travel blog on chicago

The Perfect 3 Days in Chicago Itinerary (2024 Edition)

Last Updated: February 4, 2024

If you’re planning a long weekend trip to the Windy City and aren’t quite sure what to do, keep reading for our epic 3 days in Chicago itinerary!

While Chicago is the 3rd-largest city in the US, it’s often overlooked by travellers who jet for one of the coasts.

In my opinion, Chicago is the best city in the country. New York and LA are great and all, but I’ll gladly take the friendly Midwestern vibe of Chicago instead.

Situated on Lake Michigan, the Chicago skyline is one of the most beautiful in the world. After all, it was here that the first skyscraper was built in 1885!

There’s so much going on here that you could spend a lifetime there and never run out of things to do.

With a solid Chicago itinerary, you can definitely check out the best of the city in 3 days. Let’s get to it!

Table of Contents

When to Visit Chicago

Chicago citypass, getting around chicago, loop walking tour, chicago hot dog, millennium park, art institute of chicago, willis tower, dinner and drinks, museum campus, riverwalk or river cruise, magnificent mile, chicago deep dish pizza, choose your own adventure, museum of your choice, 360 chicago, lincoln park, best hostel in chicago – hi chicago, best mid-range hotel – congress plaza, best luxury hotel – peninsula, brunch/lunch, how to spend a perfect 3 days in chicago itinerary.

Our 3 days in Chicago itinerary includes:

Shedd Aquarium
Skydeck Chicago
Field Museum
Adler Planetarium
360 CHICAGO Observation Deck
Navy PierMuseum of Science and Industry
Ferris Wheel
Crown Fountain

Looking for more awesome things to add to your Chicago itinerary? Be sure to read our guide to the best things to do in Chicago !

Travel Tips for Visiting Chicago

The first step in figuring out what to do during your 3 day Chicago itinerary is planning when you’ll visit.

Winter in Chicago can be painfully cold, which can definitely put a damper on your trip. Unless you enjoy frigid temperatures and cold, biting wind, I recommend skipping out on December-March.

Your best bet is to visit Chicago between May and October. It gets hot and crowded in the summer, but there’s so much going on that it’s worth dealing with those minor inconveniences.

Read Next: Don’t miss out on the best Chicago day trips !

Another huge tip I have before you visit Chicago is to purchase a Chicago CityPASS .

Essentially this is just a multi-use ticket that actually saves you a bunch of money (50% to be precise!) on many great Chicago attractions.

You buy the pass for USD$109, and it includes access to the following:

Skydeck Chicago and
Adler Planetarium or the Art Institute of Chicago
360 CHICAGO Observation Deck or the Museum of Science and Industry

Best of all, those entrances are mostly express or premium tickets included with the CityPASS , meaning it not only saves you money but saves you time as well.

We highly recommend you pick one up when using our Chicago itinerary to make the most of your time in the city.

Thankfully, getting around Chicago is a breeze thanks to the CTA network of train and bus lines. Chicagoans refer to the train as the “L” because it’s mostly on “el-evated tracks.”

If you’re spending 3 days in Chicago, your best bet is to just pick up an unlimited CTA pass. These cost $20 and are added to a Ventra card.

You can pick up a Ventra card at vending machines for $5 and it’s credited back to your account after you register the card. Read all about getting around Chicago on the CTA website .

You can count on the CTA getting you as far south as the Museum of Science and Industry all the way north to Lincoln Park.

Or consider jumping on and off the open-top bus that will take you all over the city!

In the city center, lots of Chicago attractions are all within walking distance as well.

Now that some of the logistics are taken care of, let’s get this show on the road for your 3 day Chicago itinerary!

Day 1 – Morning

For day 1 of your Chicago itinerary , you’ll need to hit the ground running if you want to maximize your time.

Get a nice early start, crush a substantial breakfast and some coffee, and get ready to rock.

The best way to kick-off your Chicago itinerary is by taking a walking tour of the Loop. This area of downtown is where you’ll find a majority of the sights in Chitown.

You have several options for exploring the Loop. If you enjoy meeting people and getting the insight of a local guide, you can sign up for one of the many options with Free Tours by Foot .

If it’s your first time in Chicago I suggest joining their 10 AM tour of the Loop and Millennium Park. Or if you’re really into architecture, check out their 10:30 Birth of the Skyscraper tour. Both are excellent options!

Those who prefer a DIY approach can check out the many self-guided tours of Chicago from MetroWalkz. This Architecture/Loop tour makes for a fantastic introduction to the city and is pretty easy to follow.

Whichever option you choose, you’ll get to see some of the most iconic places in the city in just a few short hours. A few of the highlights include the historic start of Route 66, the great Chicago Theatre.

READ NEXT: While you’re exploring the Midwest, be sure to check out the best things to do in Minneapolis, Minnesota !

Day 1 – Afternoon

At this point, the order in which you do things depends on which type of tour you chose. You can be flexible, as it’s a short walk between the next couple of destinations.

Before we move along with the 3 day Chicago itinerary, it’s time for lunch! If you’re down in the Loop and you want to try a local favourite, the choice is easy…

There are countless restaurants to choose from in the Loop, but you don’t want to travel all the way to Chicago to get stuck eating at some overrated chain or overpriced tourist trap.

Al’s is a classic local joint serving up the famous Chicago style hot dogs and their specialty Italian beef sandwiches.

One thing to know, a Chicago dog is an all-beef dog on a sesame seed bun. It comes topped with tomato, chopped onions, pickled peppers, relish, a pickle spear, and yellow mustard. Quite simply put, it’s heaven on a bun.

I would be remiss if I didn’t also mention Portillo’s. They also make one of the best Chicago style hot dogs out there.

While they’re a bit out of the way for today’s itinerary, keep them in mind if you’re craving another hot dog during your 3 days in Chicago (and trust me, you will).

Read More: Spending time exploring the Midwest? Be sure to check out our post on all of the best things to do in Kansas City !

Even if you visited on your walking tour, it’s worth it to double back to Millennium Park for further exploration.

There’s a lot of cool stuff to see here, including the Crown Fountain and the Cloud Gate.

The latter is commonly referred to as “The Bean” and is one of Chicago’s most popular places to take photos in the city. Don’t forget to snap that quintessential Chicago shot for the ‘gram and keep on moving.

Other Chicago attractions you must see in Millennium Park include the Jay Pritzker Pavilion, the BP Pedestrian Bridge, the Chicago Cultural Center, and the Lurie Garden.

You can easily spend a couple of hours in Millennium Park, especially on a nice day.

Buckingham Fountain and Grant Park are within this same area as well if you want to keep exploring on foot.

While there’s plenty of amazing public art in the Loop, you can’t top the collection at the Art Institute of Chicago. Art lovers will definitely want to include this on their 3 day Chicago itinerary.

Tucked away on Michigan Avenue on the south end of Millennium Park, the Art Institute of Chicago has a seriously impressive collection here and there are always new exhibits featuring modern and contemporary art.

Make the most of your Chicago CityPASS to gain fast entry into the Art Institute of Chicago.

The museum is open daily from 10:30 AM to 5 PM and stays open until 8 on Thursdays.

Day 1 – Evening

Before the day turns into night, it’s time to hustle over to your next destination of your 3 day Chicago itinerary. Try to time it just right so you make it there about an hour before sunset. Trust me, it’s worth it!

Whether or not you hit the museum, your next stop should be the Willis Tower. This is one of Chicago’s most iconic skyscraper in the city that invented them!

Formerly known as the Sears Tower, this was the tallest building in the world for 25 years. It stands at 442 meters (1,450 feet) tall and is currently the 2nd-tallest building in the US.

If you plan to visit Chicago in 3 days, you definitely need to check the Willis Tower off your to-do list.

Head to the 103rd floor to access the Skydeck Chicago and step out onto “The Ledge” – a glass balcony that lets you look straight down. You’ll want to see views of the city from this spectacular perspective!

Don’t forget, the best time to go to the Willis Tower is just before sunset. It stays open until 10 PM from March through September and tickets cost $25 for adults and $17 for children.

Once again though, no need to pay extra for a ticket, because the entrance to the Skydeck Chicago is included with your CityPASS .

To celebrate making it through a massive day 1 of the Chicago itinerary, it’s time for dinner and drinks! When it comes to wining and dining, the world really is your oyster in the Loop.

After such a big day, you may want to call it a (somewhat) early night. We’ve still got a lot of ground to cover with this 3 days in Chicago itinerary! Of course, if you want to go out and rage, go for it!

Day 2 – Morning

If you don’t have breakfast included at your hotel, I highly advise you to start day two off at Yolk’s South Loop location.

This is the perfect spot to load up with a big breakfast and coffee before another big day in the city. Go ahead and carb up – there’s going to be a lot of walking today!

After breakfast, walk across the street to check out Agora – a sculpture composed of 106 headless figures.

Keep walking east towards Lake Michigan to reach the Museum Campus. Here you’ll find the Field Museum, Shedd Aquarium, and the Adler Planetarium.

With just 3 days in Chicago, you’ll probably want to just visit one. Having been to all three, I’ll cast my vote for the Field Museum.

