easy day trips from chicago

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The best day trips from Chicago

Explore small-town breweries, bakeries and artisan shops when you embark on these easy day trips.

You don’t have to go far or spend a lot of money to enjoy a nice escape from Chicago. A simple day trip offers a fun change in scenery and is cheap and easy. Luckily, there are many exciting destinations within driving distance or accessible by train that provide the perfect getaway. Spend an afternoon soaking up the rays on beaches along Lake Michigan, go hiking near Chicago in a state park or sample a variety of beers and cheeses up north in Wisconsin. The attractions are endless, ranging from amusement parks and Japanese gardens to museums and historic lighthouses. So whether you’re low on PTO or just trying to keep travel costs down, check out our guide to the best day trips from Chicago to explore everything the Midwest has to offer.

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Top day trips from Chicago

1.  Milwaukee, WI

Driving time from Chicago: One and half hours

Getting to the Cream City requires a painless drive, but if you plan to fully indulge, ditch the car and hop on the BYOB-friendly Amtrak, which will deposit you in the heart of the city in an hour and a half. Start your day with a stack of pancakes and a round of mimosas at Sweetdiner . Meander around the Historic Third Ward and hop into home decor shops like The Home Market  or fun specialty shops like MOD GEN . Seek refuge and treats at the Milwaukee Public Market , where you’ll find a hodgepodge of the city’s best vendors, including blends from The Spice House , seafood from St. Paul Fish Company , hand-dipped chocolate from Kehr’s Candies  and vino from Thief Wine Shop & Bar . Before catching a train home, walk off the day with a trek along to Lakeshore State Park , a unique 22-acre urban oasis that juts out from the shoreline.  

2.  Fennville, MI

Driving time from Chicago:  Two hours and 20 minutes

Many Chicagoans wait until fall to venture up to western Michigan’s fruit belt. But there’s a compelling argument to be made for hitting the area a couple of months earlier, when the countryside is tranquil and stone fruits like peaches and cherries are ripe for picking. The petite town of Fennville is a great base for tasting the region’s sweet bounty in a host of iterations. Start off with a slice or two of the good stuff at local favorite Crane’s Pie Pantry , a bakery, restaurant and winery housed in a 150-year-old barn. From here, a five-minute drive will deliver you to Virtue Cider , founded by former Goose Island brewmaster Greg Hall. Reserve a spot for a guided trail tour that includes a glass of cider. Finally, make your way to Salt of the Earth for wood-fired pizza and seasonal dishes made from scratch with local and sustainable ingredients.

3.  South Bend, IN

Driving time from Chicago:  One hour and 45 minutes

There’s more to South Bend than Fighting Irish football. Check out the city’s cultured side with an afternoon visit to the History Museum , a stately Victorian mansion that was once home to the family of local industrialist and inventor James Oliver. From there, browse the local bounty at the South Bend Farmers' Market , where you can shop everything from artisan breads and doughnuts to farm-fresh fruits and veggies. When hunger strikes, head to  Café Navarre , an upscale dining spot housed in a repurposed '20s-era bank. 

4.  Madison, WI

Driving time from Chicago:  Two and half hours

Located on an isthmus between two lakes, Madison is a city that’s filled with beautiful sights—in addition to all the cheese and beer you’ve heard so much about. Begin your visit with a scenic tour of the college town on two wheels. You can rent a bike from dozens of BCycle stations , allowing you to make 30-minute trips. The Capital City trail winds around Lake Monona (the smaller of the two lakes) and provides plenty of picturesque stops for an Instagram snapshot of the skyline. Now, onto that cheese and beer: To drink like a local, head for The Malt House , a “craft beer oasis” that dates back to the Civil War era and boasts taps from local brewers like New Glarus and Central Waters. Head for Capitol Square to visit Fromagination , where you’ll find artisanal Wisconsin cheeses and knowledgeable cheesemongers to help you make a decision. Take an evening to visit the Memorial Union   Terrace , a lakefront space on the University of Wisconsin campus where you can enjoy brats, beer and live music during the summer months. 

5.  Gurnee, IL

Driving time from Chicago:  One hour

Located right off I-94, the village of Gurnee is a shopping and entertaining hub that draws 23 million visitors each year—including plenty of nearby Chicagoans. Start your day by fueling up with the brunch buffet at The Chocolate Sanctuary , where you can pile your plate with housemade bagels with lox, shrimp cocktail and chocolate-dipped strawberries. Spend some time digesting while you stroll around Gurnee Mills , which hosts more than 160 stores selling everything from sporting goods to home decor. Thrill seekers won’t want to miss Six Flags Great America , where you’ll find high-speed roller coasters and intense drop rides. On a hot day, you’ll want to plunge down the water slides and splash around the wave pool at Hurricane Harbor. If you can resist indulging in funnel cakes or turkey legs at the park, save your appetite for Primo Italian American Cuisine , where the dinner menu features black truffle ravioli and a tomahawk ribeye. Those visiting on a Friday can end the night with live music in The Parlor, Primo’s speakeasy-style lounge.

6.  Oglesby, IL

Driving time from Chicago:  Two hours

It may not be the mighty Colorado, but Oglesby’s Vermillion River offers the best rafting you’re liable to find within a quick jaunt from Chicago. A 9.5-mile run with Vermillion River Rafting will shoot you over 14 rapids, most of them class I and II. After you’ve handed over your paddle, hop in the car and head up the road to Starved Rock Lodge , where you can catch your breath and lunch on casual fare like burgers or a strawberry pecan salad at the Back Door Lounge. When you feel sufficiently refreshed, hit the hiking trails at adjacent Starved Rock State Park to spot dramatic waterfalls and explore cool glacial canyons. Unwind from your nature adventures by grabbing a nostalgic treat at The Rootbeer Stand   or check out "farm to foam" at The Lone Buffalo by Tangled Roots Brewing Company  in nearby Ottawa. 

7.  St. Joseph, MI

Golden, sandy beaches and a picturesque shoreline attract visitors to St. Joseph and its twin city Benton Harbor. You can spend an entire day out on the water with a rental from Blue Water Boat Rentals , or walk over to the St. Joseph Lighthouses — guided tours are available. If you’re hungry, you won’t have to wander far for good grub, as Silver Beach Pizza —located inside a century-old train depot—slings dependable tavern-style pies. Oenophiles, hit up a variety of vineyards and tasting rooms on the Lake Michigan Shore Wine Trail for some fine Midwestern pours.

8.  Harbor Country, MI

Driving time from Chicago:  One and a half hours

Just across the Indiana border, Michigan’s lakeside “Harbor Country” is only an hour and a half drive from downtown Chicago. Start at the north end, in Sawyer, where you can visit the original taproom of Greenbush Brewing Co.  Pair a pour of Star Chicken Shotgun IPA with some barbecue or Cajun fare. Up next, take the Red Arrow Highway down the lakeshore for great shopping, like hunting through the Harbert Antique Mall . Head back inland to the artsy community of Three Oaks to finish your day at Journeyman Distillery . A $13 tour and tasting nets you samples of 12 different spirits made in the converted corset factory. Plan to sit down for a meal at the distillery’s Staymaker restaurant afterward; you’ll need some food before getting back on the road to Chicago. 

9.  Kenosha, WI

Driving time from Chicago:  One hour and 15 minutes

About an hour north of Chicago sits this Wisconsin town filled with a plethora of things to do. Within a mile radius of the downtown area are five museums—you can gaze at dinosaur fossils and learn about the link between the prehistoric reptiles and birds at the Dinosaur Discovery Museum , or explore how the Civil War affected people on the western front at the Civil War Museum . During spring to fall, visit the Southport Lighthouse and climb 72 steps to the top for unparalleled views of Kenosha and, on a clear day, the Chicago skyline. If it’s summertime, you must check out the Bristol Renaissance Faire , where you’ll find a recreated 16th century port city populated with fairgoers dressed as knights, maidens and much more. After you’ve worked up an appetite, head over to Frank’s Diner , an almost century-old restaurant set inside an old railway car. And don’t forget to grab some cheeses and New Glarus beers at the famed Mars Cheese Castle on the way home.

10.  Rockford, IL

Situated less than 100 miles northwest of Chicago, Rockford is a surprisingly plentiful road trip destination for families. If the kids are in tow, start the day with a visit to the Discovery Center Museum , which boasts more than 300 hands-on exhibits focused on everything from light and art to color and electricity. For a dose of fresh air and nature, wander through the Anderson Japanese Gardens , a breathtaking 12-acre oasis that's filled with winding pathways, koi-filled ponds, and colorful plants. Everyone in the car will find something to love at Prairie Street Brewing Company , where bar food is elevated through dishes like Korean street tacos, Cajun mac ‘n cheese and wild mushroom quesadillas. Pick up a few cans of Screw City Light—with notes of fresh-baked bread—to take home and extend your day trip. 

11.  Cedarburg, WI

Located just 20 miles north of Milwaukee, Cedarburg is an ideal place to wind down and take things slow. The charming small town is brimming with old-world architecture, friendly Midwesterners and culture galore. If you can, plan your trip around one of the town’s seasonal events, with options including the Wine & Harvest Festival and Oktoberfest —all of which offer ample opportunities to meet local vendors and sample their wares. When you’re not rubbing elbows with the close-knit community at a street fest, make time to walk around the Cedarburg Art Museum , which hosts exhibitions from Wisconsin artists inside a former home that was designed in 1898. If wine bars are more your scene, head to Cedar Creek Winery , where you can sip your way through a $10 wine fight or enjoy a seasonal wine and cheese tasting for $25. On your way out of town, make one last stop at Amy’s Candy Kitchen to grab a hand-crafted caramel apple for the road. 

12.  Kankakee County, IL

Driving time from Chicago:  One and half hours

The Kankakee River has been a treasured area for centuries, occupied by the Illini and Miami tribes in the 17th century. Kankakee River State Park surrounds the river for about 11 miles, totaling to 4,000 acres of protected land. It’s a popular spot for fishing, canoeing, hiking and bicycling. Frank Lloyd Wright fans can visit the B. Harley Bradley House , built in 1900 and billed as the architect’s first Prairie Style home. Bring the kids to Perry Farm Park , which features a children’s museum, nature trails, playground and picnic areas. 

13.  Oak Park, IL

Drive time from Chicago:  Half an hour

You can't call yourself a Frank Lloyd Wright fanatic until you've spent the day in Oak Park, where you'll find the famed architect's home and studio as well as a smattering of other Prairie-style abodes he designed. If it's your first time, book a tour through the Frank Lloyd Wright Trust . Now that you've worked up an appetite, grab brunch or dinner at Maya del Sol , where margaritas flow like water and the ceviche is tops. Have time for one last stop? Grab a seat at Kinslahger Brewing Company , a small but mighty taproom pouring lagered brews. 

14.  Grand Rapids, MI

Driving time from Chicago:  Three hours

Summer and fall are peak seasons to visit Grand Rapids, but you’d do best to plan ahead and book your visit during ArtPrize , an international art competition in September and October when art is displayed in museums, bars, public parks and hotels. Regardless of when you go, Grand Rapids has you covered on the beer front with dozens of breweries—so be sure to bring a designated driver. First stop: Brewery Vivant for poutine and a German- or Belgian-style beer. A quick 10-minute drive will put you in the middle of downtown, where you should find parking and hoof it a while. Stop at Madcap Coffee for a post-beer pick me up before heading to City Built Brewing for creole bites and a range of beers for every palate. Finally, grab your car and head to Butcher's Union  for a dinner complete with prime cuts of beef and pours of whiskey.

15.  New Buffalo, MI

Driving time from Chicago:  One hour and 15 minutes

A charming beach town in Harbor Country, New Buffalo is popular during the warmest months. Escape the crowded Chicago lakefront and head for the sandy shores of the Mitten State, where the water’s warmer and clearer. Soak up some rays and then stroll down Whittaker Street to peruse cute shops and art galleries. Book a spa treatment at The Harbor Grand Hotel for a re-energizing experience; adventurers can rent a kayak or paddleboard from Third Coast Paddling and go exploring on the Galien River. When you need to refuel, grab a seat on The Stray Dog Bar & Grill’s bustling patio or sink your teeth into a big, juicy burger from Redamak’s . But make sure to save room for unique ice cream flavors, like Mackinac Island Fudge and Jacked Up Tennessee Toffee, at Oink’s Dutch Treat .

16.  Monroe, WI

If your cheese preferences embrace the pungent, you’ll find yourself in good company in charming Monroe, Wisconsin, gateway to a region teeming with cheesemakers specializing in varieties like Swiss and nostril-tingling Limburger. For some context, begin your day at the National Historic Cheesemaking Center , where you’ll get a crash course in south central Wisconsin’s cheesy history. Next, head to the Alp and Dell cheese store to browse more than 100 varieties of cheese, mostly from local producers, and all the wine, beer and sausage you’d want to pair them with. When you’re ready for lunch, make your way to the unapologetically old-school Baumgartner’s Cheese Store & Tavern on Monroe’s pleasant courthouse square and order the infamous specialty: a slab of Limburger on rye crowned with mustard and sliced red onions. For a chaser, stroll around the block to Minhas brewery. 

17.  Lemont, IL

Driving time from Chicago: One hour

The Village of Lemont developed as part of the construction of the canal linking the Illinois River and Lake Michigan, which also led to the discovery and development of the limestone quarries used to supply materials for iconic Illinois buildings like the Chicago Water Tower. Today, you can hop on the Metra and visit the Heritage Quarries Recreation Area , where you can walk, bike or fish along the I&M Canal (just be sure to look out for the many water birds drawn to the area). If you’re hoping for a bit more excitement, visit The Forge: Lemont Quarries . The adventure park features laser tag, a zipline and ropes courses for all ages and skill levels. Afterwards, head to the village’s historic downtown area to visit Pollyanna Brewing Company and try The Full Lemonty, their signature golden ale. You can also find the brewery’s beer on tap at Wooden Paddle , where you can watch your wood-fired pizza and other small plates being prepared before they hit your table.

18.  Holland, MI

Driving time from Chicago:  Two and a half hours

Once a stronghold of Calvinist separatists who arrived here from the Netherlands in the mid-19th century, the town of Holland continues to celebrate its Dutch heritage. To go Dutch for the day, start off with a breakfast of flaky, almond paste-filled bankets and house-roasted coffee at deBoer Bakkerij . Afterward, head across town to Veldheer Tulip Gardens , where five million of the eponymous flowers explode into bloom each spring. When hunger hits, make your way downtown for lunch and a beer at New Holland Brewing , one of the Midwest’s best-loved brewpubs. (Not sure what to sip on? Look for limited-release variations on brewery fave Dragon’s Milk, a bourbon barrel-aged stout, enriched with ingredients like cocoa nibs and peanut butter.) Wrap up your trip with a leisurely stroll around Windmill Island Gardens , a picturesque park centered around a 250-year-old Dutch windmill purchased by Holland residents in the 1960s. 

19.  Long Grove, IL

Driving time from Chicago:  45 minutes

Located 35 miles northwest of Chicago, Long Grove was founded in the 1800s by German farmers, and many of the town’s original homes and buildings are still standing. Try to visit Long Grove during one of its many delicious festivals such as Apple Fest or Strawberry Fest , when local chefs and other vendors flock to the historic downtown area to offer numerous versions of the spotlighted food. Stop by  Buffalo Creek Brewing and have a beer in their Bavarian-style taproom or in the Biergarten, which hosts live music and food trucks during the summer. Before you hit the road, swing by Long Grove Confectionery to pick up some peanut brittle or their signature Giant Myrtle, made with roasted pecans or cashews topped with caramel and milk or dark chocolate.

20.  Lake Geneva, WI

Lake Geneva has long been an accessible weekend destination for wealthy suburban Chicago families. But no matter your budget, a quick retreat to this idyllic vacation town is sure to be a blast. The town rests on Geneva Lake, an 8-square-mile body of water made for summertime fun. First things first: Get out on the water. Rent a kayak or paddleboard from Clear Water Outdoor , or take a wake surfing private lesson at Gage Marine . If you can’t get your sea legs, trek a portion of Lake Geneva’s 21-mile circumference on the Geneva Lake Shore Path and gawk at the century-old mansions that rest on the shore. When you’re hungry, Egg Harbor Café and Simple Cafe , both in the town center, offer delicious, no-fuss diner eats. If you’re feeling spendy, Baker House , a 19-century mansion-turned-hotel, offers a popular Champagne brunch with waterfront views. 

21.  Evanston, IL

Driving time from Chicago:  40 minutes

If you're short on time but craving a day away from the city, hop on the Purple Line and head to Evanston. The sweet college town is located just a few miles north of Chicago, which means you can explore the day away and still be home for dinner. Start the morning at the otherworldly Baha'i House of Worship , an architectural gem located a few miles north in Wilmette. Wander the pristine grounds before stepping inside the functioning temple, one of the oldest of its kind in the world. Up next: Fill up on colorful macarons, cakes and doughnuts at Bennison's Bakery before checking out the outdoor exhibition at the Block Museum of Art and taking a free art walk to see the 16 sculptures placed in public spaces on Northwestern University’s campus. Don't get back on the train without grabbing a brew from Temperance Beer Co. If you have the time, take a $10 brewery tour that includes samples and a souvenir pint glass. 

22.  Michigan City, IN

If you’re car-less, this small city is a perfect option for a day trip from Chicago. Hop on the Amtrak at Union Station and you’ll be in Michigan City in just over an hour. Or, take the South Shore Line and you can hop off right at the Indiana Dunes National Park , 15 miles of gorgeous sand dunes on the southern shore of Lake Michigan. Michigan City proper, too, is filled with great things to do. Visit Washington Park where you can picnic on the beach or check out the lions, wolves and other animals from around the world at the Washington Park Zoo . Hungry? Walk over to Shoreline Brewery , a gem of a microbrewery with a rotating selection of beers on tap and tasty pub grub. You can also sample local flavors at Fiddlehead , which serves high-quality comfort food including fried lake perch and grass-fed beef burgers. 

23.  Galena, IL

Driving time from Chicago:  Three hours

While this city on the Mississippi River might be best known for its resorts, you don’t need to stay the night to enjoy its mix of historical sites and outdoor activities. Start your day with brunch at Otto’s Place , where you can enjoy biscuits and gravy featuring housemade buttermilk biscuits and locally sourced sausage with a Bloody Mary or mimosa. Head across the Galena River to Nuts Outdoors and rent an electric bike to ride along the trails and into town. Take a tour of the city’s proudest attraction, the Ulysses S. Grant Home , which was gifted to the 18th president when he returned from fighting in the Civil War. If you want to learn more, you can visit the Galena & U.S. Grant Museum , which also features an offsite working blacksmith shop. That history is also on display at Galena Brewing Company , where you can sip Ult’s Dark oatmeal stout while listening to live music and feasting on a bison burger or a giant pretzel with beer cheese and house mustard.

24.  Fairbury, IL

Observant Chicago foodies may have noticed a couple of names popping up over and over again in the menu sourcing notes that have become de rigueur in these locavore-obsessed times: Kilgus Farmstead (for dairy) and Slagel Family Farm (for a range of meats). Turns out, our favorite chefs’ favorite suppliers sit just a three-mile hop from each other in the central Illinois town of Fairbury. On an hour-long tour of Kilgus , you’ll get acquainted with the farm’s herd of sweet, doe-eyed Jersey cows, learn the ins and outs of milking, and sample freshly spun soft-serve. Bring a cooler and hit the on-site store for Kilgus dairy and meat as well as goods like eggs and honey from nearby producers. Slagel has teamed up with chefs from notable Chicago restaurants to put on a program of farm dinners throughout the summer and fall. After an interactive tour and a butchering demo, you’ll retire to a picturesque barn for the main event, a family-style, BYOB meal prepared by the guest chef. 

25.  New Glarus, WI

Driving time from Chicago: Two and a half hours

Chances are you’ve already heard of New Glarus thanks the town’s eponymous brewery — which offers self-guided tours Monday through Friday and a lovely beer garden—but there are plenty of reasons to visit “America’s Little Switzerland” other than beer.  This charming, walkable town features a variety of tempting shops, hearty restaurants and themed events celebrating the town’s Swiss history and culture like the Heidi Folk Play Festival   in June . Be sure to grab a nut horn at the New Glarus Bakery , and get your fondue fix at the Chalet Landhaus restaurant. If you visit between May and October, don’t miss the seasonally-open Swissland mini golf course, featuring Alpine-themed obstacles and friendly goats. 

26.  Spring Green, WI

Driving time from Chicago: Three and a half  hours

Despite boasting a population just shy of 1,700 people, this town west of Madison has a lot going on. Most visitors are here to visit one of two sprawling complexes: Taliesin , the estate and studio of legendary architect Frank Lloyd Wright, or the infinitely weirder House on the Rock , the brainchild of artist Alex Jordan where curious travelers can explore rooms on rooms of infinity mirrors, dollhouses, nostalgic cars, circus ephemera and the world’s largest indoor carousel. When you’ve had your fill of architecture or funky assorted collections,  get a taste of traditional Wisconsin hospitality at Arthur’s Supper Club . Theater buffs can take in a show at the American Players Theatre .

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• Last Updated On
• October 3, 2023

41 Best Day Trips From Chicago — Places Nearby!

If you’re looking for a quick break away from Chicago, the great news is that you don’t have to look very far—the Windy City is surrounded by beautiful spots that make great day trips, some as close as 15 minutes away!

Everything from Illinois to Indiana is reachable, including all its impressive attractions.

Need help deciding where to go for the ultimate relaxation?

There’s no need to look far for those either–the best day trips from Chicago are right below.

1. Gurnee, IL

With 23 million visitors making their way to Gurnee every year (including Chicagoans), you know you’re dealing with one of Illinois’s most popular tourist hubs.

Sitting right off the I-94 and an hour’s drive away from Chicago, Gurnee is a hotspot, a regular feature on the list of Chicago day trips for those looking for world-class entertainment and shopping.

Start your day out with The Chocolate Sanctuary’s excellent brunch buffet and work it all off by checking out the 160-plus shops that pepper Gurnee Mills.

If you’ve got tots and adrenaline junkies in the clan, Six Flags Great America is a must-visit, with enough kiddie rides and thrilling coasters to keep everyone satisfied!

2. Cedarburg, WI

Wichita’s Cedarburg is located just two hours away from Chicago—time slows down in this delightful town, so head here if you want a leisurely day of unwinding surrounded by small-town charm.

In Cedarburg, friendly folks, rich culture, and gorgeous period architecture abound—you could spend your day here simply exploring and soaking all these in.

If you want to dive deeper into these, the Cedarburg Art Museum, a 19th-century-home-turned-art-museum is a good idea; you can also view some stunning pieces by local artists here.

The town also plays host to many fun seasonal events, including its very own Oktoberfest, but you can also enjoy great wine otherwise at the Cedar Creek Winery.

3. Evanston, IL

Want a break from the city but don’t want to travel too far, either?

Evanston should feature among the options on your Chicago trips list, being that it’s only 33 minutes away.

This little college town is home to gems such as the ethereal Baha’i House of Worship, one of only eight around the world and the oldest of the lot—the beautiful architecture, manicured grounds, and peaceful atmosphere of the temple draw hordes of visitors each year.

From here, art enthusiasts can head to the Block Museum of Art, on Northwestern University’s premises, to see the lovely sculptures, whereas food enthusiasts should consider digging into the fare at Bennison’s Bakery.

Beer enthusiasts, on the other hand, should consider making a stop at Temperance Beer Co. for the brewery tour and delicious brews.

Recommended Hotel Nearby: Graduate Evanston

4. Kankakee County, IL

If you’re looking for outdoor fun on your day trip, consider Kankakee County.

Just an hour and a half away from Chicago, the land surrounding the Kankakee River served as home to many indigenous people through the centuries and is still revered ground for many.

The Kankakee River State Park sits close to the river, sprawled across 4,000 acres of preserved land, and is a popular hub for hiking, bicycling, fishing, and canoeing.

If you’ve got kids in the clan, Perry Farm Park is a good idea, with its nature trails, children’s museum, picnic areas, and playground, whereas fans of famed architect Frank Lloyd Wright may enjoy visiting his 20th-century B. Harley Bradley House.

Recommended Hotel Nearby: Hampton Inn Bourbonnais Kankakee

5. Fairbury, IL

Foodies will enjoy a day out in Fairbury, home to the popular Slagel Family Farms and Kilgus Farmstead, both favorites among top chefs in the state.

Fairbury sits at the heart of Illinois, two hours away from Chicago.

Here, you can meet Kilgus’s lovely doe-eyed residents (of the human and Jersey variety!), get a 101 on milking, and even sample the freshly spun ice cream, all on a one-hour tour that takes you through the farmstead.

You can even stock up on their amazing ice cream if you bring a cooler with you!

At Slagel Family Farms, enjoy well-curated farm dinners that are on offer through the summer and fall months; the family-style dinner is served in a lovely barn, but not before you get an engaging tour of Slagel!

Recommended Hotel Nearby: Hampton Inn-Pontiac

Related: Activities in Chicago

6. South Bend, IN

A little under two hours away from Chicago, South Bend itself may not ring a bell—most people only hear of it through the close-by Notre Dame University—but you should consider familiarizing yourself with the city if you adore culturally rich spots.

Learn about the city at the History Museum, housed in inventor James Oliver’s Victorian manor, and if you want more museums to check out, add the Snite Museum of Art and the Studebaker National Museum to your itinerary.

From there, head to the South Bend Farmers’ Market for the gorgeous local produce.

A trip to South Bend doesn’t end without visiting Notre Dame, so make a stop here to see the lovely campus, stadium, and the stunning, Gothic-style, Basilica of the Sacred Heart.

Recommended Hotel Nearby: Embassy Suites by Hilton South Bend

Related: Best Weekend Getaways From Chicago

7. Oak Park, IL

If you worship at the altar of Frank Lloyd Wright, Oak Park is a pilgrimage that you must make.

Just 17 minutes away from downtown Chicago, Oak Park is a historic neighborhood whose primary identity is Lloyd Wright’s home and whose secondary identity is Ernest Hemingway’s home—a treat for architecture, art, and literature enthusiasts!

Start with a tour of the Ernest Hemingway Birthplace Museum and proceed to the Frank Lloyd Wright Home and Studio, both within walking distance of each other.

Other houses designed by the architect also dot the city; see if you can spot these on your trip!

End the day chilling in downtown Oak Park, or with a chilled lager at the Kinslahger Brewing Company.

Recommended Hotel Nearby: Carleton of Oak Park

8. Madison, WI

What could a capital city offer other than the usual capital-style entertainment, right?

Well, that may also be the case with Madison, but the entertainment here is top-notch and definitely worth a visit for an urban getaway.

Apart from its lovely cityscape, capitol-dotted skyline, and world-class beer, Madison offers visitors tons of attractions such as the Olbrich Botanical Gardens, city trails winding around the city’s lakes (the Capital City Trail is Insta-worthy), plenty of museums, and the Henry Vilas Zoo.

When it comes to beer, Madison leaves you spoilt for choice—take your pick from a Civil War-era taproom (The Malt House), an upscale lakefront restaurant at the University of Wisconsin (Terrace at Memorial Union), or any of the top-rated taprooms abundantly sprinkled across the city.

Recommended Hotel Nearby: Best Western Premier Park Hotel

9. Fennville, MI

Foodies don’t need much motivation to visit Michigan’s fruit belt, but if you do, petite Fennville might do the trick, with its excellent eateries that showcase the local bounty in manners that can have your tastebuds singing.

Visit Fennville at the right time of the year and try your hand at picking ripe cherries and peaches, or get your fill of these fruits in Crane’s Pie Pantry’s delicious offerings year-round, seated in a 150-year-old barn with a fine glass of wine.

Virtue Farms, a cider farm founded by brewmaster Greg Hall, is another great spot if you’re interested in cider and the cider-making process (and sampling some great cider!).

All of these are just two and a half hours away, easily accessible to all foodie travelers.

Recommended Hotel Nearby: AmericInn by Wyndham Douglas/Saugatuck

Related: Beaches in Chicago

10. Oglesby, IL

Oglesby isn’t just another quiet, Illinois-Valley river town—it’s a haven for outdoor enthusiasts, with enough recreational activities to suit any adventurer’s palette.

Sitting at the confluence of the Vermillion and Illinois rivers, Oglesby also sits close to the popular Starved Rock State Park (Illinois’s most visited) and Matthiessen State Park.

Between these two, you can cover horseback riding, golfing, rafting, fishing, canoeing, camping, kayaking, and hiking lovely forest trails (over 13 miles of it across 18 canyons in Starved Rock) in a day.

Springtime at Starved Rock also means a spectacular canyon waterfall.

If family-friendly festivals are your thing, plan your trip around the Harvest Fest in October, where fun events and cider abound!

Travel’s only under two hours, so you’ll have plenty of time to visit the attractions.

Recommended Hotel Nearby: Best Western Oglesby Inn

11. Harbor Country, MI

Harbor Country makes for a good one day trip from Chicago if you’re a fan of urban comforts, especially good beer and shopping.

An hour and a half away from Chicago, Harbor Country is home to spots such as Greenbush Brewing Co.’s original taproom and the Journeyman Distillery (housed in a former corset factory) in the north, and the Red Arrow Highway with its plentiful shopping venues spanning the lakeshore.

If you’re a fan of antiques, you’ll enjoy shopping at the Harbert Antique Mall, but even otherwise, a day spent in just the north, sampling IPAs and spirits, is a day well spent in Harbor Country!

Recommended Hotel Nearby: Fairfield Inn and Suites New Buffalo

12. Lemont, IL

Lemont is one of America’s oldest communities, having been established in 1836, and is of historic importance for the part it played in converting the state’s northern region to a commercial hub; it is from the limestone in the quarries here that many of Illinois’s iconic structures materialized.

An hour away from Chicago, Lemont is brimming with history, from its past to its authentic and preserved historic district that’s been in use since the 1800s and features on the National Register of Historic Places.

You can take a break from the history by biking, fishing, and walking in the Heritage Quarries Recreation Area, or get your thrills at The Forge: Lemont Quarries adventure park, with its rope courses, zipline, and laser tag.

Recommended Hotel Nearby: Aloft Bolingbrook

13. Long Grove, IL

The brainchild of 19th-century German farmers, Long Grove’s selling point is the many original homes and authentic period buildings that populate it—a history and architecture lover’s dream!

Long Grove sits just 35 miles (49 minutes away) from Chicago’s northwest, making it an easy day trip option.

Long Grove is also known for its many food-centered festivals, such as the Strawberry Fest and the Apple Fest, held in its historic downtown district.

Long Grove also has its own Bavarian-style alehouses, such as Buffalo Creek Brewing and Biergarten, where you can enjoy food trucks, live music, and of course, excellent beer.

Recommended Hotel Nearby: Days Inn & Suites by Wyndham Arlington Heights

Related: Fun Weekend Getaways in Illinois

14. Galena, IL

Galena ticks all the right boxes if you adore spots where history and small-town charm ooze through every pore!

Often counted among the best small towns in the country, Galena is versatile—it’s just as great for a romantic getaway as it is for a family trip.

If you’re here for the historic sites, you won’t be disappointed—the town’s past remains nearly untouched in sites such as the Belvedere Mansion, Ulysses S. Grant Home, Galena and U.S. Grant Museum, and Dowling House (Galena’s oldest building), among others.

However, it’s not just about the history at Galena—the town also has many excellent resorts, as well as outdoor attractions such as Horseshoe Mound Preserve and Apple River Canyon State Park.

The drive is about three hours long, but the knowledge you’ll gain is well worth the trip.

Recommended Hotel Nearby: Country Inn & Suites by Radisson, Galena, IL

15. Apple River State Park, IL

8763 E Canyon Rd Apple River, IL 61001 (815) 745-3302

Apple River deserves its own column—there’s an impressive plethora of things to do here for nature lovers and those wanting to unplug from the city for a day.

Nestled in northwest Illinois’s rolling hills, the state park gets its name for the Apple River that carves its way through the area’s limestone gorges.

Apple River is a hub for small-mouth bass and summer sunfish fishing, as well as trout fishing in early spring.

There are four designated picnic areas on the river’s banks, cocooned by beautiful flora and fauna, where you can use the park’s tables and grills for your own barbecue picnic.

After driving two and a half hours from Chicago, relax, take in the view, and breathe in some fresh air.

Recommended Hotel Nearby: Country Inn & Suites by Radisson, Stockton, IL

16. Lake Geneva, WI

This idyllic resort town gives you all the right reasons to visit if you’re looking for “outdoor fun meets leisure meets small-town charm”.

An hour and a half away from Chicago, Lake Geneva perfectly balances its resort-town qualities with its history and charm, thanks to a quaint downtown area, with its many local shops and eateries, and several historic buildings that offset its commercial side.

Lake Geneva is also home to many opulent Gilded-Age estates, built by affluent Chicagoans in the late 1800s; you can see these on a stroll through the 26-mile lakefront Lake Geneva Shore Path or onboard the Lake Geneva Cruise Line.

If you have an adventure in mind, there are plenty of opportunities for zip-lining, hiking, skiing, biking, water sports, and snowboarding in this year-round destination.

Recommended Hotel Nearby: Mill Creek Hotel

17. Grand Rapids, MI

Despite being geographically quite small, the city of Grand Rapids packs quite a big punch, with an international art festival that bathes the whole city in art displays and exhibits, parks sprawled across acres, and an impressive culinary scene.

A day-trip option for all ages, Grand Rapids highlights are the outdoor Sculpture Park, the Japanese Garden, the Butterfly Maze, and the Caterpillar Room.

Another interesting standout is the Frederik Meijer Gardens and Sculpture Park, 158 acres of park and museum combined.

What might also please some readers is that Grand Rapids is also Beer City USA, with craft brews that few can rival—the Beer City Ale Trail affords the best way to explore the city’s 80-plus breweries.

The travel takes about three and a half hours, but the experiences more than compensate for the time.

Recommended Hotel Nearby: Canopy By Hilton Grand Rapids Downtown

18. Holland, MI

Like the actual Holland, Michigan’s Holland comes alive with over 4.5 million tulips in early May, with tons of tourists from around the world flocking to the city for its famed Tulip Time Festival.

You can enjoy these blooms in Windmill Island Gardens and Veldheer Tulip Gardens, among other spots in the city, along with Klompen dancing, delicious Dutch food, fun parades, and foot-tapping music.

You may visit Holland for the tulips, but you’ll end up staying for the rich Dutch culture and heritage, evident in the city’s cuisine, historical architecture, windmills, the art in the Holland Museum, and the DeKlomp Wooden Shoe and Delft Factory.

Come November, the Dutch Winterfest and Parade of Lights bring their own beauty to the city; the rest of the year offers excellent shopping, dining, and beaches.

Whenever you decide to visit, keep in mind that it’s two and a half hours from Chicago.

Recommended Hotel Nearby: CityFlatsHotel Holland, Tapestry Collection by Hilton

19. Monroe, WI

If you think “cheese” when you think Monroe, you’ve hit the nail on the head—head to the “Swiss cheese capital of the USA” for some high-quality cheese, from pungent Limburger to mild Swiss cheese.

Sitting in central Wisconsin, Monroe’s cheese history goes back a long way; you can learn all about this in the National Historic Cheesemaking Center, where volunteer-led tours will take you through Imobersteg Farmstead Cheese Factory.

If you want to pick up some cheese, take your pick from over a hundred varieties at Alp and Dell, along with accompaniments such as beer, sausages, and wine.

The charming downtown area is great for a leisurely stroll, with the historic Green County Courthouse at the center.

If you love cheese, traveling for 2 hours and 38 minutes will be the simplest drive for you.

Recommended Hotel Nearby: Super 8 by Wyndham Monroe WI

20. New Glarus, WI

If you already know New Glarus, you probably do so from its world-class brewery of the same name, which is all the reason you need to visit this lovely village, but if you need more, New Glarus is also “America’s little Switzerland”.

Cute shops, charming eateries, and fun annual events shine a spotlight on the village’s Swiss roots, such as the Wilhelm Tell Festival.

The village center is especially lovely, with specialty shops, museums, and chalet-style structures with a midwestern tinge.

For a literal taste of Swiss food and beer, try Glarner Stube, Chalet Landhaus, or the New Glarus Brewing Co. (duh!), and for a historical/cultural taste of Switzerland, try the Swiss Historical Village Museum.

No need to travel thousands of miles to the Playground of Europe—it’ll only take 3 hours.

Recommended Hotel Nearby: Fairfield Inn & Suites by Marriott Madison Verona

21. Spring Green, WI

Spring Green takes a little more driving to get to (it sits three and a half hours away) but this little town draws visitors with its large architectural treasures—House on the Rock and Taliesin.

The former is artist Alex Jordan’s work, a house full of dollhouses, ephemeral circus gear, infinity mirrors, and the largest indoor carousel in the world; the latter is Frank Lloyd Wright’s studio and estate.

When the hunger pangs hit, grab a bite at the iconic Last Leaf Public House or Arthur’s Supper Club and round off the day with a performance at the American Players Theater.

Recommended Hotel Nearby: Round Barn Lodge

Related: Weekend Getaways From Minneapolis

22. Michigan City, IN

Michigan City, close to the Indiana Dunes National Lakeshore, can be easily reached in a little over an hour by road or rail and is worth visiting for its urban attractions.

Make your first stop at the Washington Park Zoo, where the tots can (safely) get up and close and personal with the residents, ranging from wolves to lions to several exotic species from different parts of the world.

Next, head to Washington Park and Beach Area for a beach picnic, walks on the pier, boat tours, kayaking, fun in the water, and plenty of family-friendly activities on the Lake Michigan coastline; if the tots don’t mind some more learning, you could alternatively visit the Old Lighthouse Museum.

Recommended Hotel Nearby: Holiday Inn Express & Suites – Michigan City, an IHG Hotel

23. Huron-Manistee National Forests

1755 S Mitchell St Cadillac, MI 49601 (231) 775-2421

Though many folks wouldn’t consider Huron-Manistee a day trip, given that it’s four hours away, it’s still an excellent option if you can make it work (and that’s highly possible!).

Occupying almost a million acres of forestland, the Huron-Manistee National Forests are Lower Michigan’s sole national forests.

Here, a ton of recreation opportunities await visitors, from fishing, off-roading, and snowmobiling to birding and wildlife watching.

The Au Sable National Scenic River, which runs through the forest, is one of the prime spots for trout fishing.

Hiking enthusiasts will enjoy the North Country National Scenic Trail winding through the forest, while the Nordhouse Dunes Wilderness Area and Loda Lake National Wildflower Sanctuary are great spots for naturalists.

Recommended Hotel Nearby: Holiday Inn Express Hotel & Suites Cadillac, an IHG Hotel

24. Chicago Botanic Garden, IL

1000 Lake Cook Rd Glencoe, IL 60022 (847) 835-5440

If you’re looking for an easy drive and glorious natural beauty, look no further than the gem that is the Chicago Botanic Garden.

Drive half an hour to the garden and be treated to 30 individual landscaped and themed gardens and natural areas spread across 385 acres, with seemingly infinite flower varieties and verdant foliage.

While walking around is the best way to immerse yourself in the spot’s beauty, there’s also a tram that will take you through the popular spots; there are also many bike trails.

Families with kids may enjoy the Children’s Growing Garden and the Nature Play Garden.

Recommended Hotel Nearby: Sheraton Chicago Northbrook

25. Abraham Lincoln Presidential Library and Museum, IL

212 N 6th St Springfield, IL 62701 (217) 558-8844

While several resources exist online and in books, there’s nothing like learning about the country’s 16th president at the Abraham Lincoln Presidential Library and Museum.

A range of immersive and interactive exhibits, such as traveling displays, documents, and Civil War-era artifacts, will teach you all about Abraham Lincoln, “The Great American Story”.

The museum also hosts several annual events, such as a scavenger hunt and art competitions that are relevant to both the president’s life and the current times, while the library is decked with newspapers, manuscripts, and tons of printed resources that unravel one of the country’s most influential leaders.

For such an Abe Lincoln fan, traveling 3 hours is going to be a breeze.

Recommended Hotel Nearby: Best Western Clearlake Plaza

26. Old State Capitol Historic Site, IL

526 E Adams St Springfield, IL 62701 (217) 785-7960

While we’re on the topic of Abraham Lincoln, here’s another Lincoln-related must-see if you’re a fan of the erstwhile President of the United States—the Old Capitol Historic Site.

This entirely reconstructed building, built in the Greek Revival style, is the site of President Lincoln’s prominent “House Divided” speech, and where he was laid in state after his assassination.

A short video in the onsite theater will give you a brief history of the Old Capitol, following which you can either take a guided or self-tour.

There are also several annual events dedicated to President Lincoln’s legacy, such as the Old Capitol Art Fair, the Abraham Lincoln Symposium, and an Annual Civil War Encampment.

Stop by from the Abraham Lincoln Library—it’s only a 3-minute walk.

Recommended Hotel Nearby: Northfield Inn Suites and Conference Center

Related: Best Weekend Getaways From St Louis

27. Peoria, IL

Peoria, once the “whiskey capital of the world”, sits in the center of Illinois, made up of four distinct neighborhoods that display its vibrant culture and art.

For interesting history lessons, head to the Warehouse District, where historic buildings find a new purpose as residences, shops, studios, and restaurants.

For upscale dining, visit the Central Business District, which also houses the Peoria Civic Center, but to truly feel the city’s pulse, head to any of the restaurants, breweries, and museums (especially the Peoria Riverfront Museum) in the Riverfront District.

For a more quirky, eclectic experience, West Main Street, sitting next to Bradley University, is a great choice.

From Chicago, it only takes under a 3-hour drive to reach this boozy city.

Recommended Hotel Nearby: Best Western Plus Peoria

28. Kettle Moraine State Forest, WI

30,000 acres of breathtaking natural splendor await visitors to the Kettle Moraine State Forest.

A great getaway for nature lovers, the state forest is a little under three hours’ worth of driving from Chicago and is full of hiking, biking, skiing, horseback riding, mountain biking, cross-country skiing, and snowshoeing opportunities.

The Kettle Moraine Scenic Drive will take you through the best of the state forest’s sights and is among the most scenic places near Chicago.

The drive will also take you through the historical Cushing Memorial Park, Wade House Stagecoach Inn, Old World Wisconsin Outdoor Museum, and Holy Hill Basilica, along with several communal, geological, and natural landmarks.

Recommended Hotel Nearby: Hampton Inn & Suites West Bend

29. Door County, WI

This is another one for nature lovers, though at four hours away, it can be quite a drive, however scenic.

If you do make the drive to Door County, though, you’ll be rewarded with splendid natural views, a ton of outdoor activities, and beautiful parks.

The star attraction is Lake Michigan, where you can take in your gorgeous natural surroundings by swimming, hiking, kayaking, and climbing up to Cave Point for ‘gram-worthy views of the area’s limestone bluffs.

A truly unique activity to enjoy at Door County is shipwreck diving and exploring the county’s 11 lovely lighthouses, with their stunning vistas.

Recommended Hotel Nearby: Gordon Lodge

30. Blaum Bros. Distilling Co, IL

9380 US Hwy 20 W Galena, IL 61036 (815) 777-1000

What started off as a rivalry between two brothers turned into a partnership, all thanks to a shared love of whiskey, giving the world the Blaum Bros. Distilling Co. and some mighty fine spirits.

Visitors are taken through the distilling process through a sensory tour, where they can smell, touch, taste, and see the various ingredients that go into the distillery’s handcrafted liquor.

The tour aptly ends in the cocktail bar and tasting room, where guests can get their fill of the distillery’s superb vodka, bourbon, moonshine, and gin—a designated driver is a must!

Gather your bibulous friends and drink to your heart’s content after a 3-hour ride.

Recommended Hotel Nearby: Irish Cottage Inn & Suites

31. Cantigny Park, IL

1 S, 151 Winfield Rd Wheaton, IL 60189 (630) 668-5161

A gift to Illinois’s Wheaton by well-known philanthropist Colonel Robert R. McCormick, Cantigny Park’s doors were thrown open to the public in 1958.

Visitors flock to the park for the many educational and recreational opportunities it presents, including two museums that pay tribute to military history and the colonel himself, respectively.

The park also has beautiful formal gardens spread across acres, a picnic area, and three miles of trails, which you can explore through walking tours.

You’ll also find an education center, a visitors’ center, a full-service clubhouse, and a youth golf academy with a 27-hole golf course to boot at Cantigny, as well as many seasonal activities for children and onsite food joints.

All these attractions are at your disposal with just a 45-minute drive.

Recommended Hotel Nearby: Hyatt House Naperville/Warrenville

Related: Places to Eat: Wheaton, IL

32. North Utica

If you adore sleepy towns and the slow-paced life, it rarely gets better than North Utica, nestled into the banks of the Illinois-Michigan canal and the Illinois River.

North Utica will especially appeal to nature, wine, and antique lovers, with its many parks, trails, proximity to four state parks, antique stores, wineries, flea markets, collectibles stores, and pottery studios.

If you’d like to learn about North Utica’s history, the LaSalle County Historical Museum is a good idea.

If it’s a family day out, get a day pass at the Grand Bear Resort and make the most of the massive indoor waterpark, sports bar, and restaurant.

Visit North Utica and see its underrated beauty; it’s only an hour and 40 minutes away.

Recommended Hotel Nearby: Hampton Inn and Suites Peru

33. White River State Park, IN

801 W Washington St Indianapolis, IN 46204 (317) 233-2434

This urban, 267-acre, award-winning waterfront park sits in downtown Indianapolis and is one of the seven districts designated as cultural districts in the city.

In White River State Park, you’ll find plenty of attractions, both historical and contemporary.

Contemporary curated attractions include the likes of Celebration Plaza, Eiteljorg Museum, the Indianapolis Zoo, the NCAA Hall of Champions Museum, Victory Field, and the Indiana State Museum.

Historical attractions include Old Washington Street Pedestrian Bridge, Historic Central Canal, and the Historic Pumphouse.

All in all, a great family-friendly day-trip option if you’re seeking 3-hour trips.

Recommended Hotel Nearby: Conrad Indianapolis

Related: Weekend Getaways From Indianapolis

34. Napierville, IL

Napierville may be small, but as the old adage goes, size doesn’t matter—this former prairie town is now an award-winning city, earning awards that designate it the best place to live and the top kid-friendly city, among others.

Despite this, Napierville still retains its small-town charm, with friendly folks and plenty of quaint attractions such as the gorgeous 158-fool Moser Tower (though now closed, you can view it from the outside), and the covered bridge, fountains, clock tower, heritage sculptures, paddle boats, and labyrinth at the Riverwalk Park.

The city’s other highlights include the 1.75-mile Riverwalk walkway that runs along the DuPage River and Centennial Beach and Grill, a restaurant-cum-beach-waterpark!

All these are only 40 minutes away from Chicago!

Recommended Hotel Nearby: Chicago Marriott Naperville

35. Indiana Dunes National Park, IN

1215 N State Rd 49 Porter, IN 46304 (219) 395-1882

Tucked into the southern shore of Lake Michigan, the Indiana Dunes National Park is a stone’s throw away from Michigan City at 48 minutes, so you could either combine the two or make a separate trip—it’s worth it, either way!

Open to visitors throughout the year, Indiana Dunes boasts pristine beaches and towering sand dunes.

There’s plenty on offer here for outdoor enthusiasts, from swimming, birding, and hiking in the summer to cross-country skiing in the winter.

Try to catch a sunset here; if you’re lucky and the day’s clear, you’ll even be able to see Chicago’s twinkling skyline.

Recommended Hotel Nearby: Spring House Inn

36. Morton Arboretum, IL

4100 IL-53 Lisle, IL 60532 (630) 968-0074

In existence since 1922, the Morton Arboretum is an outdoor museum and a naturalist haunt 40 minutes from Chicago.

With over 200,000 live plants from around the world thoughtfully exhibited across 1,700 acres, the Morton Arboretum reinforces the significance of protecting nature’s gifts and actively participating in conservation.

Despite the wide variety, each plant variety thrives in the arboretum, having been optimally placed for the best growth.

If you’re not big on learning about plant species, you can simply enjoy strolling through the tree-lined paths that circle Meadow Lake or any of the annual events hosted here, if your visit coincides.

Recommended Hotel Nearby: Chicago Marriott Suites Downers Grove

37. Nicholas Conservatory and Gardens, IL

1354 N 2nd St Rockford, IL 61107 (815) 987-8858

Sitting on the banks of the Rock River, the Nicholas Conservatory is 11,000 square feet of flowers, trees, tropical plants, garden sculptures, an infinity pond, a koi pond, and benches for visitors to sit and soak in all the natural beauty on display.

There are paths outdoors that lead to attractions such as the Riverview Terrace, waterfall gardens, lovely teahouses, Eclipse Lagoon, the Sinnissippi rose garden, Forest City Queen Riverboat dock, and Trolley Car 36 station.

For a lovely dining experience, come here on a Wednesday night in the summer and enjoy a rooftop meal on their viewing deck.

At different times of the year, you can also enjoy several temporary displays such as Breakfast with Santa and Lorikeet House.

Travel a mere 1 hour and 44 minutes to this wonderland and indulge your inner aesthete.

Recommended Hotel Nearby: Embassy Suites By Hilton Rockford Riverfront

38. Anderson Japanese Gardens, IL

318 Spring Creek Rd Rockford, IL 61107 (815) 229-9390

An hour and forty minutes away from Chicago sits the gorgeous Anderson Japanese Gardens, a garden that business John Anderson commissioned expert craftsman Hoichi Kurisu to design.

The gardens sit in the bustle of Rockford but are a world away at the same time.

The gardens are focused on three primary elements—plants, stone, and water—which Kurisu has used to build this oasis.

Guided tours will take you through the seasonal beauty on offer here, as well as the garden’s history and principles.

If you enjoy calm spaces in the midst of nature, this site must feature on your list of places to visit near Chicago.

Recommended Hotel Nearby: Extended Stay America Suites – Rockford – State Street

39. Milwaukee, WI

A slow day with plenty of great beer and Harley-Davidson—if this sounds like your jam, head to Milwaukee for your day trip.

The city celebrates its German brewing heritage, a fact that’s evident in the tons of brewpubs and breweries, historical or contemporary, spread out across the city and serving excellent craft beer.

If you’re a motorcycle enthusiast, you can’t leave Milwaukee without a visit to Harley-Davidson Museum to see the world’s oldest-known Harley and several other motorcycle memorabilia.

Milwaukee also plays host to over two dozen festivals throughout the year (hence known as the “City of Festivals”), but if that doesn’t interest you, maybe the 25 theaters, 150 parks, 75 golf courses, and the lakefront Milwaukee Art Museum will!

The quick one and a half hour travel time is a huge plus, too.

Recommended Hotel Nearby: The Pfister Hotel

40. Rockford, IL

An hour and 40 minutes away from Chicago is Rockford, a family-friendly destination with enough to keep the young and not-so-young equally engaged (yes, involving beer!).

A great way to start the day is to visit the Discovery Center Museum, where over 250 exhibits covering a range of subjects will work off all that excess energy in the kids, or the Burpee Museum with its amazing dinosaur exhibits.

After lunch, head to any of the arboretums, gardens, or conservatories in the “city of gardens”, such as the aforementioned Nicholas Conservatory or Anderson Gardens, for some quiet time before you grab a beer at the Prairie Street Brewing Company and responsibly hit the road again.

Recommended Hotel Nearby: Radisson Hotel & Conference Center Rockford

Related: Best Restaurants in Rockford, IL

41. Midewin National Tallgrass Prairie, IL

IL-53 Wilmington, IL 60481 (815) 423-6370

If you want to see for yourself why Illinois is the Prairie State, visiting Midewin should top your list of things to do outside Chicago .

About an hour away from Chicago sit this 9,000-acre expanse, home to a roaming bison herd that you may spot if luck is on your side (it’s a large park!).

However, that shouldn’t stop you from bringing your binoculars and starting your search at the Iron Bridge Trailhead and hiking three miles to the overlook point, where viewing scopes better your chance of seeing the stars of Midewin!

And there it is—a list of the best day trips from Chicago.

Since so many of these locales involve some form of alcohol, ensure that your enjoyment is responsible and always take along a designated driver.

That apart, here’s to the beauty that surrounds Chicago and a happy day out!

Recommended Hotel Nearby: Hollywood Casino Joliet Hotel

Map of Day Trips Near Chicago, IL

41 Best Day Trips from Chicago, IL for 2024

• Cedarburg, WI
• Evanston, IL
• Kankakee County, IL
• Fairbury, IL
• South Bend, IN
• Oak Park, IL
• Madison, WI
• Fennville, MI
• Oglesby, IL
• Harbor Country, MI
• Long Grove, IL
• Apple River State Park, IL
• Lake Geneva, WI
• Grand Rapids, MI
• Holland, MI
• New Glarus, WI
• Spring Green, WI
• Michigan City, IN
• Huron-Manistee National Forests
• Chicago Botanic Garden, IL
• Abraham Lincoln Presidential Library and Museum, IL
• Old State Capitol Historic Site, IL
• Kettle Moraine State Forest, WI
• Door County, WI
• Blaum Bros. Distilling Co, IL
• Cantigny Park, IL
• North Utica
• White River State Park, IN
• Napierville, IL
• Indiana Dunes National Park, IN
• Morton Arboretum, IL
• Nicholas Conservatory and Gardens, IL
• Anderson Japanese Gardens, IL
• Milwaukee, WI
• Rockford, IL
• Midewin National Tallgrass Prairie, IL

21 Best Day Trips From Chicago In 2024

Written By: ThePlanetD Team

United States

Updated On: February 19, 2024

Welcome to the Windy City! Whether a local or a traveler eager to explore beyond the skyline, our guide to the best day trips from Chicago is your ticket to adventure. We’ll show you how to swap city streets for scenic escapes, all within a day’s reach of Chicago. From charming small towns to natural wonders, get ready to discover the Midwest’s most unforgettable experiences. Pack your sense of adventure, and let’s hit the road – Chicago-style day trips await!

Table of Contents

Incredible Day Trips from Chicago

In this guide, we give you ideas for the top day trips from the third most populous city in the US. Located on the shores of Lake Michigan, many places will tempt you away from the city center. After exploring all of the awesome things to do in Chicago , from the Chicago River to historic landmarks, head to these fantastic places located within easy reach of the city.

The city is ideally located with easy border-crossing into Wisconsin, Michigan, and Indiana. It is also a great starting point for a day trip further south into central Illinois. You have four states at your fingertips – so you should carve out time for a day trip while visiting.

1. Milwaukee, WI

Milwaukee is a big deal. This major city is located on the shores of western Lake Michigan in Wisconsin – just a 1.5 hour train ride or drive north of Chicago. We’d suggest catching the train if possible, as Milwaukee is best known for its breweries. Taking guided brewery tours is one of the  best things to do in Milwaukee . Aside from its alcohol, though, it is also home to the Holler House and Milwaukee Art Museum. Don’t forget the Harley-Davidson Museum, which hosts a beautiful display of motorcycles and documents iconic biker culture. The Milwaukee Public Museum also has a large-scale European village.

If you want a fantastic day out from Chicago, Milwaukee is ideal. It has a strong sense of culture and many niche pockets of interest, like Harley-Davidson bikes and breweries. It is also a breeze to reach by train or car.

• Distance from Chicago: 1.5 hours
• How to get there: Train, bus or coach

Suggested Tour: A Group Tour to Discover Milwaukee

2. south bend, in.

South Bend has a different vibe as a university city on the St. Joseph River. It is fantastic if you are looking for a more sedate city experience. You can visit the University of Notre Dame’s iconic campus, with its classic gold-domed building. There’s also plenty of local history that you can experience in the city center, like car manufacturing from years gone by at Studebaker National Museum and the regional history at the History Museum.

South Bend is definitely slower-paced than quick-footed Chicago. However, it has lots of attractions too. Think of it as a relaxing and intellectual place to spend a day sightseeing. It has lots of fun and student twists, like cheap bars and coffee spots.