There are so many cool exhibits at the Field Museum and they’re always changing.

At the moment, they have: Inside Ancient Egypt, Bird’s of America, and Brewing Up Chicago, among others. Check their website to see what’s going on before you visit.

Tickets for the Field Museum cost $26 for adults and $19 for children for basic admission.

If you got the CityPASS, your admission is included in all three, unless you hit the Art Institute on day one. If you’ve got the pass, you might as well hit the aquarium as well.

To be honest, the aquarium is pretty sweet. Even if you don’t have the CityPASS, you should probably try to squeeze it in.

Tickets are $40 for adults and $30 for kids and you’ll definitely get your money’s worth.

Day 2 – Afternoon

There are a few cafes and food stands around the museum campus, so go ahead and grab a snack and a drink before powering on.

This is one of those days where it’s best to have a big breakfast and dinner and just graze during the day. When you’re trying to cross off so many things to do in Chicago in 3 days, you gotta keep moving!

The museum campus is the southern part of Grant Park. Known as “Chicago’s Front Yard,” this massive green space is to Chicago what Central Park is to NYC.

Take a stroll through the park to see such landmarks as the Buckingham Fountain, the Rose Garden, and the Seated Lincoln Statue. There are plenty of benches if you need to sit down and chill for a bit.

Grant Park also hosts some of the biggest events in the city, such as the Taste of Chicago and Lollapalooza.

Some are free and others cost hundreds of dollars, so be sure to check the calendar of events to see what’s happening before you book your trip.

Hug the coast and keep walking north along the Lake Michigan until you reach the Riverwalk. This scenic pedestrian path along the Chicago River is the perfect place for a leisurely stroll.

If your feet are feeling a bit tired from all the walking, you can enjoy the spectacular Chicago architecture on this fantastic river cruise instead .

Taking in the sights along the Chicago River is definitely one of the top things to do in a 3 day Chicago itinerary.

Wendella Boats has an architecture river cruise that comes highly recommended. Make sure you have your camera for this one, as you’ll get some epic views of the city.

Day 2 – Evening

I’m sure you’re ready to eat your hand by now, but you’ve just got to soldier on for a bit longer. Trust me, it’s going to be worth the wait!

On the other side of the Chicago River, you’ll find the Magnificent Mile, a short stretch of Michigan Avenue in downtown Chicago. This is the city’s premier commercial district, full of high-end shops, nice restaurants, and boutique hotels.

Along the Magnificent Mile, you’ll also see several historic skyscrapers, such as the Wrigley Building, Tribune Tower, and the Old Watertower.

The latter is home to the City Gallery, which has Chicago-focused photography exhibits. It’s totally free to visit, so you may as well check out while you’re in the area.

Even if you’re not doing any shopping, it’s worth a quick stroll along the famous Michigan Avenue. That’s because it’s leading you to…

You had the hot dog on day one, so it’s time to dig into some Chicago-style deep dish pizza.

Since it’s cooked in such a deep pan, a Chicago-style deep dish pizza can be stuffed with mountains of cheese. Of course, you can add whatever other toppings you like as well.

Now you see why I’ve been torturing you by making you walk around all day waiting for dinner! This deep dish pizza is seriously delicious and filling, so I wanted to make sure you could at least have a few slices.

There are plenty of places cooking up Chicago-style deep dish pizza, but I brought you here because two of the best are easily accessible.

Get to the corner of Michigan and Superior and you have an important choice to make. Take a left and you’ll go to Giordano’s. Hook a right and you’ll be at Gino’s East.

Just go ahead and flip a coin because you win either way. Both places are legendary for their deep dish pizzas, so you really can’t go wrong.

Not far from the Magnificent Mile, you’ll find Navy Pier. If you’re spending 3 days in Chicago on a long weekend, this is the perfect place to be on a Saturday night.

First up, you can take a ride on the Centennial Ferris Wheel. Tickets cost $18 for adults and $16 for children, but you can save a few bucks if you book online .

From the end of May until the end of August, Navy Pier also hosts bi-weekly fireworks shows. These happen on Wednesdays at 9:30 PM and Saturdays at 10:15.

To take in the spectacle, you can find a spot to stand on the Navy Pier or sign up for an evening cruise. Enjoying the fireworks as you cruise around is a great addition to your Chicago itinerary.

If you have any gas left in the tank after all of the activities at the Navy Pier, congratulations! I just ran you ragged all over Chicago on day two. That’s why it’s time to choose your own adventure!

For many, that will probably involve grabbing a casual drink from the hotel bar and getting some sleep. That’s totally fine. I’m getting to the age where that sounds like a perfect Saturday night!

For the young whipper-snappers among us, you’re probably itching to enjoy a big night out on the town. Go for it, you crazy kids!

Your options are endless. There’s live music of all varieties, comedy clubs, and just about every type of bar under the sun.

Whether you’re looking for a speakeasy that whips up creative cocktails, a classy wine & jazz joint, or just a good ole’ fashioned dive, you can find it in Chicago.

In this part of the city, one of my personal favourites is Three Dots & a Dash. This awesome tiki bar has an impressive selection of cocktails that will transport you to the Caribbean in no time.

If you’re going to go hard one night, this is the one to do it! Bars in Chicago typically close at 2 AM, but there are several that stay open as late as 4 on the weekend. You’ve been warned…

Day 3 – Morning

How early the last day of your 3 day Chicago itinerary starts depends entirely on how late your night went!

Those who already regret ordering that last round may need to sleep in a bit and smash a greasy brunch, while the go-getter set who actually slept will be up and at them. Life is all about choices, people!

Whatever you did the night before, get some food and caffeine in your system and get out there to wind down this 3 day Chicago itinerary.

Our third and final day in Chicago starts off with a leisurely museum visit. Within a few blocks of each other, you can take your pick between three excellent museums.

Art enthusiasts will gravitate towards the Museum of Contemporary Art, which highlights post-WWII art.

Those more interested in architecture and antiques may want to hit the Richard H. Driehaus Museum. It’s in a restored 19th-century mansion and brings you right back to the Gilded Age.

Chicago is very much a sports city, as people here are very passionate about their teams. Check out the Chicago Sports Museum, which is full of memorabilia and plenty of fun exhibits.

I know I already sent you to the Willis Tower on day one, but it’s still worth a trip to John Hancock’s 360 Chicago on Michigan Avenue.

This observation deck on the 94th floor of the John Hancock Building provides a whole different perspective on the city that you will definitely want to see.

Plus, if you bought a CityPASS your admission to the John Hancock building is already included! If you didn’t grab the pass, a ticket is $25 for adults or $15 for children.

Those who are feeling adventurous (and not hungover) may want to take a ride on Tilt – Chicago’s highest thrill ride.

If you need some hair of the dog instead, you can grab a ticket that includes your choice of adult beverage. Sunday Funday!

If you don’t purchase the Chicago CityPASS consider purchasing this ticket to enjoy the views from the 94th floor of the John Hancock building’s 360 Chicago.

Day 3 – Afternoon

Once you come down from 360 Chicago in John Hancock building, you have plenty of options for lunch. Within a few blocks, you can find Cuban, Vietnamese, Mediterranean, and the Chicago staple of deep dish pizza.

If you want a lunch with a view, consider eating at The Kennison. This upscale bar and restaurant offers sweeping views of Lincoln Park. The menu is modern American and they have lots of amazing cocktails and drinks.

Hop on the bus, order an Uber, or walk 30 minutes to our next destination – Lincoln Park.

There’s a lot to do in this huge park on the shores of Lake Michigan. North Avenue Beach is at the south end.

On a beautiful day in Chicago, it’s hard to beat lounging on the beach and swimming in the lake. You can also play some beach volleyball and rent a SUP or bike if you want some more activity.

In the middle is the Lincoln Park Zoo, which is totally free to visit. Sightseeing gets expensive, so this awesome free attraction is definitely one of the top things for any Chicago itinerary.

After such an action-packed 3 days in Chicago, you should definitely just take it easy and enjoy all that Lincoln Park has to offer. You’ve covered some serious ground in a short time, so congrats on that!

Day 3 – Evening

At this point in the journey, you have absolutely crushed 3 perfect days in Chicago. Order a celebratory drink or two and enjoy your last evening in the city!

What you choose to do with your final night all depends on when you’re visiting and what your interests are. That’s why it’s time once again to…

In a perfect world, the Cubs would be playing a night game while you are visiting Chicago. You could head north to Wrigley Field and enjoy America’s pastime at the 2nd-oldest ballpark in the country.

The Cubs play about 80 home games between April and September, so there’s a good chance they’ll be in town when you are. Even if you’re not a baseball fan, I recommend hitting a game if at all possible.

Chicago actually has two MLB teams. But the White Sox ballpark is way south of where you’ll be on day three and not worth the trip if you ask me.

If you’re making a trip to Chicago between October and April, you may be able to catch the Bulls (NBA), Blackhawks (NHL), or the Bears play a home game. Check their schedules to see what’s going on when you’re in town.

Those who prefer a good laugh can head back to the south end of Lincoln Park. Just a block away, you’ll find three of the city’s best comedy clubs – Second City, UP, and Zanies.

I pretty much always travel to Chicago for live music, so you know I’m going to toss that in here!

The city has an epic music scene and there’s always something playing here. Whether you’re into rock, hip-hop, jazz, electronic, blues, pop, or whatever it is you wacky Millenials listen to these days, there’s a show for you.

I usually check Jambase to see what shows are playing.

Congratulations, my friend. You made it through an insane 3 days in Chicago itinerary and experienced the best that the Windy City has to offer.

I’d say that calls for a toast! If you want to finish up with a true Chicago experience, order a shot of malort. This infamous Chicago liquor is pretty hard to describe, so I’ll let its label do the work:

“ Malort has the aroma and full-bodied flavor of an unusual botanical. Its bitter taste is savored by two-fisted drinkers .”

I’m not going to sugar coat it – this stuff is awful. It’s a rite of passage here in Chicago, though. Eat the hot dog. Drink the malort. Praise be to Ditka. You’re now a little bit Chicagoan.

After you finish that putrid shot of malort, switch to a delicious Chicago craft beer. There are plenty of choices here, including Lagunitas, Revolution, and Goose Island.

I hope you enjoyed this massive tour of Chicago!

From Navy Pier, to Millennium Park, the Chicago riverwalk, the famous Chicago hot dogs and more, visiting Chicago is never dull.

Hopefully this 3 day Chicago itinerary has been inspiring and gives you an idea of what to do in the Windy City.

Chicago Itinerary Travel Guide

Now that you know what to do with a long weekend in Chicago, I’ve gone ahead and put together a mini-guide to this awesome city to help you decide where to stay, where to eat, and of course where to drink!

Where to Stay in Chicago

You’re probably wondering where to stay, especially if it is your first time in Chicago.

Most first-time visitors choose to base themselves in downtown Chicago, and for good reason. Here are countless options for accommodation, sightseeing, dining, and nightlife.

As you might expect, staying downtown comes with a price tag. Other popular places to stay that are a bit cheaper include River North, Lincoln Park, Bucktown, and Wicker Park.

When it comes to places to lay your head, Chicago has it all. The city has 5-star luxury hotels, quaint B&Bs, dingy motels, fun hostels, and plenty of options on sites like Airbnb.

Here are a few options to suit all budgets:

Hostelling International is a trusted name in backpacker accommodation, and their downtown Chicago location is definitely the best hostel for visiting Chicago.

They have several different options for both private and dorm rooms. You can get a bunk for under $40 a night here – a steal for this fantastic location.This includes a free breakfast, and they also have free walking tours during the day and free activities at night.

That’s not all, though. They’ve also got a huge lounge with a ping pong table and a TV room with plenty of movies. Best of all, this hostel is environmentally-friendly. They have reusable products in the kitchen and recycling points all around the building.

This historic downtown Chicago hotel dates all the way back to 1893. Don’t worry – it’s had several updates over the years!

You really can’t beat the location of this place. I usually stay with friends in more residential neighbourhoods, but this is my go-to spot when I want to be in the middle of all the action.

From here, you’re just across the street from Grant Park. Many of the rooms here even boast a nice view of Lake Michigan. With rooms starting as low as $115 a night, it’s a pretty awesome deal staying here.

The 5-star Peninsula Chicago was recently named the 2nd best hotel in the country by US News & World Report. This place is fancy, people!

It’s located right on the Magnificent Mile, so it’s surrounded by high-end shops. This is definitely where the fabulous people stay.

In addition to the super swanky rooms, you can enjoy the hotel’s three different restaurants and its impressive fitness centre.

Taking up the top two floors of the building, it features a 25-meter pool and an award-winning spa. Rooms start at around $600 a night here.

Where to Eat and Drink in Chicago

I’m very fortunate to have a good friend who is heavily involved in the hospitality scene in Chicago.

I reached out to him to get a list to add to this guide. He’s never done me wrong with food & drink recommendations, so you can take these to the bank the next time you visit Chicago!

Dove’s Luncheonette
Joe’s Stone Crab: It’s a steakhouse and it’s hard to get into at night, but if you go for boozy brunch it’s great.
Parson’s Chicken & Fish: Not really brunch but just a great people-watching patio.
Big Star: Chicago classic taco joint with highly sought after patio
3 Arts Club

Bavette’s Bar & Boeuf
The Roister
Green Street Smoked Meats: A great BBQ joint and High Five Ramen is below.
Maple & Ash
Nico Osteri
Billy Sunday
Aviary (try to get down to the office)
Violet Hour
Start at Scofflaw and work your way over to Best Intentions
Longman & Eagle
The California Clipper: Been around since before prohibition!

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CHICAGO Itinerary • MUST READ! (2024)

With incredible works of public art scattered all around the city and free access to many of its museums and art centers, Chicago is a cultural hub! It’s also America’s third-largest city and the birthplace of the modern skyscraper.

This immense and beautiful city has a vibrant outdoor culture, with many activities and attractions to enjoy. You’ll find unique and delicious cuisine, fantastic outdoor fun, and great local sports. We’ve put together an itinerary for Chicago which covers all the best attractions in the city!

Pack your walking shoes and prepare to visit some iconic places. With one of the most recognizable skylines in the world and a community welcoming to travelers, you’ll have the time of your life!

Unlock Our GREATEST Travel Secrets!

Best Time To Visit Chicago

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Chicago is known as the windy city! However, many days outside of winter are balmy and perfect. All seasons are distinctly represented in Chicago. The city has hot, frequently humid summers, and wet, cool springs. Fall can be pleasantly temperate fall with a cold winter to follow. When you choose to go depends on your seasonal preferences!

Wondering when to visit Chicago? Most tourists plan their vacation in Chicago during the summer when it’s hot. However, we suggest going in early autumn or late spring, when the crowds are much calmer and the weather is mild.

Unfortunately, many of Chicago’s outdoor attractions close for the frigid winter season (November – March), so keep that in mind if you are wanting to visit during this period. It is a great time to visit if you’re coming to Chicago for its many indoor activities and don’t mind the cold!

With a Chicago City Pass , you can experience the best of Chicago at the CHEAPEST prices. Discounts, attractions, tickets, and even public transport are all standards in any good city pass – be sure invest now and save them $$$ when you arrive!

Chicago is one of the largest cities in America, with sprawling neighborhoods and lots to do in all of them. Accommodation ranges from top luxury on the Magnificent Mile to low-budget hostels in Chinatown. You can find a place for any budget and a range of interests!

The best place to stay in Chicago is undoubtedly Downtown Chicago/The Loop. It’s central and home to Chicago’s most prolific and most important landmarks, you will hardly need to leave the area and will save time and costs on public transportation! It’s an especially good idea if you’re only spending two days in Chicago.

The Loop is designed in a grid pattern, making it very navigable to first-timers. No matter where you stay in the neighborhood, you’ll find great restaurants and things to see no more than a block away.

If you’re interested in staying somewhere a little more obscure and experiencing a different side of Chicago, find a place in West Loop! It’s a great neighborhood for foodies, and there are many galleries and cafés nestled away, far from the Chicago skyscrapers (but not too far).

There are hotels, hostels, hovels and Airbnbs in Chicago so suit every budget. In fact, if you are really on a budget, you can find some cheap and comfy motels in Chicago .

If you’re looking for something that better suits you, you can also have a look at our more detailed guide on where to stay in Chicago !

Best Hostel in Chicago – Hi Chicago

This beautiful, expansive hostel is located in the heart of Downtown Chicago. It’s a great place to meet fellow travelers. It includes a pool table, bar, ping-pong table, and other great general areas.

Rooms are clean, comfortable, and gender-separated. Best of all, you get a large breakfast, a spacious locker, and guided tours of the city, all free!

To see more hostel options, check out our top picks for hostels in Chicago .

Best Airbnb in Chicago – Modern loft for 2

With this basic, convenient and well-priced studio apartment, you have access to a comfortable, queen size bed, full kitchen, on-site laundry facility, free wifi, and an awesome host who will recommend you places to visit, attractions to see in Chicago.

Best Budget Hotel in Chicago – Best Western Grant Park Hotel

A short walk from some of Chicago’s top attractions, this budget hotel is comfortable and fun. The rooms are clean, and the staff are helpful and knowledgeable. There’s an on-site restaurant, fitness center, and business center.

The beds are large, and if you book a room on one of the top floors, you’ll enjoy fantastic views over Chicago!

Chicago is not a very walkable city, as it is very large. However, walking within the neighborhoods is very doable. Most of the attractions and landmarks are centered in Downtown Chicago, so we suggest you go by foot here. Walking is also a great option because it allows you to see more of the people and culture of the city!

There are also fantastic public transport systems in Chicago. You can catch the L Train, which stops all over Chicago. It’s cheap and easy to use, navigable to first-timers and tourists.

Alternatively, you can take the bus. These stop right outside of most Chicago points of interest, making it ideal. However, it can be difficult for newcomers to navigate, and you may struggle to catch a bus that’s actually going right where you need to be!

Another great way to explore a few of Chicago’s neighborhoods is by bicycle. The city even has a Divvy bike-share system, which allows you to grab a bike from one of the hundreds of stations in the city. You can get a day-pass for these or a single fare.