The city is located just east of Chicago, on the other side of Indiana Dunes National Park, and on the lower east shore of Lake Michigan. It is best reached by car, and we’d recommend stopping off at the national park en route.

• Distance from Chicago: 2 to 3 hours
• How to get there: Car or train

3. Madison, WI

Small Madison might not seem capital-worthy, but it is actually the capital city of Wisconsin, not the major, sprawling giant of Milwaukee. This smaller city has beautiful architecture galore. You can get up close to the historic domed Wisconsin State Capitol and walk the Capital City State Trail to sightsee different city attractions. There’s a botanic garden experience, too, at Olbrich Botanical Gardens, plus a quirkier downtown area with bars and coffee shops. Madison is your best choice if you fancy a political sightseeing day trip from Chicago.

Madison is also beautifully located next to two huge lakes – Lake Mendota and Lake Waubesa. Summer leaves plenty of opportunities for water sports and sunny waterfront hiking trails. Follow this walking tour to see the city’s architecture including the State Capitol, Der Rathskaller, Bascomb Hill, and Memorial Union.

• Distance from Chicago: 2 to 4 hours
• How to get there: By car or shuttle bus

4. Starved Rock State Park, IL

Starved Rock State Park is one of the most popular attractions in Illinois. The park sits on the banks of the Illinois River and holds a collection of sandstone canyons amidst beautiful forests. The canyons were initially cut with glacial meltwater, and you can explore the scenery using a network of clearly marked wooden boardwalks. Starved Rock State Park also has tons of waterfalls, which get impressively powerful in wetter months.

Nature lovers will adore this day trip choice. Not only is the natural scenery astounding, but you can also spot wildlife like white-tailed deer and bald eagles. Starved Rock State Park covers over 2,600 acres and has 13 miles of trails, with 18 canyons to admire. It is located inland from Chicago and Lake Michigan.

• How to get there: Car

5. Cedarburg, WI

Cedarburg has serious charm. It has old-school-style houses and is frequently compared to a movie set. The town was founded in the 1840s by a mixture of predominantly Irish and German settlers and is now considered a suburb of Milwaukee. Cedarburg has many cute and aesthetic things to do, with the bonus of brewery and winery tours. You can walk the vineyards and tour brewing rooms or head to unique attractions like the Wisconsin Museum of Quilts and Fine Arts. Cedarburg is a real gem and beats to its own drum, making it a memorable day trip from Chicago.

This Wisconsin town is located just north of Milwaukee’s city center. It is best reached from Chicago by car, and you can always incorporate a stop-off in Milwaukee’s city center – parking in the outskirts and commuting in.

• Distance from Chicago: 2 hours
• How to get there: By car

6. Illinois Beach State Park, IL

If you want beaches, Illinois Beach State Park is the place to be on a Chicago day trip. The park covers over 4,000 acres, with a beautiful shore path and network of hiking trails. It is an ideal place for a beach day along the shores of Lake Michigan. However, Illinois Beach State Park is equally more than just a beach destination.

It has campgrounds and playgrounds, plus shower blocks and a nature center. Illinois Beach State Park is somewhere to spend an entire day. Start with a hike and visit the nature center before heading to Isherwood Beach, and even camping overnight if your schedule allows it.

The park is quite close to Chicago, taking less than an hour to reach by car. It’s a great day trip if you have a warm day or fancy a beach trip. Or it is the perfect adventure if you fancy camping a night to break up your classic city break.

• Distance from Chicago: 1 hour

7. Lake Geneva, WI

Lake Geneva is a beautiful resort city along the banks of Geneva Lake in Wisconsin, northwest of Chicago. As a small city out of the leading public transport lines, it is best reached by car.

Once you arrive, you are greeted by Gilded Age mansions with dramatic architecture and a scenic Shore Path that snakes around the city’s section of Geneva Lake. Historically, Lake Geneva was used as a bolt-hole for affluent Chicago residents, and looking at the city’s surrounding natural beauty, it’s easy to see why.

Admire Victorian history and Gilded Age architecture, and visit the Lake Geneva beaches. Big Foot Beach State Park has brilliant beaches, especially for a lazy afternoon. Lake Geneva is a beautiful day trip destination to unwind before revisiting Chicago’s chaotic sightseeing scene.

8. Rockford, IL

Rockford is a major city located on the banks of the Mississippi River, giving it the nickname’ River City’. Rockford is also called the ‘Forest City’ because of its history of tree felling, forests, and furniture-making industries. It is a shapeshifter with a long history and a prominent place in Illinois’ society. Nowadays, though, it is an ideal day trip candidate and is full of popular attractions and historic places. You can stop by the koi-filled ponds at Anderson Japanese Gardens, kick back in numerous public parks, or head to the Rockford Art Museum. Tinker Swiss Cottage Museum and Gardens is also brilliant.

Rockford is located in northern Illinois, right under the Wisconsin border. We’d recommend combining it with a trip to Madison, located roughly an hour above the city. It is a great stop-off point for those driving to the Wisconsin capital.

9. Indiana Dunes National Park, IN

Forget state parks if you like natural beauty – aim big with Indiana Dunes National Park. This stunning park is far more than just sand dunes and covers 15 miles of beautiful shoreline perfect for swimming and sunbathing. Indiana Dunes National Park is also a hot spot for bird watching and hiking. The national park is located on the southern end of Lake Michigan. It is a beautiful spot to visit to embrace the lake’s beauty. An entrance ticket costs around $20, and you can spend the whole day exploring the park.

Indiana Dunes National Park is located just southeast of Chicago and is ideally combined with visits to South Bend or day trips into Michigan or Indiana.

• Distance from Chicago: 50 minutes

10. Lakeshore State Park, WI

Everyone loves an urban park. This stunning park sits just off Milwaukee’s coastline. Still, we will include it as a standalone attraction since it justifies a visit on its own merit. Lakeshore State Park is best explored on foot by walking the Hank Aaron State Trail. You can enjoy city skyline views and expansive vistas over Lake Michigan. And if you are looking for a romantic day trip from Chicago, head to Lakeshore State Park at sunset with a picnic.

The state park is obviously well combined with a visit to Milwaukee. This little island state park is a beautiful spot near the city. It is located off the Historic Third Ward and accessible by a pedestrianized bridge connecting it to the mainland.

11. Monroe, WI

Monroe is pretty cool. The quirky city is known as the Swiss cheese capital. It has a vast history of dairy farming that has given it a massive cheese reputation. You can visit to take food tours – highly recommended – and try local products and produce. You should visit the National Historic Cheese Making Center Museum and the Chalet Cheese Cooperative. There’s also beautiful architecture and historic places, like the Green County Courthouse, completed in 1891. The Monroe Historic Square is in the city’s center, surrounded by shops and aesthetic scenery.

Monroe is a tiny city compared to some of Chicago’s neighboring giants. It is roughly located halfway between Madison and Rockford. It is definitely best accessed by car.

12. St. Joseph, MI

St Joseph is a scenic coastal city in southwest Michigan and an ideal day trip if you want to venture into MI on a day trip from Chicago. It sits along the shore of Lake Michigan with beautiful attractions like Silver Beach County Park and Lions Park Beach. Silver Beach is particularly cute to visit, with a 1910 carousel and restored pavilion that bring a wonderful, vintage-style aesthetic to the city. A classic red and white lighthouse is near the city’s North Pier.

St Joseph is a beautiful choice if you want one of those traditional seaside day trips. It is only a short drive from Chicago, despite the fact that you’ll be venturing through Indiana and crossing the Michigan border. Hooray for Lake Michigan’s close network of US states. It is fantastic to combine with Indiana Dunes National Park and Michigan City.

• How to get there: By Car

13. Channahon State Park, IL

Channahon State Park is an absolute must. The state park sits on some of the most historic Illinois canals, housing a restored lock tender’s house for extra historical value. You can enjoy a network of hiking trails with waterfalls, birds, and historic towpaths to snap photos of. Distance isn’t an issue when visiting inland Illinois; Channahon State Park is less than an hour’s drive from central Chicago. It is a great day trip if you want minimal travel time and an insight into Illinois’ canal history.

You can organize guided tours around Channahon State Park, including canoe trips. The state park is a designated part of the Illinois and Michigan Canal National Heritage Corridor. It is widely hailed as an essential part of the state’s history. It is a nature-given adventure park.

14. Oak Park, IL

Oak Park is a beautiful village in the suburbs of Chicago. It really packs a punch beyond pretty architecture for such a small area. Visitors can enjoy attractions like the Frank Lloyd Wright Home and Studio, Ernest Hemingway’s Boyhood Home, the National Historic Landmark of Mills Park and the Oak Park River Forest Museum. Oak Park is a quickfire selection of museums in a tiny area, accessible from central Chicago using public transport. What’s not to love? It is the perfect choice if you want trips from Chicago done easily.

It is so handy to jump on a train and be amongst dozens of museums. Additionally, its Unity Temple was recently designated as a UNESCO World Heritage in 2019. Despite all its existing attractions and offerings, Oak Park is very much up and coming in terms of visitor recognition and value for tourism.

• Distance from Chicago: 15 to 20 minutes
• How to get there: By train

Suggested Tour: Private Frank Lloyd Wright Tour from Chicago

15. grand rapids, mi.

Grand Rapids is another major city – think skyscrapers and a beautiful riverside setting with dramatic bridges. Grand Rapids has plenty of culture, with museums like the Gerald Ford Presidential Museum and Grand Rapids Public Museum. It also has a cool, safe, and walkable downtown district, which includes the Grand Rapids Art Museum, an attraction and initiative that spotlights local artists.

We like to catch a shuttle to Grand Rapids, as it has an illustrious brewery history. In particular, it is known for New Holland Brewing, and you can take guided tasting tours at the local breweries that are still running. Otherwise, driving is quicker, and you can stop off at spots like Indiana Sand Dunes National Park, St Joseph, and South Bend. You hug the lower shoreline of Lake Michigan, which is a long but very scenic drive. Ideally, rotate drivers and have a few different stops en route.

• Distance from Chicago: 3 to 5 hours
• How to get there: By car in just under 3 hours or by shuttle in under 4
• Suggested Tour: Grand Rapids Ghost Tour

16. Windmill Island Gardens, MI

Chicago might be known as ‘Windy City,’ but check out Windmill Island Gardens. This seasonal park features a 250-year-old windmill in an ode to the city’s Dutch influence. You can take self-guided tours of the park, admire the windmill, and meet guides in traditional Dutch costumes. There’s also a tulip garden, which is stunning in spring.

This is one of the leading day trips from Chicago if you want Dutch heritage, and it is even located outside of a city named Holland. Windmill Island Gardens is located in Michigan, so you’ll be driving the south coast of Lake Michigan, cutting through northern Indiana and across the Michigan border. When it comes to visiting Michigan, distance can be a concern. Is it a long day of driving? Yes. But it is incredibly scenic and a great way to combine several attractions. If you have a few drivers, you won’t have any trouble as you can just rotate driving time.

• Distance from Chicago: 2.5 hours

17. Galena, IL

Galena is an absolute gem of a charming small town, sitting on the banks of the Galena River with tons of Civil War history. The town was home to the Civil War General Ulysses S. Grant, and his former home is a State Historic Site. Of course, Ulysses S. Grant later became a US president, so his story is immortalized. Galena is a great place to visit if you are interested in politics and history. Its town center is relatively walkable and is full of stories and scenic 19th-century architecture.

Galena is right in the top left corner of Illinois, on the border of Iowa and Wisconsin. It is a fabulous add-on from Rockford or Starved Rock State Park, around 1.5 hours away by car.

• Distance from Chicago: 2 hours and 45 minutes
• Suggested Tour: Downtown Galena Food and Drink Tour

18. Michigan City, IN

Michigan City is just an hour away and is brilliant, accessible day trip material. If you want an easy trip from Chicago, Michigan City is it. Fancy a drive? You can drive there in an hour, passing Indiana Dunes National Park. Fancy a train ride? You can read or nap and reach the city in less than 2 hours. There’s lots of lakeside culture and history, with multiple lighthouses to admire and the quaint Washington Park Beach.

There’s also period history at the Barker Mansion, which showcases English-inspired decor and furnishings in a 19th-century mansion. Admire the history, have a beach day, or enjoy inner-city shopping at outlet stores. Michigan City offers loads and, at the very least, is a change of scene.

You can easily visit Michigan City; proper day-long trips are low on travel time and high on attractions. And that sums up this lakeside city.

• Distance from Chicago: 1 to 2 hours
• How to get there: 1 hour by car or 2 hours by train

19. Peoria, IL

Peoria is a beautiful city in Illinois. It was primarily established as a port city and trading center thanks to its position on the Illinois River. It is located much further inland in central Illinois. It is just an hour or so further central than Starved Rock State Park – hello, potential combined day trip.

Peoria has beautiful riverside parks, including Peoria Riverfront Park and Liberty Park. There’s also the Riverfront Museum and Peoria Historical Society. It is a lovely place to just walk and explore on foot. And the contrast between hectic Chicago and sedate Peoria is vast, making it a worthwhile day trip.

The city is located southwest of Chicago and is best accessed by car. This way, you can also stop off at Starved Rock State Park on the way.

20. Six Flags Great America, IL

What about a day at an amusement park? Six Flags Great America is a chain of amusement parks scattered across the US. And there is one on the outskirts of Chicago, creating the best day trip for fun-loving tourists. The park has water park rides, rollercoasters, and all-round fun entertainment. You can get adrenaline on rides like Sky Striker or the American Eagle. Alternatively, try the sedate, family-friendly rides like the Big Easy Balloons or Cubasco tea cups.

Everyone loves a fun day out. And Six Flags Great America is the perfect day trip to skip sightseeing and escape the city to enjoy some quality ‘fun’ time. It is the ideal place to let your hair down and has an impressive range of rides, making it suitable for adults and children. Six Flags Great America is located north of Chicago, just under the Wisconsin border. Get your tickets in advance here.

• How to get there: 1 hour by car or 2 hours by train then bus

21. Glacial Park Conservation Area

Finally, there’s the beautiful Glacial Park Conservation Area. This 3,400-acre reserve is a stunning mix of wetlands and prairie, with glacial kames and ample scenic canoeing or fishing opportunities. It is one of the most photogenic places to experience natural beauty on a day trip from Chicago. You can explore Glacial Park on foot or by water or shake things up and book a horseback riding tour. The park has a grand total of 8 miles of shared-use trails, and you’ll definitely want to bring a camera.

Glacial Park Conservation Area opens from sunrise until sunset all year round. It is ideal if you want to switch from the standard suburban park experience to a bit of rugged, remote nature.

• Distance from Chicago: 1 hour and 20 minutes

There’s so much to experience on day trips from Chicago – whether that’s Dutch heritage, rich history related to the Civil War, or riding water park rides at Six Flags America. You can embrace small-town charm at Oglesby, natural beauty and natural wonders at Indiana Dunes National Park, or craft beer at a local brewery. Chicago’s location right next to three other state borders means you have lots of diversity when choosing day trips. And the ever-presence of beautiful Lake Michigan means a constant barrage of water sports and beaches. Hopefully, you have at least 5 or 6 day trip choices.

Are you looking for more inspiration? Why not check out our guides on the  best things to do in Wisconsin  and  the best places to visit in Michigan ? We’ve also got notes on the best, most  unique things to do in Northern Michigan  specifically, so check that out if you have time to add a couple of days to the end of your Chicago trip. If you have longer, why not take a 2-3 day excursion from Chicago? It is a brilliant launchpad to discover more of the experiences in the states around Lake Michigan. Chicago’s location is by far its winning quality, and you should take advantage of it when planning day trips and excursions.

Plan your trip to Chicago with these Resources

• 29 of the Best Things to Do in Chicago
• Where to stay in Chicago: Best Areas and Hotels
• Top 10 Hot Spots to Eat in Chicago
• 23 Cool and Unique Things to do in Milwaukee, Wisconsin

Travel Planning Resources

Looking to book your next trip? Why not use these resources that are tried and tested by yours truly.

Flights: Start planning your trip by finding the best flight deals on Skyscanner

Book your Hotel: Find the best prices on hotels with these two providers. If you are located in Europe use Booking.com and if you are anywhere else use TripAdvisor

Find Apartment Rentals: You will find the cheapest prices on apartment rentals with VRBO . 

Travel Insurance: Don't leave home without it. Here is what we recommend:

• Allianz - Occasional Travelers.
• Medjet - Global air medical transport and travel security.

Need more help planning your trip? Make sure to check out our Resources Page where we highlight all the great companies that we trust when we are traveling.

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15 Spectacular Day Trips from Chicago IL

• Illinois / In the City / USA

These are the best day trips from Chicago IL.

I grew up in Iowa, and Chicago was the major city near us. I remember my older cousin taking road trips and returning with exciting stories of the big city. It wasn’t until college, after I had moved to the South, that I visited Chicago for the first time.

Chicago is situated on the shores of Lake Michigan and is a vibrant city famous for its deep-dish pizza, museums, and instantly recognizable architecture.

There’s a lot to do in Chicago already, but it also makes a great base to explore the Midwest (especially Illinois, Wisconsin, and Michigan) when you need to escape the city.

This post may contain affiliate links, where we receive a small commission on sales of the products that are linked at no additional cost to you. All opinions are always our own. Read our full disclosure  for more info. Thank you for supporting the brands that make Local Adventurer possible.

Last Updated: November 2, 2023

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• Best Day Trips from Chicago

More Chicago Day Trips Under 3 Hours

Map of the best day trips from chicago.

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Planning Checklist

More resources, 15 spectacular day trips from chicago.

When you think of the Midwest, you picture endless corn farms (there’s that, too!). But beyond the cornfields, it’s a region filled with culture and stunning landscapes, as these day trips from Chicago will prove.

1. Oak Park, Illinois

193 N Marion St #208, Oak Park, IL 60301, map

Distance:  9.1 / 15 min Things You Can’t Miss:  Frank Lloyd Wright Home & Studio, Ernest Hemingway Birthplace, Unity Temple What to Eat:   Pete’s Red Hots ,  Freddy’s Pizza ,  Rustico

Oak Park is right next to the West side of Chicago. Before the world discovered Frank Lloyd Wright, the architect spent his early days designing homes for the residents of Oak Park, and the city is a gold mine for his work.

First, take a tour of the Frank Lloyd Wright Home and Studio. Afterward, visit his Unity Temple, considered the first modern building in history. Then, stroll around a small section of Oak City to appreciate Wright’s remaining 25 homes.

There is more than one famous resident from Oak City. Renowned author Ernest Hemingway was born here, and you can tour his Victorian birthplace too. If you need a respite from architecture and interiors, you can enjoy the exotic plants at the Oak Park Conservatory.

2. Glencoe, Illinois

42.1342106,-87.7985822, map

Distance:  24.3 mi / 31 min Things You Can’t Miss:  Chicago Botanic Garden, Skokie Lagoons, Home Alone House What to Eat:   Frank & Betsie’s Restaurant ,  Bake Homemade Pizza

The village of Glencoe on Chicago’s north shore is a quick and easy day trip from Chicago. The main attraction is the Chicago Botanic Garden. Spend the day in any of the 27 gardens and stop to smell the roses (and all the other flowers).

If you’re not in a hurry to get back to the city, explore the Skokie Lagoons Nature Preserve, where you can walk around lagoons looking for wildlife or rent a kayak and enjoy the tranquil waters.

Don’t leave Glencoe without exploring the village itself. Besides charming boutiques and restaurants to peruse, there are historic homes, including 13 by Frank Lloyd Wright, and the most famous house in the area that was featured in Home Alone.

3. Morton Arboretum, Illinois

4100 IL-53, Lisle, IL 60532, map

Distance:  26.1 mi / 36 min Things You Can’t Miss:  Hiking Trails, Acorn Tram Ride What to Eat:   Manna Kitchen ,  The Bavarian Lodge ,  Burrito Parrilla Mexicana

Lisle is part of Greater Chicago, but there’s plenty to do to make it a day trip. The Morton Arboretum is a living museum encompassing 1,700-acres and hundreds of varieties of trees and plants. Spend a leisurely day immersed in green forests on any of its 16-miles of hiking trails.

Highlights include a gentle walk around the Meadow Lake or a trip into woodlands via the Heritage Trail. You can also see the entire park on the narrated Acorn Tram Ride, and in the course of an hour, you tour the arboretum’s woodlands, wetlands, and prairies.

4. Illinois Beach State Park, Illinois

1 Lake Front Dr, Zion, IL 60099, map

Distance:  47.5 mi / 1 h 5 min Things You Can’t Miss:  Swimming, Hiking Trails, Fishing What to Eat:   Taqueria Los Naranjos ,  The Shanty

Who doesn’t love a day out on the beach? The Illinois Beach State Park is no ordinary beach outing. Located along a 6.5-mile stretch of beach on Lake Michigan, this state park offers an assortment of landscapes from sand dunes, wetlands, and black oak forests.

Explore the area on any of the 5 miles worth of trails including the easy Camp Logan Trail. Afterward, relax on the sand and discover why it’s one of the most scenic beaches in the Midwest.

5. Indiana Dunes National Park, Illinois

1215 N State Rd 49, Porter, IN 46304, map

Distance:  48.9 mi / 59 min Things You Can’t Miss:  Sand Dunes, Historic Homes, Hiking Trails What to Eat:   Fiddlehead Restaurant ,  The Polish Peasant ,  Mucho Mas

Indiana Dunes National Park is a perfect escape from the city where you can breathe in the fresh air. Sand dunes hug the shore along a 15-mile stretch of Lake Michigan.

Enjoy the cover of black oak forests or appreciate the beauty of the wetlands and marsh, an ideal spot for birding and wildlife viewing. Other outdoor activities include swimming and fishing. With 50 miles of trails, you are sure to stay active.

Don’t miss the Dune Ridge Trail (0.7 miles), Paul H. Douglas Trail (3.4 miles), and the Portage Lakefront and Riverwalk (0.9 miles). The national park also protects 60 historical structures including the Bailly Homestead and a series of houses from the 1933 World’s Fair that you can tour.

See More: Complete List of National Parks by State

6. Kankakee River State Park, Illinois

5314 W, IL-102, Bourbonnais, IL 60914, map

Distance:  57.8 mi / 1 h 7 min Things You Can’t Miss:  Kankakee River, Hiking, Canoeing What to Eat:   Burgers & Beer ,  BrickStone Brewery ,  New York City Deli

Unspoiled landscapes make up the beauty of the Kankakee River State Park. Though it’s approximately an hour from the city, this one day trip from Chicago will make you feel like you’ve entered another world.

For hikers, there’s a 3-mile trail showcasing the beauty of the canyon walls featuring a waterfall. If you have a bike, enjoy the 11-mile bike path that follows along the river. You can also rent a canoe and spend the day on the river.

7. Midewin National Tallgrass Prairie, Illinois

30239 IL-53, Wilmington, IL 60481, map

Distance:  60.1 mi / 1 h 06 min Things You Can’t Miss:  Tallgrass Prairie, Bison Herd What to Eat:   The Launching Pad ,  Nelly’s Restaurant on Rt 66 ,  New China Restaurant

Midewin National Tallgrass Prairie is the only tallgrass prairie east of the Mississippi River. This unique spot guarantees a tranquil day of bird watching and hiking any of the 22 miles of trails. Hikes you can’t miss include Turtle Pond (4.0 miles), Prairie Creek Woods Loop (2.0 miles), and Henslow’s Trail (5.3 miles). You also can’t leave without seeing the wild bison herd reintroduced into the region in 2015.

8. Dayton Bluffs Preserve, Illinois

2997 IL-71, Marseilles, IL 61341, map

Distance:  79.9 mi / 1 h 21 min Things You Can’t Miss:  Fox River, Waterfalls, Native American Burial Mounds What to Eat:   Lone Buffalo by Tangled Roots Brewing Company ,  Sandi’s Bar & Grill ,  Court Street Pub

A true hidden gem in Illinois is the Dayton Bluffs Preserve, where you can experience acres of prairies, woodlands, Native American burial mounds, waterfalls, and the Fox River.

As a relatively new park, you feel like you’re in the wilderness. A 2.7-mile loop mixes the prairie and woodlands features. If you have a full day, there are smaller trails to explore in the park, too.

9. Lake Geneva, Wisconsin

201 Wrigley Dr, Lake Geneva, WI 53147, map

Distance:  82.8 mi / 1 h 31 min Things You Can’t Miss:  Lake Geneva, Big Foot Beach State Park, Black Point Estate and Gardens What to Eat:  Fitzgeralds Genoa Junction ,  Mars Restaurant & Resort ,  Joni’s Diner

In the summer, bring your swimsuit and cool off in the water, or cruise around Lake Geneva. In the winter, you can visit the Ice Castles.

On Lake Shore Path, you will pass mansions from the Gilded Age. If you have the energy, hire a bike and complete the 20-mile circuit around the lake.

To see how people lived in splendor in the past, take a tour of the Black Point Estate and Gardens or relax at Big Foot Beach State Park.

10. Milwaukee, Wisconsin

400 W Wisconsin Ave, Milwaukee, WI 53203, map

Distance:  92.2 mi / 1 h 34 min Things You Can’t Miss:  Milwaukee Art Museum, Harley Davidson Museum, Mitchell Park Domes What to Eat:   St Paul Fish Company ,  Swingin’ Door Exchange ,  The Vanguard

Milwaukee is renowned for its beer, but there is much to discover. The Milwaukee Museum not only offers visitors a cultural experience inside with its massive collection (including the most extensive collection of Georgia O’Keefe), but the outside leaves you in awe with its modern design and moveable wings.

When you think of motorcycles, Harley Davidson immediately comes to mind. Experience the history of this cultural company and view over 400 motorcycles. Or, take in the living museum of the Mitchell Park Domes, where plants from around the world thrive in different ecosystems.

11. Oglesby, Illinois

41.2954236,-89.1032013, map

Distance:  101 mi / 1 h 42 min Things You Can’t Miss:  Starved Rock State Park, Matthieson State Park What to Eat:   Uptown Grill ,  Haze Smokehouse ,  Stone Jug Barbecue

Towering sandstone canyons and picturesque waterfalls combine to make Starved Rock State Park, a must-visit if you love the outdoors. With 18 canyons and 13 miles of trails, there is endless beauty from a bird’s eye view or deep within the canyons.

Popular trails include the Starved Rock and Sandstone Point Overlook Trail, Saint Louis Canyon Trail, and French Canyon Trail.

Deep canyons and bluffs are also the dominant features of Matthieson State Park. Follow the river into the canyon to Cascade Falls. Unusual rock formations dot the 5 miles of hiking trails within the park. Take a turn on the easy Dells Canyon and Bluff Trail, or go for a more involved hike to the Vermillion River.

12. Fennville, Michigan

42.5943816,-86.1151028, map

Distance:  140 mi / 2 h 24 min Things You Can’t Miss:  West Side County Park, Fenn Valley Vineyards, Crane Orchards What to Eat:   Blue Goose Café ,  Salt of the Earth

It’s easy to forget time as you enjoy the simple pleasures found at Fennville, Michigan. Lose yourself in the stunning views across Lake Michigan at West Side County Park or relax while sipping a glass of wine at the Fenn Valley Vineyards.

You can also feel like a kid again as you pick fruit fresh from the orchard at Crane’s U-Pick Farm. The different seasons dictate what fruit is available, and the 20-acre corn maze is the highlight.

13. Apple River Canyon State Park, Illinois

8763 E Canyon Rd, Apple River, IL 61001, map

Distance:  144 mi / 2 h 23 min Things You Can’t Miss:  Nature Trails, Limestone Bluffs What to Eat :  JJ & Freddies ,  Stella’s Café & Catering

The passage of time is beautifully on display at the Apple River Canyon State Park. For millions of years, the Apple River slowly carved its way through the rocks, creating the canyons seen today. There are roughly 5 miles of trails to spend the day in serenity.

14. Holland, Michigan

78 E 8th St, Holland, MI 49423, map

Distance:  150 mi / 2 h 31 min Things You Can’t Miss:  Downtown, Windmill Island Gardens, Big Red Lighthouse, Beaches What to Eat:   Salt & Pepper Savory Grill and Pub ,  El Huarache ,  New Holland Brewing

Imagine traveling to Europe without having to leave the country. That is what it feels like as soon as you set foot in Holland, Michigan. Dutch influences are everywhere making Holland one of the prettiest cities in the US.

Downtown Holland is filled with charming shops, restaurants, and breweries. You especially can’t miss the magical Windmill Island Gardens, where over 10,000 tulips erupt in color in spring. Also, check out DeZwaan, the only authentic Dutch windmill in the US, in action.

Finish the day by relaxing on one of the many beaches and the Big Red Lighthouse, the most photographed lighthouse in Michigan.

15. Grand Rapids, Michigan

171 Monroe Ave NW, Grand Rapids, MI 49503, map

Distance:  181 mi / 2 h 54 min Things You Can’t Miss:  Frederik Meijer Gardens & Sculpture Park, Gerald Ford Presidential Museum, Grand Rapids Museum of Art What to Eat:  Butcher’s Union ,  The Green Well ,  The Mitten Brewing Co.

The Frederik Meijer Gardens and Sculpture Park is part garden and part art museum and is the one spot you shouldn’t miss in Grand Rapids. Strolling in the 158-acre site is an experience you won’t forget, with over ten different gardens and sculptures by renowned artists like Rodin and Degas.

Continuing your artistic experience, traverse Calder Plaza to behold the mammoth red sculpture La Grande Vitesse, an icon of the city. Then, continue to the Grand Rapids Museum of Art to appreciate not only 19th and 20th-century art but also the first certified LEED museum in the US.

If you’re a history buff, step back in time as you explore the museum detailing the life of Gerald Ford, the 38th president of the United States. Tour a replica of the Oval Office and pay your respects to Ford and his wife, Betty, at their final resting place on the museum grounds.

• Six Flags Great America ( 44.6 mi / 51 min,  map )
• Rockford, IL ( 88.6 mi / 1 h 31 min,  map )
• University of Notre Dame ( 94.3 mi / 1 h 42 min,  map )
• Madison, WI ( 147 mi / 2 h 23 min,  map )

Best Places to Stay in Chicago

• Get comprehensive insurance for your trip.
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• Buy a Chicago travel guide .
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• Don’t forget your in-flight essentials .
• Save money on attractions with Go City .
• 60 Hikes Within 60 Miles: Chicago: Including Wisconsin and Northwest Indiana
• Eastern USA Travel Guide
• Chicago Travel Guide
• Rand McNally Road Atlas

How many of these day trips from Chicago have you done? Any others we should add to our list?

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“Discovery consists not of seeking new lands but in seeing with new eyes ” – M. Proust

Esther + Jacob

Esther and Jacob are the founders of Local Adventurer, one of the top 5 travel blogs in the US. They believe that adventure can be found near and far and hope to inspire others to explore locally. They explore a new city in depth every year and currently base themselves in Las Vegas.

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The 7 best day trips from Chicago

Dec 11, 2023 • 6 min read

Indiana Dunes, one of the country's newest national parks, is easily accessible on a day trip from Chicago © Jon Lauriat / Getty Images

Chicago has enough cloud-poking towers, rockin’ live-music clubs and world-class museums to keep you occupied for weeks. But just beyond city limits, you can also scale sand dunes at a national park, rev a Harley and amble around wineries.

Here are seven easy day trips that are no more than two hours away from the Windy City .

1. Get into nature at Indiana Dunes National Park

Travel time: 1 hour, 30 minutes

Rustling grasses, bird-filled marshes and white-pine forests fill a whopping stretch of Lake Michigan shoreline at Indiana Dunes National Park , which feels a world away from the big city. Rugged beaches beckon, and sweet hiking trails meander up the sand and through the woodlands.

Try the 3 Dune Challenge, a view-tastic 1.5-mile climb to the park’s highest dunes: Mt Jackson, Mt Holden and Mt Tom (just to confuse you, these are in Indiana Dunes State Park , a pocket within the national park.) Biking, paddling and winter snowshoeing are other fun activities available in the park.

How to get to the Indiana Dunes from Chicago: South Shore Line commuter trains make the 80-minute trip several times daily from downtown Chicago to Dune Park station. By car, the 50-mile trip takes one to two hours, depending on traffic.

2. Admire Harleys and artwork in Milwaukee

Milwaukee  is  Wisconsin 's largest city, and it's a rollicking day trip from Chicago. Stop by the Harley-Davidson Museum to gawk at hundreds of motorcycles, including Elvis’s custom-built hog. Harleys were invented in Milwaukee, hence the big bike love. The Milwaukee Art Museum drops jaws with its kinetic “wing” that soars open and shut, as well as its outsider art and Georgia O’Keeffe paintings.

During baseball season,  Miller Park is the place to be for beers, bratwursts and the oddball sixth-inning foot race between people dressed in giant sausage costumes. Milwaukee has a reputation as a drinker’s paradise, with more bars per capita than anywhere in the US besides New Orleans. Friendly neighborhood taverns pop up on almost every corner.  Champion’s shows the local spirit.

How to get to Milwaukee from Chicago: Amtrak runs seven trains daily to downtown Milwaukee, with a journey time of 90 minutes. By car, take the I-94 for the roughly two-hour trip.

3. Tour the lakeside hamlets of Harbor Country

Harbor Country comprises several lakeside hamlets just over the Michigan border, where Chicagoans retreat for a taste of small-town life. New Buffalo is the most resort-y of the bunch, where you can catch a wave at the public beach and follow it up with suds at the Beer Church .

Three Oaks is a bohemian farm-and-arts village where you can browse Elm Street’s galleries and design shops. Antique stores and folksy delis abound in Union Pier, Lakeside, Harbert and Sawyer. Several wineries, such as Tabor Hill , surround the communities and offer tastings. 

How to get to Harbor Country from Chicago: Harbor Country is a 90-minute drive east from downtown Chicago via I-90 and I-94. While Amtrak stops in New Buffalo, the times aren’t convenient for day trips, and you’ll need your own wheels to access the other towns. 

4. Encounter the thought-provoking Illinois Holocaust Museum

Travel time: 25 minutes

The  Illinois Holocaust Museum is the third-largest Holocaust Museum in the world, after those in Jerusalem and Washington, DC. Besides its haunting Nazi-era rail car and videos of survivors' stories from WWII, the venue contains thought-provoking art about genocides in Armenia, Rwanda, Cambodia and other countries. The special exhibitions are particularly impressive.

How to get to the Illinois Holocaust Museum from Chicago:  By car, take I-94 – the 18-mile trip takes about 25 minutes. On public transportation, take the Union Pacific North (UP-N) train at Ogilvie Transportation Center to Davis Street/Evanston. Catch the 208 bus at the Davis and Maple stop and get off at Golf Rd and Woods Dr. It's a two-minute walk to the museum. The trip takes a little over an hour.

5. Walk a section of the 21-mile Geneva Lake Shore Path

Old-money Chicagoans fled to Geneva Lake in the late 1800s to escape the urban heat and chill in the true-blue, spring-fed water. It’s still high on the getaway list, and while the mansion-strewn shoreline is sometimes called “the Hamptons of the Midwest,” visitors of more modest means are just as welcome.

Nowhere is this more evident than on the Lake Shore Path, the 21-mile public trail that goes through all water’s-edge properties – right through their front lawns! – for close-up views of the mega estates. Taking a boat ride with Lake Geneva Cruise Line is a must, as is a trip to the old-school Cheese Box for hunks of aged cheddar, havarti and other Wisconsin-made goodness.

How to get to Geneva Lake from Chicago: You need a car for this day trip. Lake Geneva, the main town on Geneva Lake, is 80 miles northwest of Chicago. Take I-94 north to Wisconsin highway 50 west. The trip takes 90 minutes to two hours by car.

6. See the home of modernist architecture in Oak Park

Travel time: 45 minutes

Architect Frank Lloyd Wright lived in the leafy suburb of Oak Park, next door to Chicago, for 20 years. Fans come from all over the world to tour his home and studio where he developed the famous Prairie style, as well as to gawp at his  Unity Temple  – named a UNESCO World Heritage site in 2019 – that’s considered to be the first modern-style building.

Ernest Hemingway is Oak Park’s other famous son. He was born in a sprawling Victorian home just a few blocks from Wright’s pad. It’s now maintained as the Hemingway Birthplace Museum and gives a peek at Papa’s formative years.

How to get to Oak Park from Chicago:  It’s a simple excursion via Chicago’s public transit system. Take the Green Line L train from downtown to Oak Park station, from which everything is within a mile's walk.

7. Explore Evanston, one of the top college towns in the US

Travel time: 40 minutes

Evanston is Chicago’s neighbor to the north, a lakefront town of sprawling old houses, artisan shops and bookish cafes where college students caffeinate. Check out the quirky American Toby Jug Museum , with the world’s largest collection of character-shaped jugs (think Barack Obama, Mick Jagger and R2-D2 as ceramic pitchers), and the Baha’i House of Worship , an eye-popping temple surrounded by peaceful gardens.

Both are free, which leaves money in your pocket to rent a sailboat, kayak or stand-up paddleboard at the Northwestern University Sailing Center and get out on glimmering Lake Michigan. Otherwise, wander among the boutiques, brewpubs and brioche-laden bakeries like Hewn that pepper the walkable downtown.

How to get to Evanston from Chicago: Chicago’s L trains go to Evanston. During weekday peak times, take the Purple Line direct from downtown Chicago or take the Red Line to Howard station and switch to the Purple Line. It’s about a 40-minute trip, with departures every 10 minutes or so.

This article was first published September 2019 and updated December 2023

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BEST Day Trips From Chicago (By Car, Bus & Train)

Looking to leave Chicago for the day or even a few hours? Fortunately there are many amazing places to visit in the Midwest near the city whether you love nature, beaches, cities or small towns. Here are the best day trips from Chicago all less than 2 hours from the city.

If you don’t have a car or would rather not drive, you can also visit most of these places by train, bus or through a guided day tour.

Best Day Trips From Chicago

Disclaimer: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you.

Starved Rock State Park

Distance from Chicago: 95 miles Time from Chicago: 1 hour and 40 minutes Address: 2668 East 873 Road, Oglesby, Illinois

Starved Rock State Park is one of the top attractions in the state of Illinois. The park is an ideal spot to enjoy nature and is filled with stunning sandstone canyons and beautiful waterfalls. This is a great place for hiking with 13 miles (21 kilometers) of trails.

In addition to hiking, visitors can enjoy outdoor activities year round, including horseback riding, ice climbing, cross-country skiing, as well as fishing, kayaking, rafting on the Illinois River.

Matthiessen State Park

Distance from Chicago: 96 miles Time from Chicago: 1 hour and 40 minutes Address: 2500 IL-178, Oglesby, Illinois

Matthiessen State Park is not as popular or crowded as nearby Starved Rock State Park (less than 3 miles away) but it is just as beautiful with similar natural features such as canyons and beautiful waterfalls.

Oak Park, Illinois

Distance from Chicago: 10 miles Time from Chicago: 15-20 minutes from downtown

Oak Park is a suburb on the outskirts of Chicago. The village prides itself on its racial, ethnic, socio-economic, and religious diversity . Downtown Oak Park is home to a variety of shops and restaurants but the main draw for visitors is the architecture.

Oak Park is home to the world’s largest collection of designed sites by Frank Lloyd Wright, the famous architect. Take a walking tour of the Wright District, an area of prairie-style homes designed by Frank Lloyd Wright including the Frank Lloyd Wright Home and Studio, and Unity Temple, a Wright–designed church considered to be one of his most important structures.

For those who would rather not drive, Oak Park is easily accessible from Chicago by train (Green Line and Blue Line on the CTA and Union Pacific / West Line on the Metra ). Ridesharing services such as Uber and Lyft are also an option.

Evanston, Illinois

Distance from Chicago: 14 miles Time from Chicago: 30 minutes from downtown Chicago

Looking for an easy day trip from Chicago? Visit Evanston, a nearby suburb located on the shores of Lake Michigan. Visit and relax at the beautiful Northwestern Campus. Evanston is home to six public swimming beaches which are less crowded than Chicago beaches.

If you have more time, you can explore more of the North Shore suburbs . Must see attractions in the North Shore include the Chicago Botanic Gardens in Glencoe, the Bahá’í Temple in Wilmette and the Kohl Children’s Museum in Glenview.

For those who would rather not drive, Evanston is easily accessible from Chicago by train (Purple Line) on the CTA and the Union Pacific North Line (UP-N) on the Metra . Ridesharing services such as Uber and Lyft are also an option.

Illinois Beach State Park

Distance from Chicago: 45 miles Time from Chicago: 1-1.5 hours drive

Illinois Beach State Park , part of the Illinois state park system, is located along Lake Michigan in northeast Illinois. It is known primarily for the beach with over six miles of shoreline. The park also includes dune areas, wetlands, prairie, and black oak savanna. Activities at the park include boating, swimming, fishing, hiking, camping, and more.

Indiana Dunes, Indiana

Distance from Chicago: 50 miles Time from Chicago: 1 hour

The Indiana Dunes National Park borders the State Park of the same name. The national park offers 15 miles of shoreline along Lake Michigan’s southern shore with wide sandy beaches and towering dunes. Hikers will enjoy 50 miles of trails over rugged dunes, mysterious wetlands, sunny prairies, meandering rivers and peaceful forests.

The three highest sand dunes are all in the Indiana Dunes State Park.

In addition to beaches and hiking, Indiana Dunes offers many outdoor year round activities including bird watching, fishing, cycling, horseback riding, kayaking and paddling, snowshoeing, and cross country skiing.

New Buffalo, Michigan

Distance from Chicago: 70 miles Time from Chicago: 1 hour 15 minutes

New Buffalo, Michigan is a charming beach town on the shores of Lake Michigan. The beaches face west and have beautiful sunset views.

In addition to the beaches, a must see attraction is Galien River County Park , a beautiful park with boardwalk paths through the marsh.  For those that enjoy gambling, New Buffalo is home to the Four Winds Casino Resort .

New Buffalo has daily Amtrak service from Chicago on the Blue Water and Wolverine lines.

New Buffalo is a good base to explore various beach towns and wineries in Southwest Michigan .

Rockford, Illinois

Distance from Chicago: 85 miles Time from Chicago: 1.5-2 hours

The most popular attraction in Rockford is Anderson Japanese Gardens , a 12-acre Japanese garden. If you have more time in Rockford before heading home, the city plenty of attractions including the Discovery Center Museum (a great family museum), Nicholas Conservatory and Gardens, Burpee Museum of Natural History, Tinker Swiss Cottage Museum and the Rockford Art Museum.

Lake Geneva, Wisconsin

Distance from Chicago: 83 miles Time from Chicago: 1 hour 40 minutes

In the summer, daytrippers can enjoy a variety of activities on the water, including boating, kayaking, paddle boarding. In the winter, visitors can go skiing or snowboarding or visit the beautiful ice castles.

The highlight is the Lake Geneva Shore Path, a 21-mile trail around the lake with stunning views of the forest, water and impressive waterfront homes. Visitors can hike or take a cruise around the lake.

Read about more things to do in Lake Geneva here .

Milwaukee, Wisconsin

Distance from Chicago: 93 miles Time from Chicago: 1 hour 40 minutes

This lively city is like a smaller less touristy version of Chicago.

Milwaukee is famous for its beer -it is nationally recognized with the nickname “Brew City” due to its nearly two centuries of brewing heritage from multiple past major brewers including Miller Brewing Company, Pabst Brewing Company, and Joseph Schlitz Brewing Company. One of the best things to do in Milwaukee is to tour one of its many breweries. Another interesting attraction is the Harley-Davidson Museum.

Amtrak Hiawatha train offers frequent daily service between Milwaukee and Chicago.

Tubing on the Tippecanoe River

Distance from Chicago: 105 miles Time from Chicago: 2 hours

Tippecanoe River State Park in northern Indiana is a popular Midwest summer destination. In the summer, you can rent tubes and float along the lazy river or you can also rent canoes or kayaks from various outfitters.

South Bend, Indiana

Distance from Chicago: 97 miles Time from Chicago: 1.5 to 2 hours

South Bend is most famous for being home to the University of Notre Dame. There are many attractions on the beautiful, large campus including the Golden Dome, Notre Dame Stadium, the Basilica of the Sacred Heart and the Grotto of Our Lady of Lourdes, a replica of the famous shrine.

One of the best things to see in South Bend is the Studebaker National Museum , featuring a large collection of Studebaker automobiles drawn from the history of the company, beginning with horse-drawn carriages. They also have the carriage that Abraham Lincoln took to Ford’s Theater the night he was assassinated.

In addition to driving, South Shore Line commuter rail runs multiple daily trains between Millennium Station in downtown Chicago and South Bend Airport station.

Pontiac, Illinois (Historic Route 66)

Distance from Chicago: 100 miles

Historic Route 66 is a classic American road trip . Don’t have time to drive Route 66 all the way from Chicago to California? You can visit Pontiac and drive a portion of historic Route 66 on a day trip from Chicago.  Must see attractions in Pontiac include the IL Route 66 Association Hall of Fame & Museum , the Pontiac-Oakland Automobile Museum and the Route 66 Shield Mural .

What are your favorite day trips from Chicago ?

Planning a trip to Chicago? Check out my Chicago guides and itineraries:

• 3 Days in Chicago Itinerary + Travel Tips From a Local
• The Perfect Itinerary for One Day in Chicago (According to a Local)
• Most Instagrammable Places in Chicago
• Best Free Things to Do in Chicago

Related Posts

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15 Best Day Trips From Chicago Worth The Effort

August 13, 2022 by //  by  Midwest Explored 1 Comment

Are you looking for the best day trips from Chicago that are actually worth the effort? Then this list is for you!

Maybe you want a break from the city, or maybe you just want to explore a new city.

Planning your trip to Chicago last minute?

Make sure to book ahead. Hotels and tours often sell out the closer you get to your trip. Here are our top pics for Chicago!

Top Experiences And Tours In Chicago:

• Chicago River Architecture Cruise (Skip the Ticket Office!)
• Willis TowerSkydeck & The Ledge Ticket (Elevator express entry!)
• Navy Pier Centennial Wheel Ticket (Panoramic views of Chicago!)
• Big Bus Hop on Hop Off Sightseeing Tours (24, 48, or 72-hour options available.)

Hop Hotels In Chicago:

• Eurostars Magnificent Mile (In the heart of Chicago!)
• The Peninsula Chicago (Near museums)
• Club Quarter Hotels Wacker (Overlooking the Chicago River!)
• Hotel Blake (Close to Millennium Park.)

No matter your interests you’ll find a great day trip option on this list.

I’ve found some of the most unique, fun, and adventurous day trips to make from Chicago.

There are beautiful state parks, metropolitan cities, unique and charming small towns, and so much more.

So, lets take a look at the 15 Best Day Trips from Chicago Worth The Effort!

Cedarburg, Wisconsin

In just under 2 hours, you can find yourself in the charming small town in Wisconsin called Cedarburg.

Cedarburg is an excellent day trip from Chicago for those looking for small-town charm, but with plenty of activities.

Because Cedarburg is know for its small town atmosphere, you’ll find some really unique shops and resturants.

There is a Candy Kitchen, an Amish Craftsmen Guild, stores full of items made by local artisans, and even a shop where you can search for unique gemstones.

Cedarburg also has a wide variety of unique museums.

There is a local art museum, a local history museum, a woolen mill and textile museum, and even a museum depicting early life in Cedarburg.

No matter your interests, Cedarburg is guaranteed to have something fun for you to do, and you’ll find it was worth the drive.

Rockford, Illinois

If you drive for about an hour and a half West of Chicago, you’ll find yourself in Rockford Illinois.

The best way to describe Rockford is to call it a big-little city. It’s the fourth largest city in Illinois, but still feels welcoming in a small-town sort of way.

Rockford is also bursting with things to do.

Music lovers will enjoy checking out one of the many spots home town band Cheap Trick helped make famous.

If museums are more your thing, don’t worry, Rockford has those too. Stop by the Burpee Museum of Natural History or the Discovery Center Museum.

If none of that sounds interesting, then maybe you’ll like the Anderson Japanese Garden. It is consistently rated as one of the best Japanese Gardens in North America.

There is so much to do that you may want to turn your day trip into a Midwest weekend getaway . With the endless list of activities in Rockford, it absolutely makes it worth the hour and a half drive from Chicago.

Grand Rapids, Michigan

Grand Rapids Michigan is one of the perfect day trips from Chicago for lovers of art, food, and beer.

In fact, Grand Rapids is known as Beer City USA.

For those who want to take full advantage of all Beer City USA has to offer, you’ll want to download the Brewsader App.

The App gives you a full map of all the breweries in Grand Rapids, and after you check in at 8 of them, you’ll earn a fun Brewsader shirt to commemorate your trip.

If beer isn’t your thing, not to worry.

There are still some absolutely amazing and unique restaurants in Grand Rapids you can check out. Or you can stop into one of the cities popular art galleries.

There really are so many cool things to do in Grand Rapids .

Oak Park, Illinois Is One Of The Best Day Trips From Chicago

Oak Park Illinois is the shortest distance you’ll have to travel for a day trip on this list as it’s just under 20 minutes outside of Chicago.

Despite that, many people in Chicago, or even visiting Chicago, don’t think to explore Oak Park.

Admirers of Frank Lloyd Wright, one of America’s most prominent architects will know Oak Park though.

Wright called Oak Park home, and left his mark on many of the cities most popular homes and buildings.

Oak Park was also home to another famous architect, George W. Maher, who also designed many of the cities most prominent homes and buildings.

Ernest Hemingway was also born in Oak Park, and you can visit his childhood home that has now been turned into a Hemingway Museum.

Book Tickets Here: Ernest Hemingway Boyhood Tour

Because of Oak Park’s proximity to Chicago, many gangsters in the early 20th century called the area home, and you can now take a Gangster tour.

Oak Park is a tremendously unique option for a day trip from Chicago and you don’t even have to travel far!

Michigan City, Indiana

Michigan City Indiana is about an hour away from Chicago, and you’ll spend the whole trip driving along Lake Michigan.

So it’s no surprise that Michigan City also has its fair share of lighthouse history.

In Michigan City you’ll be able to explore the Old Lighthouse Museum and even take a tour of the Michigan City Lighthouse and Pier.

Stroll along the beach or maybe head over to the Washington Park Zoo, which is full of more interesting architecture, and of course animals.

Travelers also enjoy touring the Barker Mansion and sipping on local wines at some of the best wineries in Indiana

Monroe, Wisconsin

Monroe Wisconsin is the Swiss Cheese Capital of the USA, and just over 2 hours away from Chicago.

Cheese lovers will delight in the many, many, cheese related activities that abound in Monroe.

Monroe is a cute small town that takes cheese very seriously, and for good reason. The city has thrived for over 100 years because of it’s cheese industry.

You can pair some locally made cheeses with local beers or just explore the numerous cheese shops.

Or watch a movie at the local drive-in theater while munching on cheese curds.

The small town even holds a yearly Cheese Days Festival where you can sample all of the local cheeses while sipping a cold local beer.

Monroe is perfect for your next day trip from Chicago the next time you’ve got a serious craving for all things cheese.

This cool town is one of the best places to visit in Wisconsin.

Kankakee, Illinois

Kankakee Illinois is a cute town in Illinois just over an hour south of Chicago.

It’s full of small town charm but it still has a lot of interesting things to do, making it perfect if you’re looking to escape the city for a day.

One of visitors favorite things to do in Kankakee is taking a tour of the B. Harley Bradley House, a famous house designed by Frank Lloyd Wright.

Kankakee is also amazing for those looking for a little outdoor adventure.

The entire Kankakee County and parts of the city of Kankakee are bursting with outdoor activities.

You can enjoy some of the best hiking in Illinois , along with canoeing, kayaking, and even scuba diving in the Haigh Quarry.

Kankakee is one of the best day trips from Chicago Illinois if you’re looking for fresh air, beautiful views of nature, and plenty of small-town charm.

New Glarus, Wisconsin

America’s Little Switzerland is in New Glarus Wisconsin, just 2 and half hours outside of Chicago.

New Glarus is a small town that loves beer, cheese, and festivals. In the warmer months, they may have 3-4 festivals a month.

Typical New Glarus festivals include Polkafest, The Beer, Bacon, & Cheese Festival, The Heidi Folk Festival, Blues Brews & Food Trucks Festival, Maxwell Street Days, and so many more.

New Glarus is also known for having a selection of brews that you can only buy in Wisconsin, and some of them you can only buy in New Glarus.

If you are a beer connoisseur, you’ll love checking out one of the local beer gardens. And if you decide to stay longer here are some epic Wisconsin Airbnbs to look into.

Foodies will love checking out one of the many restaurants that serves up Swiss and Swiss inspired fare.

New Glarus is a cute romantic getaway in Wisconsin!

Holland, Michigan

Holland Michigan is a little over 2 hours away from Chicago and is one of the best day trips from Chicago that is definitely worth it.

Named after the home country of it’s original settlers, Holland is bursting with Dutch charm.

In the Spring it’s host to the Tulip Time Festival where you will get to see a riot of colorful tulips with a windmill that is straight from Holland.

Even if you can’t make it to the Tulip Time Festival, you’ll love exploring this cozy small town.

There are plenty of unique shops, restaurants, breweries, and unique Dutch gardens.

Holland is also home to one of the coolest lighthouses in Michigan , The Big Red Lighthouse.

Visitors love to view the iconic lighthouse standing proudly on it’s pier, with the bright red façade making a striking contrast against Lake Michigan.

Holland is a small town in Michigan full of charm that is definitely worth the effort to visit, any time of year.

Milwaukee, Wisconsin

If you are looking to explore a city, but you want a break from Chicago, then I suggest driving the hour and half to Wisconsin’s largest city, Milwaukee.

Because Milwaukee is Wisconsin’s biggest city, it is full of unique things to do making it one of the best day trips from Chicago!

And there are so many things to do in Milwaukee!

If you’re on a budget, take a stroll down the streets and admire the many murals on the sides of buildings. Or go window shopping and one of the many boutique stores.

You can also check out a play or musical, go on a boat tour of Milwaukee, or explore one of the amazing restaurants in Milwaukee.

If you’re a sports fan, you may want to check out one of Milwaukee’s home teams. Afterwards, you can talk about the game at one of the cities awesome bars or resturants.

Milwaukee is an amazing city that often gets overlooked, but you won’t regret making the trip out there.

Oglesby, Illinois

In just under two hours you can be in beautiful Oglesby Illinois.

Oglesby is perfect for day trippers looking for a break from the city as it is home to two beautiful State Parks.

If you’re looking for some outdoor adventure and clear air, then you’ll find that this is one day trip that is worth the effort.

At Starved Rock State Park you’ll find trails that lead you along the Illinois River and into steep sandstone canyons.

It is Illinois’ most popular State Park and for good reason. It’s accessible for all skill levels and you get to experience some beautiful views.

The other state park near Oglesby is Matthiessen State Park. The entrance for this park is just a few miles South of Starved Rock State Park.

Matthiessen State Park has similar views, but it is often far less crowded.

It is a great choice to experience fall in Illinois.

You’ll still be able to hike beautiful trails, see gorgeous Illinois waterfalls, and enjoy nature, but you’ll be far less crowded.

If you have plenty of time on one of your day trips from Chicago Illinois, you should definitely check out both state parks.

Lake Geneva, Wisconsin

Lake Geneva is a Wisconsin town about an hour and a half outside of Chicago.

It has a history of being the go-to spot for Chicago’s wealthy families during the summer.

Lake Geneva is a beautiful small town that thrives because of the large Lake Geneva, and it’s a budget-friendly day trip option.

There are so many things to do in Lake Geneva all year long that include lake activities.

But you’ll also find a charming town full of unique boutiques, restaurants, and even outdoor activities like hiking and snow sports in the winter.

In early February the town holds a Winter Fest which features the only snow sculpting championship in the United States.

Visitors get to experience massive snow sculptures, food from local restaurants, and so much more – and it’s free to attend!

In the summer, enjoy boating, swimming, and kayaking on Lake Geneva before having a meal at one of the amazing local restaurants in Lake Geneva .