On the first day of your Chicago Itinerary you’ll explore some of the city’s most iconic landmarks and beautiful places. Wear walking shoes – everything is within walking distance!

Day 1 / Stop 1 – The Art Institute of Chicago

Why it’s awesome: It’s one of the world’s greatest art museums.
Cost: $25; $35 for fast pass with audio guide .
Food Recommendation: Grab breakfast at the Corner Bakery Café.

Beautifully set out, the Art Institute is a fantastic experience and a great start to your Chicago Itinerary. Its displays are always rotating and being added to, so if you’ve been here years ago, don’t let that stop you from going again.

Admire the diverse range of art on display, broaching topics from South African Apartheid and resistance to Japanese life, to modern ideas of femininity and beauty. Attend talks on art and history in the museum! Get the audio guide and learn about the art and exhibitions as you go at your own pace.

You can spend the whole day here, but we suggest you spend 2-3 hours in the art museum. You can get a floorplan of the museum at the entrance, to help you plan your route and ensure you see everything you want to see.

Whether you love art or history or neither, this is a Chicago experience you don’t want to miss! You are permitted to take photographs, which is great, because you will really want to.

Day 1 / Stop 2 – Garfield Park Conservatory

Why it’s awesome: A green oasis under glass, it’s really something special.
Cost: Free, with an optional donation.
Food Recommendation: Find something delicious at the charitable restaurant Inspiration Kitchen.

Explore the Conservatory’s 2-acres of lush indoor display houses and exotic outdoor gardens! A beautiful getaway from the concrete jungle, the gardens host an incredible amount of flora from all over the world.

Visit the desert house for cacti and succulents, or the Palm House and Fern room, which evokes a swampy prehistoric landscape you can get lost in. In Sugar From the Sun, you’ll find botanic environments themes around water, air, sunlight, and sugar. Here you can learn about how plants make energy!

The outdoor gardens are a fantastic place to stop and enjoy a picnic, or a bit of lazing on the grass and soaking up the sun. These gardens have more to offer than grass though! The Monet Garden and Sensory Garden are wonderlands for the senses.

You can get a digital guide to the Garfield Park Conservatory for free on your phone, or just stroll around and enjoy the gorgeous plantlife. It is certainly one of the most beautiful places on our Chicago itinerary.

Day 1 / Stop 3 – Millennium Park & Cloud Gate

Why it’s awesome: The cultural and artistic hub of Chicago, the park is a must-see.
Cost: Free!
Food Recommendation: Pancake stacks at Wildberry Pancakes & Cafe.

If you’re planning a trip to Chicago, you have to visit Millenium Park. A unique town square, it’s leafy landscape is only a backdrop to state-of-the-art architecture, art and landscape design. Home to much of Chicago’s cultural offerings, you’re bound to find something amazing to do here. Family events, concerts, exhibitions, and tours are all offered!

The Park’s unique, immense outdoor concert venue was designed by renowned architect Frank Gehry and spans much of the park. This is where you’ll find much of the activity!

There is also, of course, Cloud Gate. Featured in many movies and pop culture references since its creation, Cloud Gate is the most recognizable Chicago landmark. The seamless sculpture reflects the Chicago skyline. And when you walk beneath it, it reflects you as well from myriad angles. Shaped similarly to a bean, it’s affectionately referred to by locals as ‘the bean’.

With so many artistic attractions, Millenium Park is a must-see even if you’re only spending two days in Chicago! It will charm you no matter what!

Day 1 / Stop 4 – The Field Museum

Why it’s awesome: The exhibitions are fascinating, and there’s so much to discover.
Cost: $24 – $38 ( Get an online ticket for fast access!)
Food Recommendation: Get Chicago streetfood classics at Kim and Carlo’s Hotdog Cart.

A brilliant museum for the natural sciences, Field provides an opportunity to learn and explore everything related to science and natural history! Discover dinosaurs, ancient artifacts, and groundbreaking scientific discoveries.

Research is always continuing at the museum’s extensive labs, leading global initiatives to discover more about our world. Spend a few hours exploring collections around different cultures from the past and present, fossils and meteorites that tell us about the earth’s history, and weird and wonderful animals!

Everything is consistently updated and well-maintained, with amazing attention to detail. The T-Rex skeleton is the most complete one ever found! It’s quite a thing to behold.

Insider Tip: Even if you spent the whole day here you wouldn’t be able to see everything. So, decide what you really want to see at the outset, and give yourself three hours to take in all you can!

Day 1 / Stop 5 – Willis Tower Skydeck

Why it’s awesome: The best view over Chicago.
Food Recommendation: Try Chicago’s deep-dish pizza at Giordano’s, in Willis Tower.

With a glass-bottomed deck and impeccable views, there’s no better location to watch the sunset. This is a great place to take photos of Chicago, and of course, yourself with it. In fact, your ticket includes three professionally taken photographs!

The staff is very nice and helpful, elevating the experience. There is always a line, but it moves quickly. A typical skyscraper experience, the Willis Tower is worthwhile for unparalleled views. You will be able to see most of the other stops on your Chicago itinerary!

Day 1 / Stop 6 – Comedy at Annoyance Theatre & Bar

Why it’s awesome: Get a good laugh with Chicago locals.
Cost: $5 – $12
Food Recommendation: Enjoy bar snacks or go to the nearby Ann Sather Restaurant.

A great way to spend the evening, Annoyance Theatre and Bar offers up a lot of laughs. With different acts every night, improv shows, comedy sketches, and musicals, there’s something for everyone, every night.

Comedy at Annoyance Theatre and Bar chicago

The Annoyance has played in comedy theatres all over America and has even been on TV, but their home-base is here in the windy city. Have a look at what’s on during your vacation in Chicago! You may even find a full-length cabaret or comedy musical.

With a fantastic festival-type atmosphere and tasty, well-priced drinks, you can’t go wrong. The performances are fun and creative, with a large cast and intimate setting! So grab a drink and find a seat. It’s a barrel of laughs.

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On day two of your itinerary for Chicago, you’ll see and do even more! Prepare to eat amazing food and enjoy some of Chicago’s best cultural offerings.

Day 2 / Stop 1 – Grant Park and Buckingham Fountain

Why it’s awesome: One of the biggest parks and fountains in the world!
Food Recommendation: Get some creative hot dogs at Devil Dawgs on State.

Surrounding the Millenium Park and extending far beyond it is Grant Park. This giant public park is affectionately referred to as ‘Chicago’s front yard’, and the first stop on your Chicago itinerary’s second day. Located in the central business district, you can stroll through and find hundreds of sculptures and public works of art.

Spend the early hours of the morning here while you wait for everything to open. (Chicago starts its days late). It’s a beautiful green space, and you’ll often find yoga sessions and ball games that anyone can join in!

While you’re here you have to seek out the Buckingham Fountain! Designed in 1927, the fountain is one of the largest in the world. It usually runs from 8 am to 11 pm daily, from May to October. Every hour, the Fountain produces an incredible 20-minute display! So if you’re visiting during this period, it is not to be missed.

Day 2 / Stop 2 – Chicago Cultural Center

Why it’s awesome: Beautiful building with exhibitions and events.
Food Recommendation: Grab a quick bite at Toni Patisserie & Cafe.

If you’re wondering what to do in Chicago for free, this is one of the best places to be! The architecturally stunning building is host to many wonderful things and none of them cost a thing.

Find an art show, performance piece, musical event, or something else while exploring its Art Deco interiors.

The whole building is covered in beautiful mosaics. With a giant glass dome and ornate staircases, it’s a wonderful place to go even when nothing else is going on. It’s a lovely place to relax and take in some beauty.

Day 2 / Stop 3 – Museum of Science and Industry

Why it’s awesome: Impressive, interactive exhibits and great fun.
Food Recommendation: Italian food at Piccolo Mondo.

With interactive exhibits of all kinds, the MSI brings science to life. Descend into a coal mine, float outside the international space station in a virtual reality experience, and feel and the physics of a tornado created by man!

There is so much to do, you will be enveloped in the excitement of where we’ve been and where we’re going as a species and as a planet. There’s even a behind-the-scenes tour so you can explore how such a sprawling, impressive museum and scientific center works.

One great new exhibit is Wired to Wear and is the first exhibit ever dedicated to wearable technology and where it can take us. Part of the future, it’s quite something to see this in the present and one of the best places to visit in Chicago .

Watch a film in the five-story, domed, wraparound movie theatre. The glory and intensity of nature is well-suited to such large-scale viewing. With hands-on experiments, interactive and interesting exhibits, and great, knowledgeable staff, MSI is a definite must-see on your trip to Chicago.

Day 2 / Stop 4 – Navy Pier

Why it’s awesome: A favorite for locals and tourists, this place is packed with things to do!
Food Recommendation: Find tasty seafood on the pier at Riva Crab House.

No ordinary pier, the Navy Pier has a wide and eclectic range of activities for solo backpackers in Chicago , families, couples, and friends.