No matter what time of year you visit, Lake Geneva is a Chicago day trip that is worth the effort.

Highwood, Illinois

Highwood Illinois is another small town that goes big when it comes to festivals.

Just 35 minutes North of Chicago, this charming small town is the perfect day trip from Chicago Illinois for festival lovers

There’s almost a festival every month, and they all have different themes.

For foodies, there is a Taco Festival, a Bloody Mary Festival, and a Garlic Festival.

There are also smaller music festivals, fun runs, and a Pride Festival.

One of Highwood’s most iconic festivals though is probably The Great Highwood Pumpkin Festival every October.

It is one of the coolest things to do in Illinois .

The Festival benefits the Make-A-Wish Foundation and attendees get to check out rows and rows of carved pumpkins.

Attendess of Pumpkin Fest can even bring their own pumpkins and carve them before adding them to the walls of carved pumpkins.

Highwood is a truly unique town, full of really cool festivals that are sure to make the trip out there worth the effort, no matter what time of year you go.

Indiana Dunes National Park, Indiana Is One Of The Best Day Trips From Chicago

Just under an hour outside of Chicago, the Indiana Dunes National Park is one of the coolest national parks in the Midwest.

The Indiana Dunes National Park is on 15 miles of beach on Lake Michigan’s South shore.

It is a nature lover’s dream with over 15,000 acres of preserved land full of unique hiking trails, wetlands, prairies, woodlands, and of course beaches.

From Memorial Day to Labor Day, there is a $6 entrance fee to enter the park. During the ‘off season’ though, it’s free to enter.

The Indiana Dunes is full of fun things to do, and you could spend days exploring the park making it a fun weekend getaway in Indiana!

It’s a beautiful spot, and it is definitely one of the day trips from Chicago that is worth the effort.

Madison, Wisconsin Is One Of The Cool Day Trips From Chicago

In just over two hours you can find yourself in Madison Wisconsin.

If you’re looking for a fun Chicago day trip in the summer, Madison is perfect for you.

With five lakes, spanning over 15,000 acres, in summertime there are so many things to do in Madison.

There are water sports, festivals, water front dining, and so much more.

But Madison isn’t just a fun place to visit in the summer.

You’re sure to find fun no matter what time of year you go.

There are dinner theaters, breweries, delicious restaurants, and unique boutiques. Put treating yourself at some of the restaurants in Madison on your list!

You’ll find that Madison Wisconsin is one of the most entertaining day trips from Chicago that is definitely worth the effort.

Packing List For Daytrips From Chicago

Here are some  tips on how to pack lightly

A  concealed travel pouch  may be one of the most important items you bring along when on one of your Chicago day trips! 

It is  always   important  to protect your personal information. Identity thieves are everywhere.

This  unisex RFID blocking concealed travel pouch is  lightweight and comes in several colors. It has lots of organization to give you peace of mind.

You can place it under your clothes next to your body to carry your ID safely.

If you have a pouch already that does not come with the RFID protection, as I do, these  RFID  sleeves  are the perfect solution.

This configuration comes with enough credit card sleeves that the entire family would be protected. They are slim too, so they will easily fit into your pouch or wallet. 

If you are planning on taking a lot of pictures with your phone you will definitely want to consider an  external charging battery .

This  Anker high-speed phone charging battery  is  the exact one  I carry with me on all of my trips.

It can be used on a variety of phones, not just an iPhone like I have. And wow is it fast!

I like that it holds its charging capabilities for several uses so I do not have to worry about it while out and about, and if I forget to recharge it at night, it will still be good to go the next day.

My daughter gifted me with this  FugeTek selfie stick and tripod   setup for my birthday. I absolutely love it!

It is made of lightweight aluminum and so easy to use.

It has Bluetooth connectivity and is a breeze to use for taking selfies with all those nature shots while on your Chicago day trips..

Hydration is so important when hiking. You want to remain hydrated throughout your hikes to support your immune system which in turn will be stronger to fight off any germs you will encounter during your travels. 

You will want to bring your own  refillable water bottle  with you. 

I never leave home on a trip without my  Bobble filtration bottle .  The 18.5-ounce size is perfect for hiking and it fits nicely in the pocket of a backpack.

When filled with water, it is not too heavy to carry. And the charcoal filter ensures fresh clean water whenever you fill the Bobble.

Perhaps you are traveling a long distance to Chicago Illinois and packing space is a premium in your suitcase, or in your car.

Then this  set of collapsible silicone foldable water bottles  would work well for you. Would not take up much space at all. 

You will want a  backpack or daypack  with you to store snacks, your water bottle, phone, extra clothes, etc.. when on one of your day trips from Chicago Illinois. No matter the time of day or evening.

This   foldable water-resistant backpack   would be great

It is very affordable and is available in many color options for you to choose from. The fact that it folds down into a zippered pouch will make it easy to pack!

I hope you enjoyed this list of the 15 Best Day Trips From Chicago Worth the Effort! There are so many great big cities and little towns outside of Chicago just waiting to be explored.

If you are spending a weekend in Chicago , one of these trips from Chicago would def be fun!

If you take a trip to one of these awesome places, I’d love to hear about it in the comments!

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Day Trips From Chicago

The 10 Best Day Trips From Chicago

The city of Chicago has much to offer locals and tourists; however, getting out of town and seeing what’s nearby is worthwhile. From brewery tours in Milwaukee to Dutch heritage in Holland, Michigan, to hiking in state parks or along rivers and lakes, you’ll find that the surrounding areas of the Windy City offer a plethora of experiences. Pick and choose from these nearby adventures and plan your great escape. 

Holland, Michigan

 Holland Area Visitors Bureau

While Holland is a year-round destination, with lots of Dutch shops, architecture, windmills, restaurants, and museums to explore, spring is really when this city shines. See 4.5 million tulips in bloom around the town at Veldheer Tulip Gardens and Windmill Island Gardens. The Tulip Time Festival kicks off in May with Dutch food, music, parades, and Klompen dancing.

No matter when you visit, however, be sure to stop by the DeKlomp Wooden Shoe and Delft Factory and the Holland Museum. Also, the Dutch Winterfest and Parade of Lights are worth a look-see in November.

Getting There: Located midway between Chicago and Detroit, Holland is a three-hour drive away. Take I-94 east, exit 34 to I-196, and then exit 44 to Holland.

Travel Tip: Michigan’s most photographed lighthouse is Big Red Lighthouse in Holland. Visit Holland State Park for the best view of the tower—walk the boardwalk to the north pier (wheelchair accessible). 

Indiana Dunes National Park

 Wendy Altschuler

Our country’s 61st National Park, Indiana Dunes National Park , has much to offer in a tight package. Swim and hike in the summer or snowshoe and cross-country ski in the winter. Play on 15 miles of Lake Michigan’s southern shore, watch for migrating and regular nesting birds—hawks, wetland birds, woodpeckers—and hike on 50 miles of trails that cut through and over dunes, wetlands, prairies, forests, and rivers. Keep your eyes out for threatened Pitcher’s thistle and snap photos of white-tailed deer, the largest herbivore found here. The Great Blue Heron rookery can be found along the national lakeshore as well.

Camp overnight at Dunewood Campground or fish in the Little Calumet River during the warmer months. Get the Geocaching app on your phone and find hidden containers while also enjoying nature and being outside. History buffs will enjoy visiting one of the sixty historic structures—the Bailly Homestead, Camp Good Fellow, Chellberg Farm, and a handful of houses from the 1933 World’s Fair are the most significant.

Getting There: To get to the park, take Interstate 94, exit 26 north; the Indiana Toll Road (I-80/90), exit 31 north; U.S. Highways 12 and 20, or other state roads. The Indiana Dunes Visitors Center is on Indiana State Road 49.

Travel Tip: Kids can become Junior Rangers and visit the park with a Discovery Guide. Also, park rangers can lead tours throughout the park. Stop by the Visitor’s Center to map out your adventure. 

Kettle Moraine State Forest

Getty-Wirepec 

Home to 30,000 tree-filled acres with rolling hills, grasslands, lakes, and forests, Kettle Moraine State Forest is the ideal place to enjoy the outdoors. Ride horses and bicycles, hike, cross-country ski, snowshoe, and drive the Kettle Moraine Scenic Drive to explore the kettles (depressions) left by the Ice Age. Only two hours and 40 minutes from Chicago, this destination is ideal for a day trip.

Getting There: To get to this Wisconsin State Park, located between Madison and Milwaukee, take I-90/94 west toward Milwaukee, exit 344 to US-12 west.

Travel Tip: Wade House Stagecoach Inn, Holy Hill Basilica, Cushing Memorial Park, and numerous geological landmarks and small towns can be seen along the drive. 

Lake Geneva

Daniel Nicholson / 500px / Getty Images

If you want to see Gilded Age mansions built by well-heeled Chicagoans, visit the lakeside Shore Path in Lake Geneva. The area also offers shopping, diverse dining, local beaches—including Big Foot Beach State Park—and outdoor fun. Stay overnight at a campground or Bed and Breakfast, ride the U.S. Mailboat and watch jumpers deliver mail while the boat keeps moving, go kayaking, visit a winery or brewery, or hit a round of golf—there’s something to do for every age and ability at Lake Geneva.

Getting There: Take 294 north toward Wisconsin, continue to I-94 west, and exit at 344 onto WI-50 toward Lake Geneva.

Travel Tip: Request a free Visitors Guide at Visit Lake Geneva.

Chicago Botanic Gardens

 Getty/N. Vivienne Shen Photography

Just one hour north of Chicago sits Chicago Botanic Garden , a haven for plants and flowers from around the globe. Plan on spending a few hours here, exploring the grounds, having lunch or a snack at the Garden View Café, and shopping for unique items in the Garden Shop. A cart positioned just over the bridge from the Visitor Center lets you know what is currently in bloom so that you can make the most of your visit.

Admission is per person; buy tickets in advance to get the best pricing and to ensure your preferred date and time; a parking fee is purchased separately. Admission includes summer attractions such as Butterflies & Blooms, Grand Tram Tour and Model Railroad Garden.

Home to nearly 30 different display gardens spread over almost 400 acres; these gardens give visitors a chance to learn about various plant collections. This living museum is well-known for its Bonsai Collection, Japanese Garden, English Walled Garden, Dwarf Conifer Garden, and multiple greenhouses that nurture rare, edible, seasonal, and flowering plants from around the world.

Getting There: From Chicago, take the Kennedy Expressway (I-90/94) west to Edens Expressway (I-94) and U.S. Route 41. Take the Lake Cook Road exit and drive a half-mile east to the destination.

You can also take the Metra train on the Union Pacific North Line and get off at the Braeside station. From there, walk just under a mile to the gardens on the North Branch Trail, which is quite lovely.

Travel Tip: Kids love the Model Railroad Garden, open half of the year, which features 18 trains chugging along over bridges, through tunnels, and past nearly 50 different American landmarks. 

Starved Rock State Park

Getty/Rudy Balasko

Starved Rock State Park is a family-friendly—and dog-pro—park that features lofty sandstone bluffs that loom large, especially in contrast to the flatlands that the state is known for. See 15 canyons, towering trees, flora and fauna, and waterfalls while you hike along the Illinois River. The most scenic waterfalls—especially after snowmelt or rain—can be found in French, Wildcat, and Kaskaskia canyons.

Getting There: Starved Rock is about 90 miles west of Chicago, south of I-80, near the town of LaSalle.

Travel Tip: Crowds over holidays and weekends in the summer months can be obtrusive—visit during the week if possible or in the off-season.

Six Flags Great America

 Six Flags Great America

Six Flags Great America has a brand new ride to lure in visitors: Maxx Force, a record-breaking roller coaster. Reaching speeds of 78 miles per hour in just under two seconds, this ride features the fastest and tallest inversion of any roller coaster in the world. Also, the park has over 30 different rides and attractions, a 20-acre water park, various shows and themed entertainment, character meet-ups, and four different children’s areas for the younger crowd.

Getting There: From the city, take I-94 or I-294 west, drive for just under an hour, and exit at Grand Avenue (Route 132) in the village of Gurnee. Six Flags will be just off the ramp on the right.

Travel Tip: The entrance to the park is often busy during peak summer months (parking in the overflow parking is a good sign that there’s a long line at the door). Arrive early, before the gates open, to avoid long waiting times. Also, park hours are subject to change and do so seasonally, so be sure to check the website for operating hours. 

Milwaukee, Wisconsin

Walter Bibikow / Getty Images

From macro to micro, Milwaukee, also known by the moniker Brew City, has pints for everyone’s taste buds. Pabst, Schlitz, Blatz, Miller—all well-known Milwaukee favorites. This beer-happy city’s roots trace back to German immigrants from the 19th century—they brought their brewing know-how with them.

The Bavarian Bierhaus , a German beer hall with a restaurant, beer garden, and brewery, is a resident favorite. City Lights Brewing Company is another great option, especially for history buffs—the brewery is located in the 115-year-old Gas Light Building. Historic architecture and modern-day brewing techniques are the highlights of the tour, available on Fridays and Saturdays. Milwaukee Brewing Co. offers weekend “Beer in Hand” tours through its craft brewery, where you can sample seasonal delights and use the token for a free beer at bars nearby.

Getting There: Located on the shores of Lake Michigan, 90 minutes from Chicago, Milwaukee is accessible by train or car. From Chicago, by car, take I-294 north to 94 west. Exit at I-794 east (exit 310 C). Or, take the Amtrak from Chicago to Milwaukee, getting off downtown at Milwaukee Intermodal Station.

Travel Tip: Of course, there are lots of breweries to choose from, and you may want to join an organized walking or shuttle tour. Visit Milwaukee is an excellent resource for planning out a beer tour. 

Abraham Presidential Library and Museum

Randy von Liski / CC BY-NC-ND 2.0 / Flickr

Learning activities, hands-on exhibits, civil war artifacts, and more bring people from all over the world to this museum and library. You’ll have the chance to immerse yourself in the history and stories of America’s 16th president of the United States.

Getting There: Take I-290 east to I-355 south to I-55 south, exit at 98 B onto IL-97 west.

Travel Tip: Many events and special happenings occur throughout the year. Be sure to check the museum’s website to see if the scheduled activities align with your plans. 

Morton Arboretum

Special days throughout the year allow dogs inside the Morton Arboretum . For only $5 per dog, leashed animals can hike the trails, receive a bandana, and meet other canines as you explore the arboretum. The Tails on the Trails event is full of vendors, activities, and contests (how fast do you think your dog can lick peanut butter off of a spoon?).

Getting There: The Morton Arboretum, just west of I-355 and north of I-88 on Illinois Route 53, is located 25 miles west of Chicago.  

Travel Tip: Make sure your dog is up-to-date on vaccinations and is friendly around humans and other dogs. 

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9 Spectacular Must-Do Day Trips From Chicago (2024 Guide)

• Last Updated: February 4, 2024

Looking for a good day trip from the Windy City? Here are 9 amazing day trips from Chicago that include state parks, beaches, historic sites and more.

Chicago is a city of mouthwateringly good deep-dish pizza, pristine architecture, and an enriching atmosphere. Full of top-notch restaurants, eye-catching fashion, and upscale attractions, the Windy City is a place people travel from all over to visit.

A place of innovation, Chicago is constantly up to speed with new trends – or establishing the trends for everyone to catch onto.

Of course, as the birthplace of modern architecture, this is not a big surprise. Still, a visit here catches one’s eye with the fascinating designs and structures of the buildings within the third largest city in the United States. 

While visiting this trendy city, we recommend spending a day outside Chicago to see nearby top attractions like state parks full of hiking trails. There is so much to see outside the town center of Chicago, so why not add a day trip or two to your Chicago itinerary ?

The best way to get around is to rent a car and explore on your own! We recommend Rental Cars , which has the largest range of vehicles for the best value on the market.

Table of Contents

What Is There To See And Do?

Getting there and away, best time of year to visit, the 9 best day trips from chicago.

It’s time to spread your wings and leave the city on an incredible day trip. Take your pick from our curated selection of the 9 best day trips from Chicago. From living in luxury in Lake Geneva to exploring the rich history and architecture of Oak Park, get ready to have the time of your life.

Find more of the best things to do in Chicago here !

1. Starved Rock State Park

• Distance from Chicago: 91 miles/146 km
• How Long it Takes: 1½ Hours

Settled along the Illinois River, Starved Rock State Park is an oasis teeming with seasonal waterfalls, towering sandstone canyons, thriving wildlife, and scenic hiking trails.

However, the most well-known landmark at the park is the cliff the park is named after – Starved Rock. This imposing sandstone cliff is a natural landmark that holds history. 

Archaeological excavations have been run at Starved Rock for further research to verify information shared throughout history. In 1683, the French used Starved Rock to establish a fort called Fort St. Louis. It was later abandoned in 1691. 

The sandstone cliffs were named “Starved Rock” by Native Americans in 1770 after what is estimated to be about 2,000 Native Americans died atop the cliffs. This was after the Potawatomi Indians attacked the Peoria Indians.

As a result, the Peoria Indians were trapped on the rock and suffered starvation. 

Today, Starved Rock State Park has become a favored spot to sink into nature’s beauty. People come from all over to see Starved Rock and other popular landmarks, including the St. Louis Canyon Falls.

The St. Louis Canyon Falls towers an impressive 80 feet, one of the highest waterfalls in Illinois. In summer and spring, visiting these falls is one of the top activities to do at the park. You can also go kayaking , canoeing, or try other water sports.

Top attractions in the park include:

• St. Louis Canyon Falls
• Aurora Canyon
• Illinois Canyon
• Starved Rock State Park Lodge 

Popular hiking trails:

• St. Louis Canyon Trail
• River Trail
• Bluff Trail
• French Canyon Trail

There are two popular methods of getting to Starved Rock State Park from Chicago without a car. The first is taking the train from Chicago Union Station to Mendota Amtrak Station. The second would be to take a taxi, which can be much more expensive but is a quicker route.

We recommend visiting from April to September as it’s ideal weather for outdoor activities. If you’re an avid birdwatcher, then the best time of year to visit Starved Rock State Park to see the eagles is in January and February. 

The spring is the best time to see the waterfalls as they are seasonal and fed by heavy rains often experienced during the spring.

The summer is the most popular time to visit Starved Rock State Park. Unfortunately, this is when the park can get overcrowded, resulting in the park cutting off entry for visitors, as many people come to kayak and raft on the river. 

2. Lake Geneva

• Distance from Chicago: 83 miles/134 km
• How Long it Takes: 1 Hour 45 Minutes

A resort city, Lake Geneva, was named “Newport of the West” after the American Civil War. The year-round resort city was where rich Chicago residents constructed their summer homes. Some famous names that visited the area include General Sherman and Mary Todd Lincoln. 

This area has a rich history, where ancient Oneota Tribes of the lost Hopewell Culture Indians once thrived. Archaeological evidence suggests that the Oneota Tribes had an advanced civilization here in 1,000 BC.   

Today, Lake Geneva is one of the best weekend getaways from Chicago. A day trip or weekend trip here is worth taking because of its natural beauty, impressive architecture, and luxurious resorts.

Take your pick of boating on the lake, hot air ballooning over the resort city, joining a history tour, or sinking into luxury with a spa day at The Abbey Resort.

Examples of popular things to see include:

• Riviera Beach
• Big Foot Beach State Park 
• Lake Geneva Shore Path
• Royal Oak Farm 
• Safari Lake Geneva

There are no trains directly connecting Chicago to Lake Geneva. Another option would be to take the train from Chicago Union Station to Fox Lake. From there, snag a taxi to this Wisconsin resort city. 

To catch some sun outdoors by the lake, the best time to visit Lake Geneva is in the summer. This is the optimal time for weekend getaways or day trips from Chicago. The days get hot, so wear sunscreen and bring plenty of water to stay hydrated.

Have 3 days to spare in Chicago? Check out our ultimate 3-day itinerary ! 

3. Indiana Dunes National Park

• Distance from Chicago: 39 miles/62 km
• How Long it Takes: 1 Hour

One of the best day trips from Chicago, Indiana Dunes National Park is thriving with natural wonders with over 50 miles of scenic trails to observe these eye-catching features. A road trip through here is sure to be a beautiful one!

The park has one of the most biologically diverse habitats in the United States, including wetlands, shorelines, prairies, and sand dunes. This includes the 15 miles of Indiana Dunes National Park beaches stretching down Lake Michigan’s southern tip. 

Though the beach is one of the top things to do when visiting Indiana Dunes National Park, the park is also notorious for its rich history.

The Bailly Homestead, a National Historic Landmark, was the home of one of the first settlers in the area, Joseph Bailly de Messein. This fur trader’s trading post acted as an in-between for travelers from Detroit to Chicago. 

Top attractions in the park:

• Chellberg Farm
• Bailly Homestead
• Kemil & Dunbar Beaches
• Paul H. Douglas Trail 
• Great Marsh Trail
• Cowles Bog Trail
• Dunes Succession Trail (Diana of the Dunes Dare)

The best way to get to Indiana Dunes National Park is by renting a car. Unfortunately, there are no methods of transport that take you directly to the park. You can take a taxi, but it will be quite expensive!

Summer is the best time of year to visit Indiana Dunes National Park. This is when the beaches are open and prime for sunbathing and swimming. Other activities like fishing and hiking to see the sand dunes are also great at this time. 

4. Silver Beach County Park

• Distance from Chicago: 98 miles/157 km 
• How Long it Takes: 1 Hour 45 Minutes 

Bordering four states, Lake Michigan seeps into Illinois, Indiana, Michigan, and Wisconsin. Though Lake Michigan is technically within access of Chicago, with popular attractions like the Navy Pier and Millenium Park, one of the top day trips from Chicago is Silver Beach County Park.

Located at the mouth of the St. Joseph River on Lake Michigan’s southern shore, Silver Beach County Park has lots of picturesque viewpoints.

The long, clean stretch of beach has become a top tourist destination with upgraded renovations made to the park to promote accessibility and convenience. 

Access to Silver Beach County Park is free, though parking can be tricky depending on how busy it is. The barrier-free walkway gives easy access to the South Pier, Dunes Pavilion, concession stand, Shadowland Pavilion, and restrooms.

Using the park’s sidewalks along the beach, you can reach the Silver Beach Center, find the Whirlpool Compass Fountain, and take a refreshing stroll to downtown St. Joseph.

Cool things to see in the area:

• Silver Beach Carousel
• Krasl Art Center
• Harbor Shores Golf Club
• Whirlpool Compass Fountain

There are several ways to get to Silver Beach County Park from Chicago without a car. The first is a train ride from the Chicago Union Station to St. Joseph-Benton Harbor, Michigan.

The second is a bus ride from the Chicago Bus Station to Benton Harbor and a taxi to Silver Beach County Park. The third would be getting a taxi or renting a car to reach Silver Beach County Park. 

Silver Beach County Park is open daily from dusk to dawn. For swimming, the best time of year to visit is usually anywhere from July to September. Lifeguards are on duty at the park from June to August. 

Exploring more of the Midwest? Check out our list of the best things to do in Minneapolis, Minnesota !

5. Anderson Japanese Gardens

• Distance from Chicago: 85 miles/137 km

One of the highest-quality Japanese gardens in the United States, the Anderson Japanese Gardens is among the most rewarding Chicago day trips.

The authentic Japanese garden inspires by its refined outdoor setting that has been maintained and designed with the highest standards.

The Anderson Japanese Gardens were designed by Hoichi Kurisu, who established many other Japanese gardens, including the one at the Samaritan Lebanon Community Hospital that won the Healthcare Environment Award in 2006 for Landscape Design. 

Exuding eloquence and grace, this location soothes the soul as guests stroll through the thriving landscapes.

Yoga sessions are taught within the gardens in the Hatha Yoga tradition amongst the refreshing air of the gardens. There are beginner, intermediate, and advanced classes for Tai Chi led at the gardens to encourage relaxation and mental focus. 

Fun things to do here include:

• Amanda Stivers yoga
• Sound & gong bath
• Awareness walks

Other fun things to do in the area include:

• Rockford Art Museum
• Laurent House
• Prairie Street Brewing Company
• Nicholas Conservatory & Gardens
• Burpee Museum of Natural History
• Discovery Center Museum

Take the bus from the Chicago Union Station to Rockford Amtrak Station. From there, hitch a ride on a taxi.

Another option is to take the subway Jackson-Blue to O’hare in Bensenville. Once you reach the station, hitch a bus ride from the Chicago – O’hare Airport to the Rockford Bus Terminal. Then, grab a taxi to reach the gardens.

Taking a car is the second best option for a more cost-effective option, but it is more convenient than taking the bus and taxi to reach Anderson Japanese Gardens.

The best time to witness the stunning transition of the leaves as they turn color at Anderson Japanese Gardens is in Fall, from September to October. However, summer is the peak season, so if you want to avoid the crowds stick to visiting in the spring or fall. 

6. Oak Park

• Distance from Chicago: 10 miles/15 km
• How Long it Takes: 20 Minutes

Within a short distance from Chicago, Oak Park is a historically rich village place to visit. It is also considered one of the best places to live in Illinois, intertwining suburban and urban living in one favorable family-friendly location. 

There are plenty of activities in the area, with family-friendly attractions like the Brookfield Zoo and the Galloping Ghost Arcade. The arcade is the largest video arcade in the United States. Oak Park is notorious for its trendy restaurants like Maya Del Sol or Hemmingway’s Bistro. 

If you’re a history buff or appreciate architecture, you’ll love this beautiful spot. Renowned architect Frank Lloyd Wright showcased his talent here for the first 20 years of his career.

Walking tours take visitors past significant historical and architectural sites such as Wright’s home, the Frank Lloyd Wright Home and Studio. 

There is also the home of famed author Ernest Hemingway, who grew up in Oak Park. The Ernest Hemingway Foundation restored Hemingway’s home, and now tours of the author’s birthplace are given. Join a guided architecture tour to learn all about the history and creativity of the area’s top attractions!

Top sights here include:

• Frank Lloyd Wright Home and Studio
• Ernest Hemingway Birthplace Museum
• Brookfield Zoo 
• Oak Park Conservatory

There are lots of convenient ways to get from Chicago to this charming village. The train at Chicago OTC and the subway both head straight to Oak Park at inexpensive prices. The fastest way to get there would be a taxi, though this will run a little more costly than the subway or train. 

The Line 20 bus also comes here at an affordable price, though it will take longer to reach your destination as stops are included. 

Oak Park’s busiest month is from May to July. However, we recommend visiting anywhere from August to October if you want to avoid the crowds and high prices for these tourist-heavy months. 

Read next: The 21 Best Things To Do In St Louis, Missouri

7. Holland, Michigan

• Distance from Chicago: 152 miles/245 km
• How Long it Takes: 2½ Hours

Notorious for its award-winning breweries, Holland, Michigan, is only a few hours from Chicago and worth the trip. 

Holland’s natural beauty and charm are one for the books, with its lush nature, flower-speckled fields, and waterfront views.

The city is home to numerous parks to choose from for a picturesque stroll through nature with outstanding vistas. Holland’s downtown is thriving with locally-owned businesses to shop at.

The historic area was named one of “America’s Prettiest Towns” by Forbes magazine, with its cobblestoned sidewalks, live performances, and award-winning eateries and breweries to choose from. 

The Windmill Island Gardens is one of the top attractions in Holland. The gardens feature a 251-year-old windmill called De Zwaan. It is the only authentic Dutch windmill working in the nation.

Holland State Park is another largely popular attraction. The park showcases its iconic “Big Red” lighthouse for breathtaking sunset scenery and long stretches of beach on Lake Macatawa and Lake Michigan.

Many travel to the park to go camping, fishing, paddleboarding, sunbathing, and more for one of the best weekend trips from Chicago.

• Windmill Island Gardens
• Holland State Park
• Holland State Park – Macatawa Campground
• Big Lake Brewing
• Saugatuck Dunes State Park

For those without a car, there is a direct connection by train from the Chicago Union Station to the Holland Amtrak Station. However, if you have a car or can rent one, that is the only other option to get back and forth to avoid ridiculous fees for a taxi. 

We recommend visiting Holland in spring when the flowers bloom to see the tulips that the area is known for. They usually bloom around late April and continue to bloom to mid-May.

Visiting Holland in the summer is extremely popular, so if you don’t mind crowds and want to catch some sun, take a trip to the city to soak in the sun and picturesque views. 

8. Peoria, Illinois

• Distance from Chicago: 173 miles/267 km
• How Long it Takes: 3 Hours

Nestled along the Illinois River, Peoria is a bustling shipping center and agricultural production zone. Presenting a suburban feel, the city has family-friendly attractions to savor. It was once known as the Whiskey Capital, with 40% of alcohol produced in the United States coming from Peoria in 1890. 

On the city’s historic Distillery Row along the Illinois River, visitors can taste Peoria’s specialized whiskey distilleries that have maintained the city’s legacy.

There is much to see and do in Peoria. Designed by Pritzker Prize-winning architects John Burgee and Philip Johnson, the Peoria Civic Center is a hotspot attraction in downtown Peoria. The center showcases an exhibit hall, an arena, and a theater that hosts live entertainment for comedians, Broadway shows, concerts, and more.

The Luthy Botanical Garden is a refreshing stroll through themed gardens, including a children’s, Japanese, rose, and herb garden. It was also the first botanical garden in the state.

For a fun new experience, hitch a ride on this guided architecture cruise to experience the iconic architecture along the Chicago River. 

Top things to do include:

• Peoria Civic Center
• Peoria Riverfront Museum
• Louisville Slugger Sports Complex
• Forest Park Nature Center
• Luthy Botanical Garden

The cheapest method of getting to and from Peoria from Chicago is by driving. Another method of taking the train from the Chicago Union Station to Peoria Amtrak Station. This route will take longer than the alternative of going by car. 

The most popular time to visit Peoria is in the summer. However, if you’re looking for cooler weather, we recommend visiting the city in September to early October when the weather is getting cooler.

Read next: 23 Best Things To Do In Kansas City, Missouri

9. Michigan City

• Distance from Chicago: : 60 miles/96 km
• How Long it Takes: 1 Hour 15 Minutes

The source of Michigan City’s name is initially confusing for many. The city was not named after the state of its namesake but Lake Michigan that it is near. Michigan City is a favored tourist spot thanks to its convenient location near top attractions such as Indiana Dunes National Park and Lake Michigan. 

The city has a rich history with a small-town charm, and history buffs will be pleased to find the city flooded with attractions.

The historic city preserves its oldest structure, a lighthouse established in 1858, at the Old Lighthouse Museum. It was the home of the creator of Wikipedia, Howard G. “Ward” Cunningham, who grew up in the city.

The Barker Mansion is an English manor built in 1857, preserving period furnishings from the Gilded Age. It is part of the National Register of Historic Places and is open for tours.

Michigan City is a rewarding day trip from Chicago. Other than its historical attractions, there are nature-based activities such as Friendship Botanic Gardens and Indiana Dunes National Park. Go for a relaxing evening or tour the vineyards at Shady Creek Winery. Or test your luck at the Blue Chip Casino Hotel Spa.

Top attractions include:

• Washington Park Zoo
• Friendship Botanic Gardens
• Shady Creek Winery
• Blue Chip Casino Hotel Spa
• Michigan City Lighthouse and Pier

In Chicago, there are direct routes to take on the buses and trains that head to Michigan City from Chicago. Other than that, the only other inexpensive way to reach Michigan City is by driving. 

Ideally, summer or early fall in September is the best time to visit Michigan City to savor outdoor activities while in town.

Unfortunately, the winter months are frigid, from November to February. Therefore, we recommend not visiting during these months if you plan on spending time outdoors at the parks or gardens. 

DISCLAIMER: Some of the links in this article are affiliate links, which means if you book accommodation, tours or buy a product, we will receive a small commission at no extra cost to you. These commissions help us keep creating more free travel content to help people plan their holidays and adventures. We only recommend the best accommodations, tours and products that ourselves or our fantastic editorial team have personally experienced, and regularly review these. Thanks for your support, kind friend!

Alesha and Jarryd

Hi, We’re Alesha and Jarryd!

We’ve been traveling the world together since 2008, searching for the planet’s best destinations and adventures.

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The 25 Best Day Trips from Chicago for Every Style of Adventure

Whether you’re looking to escape your hometown or planning a trip to the Windy City and seeking some detours, try any one of these day trips from Chicago!

Chicago Illinois is one of America’s great cities. It is also perfectly situated for exploring. Home to the world’s first skyscrapers, Chicago is the third-largest city in the United States, and rather surprisingly so, as it seems to rise out of nowhere, from the middle of the cornfields. The city buts up against vast Lake Michigan and is home to the Cubs, The White Sox, and ‘Da’ Bears, and has the “world’s largest free-admission food festival:” The Taste of Chicago . It also happens to be home to the world’s best pizza (sorry New York). Chicago is an awesome city to explore, but nature lovers, and those looking to escape the city life, will find no shortage of great day trips from Chicago!

If the Windy City is your home, or you have spent a few days exploring, and you are ready to head for less hectic surroundings, Chicago is also perfectly situated for great day trips and weekend getaways. In this guide, we will show you some of the best day trips from Chicago to catch your breath and slow down a bit. Within a three-hour drive from Chicago, you can find wineries, amusement parks, charming Dutch towns, and beautiful state parks, a trip for every kind of adventurer!

Scavenger Hunts in Chicagoland

Before you head out to the surrounding areas, let us take you on a proper tour of the Windy City, with our Chicago Loop Scavenger Hunt . This app-led adventure will take you through the heart of Chicago on a journey filled with photo and trivia challenges meant to rack the brain and cause intense laughter. Our hunts are informative and tons of fun!

25 Day Trips From Chicago

Disclaimer: The distances and time recorded in this guide were taken from Google Maps at the time of writing. They are driving distances from Downtown Chicago. They may vary drastically depending on what day and time you choose to make your trip. We advise that you double-check the timing while planning your day. Also, bear in mind that many of these destinations can be reached by train or metro and may be faster that way!

1. Rockford

​Distance: 95 miles

Travel Time: 1 hr 40 mins

Rockford is a great day trip from Chicago for those with kids on board. Head straight for Discovery Center Museum , and let your kids dive into more than 300 interactive exhibits. They will playfully learn about air and flight, agriculture, their own bodies, and even the science behind color, light, and electricity. The museum is part of the great Riverfront Museum Park Campus. So, you can very easily make a full day (or two) without even leaving the park. Stop next door at the Rockford Art Museum, and then head to the Burpee Museum of Natural History(they have a baby T-rex.) 

Once you’ve had your fill of artifacts and art, the Anderson Japanese Gardens offer some much-needed fresh air. The gardens cover 12 acres and are filled with beautiful koi ponds and walking paths through the well-manicured flower and botanical gardens. The gardens are actually on the private property of businessman, John Anderson. After visiting the Japanese gardens in Portland, he fell in love with the zen and brought it home to his very wet backyard in Rockford. 

If you prefer your plants tropical, then head for the 11,000 acres of Nicholas Conservatory . Rock Cut State Park is a great place for a picnic or to stretch your legs on the lovely trails. Rockford also has a distinctly Swedish history on display at the Erlander House Museum. You can also try out traditional Swedish food at the Stockholm Inn . From exploring the land of ancient dinosaurs to chowing down on Swedish meatballs, Rockford Illinois is the perfect day trip from Chicago for families.

2. Chicago Botanic Garden

Distance: 25 miles

Travel Time: 43 mins

The Chicago Botanic Garden is in the suburb of Glencoe, just north of the city. Not only does the garden boast over 385 acres of natural beauty. They also have fun programs throughout the year to entertain your crew. The model railroad is interesting and displays scale models of several popular American landmarks. Make sure to download the Model Railroad BINGO game before you go. 

From November to January, The Chicago Botanic Gardens are transformed into one of the most impressive Christmas light installations in the Midwest. It’s so much more than Christmas lights, with a cacophony of light art installations falling from the sky and popping up from the earth. Traversing the gardens during the holidays is nothing short of magical! Tickets sell out very fast though, so make sure to book early.

The gardens are a quick trip from Downtown Chicago and the perfect place to get away from the city for a little nature break.

3. Oak Park 

Distance: 9 miles

Travel Time: 22 mins

Oak Park is a suburb just east of Downtown Chicago. The city prides itself on diversity in every walk of life. So, it is an eclectic city, where everyone, and every way of thought, are not only accepted but treasured! It also happens to be the perfect day trip for architecture lovers. Oak Park was the home to the famous Frank Lloyd Wright Home and Studio and showcases his own home, plus several more of his perfectly designed houses. Guided tours can be booked through the Frank Lloyd Wright Trust . You can also do a walking tour through Wright District, just make sure to see the incredible Unity Temple, a church Wright designed that is stunning and unexpected, in that FLW kind of way. 

4. Brookfield Zoo

Distance: 17 miles

Travel Time: 29 mins

The iconic Brookfield Zoo has been entertaining and educating families since 1934. The zoo covers 216 acres of natural animal habitats that are home to more than 2,000 animals. Visit the new baby wallabies, see the dolphin show, or get up close and personal to the resident Polar Bear. Travel to the Savannah to meet giraffes, rhinos, and zebras, before heading for Tropic World and coming face to face with a giant gorilla. Brookfield is a leader in conservation and animal care, as well as public and advanced zoological education. If you are unable to visit, send them a donation instead. They are doing some great work!

5. Springfield, Illinois

Distance: 218 miles

Travel Time: 3 hrs

Okay, Springfield is pretty far for a day trip, definitely pushing the boundary, but it can be done if you leave early. Springfield is a great destination if you are interested in history. It’s Illinois’ capital city and home to the beautiful Old State Capitol building. The old girl is a Greek-Revival masterpiece that is full of history. Honest Abe gave his famous “House Divided” speech from here, and he also lay in state here for a couple of days after his 1865 assassination. 

Visitors can tour the Capitol on their own or take a 30-minute docent-guided tour. The grounds also host several special events throughout the year including Civil War Encampments and Holocaust Remembrance Day. 

While in Springfield, you can also tour Lincoln Home , a national park celebrating the life and legacy of the 16th president. It was the only home ever owned by President Lincoln and the docents here do a great job walking you through his life from rural Kentucky to the White House. After that, you might as well stay on the Lincoln train and head for the Abraham Lincoln Presidential Library and Museum . You will be a bonafide Lincoln expert by the end of the day!

For a little fresh air, head over to the trails at the Adams Wildlife Sanctuary . This urban park is 40 acres of trails and woodlands, right in the center of Springfield. The estate belonged to long-time Springfield natives, the Adam’s Family (not the creepy ones). The home was built in 1869 and inhabited by the family until the death of Miss Margery Adams in 1983. It’s quite an oasis and definitely worth a stop. 

Truthfully, Springfield is much better suited to a weekend getaway or more. In addition to what we already detailed, the city also offers modern government sites like the Ilinois Governor’s mansion. It’s the home of the 1908 Race Riot Walking Tour, The Air Combat Museum, and The Camp Butler National Cemetary. There are plenty of great restaurants and breweries to explore too!

6. Kalamazoo, Michigan

Distance: 146 miles

Travel Time: 2 hrs 15 mins

Kalamazoo is loaded with fun activities. Gilmore Car Museum has a huge collection of vintage and antique cars. Actually, it has one of the top five automobile collections in the US, with more than 300 fully-restored pieces including rare Studebakers and Model A’s. The museum covers 90 acres and is a must-see for car and motorcycle lovers. 

The Air Zoo Aerospace and Science Museum is a blast. See a replica of the Wright Flyer, WWII Hellcats, and the final remaining Blackbird Stealth Plane. The museum also has a spacecraft wing with a 1970s replica command module and shuttle. The kids will love the interactive exhibits and flight simulators. 

Other things to do in Kalamazoo: (yes, Kalamazoo is the funnest word ever, and it is very hard to refrain from over-rhyming) Anway, visit the Kalamazoo Nature Center with its forest footpaths and butterfly gardens, and the oldest brewery in Michigan, Bell’s Brewery . While you certainly can’t cover all of Kalamazoo in a day, you can see a lot. It’s one of the best city getaways from Chicago.

7. Skokie, Illinois

Distance: 15 miles

Travel Time: 23 mins

Skokie is home to The Illinois Holocaust Museum , the second-largest Holocaust museum in the United States. It covers over 65,000 square feet, all dedicated to the horrors of the Holocaust and the memories of the survivors. The museum is a labor of love from the Chicago area Holocaust survivors. They opened the tiny, store-front memorial, in Skokie, in the 1970s, when the city was being threatened with neo-nazi marches and parades. In 2009, they scored a major upgrade to the new, modern museum, and it is definitely worth a visit!

Just in case a trip to Italy isn’t in your near future, no worries, Skokie also randomly has a half-sized replica of The Leaning Tower of Pisa known as “The Leaning Tower of Niles.” The Skokie Northshore Sculpture Park is also the perfect place for a picnic and a stroll!

8. Evanston, Illinois

Distance: 14 miles

Travel Time: 37 mins

If you are looking for a true day trip, Evanston is an easy jot north of Chicago. We recommend starting at the Baha’i House of Worship , which is actually a bit north of Evanston, in Wilmette. The architecture is out of this world. It’s unique and extremely beautiful! 

Evanston also has some quirky museums. The Block Museum of Art is located on the camp of Northwestern University. It’s an outdoor sculpture museum showcasing 16 works of art. Take a walking tour for something free to do in Evanston. The Halim Time and Glass Museum has an incredible collection of stained glass, as well as clocks from around the globe. The American Toby Jug Museum has the largest collection of its kind in the world, with over 8,000 Toby jugs (Philpots) and character jugs. Evanston also contains several small house museums detailing the history and culture of the area. It’s the perfect day trip for the art and history lover!

9. Lake Geneva, Wisconsin

​Distance: 83 miles

Travel Time: 1 hr 30 mins

Lake Geneva is a resort lovers paradise. It has long been a haven for wealthy Chicago families. If you want to spend your day sipping cocktails and gazing at the natural beauty of Geneva Lake, then there is no shortage of fancy resorts to choose from. 

However, you don’t need to be super wealthy or even step foot on a resort to enjoy Geneva Lake. Outdoor sports are king here too. Rent a paddleboard or kayak to cruise the lake or stroll around Lake Shore Path, where you can admire the incredible mansions. The 26-mile trail was once a Native American path used to travel between several Potawatomi Tribal villages. The trail was later used by migrant workers, and finally, after The Great Chicago Fire of 1871, several wealthy families escaped the city and built their new summer palaces on the shores of Geneva Lake. 

You can now stroll the path with the beauties of nature on one side and man-made beauty on the other. The mansions are inhabited, so please stay on the trail and be respectful of private property. Once you are done strolling, take a dip in the cool waters and relax in the sun on Riviera Beach. Lake Geneva is the perfect day trip from Chicago for water lovers and those who just want a relaxing day outside!

10. Morton Arboretum

Distance: 26 miles

Just west of Downtown Chicago, in the suburb of Lisle, the Morton Arboretum where you can learn everything ever wanted to know about trees. These guys are a little obsessed, in the best way! The arboretum is exceptional in the fall when the leaves are changing colors, but they also have special events year-round for adults and children, including marathons, holiday light installations, and whiskey dinners. The park offers a guided tram tour that is well worth your time as well. There are over 16 miles of trails to explore and a Children’s Garden where kids can splash in the streams and climb and slide on nature-themed exhibits made just for them! It’s beautiful. It’s fun, and it’s a great relaxing day away from the city. 

11. Michigan City, Indiana

Distance: 60 miles

Travel Time: 1 hr 5 mins

Michigan City lies on the southern border of Lake Michigan. The Century of Progress Historic Homes is a collection of buildings from the 1933 Chicago World’s Fair that was moved by barge to Beverly Shores. Once a year the buildings are open for tours in conjunction with the National Parks Service. The houses are incredibly modern-looking and must have been a sensation in 1933. Four of the houses are inhabited by sub-leasers who worked in conjunction with the park service to renovate and preserve the homes.

Move on to the Old Lighthouse Musem , the oldest lighthouse in Indiana, or stroll around the Washington Park Zoo . Michigan City has some great breweries to explore as well, but its real claim to fame (and the reason it makes this list) is Indiana Dunes National Park . This park is beautiful with over 50 miles of trails and 15 miles of shoreline. It used to be called the Indiana Dunes National Lakeshore, and the wide swaths of beach, flanked by towers of sand are still certainly the main attraction. The state park of the same name is right next door, and it showcases the three tallest sand dunes. Bird-watching is a favorite past-time here, along with horseback riding in the summer and snowshoeing in the winter. Kayaking or fishing on the lake is also a great way to spend a few hours! 

12. Holland, Michigan

Distance: 151 miles

Travel Time: 2 hrs 20 mins

Holland is in one word … adorable! Dutch, Calvinist settlers arrived in the region, in the mid-1800s. They built a village resembling their homeland, and Holland is still the go-to place to experience Dutch culture in the area. There is even a tulip garden, how very Dutch! Veldheer Tulip Gardens has over 5 million tulips. We would suggest visiting Holland in the spring so that you get to experience the flowering! 

Several restaurants and breweries around town offer traditional foods from the Netherlands, and when you feel sufficiently fat, head for Windmill Island Gardens , because no Dutch town would be complete without some windmills. The center-piece mill is over 250 years old and was transported to the area in the 1960s. For a bit of the international in a day trip from Chicago, you can’t beat a visit to Holland!

13. Starved Rock State Park, Oglesby Illinois

Distance: 93 miles

Starved Rock State Park is just outside the city of Oglesby. It is the go-to hiking location for Chicagoland. The beautiful park includes strange rock formations, that are unexpected in the Illinois flatlands, and over 13 miles of hiking trails along the Illinois River. The park is beautiful year-round. In the spring, all the waterfalls are at peak flow, tumbling over the walls of the 18 canyons in the park. A visit in the autumn will treat you to all the fall-foliage color changes. 

While you are in the area, be sure to check out Matthiessen State Park as well. It is only 3 miles away from the more popular (and crowded) Starved Rock State Park , and as you would imagine, it has all the same beautiful waterfalls and forested trails.

Nearby, at the Vermillion River, adventurers can enjoy some of the best river rafting in the region. The river has 14 rapids, mostly Class 1 and II, so it’s manageable for families, even with young kids. The Starved Rock Lodge is a great place to catch lunch or dinner, or should you decide to stay the night, you can snag a beautiful room. For nature lovers and adventurers, you really can’t beat a day trip to Oglesby. 

14. South Haven, Michigan

Distance: 123 miles

Travel Time: 1 hr 56 mins

South Haven is one of the best small towns on Lake Michigan. It is the home of the Michigan Maritime Museum The museum has permanent and rotating exhibits, highlighting Michigan’s maritime history and shipwrecks, but the favorite is the interactive Friends Good Will . It is a replica of an 1810 Top-Sail Sloop that is available for sailing tours. Guests can take a cruise on the replica tall ship, just like a sailor in the War of 1812. While the old girl is a bit creaky, it’s a pretty cool experience. 

Other than the museum, South Haven also offers some great outdoor activities. Bikers will love the over 30-mile Kal-Haven Trail, which links South Haven to Kalamazoo. Bikes can be rented from several shops in town. Van Buren State Park offers beautiful Lake Michigan beaches to lounge on too. If you happen to be in town during August, you can celebrate with the locals at the Blueberry Festival . The town comes alive with live music, pie-eating contests, a 5K, and all other-manner of blueberry-themed events. 

15. Galena, Illinois

Distance: 164 miles

Travel Time: 2 hrs 40 mins

Galena is a great day trip destination for history buffs. Galena was home to General Ulysses S. Grant and his family and features several prominent historic sites. Grant had actually ended his military service by the time he moved to Galena in 1860 and was working as a store clerk, but when the Civil War broke out, he was called back into action. The Ulysses S. Grant Home was presented to the war hero upon his return in 1865 by the citizens of Galena. He lived there until taking his spot in the White House years later. 

For more Grant-centered info, head to Galena & U.S. Grant Museum . It explores the history of Galena, including exhibits on blacksmithing, leatherworking, and lead mining. Both the Gran Home and the museum are housed in beautiful, red-brick Italianate villas. Speaking of Italianate mansion, consider spending the afternoon at the Belvedere Mansion and Gardens !

For the paranormal folks out there, Galena also happens to have several haunted locations. Join a ghost tour for an evening of spooky fun!

16. Fairbury, Illinois

Distance: 107 miles

Travel Time: 1 hr 45 mins

Fairbury is a road trip for the foodies. Fairbury is the location of two farm-to-table sites that service restaurants all over Chicago. Kilgus Farmstead is a dairy farm offering 1-hour tours detailing the milking process and the making of homemade ice cream, complete with samples! Slagel Family Farms specializes in hormone-free, farm-raised meats. They also offer interactive tours, complete with butchering demonstrations, followed up by a full farm-fresh dinner. The dinners take place in their charming barn, and make for a perfect date night! Make sure to stop by each farms’ grocery store to stock up on fresh eggs and other local goodies from nearby farms.  

17. Monroe, Wisconsin

Distance: 137 miles

Travel Time: 2 hrs 12 mins

Our second foodie location is the village of Monroe. Monroe is in the middle of cheesemaker territory! Learn all the ins and outs of the cheese industry at the National Historic Cheesemaking Center , then head for Alp and Dell where you can find more cheese varieties than you ever imagined. They are almost all local, and the staff there are experts. They can help you make wine and beer pairings like a pro. Take a walking tour of the town and visit cute Courthouse Square. The Green County Courthouse is on the National Registry of Historic Places and has lovely Romanesque architecture. Take the interactive tour and have your picture made in a judges gown and gavel!

If you want to spend a bit of time outside, hike part of The Badger Trail, a 40-mile journey that links to Madison. It traverses several small towns, wooded areas, and old tunnels, and it’s the perfect way to spend an afternoon outdoors. 

18. Peoria, Illinois

Distance: 128 miles

Travel Time: 2 hrs 28 mins

Peoria has had a huge revitalization over the last few decades. The old Warehouse District is now a conglomerate of unique art galleries, funky boutiques, and yummy eateries. The Riverfront District has seen even more gentrification and is full of breweries, museums, and even a really great farmer’s market on the weekends. Peoria seems to always be having a festival by the water, and when they aren’t, you can take a ride on a historic riverboat. 

Wildlife Prairie Park is located just outside Peoria. It consists of 1800 acres and is home to over 150 animals. The park has its own tourist train and a safari bus, so you have two choices for tours. You can make a full day of the park. Encounter the animals. Hike or bike the miles of trails, play disc golf or go visit the lakes.

Whether you are a shopper, a group of friends looking for a unique night out, or a nature lover, Peoria is a great day trip for you!

19. Milwaukee, Wisconsin

Distance: 86 miles

Travel Time: 1 hr 25 mins

The little city of Milwaukee on the shores of Lake Michigan has made quite a name for itself. It is famous for Summerfest Music Festival . The Milwaukee fest has been rocking for over 50 years and plenty of Country Music and Rock and Roll Hall of Famers have graced the stage there. With 11 stages rocking at once, it is a pretty epic show. 

The Milwaukee Art Museum has a stunning collection and is housed in a seriously innovative building. Many families argue that the Betty Brinn Children’s Museum is one of the best in the USA. Betty Brinn spent her childhood in foster homes and orphanages, so her rise to a successful place in the Milwaukee business world was an impressive one. She spent her life advocating for disadvantaged women and children, and the museum is her legacy.

Milwaukee is home to legendary beer maker, the Pabst Brewing Company. The Pabst Mansion is now on the National Register of Historic Places and offers guided tours. It’s a monster. The huge Harley-Davidson Museum is a top tourist attraction as well. 

Honestly, we would recommend that you give Milwaukee a full weekend unless you just want to visit one or two specific sites. It’s a great city, and there is a lot to see!

20. Grand Rapids, Michigan

Distance: 179 miles

Travel Time: 2 hrs 45 mins

Grand Rapids is the premier location for beer lovers. The city is loaded with great microbreweries. Grand Rapids is also home to some great museums, including the Gerald R. Ford Presidential Museum, the Grand Rapids Art Museum, and the Grand Rapids Children’s Museum. 

If you happen to be in town during ArtPrize, then lucky you. The annual event wraps the city in new and innovative art. It’s an outdoor/indoor art competition usually lasting 18 days. Artists create works that are displayed in galleries, museums, public parks, and even restaurants and bars. The whole city is transformed, and it is definitely worth seeing if you are in the area1 

Our ultimate guide to “ The Best Things to Do in Grand Rapids ” will give you more great ideas should you decide to stay a little longer in Grand Rapids.  

21. Explore the Sunflower Fields

Distance: 41 miles to Johnson’s (Other farms vary.)

Travel Time: 47 mins to Johnson’s (Other farms vary.)

From early July to late September, the fields surrounding Chicago are ripe with happy Sunflowers. The yellow beauties are not only soothing to the soul, but they are the perfect day trip for photographers. Whether you are a landscape photographer, you need a perfect family photo, or you just want a color Instagram selfie, the flower fields are for you! There are many private farms with varying degrees of availability, but one of the biggest and best is Johnson’s Farm. Not only do they have over 20 acres of sunflowers, but you are also allowed to pick them! They also offer a Fun Farm for children complete with an obstacle course, pedal karts, train and tram rides, a goat farm, and a jump pad. It’s a full day of fun!

Each farm has different rules about photography. Some require you to book an appointment in advance and pay a photographer’s fee if you plan on bringing professional camera equipment. 

22. Fennville, Michigan

Distance: 141.3 mi

Travel Time: 2 hrs 15 min

Fennville is in Michigan’s fruit belt. Chicagoans flock in droves to the country to pick peaches, cherries, and apples, depending on the season. Fennville is our favorite town to make a home base. Crane Orchards is popular for U-pick tours, and the hard ciders at Virtue Farms are top-notch. They supply many of the local restaurants in town with fresh goodies, but you can also sip a cider right on their beautiful property. Featherstone Antique Mall is a great place to peruse for treasures. There is no better pie than what you will find at Crane’s Pie Pantry . Plus the adorable restaurant/bakery/winery is located in the most charming centuries-old barn! It’s lovely. 

In June, you can enjoy the Fenn Valley Wine Festival , a celebration of live music and local wines. No matter what you do in Fennville, end your day at Salt of the Earth , everyone’s favorite farm-to-table local eatery.

23. Southbend, Indiana

Distance: 96 miles

Travel Time: 1 hr 35 mins

Home to the Notre Dame Fighting Irish, Southbend India is a pretty typical Midwestern city. There is a great History Museum housed in a lovely Victorian Mansion, and the city has a wonderful farmer’s market, but Notre Dame really runs the show here. The student population is 20,000 strong and the campus is beautiful. Take a tour of the campus noting the gold dome of the Main Building, the Basilica of the Sacred Heart , and the Grotto of Our Lady of Lourdes . The University of Notre Dame is older than the city of Southbend, itself, and tradition runs deep! It’s the perfect day trip for football lovers!

24. Madison, Wisconsin

​Distance: 147 miles

Flanked by lakes, Madison is the capital of Wisconsin and a long but good day trip from Chicago. Madison is another university city, so the vibe is young and fresh. History lovers, start with a tour of the Wisconsin State Capitol building. Not only do you learn a little about the city and see some beautiful architecture, but you will also walk through one of the best farmer’s markets in the region, so come hungry! It’s open every Saturday from April to November.

The farmers’ market isn’t the only place to get good food, though, Madison is loaded with fancy cheeses and craft beers. One of the local favorites is the Malt House . The dive has been serving up brew since the Civil War years and has plenty of local goldens on tap. For those fancy cheese lovers, head to Fromagination , where you can sample artisanal cheese and learn all about pairings from the cheesemongers. 

Biking is a big thing in Madison, and their local BCycle stations allow you to rent a bike for 30 minutes segments and explore the trails around Lake Monona. We also highly recommend a stroll through the Olbrich Botanical Gardens !

Tired and ready for a beer? Try our Madison Bar Crawl Scavenger Hunt and find all the best brews!