Go for a ride on the iconic Centennial Wheel, with fantastic views over Chicago and Lake Michigan. Explore virtual reality or test your strength on the climbing wall. Navy Pier is also the primary departure point for many lake cruises and bus tours, so its the perfect place to go if you have a little more time than expected!

You’ll find public art and exhibitions, cultural attractions, a great variety of shopping opportunities, and of course, amazing restaurants. With such an eclectic range of activities, it could be the only thing on our Chicago Itinerary!

Day 2 / Stop 5 – Wrigley Field

Why it’s awesome: Baseball has been played here for over 100 years!
Cost: $13 – $154 for a game
Food Recommendation: Get something at the lively sports bar Murphy’s Bleachers.

Wrigley Field is a great American Ball Park with great, enthusiastic fans and a fun environment and vibe. Everything is well run with helpful and friendly security and staff, and well-maintained restrooms.

Across the street from the field, you can find plenty of sport-themed pubs and bars. Go after the game, and celebrate your team’s win or mourn their loss with people who are doing the same. It’s great fun, either way.

With over 100 years of iconic baseball games here, it’s a great place to spend a few hours and feel the spirit of Chicago. Recent renovations to the field add convenience to the ambiance of history, and as per tradition, you can buy hotdogs and beers at in-house vendors before taking your seat.

If you are more interested in the famous field than the game, you can go on a Wrigley Field tour! These last 90 minutes, and allow you to experience the beauty and charm of the historic field and learn about its captivating history.

Day 2 / Stop 6 – Magnificent Mile

Why it’s awesome: Admire skyscrapers and boutique shops in this world-famous upscale shopping district.
Food Recommendation: Mediterranean food at The Purple Pig.

Chicago’s premier commercial district, the Magnificent Mile, is where to go to get all your Chicago shopping done! More than this, it’s a great place to explore for its luxurious and posh atmosphere, with high-class fashion outlets, restaurants, and hotels.

We love window shopping in this district and people-watching! There are also numerous Chicago landmarks , including the Chicago Water Tower and the John Hancock Center. In fact, there are over 50 landmark structures here!

Stroll down the long, beautiful avenue and admire so much of what makes Chicago a great international destination, right in one city center. It’s also nicknamed the Million Dollar Mile. Walking down it, you’ll understand why!

At night, everything lights up beautifully. Turn into a few taverns and art galleries for a laid-back and enjoyable cultural bar-hopping experience. Hopefully, you’ll meet a few locals!

Day 2 / Stop 7 – Jazz at Blue Chicago

Why it’s awesome: Fantastic blues and jazz and a great vibe
Cost: $10 – $12
Food Recommendation: Try Peruvian food at Tanta Chicago

Don’t worry if you’re not spending the weekend in Chicago! With live Chicago Blues seven nights a week, this is the perfect end to your two day itinerary in Chicago. This blues bar is the perfect place for it – a traditional ‘hole in the wall’ style establishment with well-priced drinks and an old-school atmosphere.

The world-renowned blues bar has been running since 1985 and is packed with locals and foreigners every night. Be sure to book beforehand or go early, and keep in mind that only adults over 21 may enter.

Chicago Blues is an eclectic style of blues and jazz music which came about with the migration of African Americans from the South to the Midwest. The performances at Blue Chicago reflect this rich, powerful and difficult history, with great energy and a surplus of talent.

An important part of Chicago’s history and culture, this music is a celebration of life. to watch it and participate in continuing a proud musical tradition is really something special, and certainly one of the best things to do when spending a weekend in Chicago .

This beautiful, expansive hostel is located in the heart of Downtown Chicago.

Free Breakfast

Chicago River Cruise | Chicago Food tour | Richard H. Driehaus Museum | Mob and Crime Bus Tour | Football Game at Soldier Field

If you’re spending three days in Chicago or more, these are the best activities and attractions to include in your Chicago itinerary! They’re a great way to explore the city and learn more about that unique Chicagoan culture.

Chicago River Cruise

Relax with a drink while cruising along the river.
Get insight into landmark buildings and marvel at the legendary architecture.
A 75-minute cruise on a state-of-the-art vessel.

Spend some time exploring one of the biggest Chicago attractions – the gorgeous river. On the architecture tour, you’ll cruise along all three branches of the Chicago River, spotting your favorite landmarks and learning about the city.

From the Navy Pier, you can catch numerous different types of cruises to suit your interests, like a dinner cruise, buffet cruise, or sport-themed cruise. You can also choose between different types of boats!

Our top choice is an architectural river tour, offering a captivating exploration of Chicago’s hidden gems and iconic landmarks. Among others, you’ll see Tribune Tower, the Wrigley Building, Marina City, and Willis Tower.

Relax and enjoy a drink from the bar. The cruise is 75-minutes, just enough time to relax and recover your energy before plunging back into Chicago’s central city hub!

Chicago is known as the birthplace of the skyscraper, and the home of modern American architecture. There is so much to learn and appreciate here. On the tour, you will have an expert guide, with facts, anecdotes, and answers about all of Chicago’s attractions!

Skip the ticket office and proceed directly to boarding by pre-purchasing your ticket online . One of the world’s most beautiful cities and a thriving modern metropolis, Chicago is well worth exploring this way.

If you want a more unique and exciting way to see the river and Lake Michigan, then consider chartering a yacht at an affordable price.

Chicago Food tour

Join a fun and enthusiastic foodie guide while touring Chicago.
Sample some of Chicago’s best culinary offerings.
Get insight into the art, architecture and everyday life of the metropolis.

This foodie Chicago walking tour is a simple classic – stroll through the city learning more about it from a local, while trying all of its best and most exciting foods.

Your guide is knowledgeable and friendly, and will tell you about much more than just the food! The city has so much to see and explore and has such an interesting history, including famous 1920s gangsters like Al Capone. It’s fantastic to explore it with a local, who knows all the best and worst things about the city. You can also get tips on how to explore Chicago’s food and dining scene some more if you’re interested.

Chicago is famous for its American-style food innovations, like the deep-dish style pizza, and Chicago-style hot dogs. You’ll dig into some of these, among other foods! The tour lasts three-hours long, so you have ample time to eat and explore.

You will also get to meet new people on your tour, and enjoy your meals with new friends, laughing and chatting. It’s a great way to meet people while traveling, and also a great Chicago activity to do with friends and partners.

Richard H. Driehaus Museum

Explore an old mansion to see how the well-to-do lived during the Gilded Age.
Contemporary art contrasts with old-style luxury and decadence.
A guided tour is only $5 extra and contributes immensely to the experience.

If you’ve ever wondered what a home looked like in the late 19th century Art Deco period, this is the perfect place to be in Chicago! The museum was once the mansion of Samuel Nickerson and his family, a local banker. Now, after two restorations over the years, it explores the art, design, and architecture of that period to the present.

The permanent collection of period decorative arts suits their surroundings perfectly. Educational and cultural programs contribute to exhibitions which contextualize the Gilded Age and illuminate the vibrant history and culture Chicago.

Enjoy all the little details that make this museum stand out among much larger ones in the country. Each detail is unique, many inspired by locations around the world, others by jazz, music, and the urban culture of Chicago.

Year round the museum features rotating exhibits of modern and contemporary art, which contrasts with the location in interesting and beautiful ways. Spend a few hours here- the more you look, the more you will see.

The staff is also very passionate about their work, and the guides are knowledgeable. In fact, we certainly recommend the guided tour. There’s so much history here, beyond the aesthetic. You will want to learn more about it!

The Museum is located just steps from the Magnificent Mile, and is easy to find! It’s one of Chicago’s lesser-known attractions, so it’s a great place to relax and enjoy the peace.

Mob and Crime Bus Tour

Hear about how some of the world’s most famous mobsters conned their way through the city
Ride comfortably in a luxury bus, unaffected by Chicago’s unpredictable weather
Stake out notorious crime scenes and Chicago landmarks

An alternative way of experiencing Chicago is the Mob and Crime bus tour . It’s not for the faint of heart, though, exploring the sites of Chicago’s most famous and notorious crimes took place. It’s the perfect activity for those rainy or windy days when you can’t explore Chicago on foot.

See famous Chicago crime scenes from the 19th century through to modern times. You’ll learn about Al Capone, the Untouchables, the Chicago Mob, Terrible Tommy O’Connor, the Chicago Black Sox, Leopold and Loeb, Cap George Streeter, and more. You’ll also hear about some of the most daring heists in history!

Visit the historical criminal courthouse, an architectural landmark where some of the biggest cases were tried. Stake out other landmarks and learn about the darker, more criminal side of their history. For a time, gangsters ran Chicago . They are a large and important part of Chicago’s making and rich history.

You will also have the opportunity to leave the bus and walk the path that notorious Chicago gangsters John Dillinger and Hymie Weiss followed just before their deaths. It’s gory and intense, and a good deal of fun and intrigue.

Watch a Football Game at Soldier Field

Watch Chicago’s famous sport with enthusiastic fans.
Enjoy the iconic stadium, which has housed some of NFL’s most famous games.
More than just sports, you can watch live performances too.

On the third day of your itinerary in Chicago, go watch a football game! Most games are of course played on weekends. The Bears, Chicago’s local team, have more regular-season and overall wins than any other NFL team. The team and the stadium have a rich history and a loyal following.