25. Gurnee, Illinois

Distance: 44 miles

Travel Time: 45 mins

Gurnee is a getaway for shoppers! Gurnee Mills is a huge shopping complex with over 150 stores. Whatever it is you need, you can find it here. If you hate shopping, no worries. Gurnee is famous a popular destination for one other reason— Six Flags Great America . The giant amusement park is full of traditional coasters and waterslides and wave pools at Hurricane Harbor Water Park.

For thrills seekers, shoppers, and families, Gurnee Mills is the perfect Chicago day trip!

Closing Thoughts

Chicago Illinois is a thriving city with plenty of action, but within just a few hours of the chaos, you can explore quiet state parks, wander lush sunflower fields, learn Civil War history, and enjoy the fruit of the vine. We hope you found your next day trip idea here. Use the comment section to let us know where you’re going!

For more vacation ideas, check out our guide to the best day trips from Boston ! And keep your eyes on our travel blog for more tips and travel ideas.

Frequently Asked Questions

There are several great day trips from Chicago ! The city is perfectly situated to visit small towns around Lake Michigan. Popular choices include Grand Rapids, Madison, and Milwaukee.

Start with a scavenger hunt of the city , then take a day trip from Chicago to the Dutch village of Holland, tour Notre Dame in Southbend, or spot wildlife in Peoria.

The windy city is surrounded by rural areas, perfect for hiking, kayaking, and exploring. That means there are some fantastic day trips from Chicago , like Starved Rock State Park and the Indiana Dunes.

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5 Best Day Trips from Chicago

By Joseph Hernandez and Jessi Roti

Are you visiting Chicago but your wanderlust feels like an itch you can’t scratch? No worries. The city is the gateway to the rest of the Midwest, and there are plenty of trips within a short drive or train trip that require only a day or two to explore and enjoy. Check out a painterly tulip farm in Michigan or devour the craft beer and cheese curds in Wisconsin. Whether you pick Milwaukee or Lake Geneva, Wisconsin; Oak Park or Mount Vernon, Illinois; or Holland, Michigan, these excursions prove the Midwest is anything but fly-over country.

Click the link to read our complete Chicago city guide .

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission.

MILWAUKEE, WISCONSIN

Want out of Chicago but still need to feel the pulse of a buzzing metropolis? Milwaukee is your next stop. While known for its beer and brats, the city’s pride in its past is equally undeniable upon arrival. With the dedicated revitalization of neighborhoods such as the historic Third Ward, Lincoln Village, and others, visitors are kept busy by specialty shops, galleries, and restaurants, as well as more growing, creative businesses. With access to Lake Michigan and a number of other rivers with paved pathways, there are plenty of nooks downtown for taking a break to take in the view. Milwaukee has a little bit of it all.

Milwaukee Public Market Arrow

This bustling public market is stuffed with local shops and restaurants in the heart of Milwaukee's historic Third Ward neighborhood. Each of the vendors are independently operated, and each offer different food and shopping experiences. The market invites you to divide and conquer, so bring your most inquisitive or adventurous friend to sample each of the vendors. Create a DIY tapas-style crawl, or shop vendors for tasty souvenirs.

Lakeshore State Park Arrow

Located in the heart of Milwaukee, Lakeshore State Park is an urban escape. Twenty-two acres of lakefront trails and paths look out onto Lake Michigan, with fishing areas, a watercraft landing for canoes and kayaks, and connecting access to Summerfest, Milwaukee's annual large-scale music festival. Trails are clearly marked with little chance of getting lost, where leisurely walkers and cyclists are soaking in the views.

Milwaukee Art Museum Arrow

The lakefront Milwaukee Art Museum is a vision in and of itself. The gleaming white Santiago Calatrava structure, with dramatic wings and stunning dorsal fin, hints at the talent within the quiet galleries inside. With a collection of over 25,000 works, the Milwaukee Art Museum is one of the largest museums in the country. The galleries feature everything from folk art to contemporary American, across all disciplines like prints, sculptures, and paintings. Wisconsin native Georgia O'Keefe features prominently—the museum owns much of her work—alongside European artists Gustave Caillebotte, Claude Monet, and Joan Miró.

Jessica Puckett

Olivia Morelli

Rachel Chang

Schuster Mansion Bed & Breakfast Arrow

Let Schuster Mansion comfort you in history and elegance, at the level of your choosing. Upon arrival, you'll be struck by it's rusty, red coloring—a blend of red sandstone, red brick, and red terra cotta trim. The mansion's stand-out coloring only hints at the interior design. Rooms are spacious, and each comes with a vintage, claw foot tub that taunts you with the promise of a luxurious bubble bath. Enjoy the lush, relaxing Victorian Garden or help complete the ever-ongoing jigsaw puzzle in the Ladies’ Parlor. Planning on visiting ahead of the winter holidays? Schuster's Christmas decor is second to none.

Holler House Arrow

Founded as Skowronski's in 1908 in the Lincoln Village neighborhood, the noisy tavern was renamed Holler House after a local woman complained about the ruckus emanating from inside. But the bar has seen many boozy hijinks in its century-plus existence. Known for its raucous bowling nights—in a slight basement alley featuring two lanes that happen to be the oldest, sanctioned tenpin lanes in the United States, still set by hand—Holler House is where you can go to really let loose. In addition to playing a game or two, there’s a full bar, but this is much more of a beer and a shot establishment .

OAK PARK, ILLINOIS

Sharing a border with Chicago’s West side, suburban Oak Park is accessible via the CTA’s Blue and Green Lines as well as Metra trains. But its proximity to the urban hustle doesn’t disrupt its refreshing slow pace. Enjoy its homegrown Arts District, unique boutiques, cafés, and rich cultural record—including being the home of actress Betty White and novelist Ernest Hemingway. Known for its abundance of Prairie School architecture, thanks to natives such as Frank Lloyd Wright, the neighborhood also makes for great self-guided tours on bike or on foot. Whether you’re a fan of local history or everyday whimsy, a visit to Oak Park is worth it.

Frank Lloyd Wright Home and Studio Arrow

Designed, worked, and lived in by one of the biggest names in American architecture, the Frank Lloyd Wright Home and Studio preserves the Prairie School founder's original architectural studio and his adjacent home where he experimented with early ideas. Wright designed the buildings and filled them with his own furniture designs, too, a marriage that offers a comprehensive look at Wright's insistence on design integrity.

Pleasant Home Arrow

Set in Oak Park's sprawling Mills Park and designed in 1897 by architect George W. Maher, this home is a National Historic Landmark and the only Maher building open to the public as a museum. While Frank Lloyd Wright is the bigger name, his peer Maher helped usher in the Prairie School of architecture with Pleasant Home's design, helping to influence the blending of oeuvres that defined the style. This 30-room museum showcases late 19-century craftsmanship, from intricate art glass to custom woodwork throughout.

LAKE GENEVA, WISCONSIN

A once-popular summer vacation destination for wealthy urbanites, Lake Geneva has managed to preserve much of its Gilded Age lure. Think a little Great Gatsby in the Midwest. Though tastes have changed, Lake Geneva has managed to stay at the top of many travel recommendation lists—mainly for its year-round resort-like atmosphere and attractions. A place that’s almost always prepared for tourists has its perks and one of this Wisconsin town’s is its genial nature, whether you’re perusing different markets or rubbing elbows at the bar. Visitors can also explore local arts culture. Scenic, lakeside paths and parks are calling your name. Or if you’re feeling adventurous, fly above it all in a hot air balloon.

Lake Geneva Shore Path Arrow

With 26 miles hugging the shores of well-trodden Lake Geneva, the Shore Path is not exactly removed from the Realm of Man, but it is a scenic stroll nonetheless. Wealthy Chicagoans flocked to Lake Geneva in the 19th century, especially after the Great Fire in 1971. You'll find stunning former estates and opulent lawns. By public ordinance still in effect today, property owners leave at least 20 feet of space available to the public, with some offering benches to rest or art installations to view and interact with as you make your way around the path.

Baker House Arrow

Baker House, constructed in 1885, houses an opulent Gilded Age parlor, with sunny lakeside views, and homey digs. Guests flock there for its old-school charm and luxurious furnishings, trying to tap the wealthy turn-of-the-century vibe that attracted well-heeled vacationers to Lake Geneva in the first place. For turn-of-the-century charm and opulence, Baker House delivers on all fronts.

Studio Winery Arrow

Exposed steel beams, warm wood wine racks, and art made by Studio Winery's artist owners create a warm, convivial atmosphere for wine drinking. The large room features many high-top tables for groups to sit and enjoy, plus a small stage for visiting music acts. The wines aren't technically fine wines, but they're fine wines—get it? The Musician series wines take their name from famous musicians, using local varietals and range from dry to sweet. Meanwhile, the premier tasting wines feature more elegant, classic European varietals, like viognier, syrah, and cabernet sauvignon.

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Housed within Lake Geneva's Fancy Fair Mall, this indoor artisan market is open year-round, showcasing original wares by more than 100 makers from across the country. Queen Bee’s curated collections cater to all ages, so even kids will be able to make a day out of shopping and supporting small business. Whether you’re looking for hand-forged, industrial lamps, a housewarming gift for a friend who you know loves a sassy statement mug, candles, decorative signage, or unique clothing, the market is a great place to find one-of-a-kind, useful souvenirs from your visit.

HOLLAND, MICHIGAN

Holland’s Dutch immigrants are celebrated in the aesthetics and traditions of this shore town’s varied restaurants, shops, attractions, and architecture. You’ll notice antiqued windmills, re-envisioned Germanic villages, dainty gardens, and millions of tulips, which give it the nickname Tulip City. Stroll or hike through the park before taking in the sunset over Lake Michigan, then go out for drinks. While there’s plenty of activity to occupy you during the day, the star-gazing Holland’s country outskirts allow for is unparalleled. What better way to end a day? Play Sufjan Stevens’ Greetings from Michigan album on your way up, track 7—“Holland.”

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Located on a quiet country road, Castle in the Country is a quaint, 100-year-old Victorian that screams iconic American dream home. The bed and breakfast, with its millennial pink painted details, wrap-around porch and just-so hanging planters, is an adorable escape out in flat, picturesque countryside. Castle in the Country's seclusion is its biggest draw. Far away from city lights, you'll be beneath star-filled skies and amidst wide-open spaces. The luxurious digs and clean country air are enough reason to book a stay.

Windmill Island Gardens Arrow

Want a taste of old-school Europe? Holland's Windmill Island Gardens, a 36-acre park of even-keeled fallow land, manicured gardens, and quaint recreation Dutch shops is such an escape. The main attraction at Windmill Island Gardens is its namesake, DeZwaan ("The Swan"), a windmill built in 1771 but purchased and imported from the Netherlands in 1964. The working mill still grinds flour, available for purchase in the "Little Netherlands" shops, which also sell kitschy crafts like pottery and wooden shoes. With 100,000 tulips planted annually, the gardens also participate in Holland's famed Tulip Time festival, with activities for kids and adults alike.

Veldheer Tulip Gardens Arrow

With over five million tulips planted annually, Veldheer Tulip Gardens is a sight to behold come spring-time. The manicured lawn explodes in color, much like you'd expect in the real Holland, with tulips of every hue brightening the landscape. Though you're not allowed to pull the tulips from the ground, plenty of bulbs are available to order, as are other flowering plants. You think it's just all pretty flowers here? Think again. Veldheer also started a breeding program for American bison, with a herd of 20 available for viewing, with educational programing for the public. Veldheer’s grounds also include the DeKlomp Wooden Shoe Factory—a perfect gift to snag before you go.

Butch's Dry Dock Arrow

This stylish bistro is a welcome respite, with white table cloths, warm lighting, and local art on walls. A small list of tightly curated wines spans the globe, but the draw here is Butch's 200-plus beer selection, spanning micro, craft, and imported beers and ciders. The menu is a selection of New American classics, and Butch's prides itself on working closely with local purveyors, listing its local partners prominently on the website. When in Holland, head here for a sophisticated, special dinner that is elevated but unfussy.

New Holland Brewing Arrow

Founded in 1996, New Holland Brewing is one of the country's pioneering microbreweries. At its corporate headquarters in downtown Holland, you'll find the brewpub. The sprawling, two-floor pub is familiar in the way that breweries can be, that is, exposed ducts and bricks, tin ceilings and numerous myriad high-tops occupied by imbibers is familiar. From cask-poured stouts to limited releases, growler fills and special brewpub-only offerings, New Holland serves upwards of 20 brews at any given time. Head there for a low-key lunch or dinner. Meet new friends or catch up with old ones over cold brews in relaxed digs.

deBoer Bakkerij Arrow

This family-run spot has been baking in Holland, Michigan for four generations, adding the cozy breakfast and lunch restaurant in 2008. The bakery bustles with to-go diners in the mornings, with cafe bar seating, benches, and banquettes for restaurant diners. The high ceilings and bright lights make for an airy space. DeBoers started as an authentic Dutch bakery, so it's safe to assume that the baked offerings are on lock: Challah, cracked wheat, San Francisco sourdough, French baguette, marble rye—the list goes on.

Tunnel Park Arrow

Along the shores of Lake Michigan, this 22-acre park is a popular place for swimming, sunbathing, and picnicking—but it’s called Tunnel Park for a reason. What locals consider the best spot to watch the sunset, a unique archway built through a dune gives way to pure, unobstructed views of orange and amber skies. You may even spot a sailboat or two.

MOUNT VERNON, ILLINOIS

Small town Mount Vernon (named after President George Washington’s Virginia plantation) has all the modest charm expected from Southern Illinois, and passionate locals are at the heart of efforts to bring more tourism to their town. Home to Rend Lake, a groovy vinyl record shop, comforting spots to grab a bite, the Cedarhurst Center for the Arts, and plenty of wide open spaces, Mt. Vernon might not be what immediately comes to mind when one thinks about visiting the Prairie State—but its surprising creative spirit may just capture a spot on your return travel list.

Main Street Records Arrow

At the only locally-owned vinyl LP shop in town, wafting incense will greet you ahead of your dive into the expanse of classic rock albums, R&B, and jazz albums, rare imports, and more, among plenty of band t-shirts to show an even deeper allegiance to your favorite acts. A number of CDs and concert DVDs are also available in the store’s collection, but management is positive it can track down any disc you’re after.

King City Books Arrow

Though King City Books’ is under renovation, the shop’s reputation precedes it—diehard patrons sing its praises for the reads and espresso bar it houses. It's the only indie bookstore within 60 miles, making its devoted fan base even more important. The shop is dedicated to elevating local authors and selections fit for all ages, including mystery and YA. Locals are devoted fans of this book shop and are eagerly awaiting its return, as are musicians and artists who took advantage of the shop's open mic nights.

Cedarhurst Center for the Arts Arrow

Across the Cedarhurst Center's 90-acre campus, early 19th and 20th century paintings and modern sculpture are showcased. Most of the collection is from that of the museum's founders John and Eleanor Mitchell. Take a stroll or drive through the Goldman-Kuenz Sculpture Park for some perspective. Across the center’s 90-acre campus, works by John Kearney, Chakaia Booker, Deborah Masuoka, Tom Orr,and many more are thoughtfully placed for guests to develop a deeper appreciation for modern sculpture. Inside, the Bonan Permanent Collection is at the heart of the museum—an abundant celebration of paintings by early 19th and 20th century American masters, both renowned and unsung.

Rend Lake Arrow

Rend Lake offers a slew of water sports and other outdoor activities that are difficult to properly enjoy within Chicago city limits. Known as “Southern Illinois’ playground,” you could plan a day’s worth of events based solely on what the lands have to offer. Hit one of the lake’s two beaches (but prepare to pay a daily fee) or take advantage of the thousands of acres of open water for skiing, jet skiing, wake boarding, or tubing.

Sidwell Friends Bed and Breakfast Arrow

Nestled between the trees, this quaint bed and breakfast offers a glimpse at simple, sophisticated small-town living. With boutique amenities, lovely gardens, and owner Mr. Sidwell's library of books and art collection, this stay encourages serenity at both the start and end of your day. Each morning, you’ll be greeted with a full, home-cooked breakfast and probably a look or two from Sidwell’s resident English Bulldog. She doesn’t have the run of the house, but she’s certainly one of the ladies of it. The bed and breakfast is blocks away from the Cedarhurst Center for the Arts, a few miles from Rend Lake, and other Mount Vernon sites including wineries.

Jimmie James Blue Goose Arrow

This unassuming gyro shop has been a Mt. Vernon staple ever since it began serving Greek comfort food in 1978. The menu hasn’t changed much over the years (it’s still cash only), and neither has the décor, but it’s part of why the place is so beloved. Get a gyro and fries with a piece of baklava on the side, kalamata olive salad, or—if there’s a bit of chill in the air—warm up with a bowl of gyro stew: the juicy, tangy bite you love served in a rich, brown broth with chunky veggies and potatoes. The stew is the entree to choose for something quintessentially Jimmie James.

Farmhouse Bakery & Cafe Arrow

Locals frequent for breakfast, lunch, and dinner as well as shop the small grocery inside the cafe. But rowdy, this cafe is not. The café offers a number of housemade lemonades, smoothies, hot and iced teas, coffees and frappes, and soft drinks. With its down-home appeal, pies, pecan rolls, biscuits, donuts, and scones all have the feel of grandma’s hands. Stop in for breakfast or lunch—which includes everything from panini to lasagna and meatloaf—or homemade ice cream after a day at the lake.

Fenn Valley Vineyards Arrow

This longtime, family-owned vintner features a warm, rustic tasting room, tours, and wine-pairing dinners in a convivial atmosphere. The winery hosts majority group tastings for special occasions and picnics. As the wine continues to flow, so does conversation. During select times of year, the vineyard offers specially designed tours involving food and wine. Picnics include a hearty charcuterie board, choice of three bottles of wine or 3-4 packs of hard cider, and a battery-powered speaker with cables to connect to your phone or tablet.

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11 Unforgettable Day Trips from Chicago

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Chicago is a wonderful city in the USA worth visiting because of the food scene, nightlife, and architecture. Chicago has so many museums and neighborhoods to explore. Once you’re done touring the city, don’t miss the opportunity to take some day trips from Chicago!

Sometimes the busyness of the city can be overwhelming both for residents and travelers. Taking a day trip (or three!) allows you to breathe some fresh air and see more of the state of Illinois. 

By adding a few extra days to your itinerary, you can spend your time taking a few Chicago day trips. You can also easily visit nearby states like Michigan and Wisconsin since Chicago borders them. 

Here are the top ten day trips from Chicago and what you can expect on each of them.

This post may contain affiliate links, which means I’ll receive a commission if you purchase through my links at no extra cost to you. Please read the full disclosure for more information.

Visiting Chicago 

Heading to Illinois? Chicago is usually the first stop for most travelers to the state. A weekend in Chicago is enough to see all the best sites, but you can easily spend a few weeks or more. 

After a few days of sightseeing and touring around Chicago, here are the best places to visit near Chicago and what to do in each place:

• Cycle around Lake Geneva
• Grab a beer in Milwaukee 
• Go fruit picking in Fenneville 
• Visit the small town of Gurnee
• Go to a tulip festival in Holland, Michigan 
• See the flowers blooming at Chicago Botanic Gardens 
• Go horse riding in Indiana Dunes National Lakeshore 
• Take a guided tour through the Anderson Japanese Gardens
• See the Discovery Center in Rockford 
• Go to a festival in Cedarburg 
• See bison in the Midewin National Tallgrass Prairie

Click the link to go directly to the section below. Or scroll down to read them all!

1. Cycle Around Lake Geneva 

Lake Geneva is one of the best day trips to take in the warmer months. It’s a small city on the shore of Geneva, Lake in Wisconsin. The city is a resort town with many hotels, shops, and tourists. 

The Lake Geneva Shore Path is the main attraction. It’s 21 miles long and is perfect for biking and walking. Lake Geneva also offers cruises for those that want to be out on the water. They have daytime and sunset cruises. 

You can easily head back to Chicago in the evening if you want to since the drive is only about an hour and 40 minutes. Before leaving the area, make sure to walk around the city center, where there are some great boutique shops. 

Getting to Lake Geneva

Renting a car is the fastest and easiest way to get to Lake Geneva. It takes about an hour and a half when you drive along I-94 W and WI-50 W. There is also an option to take a train, but I don’t recommend it as it includes transfers, and the journey can take up to 3 hours.

2. Grab a Beer in Milwaukee 

If you want to head to another nearby city, you can head up to the state border and be in Wisconsin in about an hour and 35 minutes. 

Milwaukee has plenty of things to do, but beer lovers will love this city the most. Craft breweries can be found all over the city, along with microbreweries. Many of the older breweries have a long history and even offer historical tours. 

Here are the best places not to miss:

• Lakefront Brewery : Offering seasonal beers with local ingredients, this brewery is one of the most famous in Wisconsin. They have a diverse selection of flavors. Everyone in your group should be able to find something they like, including those who are gluten-free!
• City Lights : Famous for its coconut beer, City Lights is in a historic building that also offers tours. They have a really nice patio outside where you can see the Menomonee River. 
• Eagle Park Brewing: This brewery has many different options, including milkshake IPAs, hazy IPAs, and hard seltzers. It’s a large brewery, so you can always find seating, even on the weekends or other busy periods. 

Getting to Milwaukee

If you have a car, it’s easy to get to Milwaukee in about an hour and a half using the I-94 W. You can also take a train, as Amtrak stations are in both cities. Hiawatha Service is the most common way to travel between the two cities.

3. Go Fruit Picking in Fenneville 

Around 2.5 hours from Chicago, Fenneville is one of the best day trips from Chicago. It’s in the fruit belt of Michigan, so it’s a great place for fruit picking. In the fall, you can pick fresh apples; in the summertime, you can get peaches and cherries. 

Pleasant Hill Farm and Crane Orchards are the most popular places for fruit picking. 

Before heading back to Chicago, stop by Crane’s Pie Pantry . It’s a beautiful winery and restaurant in a historic barn. They have amazing food and pies made with fresh fruit from nearby farms. 

Getting to Fenneville

The fastest way to get to Fenneville is to rent a car. The journey will take you about 2 hours and 20 minutes when you use I-94 E.

4. Visit Gurnee

Just one hour from Chicago, Gurnee is another of the best weekend road trips from Chicago. It’s home to Six Flags of America , so many rollercoaster fans come here for the weekend to get their adrenaline pumping. 

If you’re not an amusement park fan, there are many other things to do in Gurnee, including:

• The Chocolate Sanctuary : This restaurant has a nice breakfast buffet, including freshly baked bagels. The chocolate-covered strawberries are a popular item on the menu. 
• Illinois Beach State Park: Come here in the summer to lounge on the beach, pick wildflowers, and spot more than 600 different species of plants. 
• Only Child Brewing Company : This brewing company has something for every palate, including IPAs, citrus fruit beers, and beers aged in wine barrels. 
• Lambs Farm : A small farm that’s also an animal shelter, Lambs Farm is a nonprofit that employs people with disabilities. You can spend time with the animals, grab a treat at the bakery, and play mini golf. 

Getting to Gurnee

The only option to get to Gurnee from Chicago is to rent a car, as there are no good bus or train options. The drive only takes about 45 minutes on I-94 W, making it a super easy day trip.

5. Tip Toe Through the Tulips in Holland 

This small town in Michigan is 2.5 hours from Chicago. Spring is the best time to visit, so you can see the tulips in bloom. At the peak in spring, the town boasts over 4.5 million tulips. 

The best places to see the tulips are Windmill Island Gardens and Veldheer Tulip Gardens . 

There is also a tulip festival in early May that is worth checking out. You can try Dutch food, see traditional Dutch dancing, and even watch a few parades that go through the city center. 

There’s also the Holland Museum , which you should check out if you’re interested in Dutch culture and cuisine. 

Spring is the best time to see the tulips, but it’s not the only time of year when there are festivals. Come in late November if you’re interested in the Parade of Lights or Dutch Winterfest. 

Getting to Holland

There are a couple of options for getting to Holland from Chicago. One is to rent a car, and the other is to take the Amtrak train . Many people choose to take the train as no transfers are, making it an easy journey.

The train will take about 3 hours. It can be pricey, though, with tickets costing up to $90 one way. If you travel with many friends, it might be cheaper to split the cost of a rental car and fuel.

6. See the Flowers Blooming in Chicago Botanic Gardens

For one of the best short trips from Chicago, you can drive about 35 minutes to get to the Chicago Botanic Gardens. The landscaping is beautiful, and flowers bloom through spring, summer, and early fall. 

The botanical gardens are divided into thirty separate smaller gardens, all with distinct flora and fauna. 

Once you get to the gardens, you can download an app on your smartphone that guides you down the different pathways in the park. A voice narration provides information about the different flowers and garden designs. 

On-site, there is a small restaurant and cafe . There is also a bike rental shop, as some parts of the gardens allow cycling. 

Chicago Botanic Gardens is located at 1000 Lake Cook Rd, Glencoe, IL 60022, United States . They’re open from 10 a.m. to 6 p.m. Tickets start at $11.95. 

Getting to Chicago Botanic Gardens

You’ll definitely need to rent a car to get to Chicago Botanic Gardens from Chicago. The easiest way to get there is to use I-94 W and then get off onto US 41. It will take you just under 30 minutes to get there.

7. Go Horse Riding in Indiana Dunes National Lakeshore 

If you’re interested in a one-day beach trip from Chicago, head to the Indiana Dunes National Lakeshore, just an hour outside of Chicago. The shore is about 15 miles long and is perfect for relaxing when the weather is warm. 

There are also many trails around the shore to go hiking, biking, or horse riding. If you’re interested in birding or want to explore more of the lakeshore, stop at the visitor’s center and ask to go on a walking tour led by one of the park rangers. 

Indiana Dunes National Lakeshore is located at 1215 N State Rd 49, Porter, IN 46304, United States. It’s open from 7 a.m. to 11 p.m. Entrance tickets are $15 if you don’t have a car and $25 if you do have a car. 

Getting to Indiana Dunes National Lakeshore

There is a bus option to get to the lakeshore, but I don’t recommend it as it makes the day very long, and the buses don’t come super often. Renting a car is your best option, and it takes about 45 minutes to get here from downtown Chicago.

8. Tour the Anderson Japanese Gardens 

For another of the best Chicago road trips, head about an hour and 40 minutes outside of the city to Anderson Japanese Gardens. You can walk down the quiet, peaceful trails and see the gardens John Anderson and Hoichi Kurisu designed. 

You can also take a guided tour. The guides can tell you more about the plants and the garden’s design. 

Open in 1978, the gardens were designed using different plants, water, and stones to provide a more authentic Japanese garden feeling. 

The Anderson Japanese Gardens are located at 318 Spring Creek Rd, Rockford, IL 61107, United States . Hours vary by season , and they are closed during the winter months. Tickets are $11.  

Getting to Anderson Japenese Gardens

To get to the gardens from Chicago, your best choice is to rent a car. If you drive along I-90 W, you can reach the gardens in about an hour and a half.

9. See the Discovery Center in Rockford, Illinois

Anderson Japanese Gardens is located in Rockford. So, after visiting the gardens, you can stay a little longer and explore this charming small town. 

This is a great place to visit if you bring the kids, as there are many family-friendly activities like the Discovery Center Museum .

You need to make reservations online before coming. There are over 250 exhibits to visit, so you can easily spend a whole day here. 

If you’re not with the kids, head to Prairie Street Brewing . Along with great local beers on tap, they also have bar food with a twist. Try the spicy mac ‘n’ cheese or the Asian street tacos. 

Getting to Rockford, Illinois

If you don’t want to rent a car, you can take a bus from Chicago to the Amtrak Station in Rockford. From there, you must take an Uber to the Discovery Center Museum.

If you choose to rent a car, you can drive directly to the Discovery Center on I-90 W.

10. Go to a Festival in Cedarburg, Wisconsin 

This cute town in Wisconsin is about 20 miles from Milwaukee and 2 hours from Chicago. Many family-owned places exist, including the wine bar Cedar Creek Winery and a famous candy apple store called Amy’s Candy Kitchen .

The city is also well known for having festivals in the fall that attract many different visitors, including Oktoberfest and the annual Wine & Harvest festival .

Getting to Cedarburg

Definitely rent a car to get to Cedarbug, as bus and train options are super limited. it takes about 2 hours to get to Cedarburg from Chicago.

11. See Bison at Midewin National Tallgrass Prairie

You might already know that Illinois is nicknamed the “prairie state.” This is because there are tons of uninhabited land where animals, like bison, roam freely.

To get a close-up look at these incredible animals, head to the Midewin National Tallgrass Prairie.

The place is pretty large, so you might have to spend several hours looking for the bison. Most travelers can spot them from the Iron Bridge Trailhead. You should also consider bringing a photo lens that can zoom in or a pair of binoculars so you can see the animals better.

There are also a few hiking trails throughout the prairies where you can see other wildlife and their natural habitats.

Getting to Midewin National Tallgrass Prairie

The only way to get to the prairies is to rent a car, as they are in a pretty rural area. You can drive along I-55 S to get here, and the journey will take about an hour.

Top Things to Do in Chicago

Planning on spending time in Chicago in between a few fabulous day trips? Here are the top things to add to your Chicago bucket list:

• The Art Institute of Chicago : All art lovers should head here on their first day in Chicago. The permanent exhibits showcase pieces of art from all over the world. Make sure to check the calendar to see which rotating exhibits they have while you’re visiting. 
• Cloud Gate : This is the famous mirror bean that you have probably seen many photos of while planning your trip to Chicago. It’s an iconic piece of Chicago history that is worth seeing. 
• Millennium Park : The perfect place in the city for people-watching, grabbing a snack, and relaxing. In the winter, there is an ice rink where you can go skating. 
• Eat deep-dish pizza: Eating pizza is a must while in Chicago. The best places to enjoy pizza in the city are Giordano’s and Lou Malnatis . 
• Gaze at the architecture: One of the first things you’ll notice when walking around Chicago is the beautiful buildings. Try to join a walking tour so you can be sure not to miss any of the best architectural spots. 
• Hit the clubs: Chicago is known for having an amazing nightlife scene. If clubbing isn’t your vibe, there are many laid-back bars around the city as well. Raised Urban Rooftop Bar is one of the best places to drink, with nice views of the skyline. 

How to Get to Chicago 

Chicago has a huge international airport, making the city very accessible for domestic and international travelers. Chicago O’Hare Airport (ORD) has daily flights from locations all over the world. 

You can find flights on American Airlines , Delta , and cheaper carriers like Spirit and Frontier. International airlines like KLM , Ethiopian Airlines , and Turkish Airlines also fly to Chicago. 

When to Visit Chicago 

Chicago has brutally cold winters, so it’s best to avoid coming to the city during that time. The months with the mildest weather include April through October. If you really hate chilly weather, the latest you should come is in September. 

The summer and early autumn months also have many different festivals making it a great time to be in the city. 

Don’t Miss These Incredible Day Trips from Chicago! 

From small local towns to state parks to famous botanical gardens, there are some amazing day trips from Chicago. While many more didn’t make this list, these are the ten best day trips to check out when you’re in the Chicago area. 

Are you heading to Chicago? Which of these day trips are you going to take first?

You Might Also Like

• The 12 Best Places to Stay in Chicago: Areas & Accommodations
• What to Do in Chicago for a Weekend

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This post was contributed by Natalie Castle. Natalie has been traveling mostly solo for the past 6 years internationally and across the United States. She loves seeing new destinations, especially where she can go to the beach or go for a long hike. She discovered her love for travel writing a few years ago and hopes to encourage other people to begin solo traveling through her writing. When she’s not working, you can find her with a glass of red wine planning her next trip.

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10 Easy Weekend Getaways from Chicago—No Flights Required

Escape chicago for a few days with one of these 10, drivable weekend getaways and short road trips starting in chicago..

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Door County, Wisconsin, is one of the many easy-to-reach day trip destinations from Chicago.

Photo by Bailey Berg

Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location : With prime real estate on Lake Michigan, the Midwest city is about as far by car from Minneapolis (six hours) as it is Toronto (eight hours) and Nashville (seven hours). In this sense, it’s an ideal jumping-off point for a drivable trip. There are several weekend getaways from Chicago, whether you want to put some serious miles on your car or be somewhere new by the time your kids are done watching Cars. Read on for ten easy weekend getaway ideas from Chicago.

What cities are under three hours from Chicago by car?

• Milwaukee, Wisconsin (1 hour, 30 minutes)
• Madison, Wisconsin (2 hours, 25 minutes)
• Grand Rapids, Michigan (2 hours, 47 minutes)
• Peoria, Illinois (2 hours, 41 minutes)
• South Bend, Indiana (1 hour, 39 minutes)
• Indianapolis, Indiana (2 hours, 56 minutes)

The Dane County Farmers’ Market in Madison is one of the largest in the U.S.

Photo by MarynaG/Shutterstock

Geneva, Illinois

• Distance: An hour by car
• Best for: Singular art and great shopping

OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa , located on the Fox River, and set out to explore the city’s walkable downtown on foot. Public art abounds here, as do independent shops and restaurants (all told, there are more than 150 of them in the historic district).

Michigan City is a breath of fresh air not far away.

Photo by Andy Konieczny / Shutterstock

Michigan City, Indiana

• Distance: An hour and a quarter by car
• Best for: Hiking (and swimming for the brave)

On a clear day from Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park ; in Michigan City proper, attractions include the 19th-century Barker Mansion —listed on the National Register of Historic Places—and family-friendly Washington Park Zoo .

A lighthouse in New Buffalo, Michigan

Photo by Suzanne Tucker/Shutterstock

Harbor Country, Michigan

• Best for: A beach and wine combo trip

Comprising the eight towns of Michiana, Grand Beach, New Buffalo, Three Oaks, Union Pier, Lakeside, Harbert, and Sawyer, Harbor Country is a favored weekend escape from the Windy City, thanks to its beach and country offerings. There are also a number of world-class wineries and breweries in the area, including the popular Lehman’s Farmhouse and Dablon Vineyards and Winery , in nearby Baroda.

Milwaukee is home to one of the largest German populations in the U.S.

Photo by Jayne Lipkovich / Shutterstock

Milwaukee, Wisconsin

• Distance: An hour and a half by car
• Best for: Brats and brews

Milwaukee has a rich German heritage, which means the city is full of places to get a good beer and brat (and more beer, if that’s your thing). Both Pabst Blue Ribbon and Miller are based here, but don’t sleep on the smaller guys, including Milwaukee Brewing and Lakefront .

Mary stands atop the Golden Dome of the University of Notre Dame Main Administration Building.

Photo by Jonathan Weiss/Shutterstock

South Bend, Indiana

• Distance: An hour and forty minutes by car
• Best for: Whitewater rafting

There’s more to South Bend than Fighting Irish football, though we absolutely cosign the idea of a walk around Notre Dame’s scenic campus. Hit the rapids on East Race Waterway , North America’s first artificial white-water course, which cuts through the city, or visit the historic Robinson’s department store to throw your own pottery at the Pigeon and the Hen . Play arcade games—for free!—at the Garage Arcade and Bar , which has all the classics, Galaga and Ms. Pac-Man included.

The Fredrick Meijer Gardens spans 158 acres and features a host of outdoor art exhibits.

Photo by SNEHIT PHOTO / Shutterstock

Grand Rapids, Michigan

• Distance: Around three hours by car
• Best for: Beer, of course, but also outdoor sculptures

Voted “Beer City USA” in several national polls, Grand Rapids is known for its suds: Check out the Beer City Ale Trail , a map showcasing all of the options in the city. For food, we’re partial to strolling Downtown Market , which counts more than 20 vendors in the hall south of Heartside Park (a perfect picnic location, if you ask us). For an outdoor experience that requires a bit more activity, head to the 158-acre Frederik Meijer Gardens & Sculpture Park : here, you’ll find art by Auguste Rodin as well as a hall dedicated solely to carnivorous plants.

A dinosaur breaks out of the Children’s Museum in Indianapolis.

Photo by James Kirkikis/Shutterstock

Indianapolis, Indiana

• Distance: Three hours by car
• Best for: Museums, both traditional and quirky

Indianapolis is an incredible museum city. Although two of its most popular attractions are the Children’s Museum and the sprawling indoor-outdoor Indianapolis Museum of Art , don’t miss some of the city’s quirkier options: the Indiana Medical History Museum (not for the faint of heart) and the Kurt Vonnegut Museum and Library . Visit Indy’s famed City Market to sample more than 25 locally owned eateries; when you’ve had your fill, descend underground on a public catacombs tour, which takes place on the select Saturdays, May through October, between 10 a.m. and 3.15 p.m. (Private tours can be booked with Indiana Landmarks .)

Ann Arbor is known for its university, but a host of delights awaits all visitors.

Photo by Dark Vader / Shutterstock

Ann Arbor, Michigan

• Distance: Around three hours and 45 minutes by car
• Best for: Adventures on the river

Activities for all seasons abound in Ann Arbor, best known as the home of the University of Michigan. Tube, kayak, SUP, or canoe down the peaceful stretch of the Huron River—accessed from the 69-acre Gallup Park—or stroll U of M’s famed Matthaei Botanical Gardens and Nichols Arboretum . Be sure to make time for the city’s Kerrytown Market and Shops , a picturesque neighborhood full of independent boutiques and restaurants. ( Zingerman’s Deli , one of the best spots in Ann Arbor for a sandwich, is here.)

An aerial view of Door County, Wisconsin

Photo by Matt Sampson Photography/Shutterstock

Door County, Wisconsin

• Distance: Four and a half hours by car
• Best for: Exploring rugged coastline

A 70-mile-long peninsula, Door County is often called the “ Cape Cod of the Midwest” —and rightfully so. Just 50 miles northeast of Green Bay, Door County has stunning coves, cherry orchards, harbors, lighthouses, wineries, and some 300 miles of coastline. Newport State Park is an International Dark Sky Reserve , and the 900-acre Rock Island State Park has no cars; for a dose of small-town charm, stop by Ephraim, a Scandinavian-style village .

Traverse City might be a bit further away, but it’s worth the drive—especially in the fall.

Photo by Gary R Ennis Photos / Shutterstock

Traverse City, Michigan

• Distance: Five hours by car
• Best for: Exploring shops and galleries in a justifiably popular small town

No wonder Traverse City was named one of the sweetest small towns to visit in summer : a lakeshore beauty with art deco architecture, the city is beloved by many Chicagoans (including Oprah herself). One of Traverse City proper’s most popular attractions is the Village at Grand Traverse Commons: a hospital complex from the 19th century, the historic venue has since been reborn into a mixed-use space, with shops, restaurants, footpaths, and art galleries. Northwest of Traverse City is Leelanau Peninsula, which is home to the striking Sleeping Bear Dunes National Lakeshore .

Where can I go by train from Chicago?

No car? No problem. You can get virtually anywhere from Chicago by train: Memphis is 10 hours by rail; Seattle is 46. But for a weekend getaway, we’re partial to these picks:

• Indiana Dunes National Park (the South Shore Line from Chicago’s Millennium Station stops at four stations in the park )
• Milwaukee, Wisconsin (about 90 minutes by Amtrak from Chicago’s Union Station)
• Kalamazoo, Michigan (about two hours by Amtrak from Chicago’s Union Station)
• Grand Rapids, Michigan (about four hours by Amtrak from Chicago’s Union Station)

Of course, there’s plenty to do in Chicago itself before you head off; it was ranked number 2 in the best cities in the U.S. for 2023 , after all, thanks to its top restaurants , world-class museums, and abundant hotel options. On the other hand, if you’re feeling really adventurous, you could always take the ultimate epic road trip: 2,448 miles all the way to Santa Monica , California.

Happy weekending.

This article originally appeared online in 2020; it was most recently updated on August 31, 2023, to include current information.

When you purchase through links on our site, we may earn an affiliate commission. Details here .

15+ Must-Do Family Friendly Day Trips from Chicago

Cindy Richards

As a native Chicagoan, I’ve spent a lifetime exploring the surrounding area — suburbs reachable by public transit as well as small towns within a few hours’ drive of the Windy City. From glistening lakeshore towns to historic sites to natural wonders, these are some of my family’s favorite day trips from Chicago.

Day Trips in Illinois

Growing up, we tended to hug Lake Michigan on our family road trips , mostly heading into Wisconsin or Michigan. But once I had kids, we discovered the wonders of what we Chicagoans call “Downstate Illinois.”

Starved Rock State Park

This lovely spot two hours from Chicago was our go-to hiking spot when the kids were young. Lining the shores of the Illinois River, Starved Rock State Park has 13 miles of trails that wind along fascinating rock formations you wouldn’t expect to find in the flatlands of Illinois. The area was formed more than 425 million years ago during an intense warming period after the glaciers melted and left behind soft sandstone in the Illinois River Valley.

Visit here in spring when the winter thaw leads to waterfalls in all 18 canyons or in the fall when the leaves are at their most colorful. It’s one of the best places to see gorgeous fall colors in the Midwest.

SheBuysTravel Tip: Bring a change of clothes and the kids’ rain boots if you visit in the spring — they will get wet and muddy!

If you plan to spend the weekend, there are campground options, as well as the lovely and historic Starved Rock Lodge that was built by the Civilian Conservation Corps in the 1930s. But the kids might prefer the water park at nearby Grand Bear Resort .

Matthiessen State Park

This is the lesser-known cousin of Starved Rock. Located just a few miles south, Matthiessen has similar geology and terrific hiking trails. It’s a don’t-miss spot if you’re visiting the area in mid to late July. That’s when the sunflower fields are in full bloom.

OK, Chicago snob here. I grew up making fun of Rockford. That ended once I visited when my kids were 8 and 10. I had to pry them out of the Discovery Center Museum ! Mostly indoor, it has multiple levels full of hands-on learning fun. But I did pry them away so my dinosaur-loving family could head to the Burpee Museum of Natural History to meet Jane, the juvenile T-rex. We spent so much time there that we never made it to the Rockford Art Museum.

If you’re looking for outdoorsy things to do in Rockford in the summer, head to The Anderson Japanese Gardens . While it might seem a little odd to find a Japanese garden in the heart of the Midwest, this superbly zen spot comes courtesy of a Rockford businessman. Inspired by a visit to a Japanese Garden in Portland, Oregon, John Anderson decided to transform his swampy backyard along Rockford’s Spring Creek into a peaceful, Japanese-style landscape. For a more tropical experience, try Nicholas Conservatory and Gardens.

Just a 20-minute L line ride on the Green Line from downtown Chicago, Oak Park is the first suburb west of the city and it’s a mecca for architecture lovers who flock there to see the Frank Lloyd Wright Home and Studio .

Chances are that won’t get your kids too excited. Mine weren’t when they found out they would be visiting the Home and Studio on a school field trip. I had always wanted to see it, so I volunteered to chaperone. I listened to the 3rd and 4th graders complain all the way there. Then I watched with a smile as they were engrossed in stories about Wright’s kids having pillow fights over the partition wall that separated the boys’ and girls’ bedrooms. And I said no when my kids begged me to buy them a set of the building blocks Wright used as a kid that set him on his life’s path.

Chicago Botanic Garden

My brother-in-law lives a half mile from the Chicago Botanic Garden in north suburban Glencoe, so I’ve visited enough times that I nearly failed to include it in this roundup. It feels almost like a neighborhood park. But it is So. Much. More. The Botanic Garden is 385 acres of gardens and natural areas and is home to a renowned Bonsai Collection.

Take kids in the fall to see the model railroad with its scale models of US landmarks. Or visit during the holidays to see one of the best Christmas lights displays in the Midwest. Before you go, download the  free Model Railroad BINGO game  to play with the kids.

SheBuysTravel Tip:  Strollers are not allowed, so plan to bring a Baby Bjorn or some other babywearing device for kids who are too young to walk the entire time you’re visiting.

Morton Arboretum

Located in west suburban Lisle, the Morton Arboretum is extra popular in the fall when Chicagoans drive through this “great outdoor museum” of trees to see the fall colors.

But I’ve been there to walk the 16 miles of trails (it’s dog friendly) and even to see a play that moved from one idyllic setting to the next as the play progressed. (Unfortunately, there were a lot of bees that summer and I spent more time watching them buzzing around than I did watching the actors.)

A Children’s Garden aimed at letting kids learn while they’re having fun has two sections: Backyard Discovery Gardens and Adventure Woods, linked by the Central Plaza. Kids can splash through secret streams, climb colossal acorns, and slide down giant tree roots while they learn about plants they might find in their own backyard and beyond.

This town just south of the Illinois-Wisconsin state line is home to Six Flags Great America amusement park . This is where Chicago kids head for thrilling roller coasters and scary Halloween experiences.

Adults, of course, are welcome to join the kids. But the secret Chicago moms know is this: The amusement park is across the street from Gurnee Mills, a giant shopping mall. So if your kids are old enough to do the amusement park on their own and you’re more into shopping than thrills, this is the day trip that works for parents as well as tweens and teens.

Gurnee also is home to a Great Wolf Lodge indoor waterpark, always a hit with my kids.

This northern suburb is home to the third-largest Holocaust Museum in the world. The Illinois Holocaust Museum has more than 500 artifacts donated by Chicagoland Holocaust survivors. There’s an authentic German rail car, impressive galleries and contemplative spaces, both indoors and out.

Read More: Food and Fun in Charming Galena, Illinois

Wisconsin Day Trips from Chicago

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This small city on the banks of Lake Michigan just 90 minutes north of Chicago is home to one of the best children’s museums in the country — the Betty Brinn Children’s Museum . It’s also home to a gorgeous art museum that is just as beautiful on the outside as it is on the inside. The Milwaukee Art Museum is capped with a moveable sunscreen with a 217-foot wingspan that unfolds and folds twice daily.

With older kids, don’t miss a visit to the terrific Discovery World science museum . When I visited, I saw just as many dads paying with the hands-on exhibits as kids.

Milwaukee is famous for its Summerfest music festival. When I attend, the music was great and plentiful and much of it was included in the festival admission. But the beer was flowing freely and there were lots of overly imbibed visitors. I was there without kids, so I managed just fine. But I would not have been happy and relaxed if I had brought younger kids.

Lake Geneva

Just 85 miles north and a little west of Chicago, Lake Geneva is the summer playground for Chicagoans. The lake is the draw here. You can take a boat ride, lounge on one of the small beaches, or walk a portion of the 26-mile Lake Shore Path to ogle the multi-million-dollar mansions that line the lake.

This is also what passes for a ski resort in the Midwest. The Mountain Top at Grand Geneva Resort & Spa has 20 downhill ski runs, complete with chair lifts.

SheBuysTravel Tip: The best way to see the lake is via the U.S. Mail Boat Tour . It’s just what it sounds like — mail delivery via boat. The post men and women literally jump off the boat to deliver the mail, then hop right back on — just the way it’s been done for a hundred years. Except now tourists can ride along.

Elkhart Lake

This tiny lakeside town lacks the big tourist draw of Lake Geneva, but that makes it an even better destination, if you ask me.  Elkhart Lake  offers plenty of small town charm and its own brand of luxury at the lakefront Osthoff Resort. It’s been one of my family’s favorite Midwest destinations for years.

It’s 150 miles north of Chicago, which makes it a stretch for a day trip. Besides, you’ll want to spend at least one night at the Osthoff . The condos are luxurious and the resort offers lots of fun activities. You can rent a tandem bike and pedal your way around the area. (Or, if you’re like my husband and me, you can try — and then turn in the tandem and rent two regular ol’ bikes instead.) My kids loved the horse-drawn hay ride, swimming in the warm lake waters and the resort pool.

Also 150 miles from Chicago, Madison can be a stretch as a day trip from Chicago. But it’s definitely worth a visit. The state capital is home to the University of Wisconsin-Madison (go, Badgers!), which sits on the shores of Lake Mendota. It’s a college town, which means the area is filled with bars and affordable food options.

Drag the kids along on a free tour of the State Capitol building. They’ll be a little bored, but seeing the architecture is worth putting up with some sighs from bored kids.

On the sidewalks that ring the capitol building is one of the best farmers’ markets I’ve ever seen. Buy the kids some fresh Wisconsin cheese curds and watch their faces light up when the cheese curds squeak as the kids bite into them. The squeak proves they’re fresh! The farmers’ market sets up each Saturday morning from mid-April through the first week in November. It claims to be the largest producer-only farmers’ market in the U.S.

Indiana Day Trips from Chicago

Indiana dunes national park.

I grew up spending hot summer days at the Indiana Dunes National Lakeshore. It became the 61st  US National Park  in 2019 when 15 miles of the lake shore were designated a national park. It didn’t change the experience, though. It’s still an incredible natural resource, with miles of trails for hiking and biking and wide open waters for swimming, kayaking, canoeing and rafting. (Beware: Lake Michigan waters can be coooooold!)

The lakeshore is a year-round attraction, with gorgeous winter vistas across the water and the hiking trails open for walking and cross-country skiing.

It’s a short 45-minute drive from Chicago to Indiana Dunes. At the end of a day at the beach, head to Chesterton or Michigan City for dinner with a craft beer at one of the family-friendly spots that are popping up all over.

Indianapolis

The Indiana state capital is 185 miles southeast of Chicago, so not really a day trip option. But it’s well worth a visit for a weekend getaway.

The city was a sleepy town when I was growing up, but today it’s a thriving metropolis with a vibrant downtown, great pro and semi-pro sports, the  best children’s museum in the country  and lots of fun  free things to do with kids .

Michigan Day Trips from Chicago

Southwest michigan.

Chicagoans flock to the towns that hug the southwest Michigan lakeshore — from New Buffalo to Saugatuck — for the wide sandy beaches and lake town vibe. But the area is also a rural and agricultural gem with wineries, u-pick farms, horseback riding and farm-to-table foodie fun.

While the tourist draw is the “big lake” — Lake Michigan — the state is dotted with small inland lakes perfect for kayaking, canoeing, rafting and swimming. If you happen to have your own kayak or canoe, strap it to the roof of the car and bring it along. Most lakes have public access ramps for launching small boats.

My parents piled us in the car one spring to make the 150-mile trek to Holland for the Tulip Time Festival. I have vivid childhood memories of a looming windmill, what felt like miles of brightly colored tulips and the wooden shoes I talked my dad into buying. I’m sure he regretted it every minute I spent clomping across our hardwood floors until I outgrew those wooden shoes!

The Dutch-inspired town is home to more than 5 million tulips blooming throughout the town and the tulip festival in early May wins accolades every year.

My now young adult children live in Detroit, so our road trips there take us right past Kalamazoo. Each time, my husband and I share the memory of taking our son and his best pal there to visit the Air Zoo . This world-class, Smithsonian-affiliated aerospace and science museum had a flight simulator! The boys, then both 13, had to be dragged out at the end of the day so we could drive home.

These days, my hubby longs to make a stop in Kalamazoo to tour the  Gilmore Car Museum . It claims to have one of Michigan’s largest collections of classic and vintage automobiles.

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10 Best Weekend Getaways From Chicago

Waterfalls, wildlife, and lots of small-town charm await.

Elizabeth Rhodes is a special projects editor at Travel + Leisure , covering everything from luxury hotels to theme parks to must-pack travel products. Originally from South Carolina, Elizabeth moved to New York City from London, where she started her career as a travel blogger and writer.

With fascinating architecture, great museums, and plenty of delicious local eateries (deep dish pizza, anyone?), Chicago has a lot to offer tourists and residents alike. That said, we could all use some respite from the urban hustle and bustle every so often. We've rounded up the best destinations within easy reach of the Windy City, from lakeside escapes to state and national parks. Whether you're looking for beautiful landscapes or small-town charm, these quick trips are sure to please every type of traveler. Here are our top 10 weekend getaways from Chicago.

Starved Rock State Park, Illinois

Wander among towering trees to find waterfalls and wildlife at Starved Rock State Park , located on the Illinois River about an hour and a half from Chicago. It's the perfect choice when you want to trade skyscrapers for the great outdoors. In the spring, heavy rains make the waterfalls especially active, and in the fall, the leaves turn beautiful shades of orange, red, and yellow. Stay within the state park at the Starved Rock Lodge , or opt to spend the night in nearby Ottawa, a charming little town with eclectic restaurants, independent shops, and more.

Indianapolis, Indiana

Just a three-hour drive from Chicago, "Indy," as the locals know it, offers plenty to do. Kids will love The Children's Museum of Indianapolis and the Indianapolis Zoo , while sports fans will want to check out the iconic Indianapolis Motor Speedway . The hip Broad Ripple neighborhood has nightlife, dining, shopping, and more, and the Massachusetts Avenue Arts District offers theaters, galleries, and independent boutiques. History lovers can book a stay in one of the 1920s Pullman train car rooms at the Crowne Plaza Indianapolis Downtown-Union Station .

Saugatuck, Michigan

Summer is the perfect time to visit this lakeside town, located just under two and a half hours from Chicago. Lounge on the sandy shores of Oval Beach or Saugatuck Dunes State Park , rent a boat and explore Lake Michigan, browse the art galleries, or check out the local breweries. After a day enjoying some of Lake Michigan's most pristine beaches , rest your head at one of the adorable inns or bed-and-breakfasts in town.

Lake Geneva, Wisconsin

For another nearby waterfront escape, head an hour and a half from Chicago to beautiful Lake Geneva . During the summer, you can get out on the lake, sunbathe on its beaches, or go zip lining, among other outdoor activities. During the winter, check out the Ice Castles , an awe-inspiring display of illuminated, human-made icicles that you can walk through.

Milwaukee, Wisconsin

An hour and a half north of Chicago on Lake Michigan, Milwaukee is teeming with great museums and even better beer. Pabst Brewing Company and Miller Brewing Company call this city home. Today, you can toast to the city's beer heritage by trying these classics or visiting one of the many local craft breweries. The Milwaukee Public Museum is a must-visit — it has fossils, a European village, a full-size display recreating the streets of Milwaukee in the late 19th and early 20th centuries, a butterfly garden, and more. Other sites worth visiting include the Milwaukee Art Museum , the Harley-Davidson Museum , and the Mitchell Park Horticultural Conservatory, also known as The Domes .

Indiana Dunes National Park, Indiana

Just under an hour's drive from the city, Indiana Dunes National Park is perfect for a quick getaway. You can even make it a day trip if you're short on time (it's accessible from the South Shore Line, so you don't even have to drive). This national park covers 15 miles of Lake Michigan's shoreline, making it ideal for a relaxing weekend away from Chicago. Go for a hike along the dunes, fly a kite on the beach, enjoy horseback riding, or check out the historic 1933 World's Fair Century of Progress Homes .

Madison, Wisconsin

Wisconsin's capital city is just over two and a half hours from Chicago, and it offers something for every type of traveler. Food lovers will want to visit the National Mustard Museum and try fresh ice cream at the Sassy Cow Creamery , located 20 miles from Madison. Meanwhile, outdoorsy types will love kayaking or taking a cruise around the lake during the summer, or snowshoeing in the winter. Families can check out the Madison Children's Museum and the Children's Theater of Madison for kid-friendly entertainment.

Holland, Michigan

Holland is a unique destination about two and a half hours from Chicago. The city's Dutch heritage is evident in its famous attractions like the Windmill Island Gardens , De Klomp Wooden Shoe and Delftware Factory , and Nelis' Dutch Village . The yearly Tulip Time Festival is another great reason to head to this quaint Michigan town — millions of tulips are planted across Holland, so visit in spring to see the beautiful flowers in bloom.

Wisconsin Dells, Wisconsin

For a family-friendly getaway, opt for a weekend trip to Wisconsin Dells, a three-hour drive from Chicago. This area, known as the "water park capital of the world," is packed with attractions kids will love. One of them, Noah's Ark Water Park , is the largest water park in the United States. For the ultimate relaxation, take a scenic boat ride through the Dells or visit one of the local wineries or breweries.

Geneva, Illinois

Just an hour outside of Chicago, you'll find Geneva, an ideal destination if you're looking for a small-town getaway. Wander the quaint downtown, check out the murals and outdoor sculptures, and browse independent shops selling antiques, jewelry, chocolate, ice cream, and more. The Fabyan Forest Preserve , with its mid-19th-century windmill, is just a few minutes' drive away.