Join The Bears’ passionate fans, cheering on the home team, or watch a game with your favorite team! It’s the kind of good sports fun that doesn’t require you to have too much knowledge or enthusiasm for the game itself. Just enjoy the action and the great vibe!

Soldier Field is an iconic football stadium, easy to get around and has lovely, efficient staff. They’re attentive and organized, which is good in a 60,000 seat stadium! Interestingly, it is still the third-smallest stadium in the NFL.

Of course, the stadium also hosts massive concerts, so if you’re more interested in music than sports, have a look at what’s playing when you’re in Chicago .

So how safe is Chicago? Well most of Chicago is very safe for tourists, and you’ll have no trouble walking around and exploring during the day and night. There are, however, some neighborhoods that are better to avoid.

In these areas, gang violence and other criminal activities occur. They are quite clearly sketchy, though, and far from Downtown Chicago where you’ll spend most of your time exploring.

Pickpockets are reasonably common in very busy areas, and we suggest you keep your belongings firmly by your side. Muggings also occur, particularly at night. These can be avoided by staying on well-lit, well-populated streets and avoiding dark or dingy areas. Thieves sometimes operate on the subway, so it’s best to avoid it when out of peak times (7am-9am and 3pm-6 pm).

Neighborhoods to avoid, particularly at night, are the far West Side of Chicago, which has very few tourist attractions and the Fuller Park area. Parts of Downtown Chicago get empty at night, and therefore risky. North Side remains safe throughout the night, and you can walk comfortably here as long as you take the common-sense safety precautions.

Natural hazards do occur occasionally, but their safety risk tends to be low. There is, however, a higher risk during winter.

Don’t Forget Your Travel Insurance for Chicago

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SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

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Chicago is near to four different states! You can get to other great cities easily and explore the beautiful surrounding area on these day trips from Chicago.

Chicago to New York City Day Trip by Air

The best of the day trips from Chicago has to be New York by air! Fly to the Big Apple, where you’ll hop on a sightseeing bus and spot the greatest of New York’s world-famous landmarks, like the Statue of Liberty!

The tour is very laid-back, with time to take in a show, do some shopping, or set out on a little extra sightseeing!

The tour includes a round trip from Chicago, a two-course lunch in Times Square, and your sightseeing bus trip. So different to Chicago and yet so close. It’s a fantastic part of the Chicago trip itinerary!

Tour of SW Michigan Wine Country from Chicago

Touring America’s beautiful wine country is the perfect day trip. You’ll tour the scenic countryside and visit three wine farms! Enjoy wine tastings at each of them and a gourmet lunch.

Learn about winemaking and how the grapes in Michigan differ to those found in France’s Napa. Have a delicious meal overlooking a vineyard and enjoy some time walking through and learning about the farms.

The tour includes tastings, lunch, bottled waters, and a departure toast to start things off right! Get to know the people on your tour and enjoy leaving the city behind for a day.

Chicago Grand City Tour & 360 Chicago Observation Deck

This half-day tour of the city is one for the books! Travel through the north and south financial districts, admiring iconic buildings and sculptures. Experiencing the vitality and excitement of Chicago’s central hub.

Enjoy views of Lake Michigan and Jackson Park where the Colombian Exposition of 1893 was held to celebrate the founding of America.

You will also look out from the top of the John Hancock Building, and try to identify all four states! The tour is a great activity to bring friends who only have one day in Chicago.

If you fancy enjoying the windy cities magnificent skyline with a cold (alcoholic) drink, then try to find one of Chicagos rooftop bars – but drink responsibly!

Detroit: The Rise, Fall & Renewal Walking Tour

Fly to Detroit, where you can explore the very different American city with a walking tour before setting out on your own. On the tour, you’ll explore the social and economic upheavals of Detroit through its architectural landmarks, learning all about the city and its complex history!

The tour is a great introduction to the city. You’ll see some of the world’s tallest vacant buildings, and most beautiful modern landmarks. Chat with fellow tourists and a knowledgeable local.

Get tips on where to go next, and source out some of Detroit’s finest food at restaurants like Selden Standard.

Milwaukee Scavenger Hunt Adventure

Catch a short flight to Milwaukee, where you can join an exciting and fun scavenger hunt adventure! One of the best ways to explore the city, you’ll use your surroundings to solve clues and complete challenges.

You can stop and go as you please, and take as much time as you need, admiring and learning about the attractions as you go along. It’s a really laid-back trip, and a great experience for couples, friends, and families.

You use your smartphone to play the game and navigate the historic streets of Milwaukee, enjoying its modern and unique culture.

Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.

It looks exactly like a normal belt except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)

Find out what people want to know when planning their Chicago itinerary.

How many days are enough in Chicago?

You’ll want to spend at least 3 days in Chicago, as the city is not very walkable. 4-5 days are ideal for seeing all the attractions and discovering the various neighbourhoods.

What should you include on a 3 day Chicago itinerary?

Don’t miss out on these Chicago highlights: – Millennium Park & Cloud Gate – Chicago Art Institute – Grant Park – Navy Pier

Where is the best place to stay for a weekend in Chicago?

Downtown Chicago is the best place to stay for a short trip. It’s super central, surrounded by the city’s top attractions, and bursting with eateries and nightlife.

What are the best day trips from Chicago?

The Chicago to New York City by Air day trip is the ideal way to spend an extra day. The Detroit Walking Tour and Milwaukee Scavenger Hunt Adventure are also very popular.

With so many world-class museums, sports centers, places of culture, music, food and fun, Chicago is one of the best cities in the world.

You can explore the history of the city, and the natural history of the world! Or stroll through its public parks, and later take in the earth’s most incredible flora. Chicago brings together elements of our whole world in ways unique to the vibrant city.

Even if you’re traveling on a shoestring budget, you can travel to Chicago and make the most of what the city has to offer! With our Chicago itinerary, you will certainly never have a dull moment.

Pack walking shoes, an umbrella, and be sure to bring your camera. You will want to capture the immense skyscrapers as well as the little details that make Chicago iconic!

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

Aiden Freeborn

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That’s a really thorough itinerary, kudos!

Sun Country Airlines is a low-cost airline. The airline offers a range of domestic and international flights to popular vacation destinations at affordable prices. In terms of Sun Country Cancellation Policy it allows passengers to cancel their reservations within 24 hours of booking without incurring any cancellation fees.

YOu should check out the FREE professional Chicago Blues Jam at 9pm at the bar: “West on North.” This is a restaurant bar that 20-30 of the best blues players in Chicago show up to and Jam together. INcredably prepared musicians and nothing is practiced. This is led by singer Ya Ya Townsend. Raw, dirty, improvisation with real heart. The most real Chicago blues fun I have had and the cost for entering $0.

I have always wanted to visit Chicago I’m seriously in love with this type of blog as they highlight all of the best things in every city.

Chicago Itinerary: The Ultimate Travel Guide

Categories Domestic Travel , Travel

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Top Things to do in Chicago, by Travel Blogger What The Fab

So excited to share my Chicago itinerary with you today!

Chicago is one of those cities in the U.S. that I had been wanting to explore for a long time, and people were always surprised that I hadn’t been there yet.

I finally made it out to Chicago for a work trip, and Omied and I extended it into a play trip as well. We ended up visiting during the perfect time of year when the weather was amazing, in early September.

We absolutely loved this city—Omied of course was gaga over the architecture and even I found it to be super interesting to hear about all the famous architects and their stories.

Pssst, heading to Chicago? Don’t miss these travel guides to help you plan your trip!

Where to Stay in Chicago Chicago 3 Day Itinerary Day Trips From Chicago Famous Chicago Food You Have To Try

There’s so much to do, see and eat in Chicago (be sure to purchase a Go City Chicago pass here to save money on top attractions). Here’s how we packed in everything we wanted to hit up in the Windy City.

5 Day Chicago Itinerary

Chicago itinerary: day 1.

We stayed at The Gwen Hotel, which is part of Starwood’s Luxury Collection.

The hotel is absolutely gorgeous, and I adored its art deco vibes. You can see more pics just of The Gwen in this post .

Its central spot on Magnificent Mile means you really can’t beat the location. We were able to walk or take a short uber ride to most places.

In case The Gwen is fully booked, I also recommend the Western River North Hotel located right in downtown Chicago.

Lunch at Cold Storage

We kicked off our foodie tour with lunch at Cold Storage.

This seafood spot had amazing oysters, delicious spreads, and yummy lobster rolls. We finished lunch with a super decadent ice cream sundae, that they are also famous for.

The Best Chicago Itinerary, by Travel Blogger What The Fab

Millennium Park

After lunch, we went over to Millennium Park to walk around.

Millennium Park is famous for all of the incredible, free concerts and events that it hosts, and there happened to be a jazz festival going on when we strolled by.

We also popped over to see The Bean (formally known as Cloud Gate), which was pretty cool but definitely crowded in the afternoon (we came back early in the morning the next day to shoot the above photos).

Cindy’s Rooftop

We hopped just across the street to visit Cindy’s Rooftop, which I’d heard so much about and everyone told me was a must-do in Chicago, even though it’s a tad touristy.

I can see why it’s such an attraction, with its gorgeous views overlooking Millennium Park and fun drinks (terribly slow service, though).

The Ultimate Chicago Travel Guide, by Travel Blogger What The Fab

Architecture River Cruise

An Architecture River Cruise is another must-do if it’s your first time in Chicago.

I promise even if your husband isn’t an architect, you’ll still find it interesting. Plus floating down the river gives you an awesome perspective of Chicago’s beautiful buildings.

We booked ours so that we’d be out on the river around sunset, but be sure to book ahead if you’re looking to do the same, as sunset rides fill up fast.

Blue Chicago Jazz Club

Omied and I love to find local spots for live music when we’re traveling, and we had a few recs for jazz clubs.

We popped into Blue Chicago Jazz Club and loved the vibe there—it was so much fun!

Girl and the Goat

After watching Anthony Bourdain’s No Reservations episode in Chicago, I was dying to visit Stephanie Izard’s Girl and the Goat.

She’s the first female winner of Top Chef and has built an empire of noteworthy restaurants in Chicago, with Girl and the Goat being the most popular (and infamously tough to get a reservation, so again, book ahead).

I looooved our dinner here. 10/10 would do again. It’s a super romantic spot and the food was fabulous. Definitely get the green beans, lamb ribs, and ratatouille focaccia with feta and tomato jam.

Ugh, my mouth is watering just thinking about those dishes!

Chicago Itinerary: Day 2

Duck Duck Goat

Back to back Stephanie Izard! Duck Duck Goat is her dim sum restaurant, and we had an incredible brunch here.

Seriously some of the best dumplings I’ve ever put in my mouth. The octopus salad, char sui bao, duck and goat spring roll, crab rangoon were all absolutely to die for.

This was one of my favorite meals of our trip, so I’d highly, highly recommend this place!

Museum of Contemporary Art

The MoCA had an exhibit on Murakami, and Omied and I really like his trippy and weird art so we spent a couple of hours there.

If you’re not into art museums, there’s also the Field Museum and Adler Planetarium to check out.

Petit Margeaux

For an afternoon pick-me-up, we stopped by Petit Margeaux, the cute sister café of Michael Mina’s Margeaux restaurant at the Waldorf Astoria.

We had some insanely delicious snacks, including foie gras (because I can’t say no to foie when I see it on the menu).

The outdoor seating at the café is really cute and pleasant, so it was a nice spot to relax before continuing on with our exploring.

As the sun was setting we headed back in the direction of our hotel and made our way over to the Riverwalk.

I think it’s so cool that Chicago has a river running through it, and apparently it’s the only city in the U.S. with a river. This area is so beautiful, especially as dusk sets in and all the skyscraper lights turn on.

We sat outside along the river watching the boats go by, and it seemed like the perfect evening.

Until we got caught in a torrential downpour that suddenly started and caught us totally off guard.

Pequod’s

I quickly learned that there are only three acceptable places to get deep-dish pizza in Chicago, and they are Lou Malnati’s, Giordano’s, and Pequod’s.

I also learned that not all three are created equal in each local’s eyes, and everyone has their favorite.

Each Uber driver I had told me I had to go to Giordano’s, the others are terrible. It was pretty funny to see them get all riled up when I told them my previous Uber driver said the opposite, and that I had to go to Giordano’s.

In the end, we decided on Pequod’s, and omg was their deep-dish delicious.

Chicago Itinerary: Day 3

The Highline Bar

I had a coworker who was from Chicago and she used to rave about their Bloody Mary bars. “No one does it like Chicago,” she told me.

“Why doesn’t SF have a Bloody Mary bar with all the fixings? Screw bacon, celery, and cheese cubes. That’s so uncreative.

Think mini sliders, chicken wings, mac and cheese balls. These can all go on your Bloody Mary skewers.

People in the Bay would go ape shit for it!” Clearly, I needed to try one of these fabled Bloody Mary bars, and we found The Highline Bar’s Sunday Bloody Mary brunch to help fill that void in my life.

It was so much fun piling on all the goodies for my Bloody masterpiece (A doughnut? Sure, why not? A bag of flaming hot Cheetos? Hell yes.) and while we left feeling bloated from all the sodium, it was totally worth it.

If you end up loving this spot then you have to explore more of the River North area for great restaurants and bars.

Oak Street Beach

Besides having a river running through the city, I also think it’s super cool that one side of Chicago backs up against the beaches of Lake Michigan.

We went over to Oak Street Beach to watch the volleyball players kill it (and basically be the opposite of us—fat, bloated blobs after Bloody Mary brunch), and to relax on the beach a bit.

Be sure to check out North Avenue Beach too if Oak Street gets too crowded.

London House

After hanging at the beach for the afternoon, we freshened up at the hotel and then walked over to the London House to have drinks at their rooftop bar.

Fair warning, this place draws a crowd that is douchey as hell (too many tight, black v-neck shirts paired with gold chains to count), but the view is pretty awesome.

We watched the sunset from up here and it was worth the long line and other general douchebaggery to get in.

Second City Comedy Show

Everyone told us we had to catch a comedy show in Chicago, and that Second City (where the likes of Tina Fey and Amy Poehler practiced comedy) was the place to do it.

They had several different shows going on and we picked this cast/show , which does a fresh show based on current events (and the bizarre political times we’re living in).

You guys, it was hilarious. Some of the sketches were short and sweet, some required audience participation.

My fav was a cheesy baby-making music song (think the tune of Dick in a Box) about how this guy needed to know if the girl he was on a date with voted for Trump. So good.

Greek Islands

Apparently, the Greek Islands have been around for ~50 years and have been known as THE place to have Greek food in Chicago.

We had a really good meal here, including the flaming cheese, lamb chops, and gyros, but to be honest, I think it may not be as good as it was decades ago since my dad was raving about how insanely delicious it was back in the day, but we left feeling like it was just good.

Chicago Itinerary: Day 4

Lincoln Park Zoo

We spent all afternoon at the Lincoln Park Zoo, which was so much fun. They have so many awesome animals there and I had kinda forgotten how fun it is to go to the zoo!

If you like the zoo, be sure to check out the Shedd Aquarium to see beautiful aquatic animals.

3 Arts Club Café

We had lunch at the uber posh restaurant inside the Restoration Hardware.

This place is an Instagrammers dream, but unfortunately, they asked us to not take photos (you know I still had to sneak one with my phone), because it’s that type of place where they think their clientele is so bougie that they’d be pissed to be captured in a photo.

Be sure to make rezzies in advance, because without it you’re looking at a two-hour wait during the weekend.

Shopping at the Magnificent Mile

You can pretty much shop ’til you drop in Chicago.

The Magnificent Mile is made up of three vertical shopping centers and has basically every store your little heart could desire.

We knew we wanted to go to Au Cheval for dinner, and that they don’t take reservations, so we put our name in and were greeted with a two and a half hour wait.

That’s ok though, we were prepared and had already scoped out some great bars nearby!

Might I recommend The Allis (in Soho house), RM Champagne Bar , and Bad Hunter next door as great spots to grab cocktails while you wait for your table.

Okayyyy first of all, yes the wait is worth it, especially since you have so many fun bars nearby to choose from while you wait.

And second of all, if you go to Au Cheval and don’t get their burger, you’re doing it wrong. SO. GOOD.

We also got the bone marrow because we’re fatties. #noregrets

Chicago Itinerary: Day 5

Willis Tower Skydeck

Gotta do the sky deck! Pro tip: when you’re facing the windows with the glass bottoms, you might be tempted to go to one of the shorter lines for the windows on the left, but they are shorter for a reason.

The window on the very right is the one with the best views, so if you’re going to wait in line and get that shot for Insta, you might as well make it worth your while.

It’s definitely a trip to stand on a glass floor 1,450 feet high!

Kayaking on the river

Omied and I love kayaking, and this is another really fun way to see the Chicago river and buildings from a different perspective.

Portillo’s

Clearly, we had to try a Chicago-style hot dog. After trying it, I’m not exactly sure what all the fuss is about, but if you’re going to try a Chicago-style hot dog, I’m told this is THE place to do it.

If you’re not about that hot dog life, I’d also recommend Little Goat Diner . Yes, another Stephanie Izard restaurant.

Clearly, I love this woman’s food. The chicken pot pie and Rueben sandwich were both killers!

If you are spending more than 5 days in Chicago, I would recommend getting the Chicago Citypass .

You get to visit 7 of Chicago’s best attractions like Shedd Aquarium , Skydeck Chicago , The Art Institute of Chicago, and 360 Chicago Observation Deck in the John Hancock Center Building.

I would also recommend spending some time at Grant Park , the Chicago Cultural Center , Wrigley Field, Chicago Water Tower, and the Navy Pier .

Phew, looking back at our itinerary, that was a lot of things! There’s just so much to do in Chicago, and we had the best time exploring!

I know there are other things (especially restaurants!) that we didn’t get to try so tell me, what else do I need to hit up the next time I’m there?

You can tag me (@ wtfab ) on insta so I can see where in the world you’re traveling from.

Heading to Chicago? Check out my other Chicago travel guides here.

Where to Stay in Chicago Chicago 3 Day Itinerary Gwen Hotel, Chicago Day Trips From Chicago Famous Chicago Food You Have To Try Top 11 Chicago Black-Owned Restaurants 22 Best Indoor Activities Chicago Has to Offer 20 Fun Things to Do in Chicago at Night 18 Most Instagrammable Places in Chicago

It is recommended to spend a minimum of 3 days in Chicago, but a week is best.

The best time to visit Chicago is in late spring, early summer, and early fall since the weather is the best. These months are May, June, September, and October.

Yes, Chicago is a great place to visit! There are so many fun activities to do, amazing places to visit, and amazing restaurants to eat at.

Elise Armitage is an entrepreneur and founder of What The Fab , a travel + lifestyle blog based in California. At the beginning of 2019, Elise left her corporate job at Google to chase her dreams: being an entrepreneur and helping women find fabulous in the everyday. Since then, she’s launched her SEO course Six-Figure SEO, where she teaches bloggers how to create a passive revenue stream from their website using SEO. Featured in publications like Forbes, Elle, HerMoney, and Real Simple, Elise is a firm believer that you can be of both substance and style.

Best snorkeling in Florida Keys itinerary, by travel blogger What The Fab

Jazmin Marie

Tuesday 21st of February 2023

Love this itinerary. Thinking about having a staycation in Chicago and staying at the Gwen - that place looks so gorgeous.

Elise Armitage

Wednesday 1st of March 2023

It's beautiful!! You'll love it.

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The Perfect Itinerary for 3 Days in Chicago

Chicago is one of the United State’s greatest cities. It’s architecturally gorgeous, a center of art and culture, and one of the best places for live music in the world. Even better, it has a more laid-back and friendly vibe than New York and San Francisco (the Midwestern charm is real!).

You could spend weeks exploring the food scene, relaxing in Millenium Park, and hanging out at a different blues club every night. But a long weekend is enough to see the highlights. So I put together this 3 days in Chicago itinerary to help you make the most of your time.

Disclaimer: This post contains affiliate links.

Weekend in Chicago Itinerary

Day 1 of 3 days in chicago itinerary, breakfast: dollop coffee co..

Before you start your exploration of Chicago in earnest, fuel up with a pastry and caffeinated beverage at this third-wave coffee shop, conveniently located near Navy Pier. The almond croissants are the perfect compliment to your morning pick-me-up. There’s no better way to kick off your 3 days in Chicago itinerary.

Explore Navy Pier

Pull up a chair at one of the lakeside bars for a Bloody Mary with sweeping views over Lake Michigan. Take a ride on the giant Ferris wheel to see the towering skyscrapers all around. Or do as the locals do: rent a bike and pedal around the lakeshore, looking for the perfect beach to sink your toes into the sand.

Eat Chicago deep dish pizza

Since deep dish pizza is so piled with toppings, it takes awhile to cook — expect to wait at least an hour after you order for your pizza to arrive. Sausage is the classic topping.

Go on an architecture cruise along the river

On October 8, 1871, legend has it that a cow on the O’Leary family farm kicked over a gas lantern. While the sequence of events has never been verified, one thing is for sure — over the next three days, a massive fire raged through the entire city of Chicago, killing hundreds of people and laying waste to much of the predominantly wood construction in the city.

In the aftermath of the Great Chicago Fire , with hundreds of thousands of people left homeless, the city had to rebuild — and fast. Residents had learned their lesson about constructing a city from wood. So they shifted to constructing steel-frame buildings, leading to the development of some of the first modern skyscrapers. The end result is today, Chicago has a totally unique skyline.

The best way to explore the architecture and learn about its history is by taking a boat tour along the river.

Most tours start from Navy Pier and take about 75 minutes. You sit on the deck and your trip is narrated by a knowledgeable and entertaining guide. You’ll learn about the different architectural styles and the role architecture has played in the city’s history, starting with the initial post-fire reconstruction and ending with the Sears Tower. It’s a great way to get oriented early on during your 3 days in Chicago itinerary.

You can book a tour on Viator in advance.

Dinner: Xoxo

If you’re a fan of Mexican food, you can’t miss Xoxo when you spend 3 days in Chicago.

The main focus of the menu is tortas or Mexican sandwiches. They sound simple but they are so, so delicious — especially the Woodland Mushroom one. Even better, all the ingredients are locally and sustainably sourced. Other Mexican street food is available if you want something lighter.

The chef behind Xoxo — Rick Bayless — has two other restaurants in the area. Topolobampo is high-end and you will need a reservation (weeks in advance). Frontera Grill is somewhere in the middle and if you go at an off-peak time, you can probably get in without a reservation.

Drinks at Signature Room

Close out your first day in Chicago with drinks at one of the city’s most epic rooftop bars.

The Signature Room is on the 95th floor of the John Hancock Building. The views over Navy Pier and the entire downtown area are nothing short of spectacular.

You’ll have to wait in line for probably half an hour on the ground floor before taking a harrowing elevator ride up to the bar. If you have a large group you may have to wait a second time once you’re inside. But it’s all worth it when you land a window seat. The only cost is an overpriced beer (figure on paying $12).

The best time to visit is on a Saturday night around 9:30, when you can watch the fireworks show over Navy Pier.

Sorry gentlemen — the best view in the bar, and arguably the best view in all of Chicago, is from the window in the ladies’ restroom.

Day 2 of 3 Days in Chicago Itinerary

Walk down the magnificent mile.

The Magnificent Mile is Chicago’s answer to 5th Avenue in New York. It’s a high-end shopping street surrounded by skyscrapers that leads straight into the heart of the business district. Start at the north end and head toward Millennium Park.

Even if you’re not a shopper, it’s worth exploring the Magnificent Mile for the architecture and landmarks you’ll find along the way. You’ll pass some of the tallest buildings in the city, including the John Hancock Building. The best view is from the Michigan Avenue Bridge, which is surrounded by historical landmarks.

Explore public art in and around the Theater District

Where can you see magnificent Picasso sculptures for free, randomly located in the heart of a major city? Only in Chicago.

The Theater District and the area around it has the highest concentration of public art. It’s most famous for Picasso’s “Untitled,” but there are dozens of other sculptures in the area. Flamingo and Monument with Standing Beast are worth going out of your way for.

When you need a break from walking around, pop into Intelligentsia for a great cup of coffee. Then, head over to the Chicago Cultural Center and see if they have any special exhibitions on display. The work here is often more political and 21st-century. It’s free to visit and the building is architecturally beautiful, so it’s worth strolling through even if modern art isn’t your thing.

Lunch: Native Foods Cafe

It can be hard to find decent, healthy, affordable food in the Loop (the downtown area) on weekends. But Native Foods Cafe has you covered. Looking for more money-saving tips? Check out this post .

The all-vegan menu features sandwiches, salads and main courses from around the world. Die-hard carnivores might feel deprived, but there are plenty of satisfying chicken-that-isn’t-really-chicken options.

The Art Institute of Chicago

A rival to the best art museums in Paris and New York, the Art Institute of Chicago is the one must-visit museum when you have 3 days in Chicago.

Most people come for the impressionist work, but there’s plenty more here covering a huge span of art history.

Tickets cost $25. You could rush through in about two hours, but allow the whole afternoon to really take it all in. You can get a coffee or tea at two cafes inside if you need a break from art-gazing.

Dinner: Picnic in Millennium Park

Stop by Pastoral before 6 pm (or order in advance) to grab a picnic dinner. This deli serves serious sandwiches and takeaway beer and wine and is in a perfect location to bring your meal to Millennium Park. Cured meats may be the specialty but the Farmhouse Veggie is to die for.

After you eat, explore the park itself. The highlight is the Cloud Gate statue (more commonly known as the “Bean”), where you can see the city’s skyline reflected in its metallic coating. There are a couple interesting fountains and other works of public art on display in the park as well.

Then, spend the evening listening to live music — available throughout the summer at the park’s main stage. Find a spot on the grass to sit down and listen to the world-class blues and jazz performers Chicago attracts.

Day 3 of 3 Days in Chicago Itinerary

Pilsen and the mexican art museum.

Chicago has a large Mexican community, which forms a huge part of the city’s history. The center of the community is in the neighborhood of Pilsen. This area is pretty off the beaten path for tourists, so it’s a good way to get under the city’s skin during your 3 days in Chicago itinerary.

Start your neighborhood exploration at Cafe Jumping Bean . It serves good coffee and delicious pastries, among other breakfast specialties. It feels like a community gathering spot and it’s very friendly.

Then, head over to the Mexican Art Museum . This is the largest collection of Latino artwork in the United States. If you’re at all interested in the fascinating, diverse world of Mexican art, it’s worth spending at least two hours here. It even has free admission.

The museum includes traditional artwork, a large collection of folk art, and modern art created by both Mexicans and locally based Mexican-Americans. It walks you through the history of the Pilsen neighborhood and the Mexican community in Chicago as well.

After you visit the museum, spend some time wandering around and checking out the colorful street art, which has very strong Mexican influences. Even the “L” (subway) stations are elaborately decorated.

Finally, grab lunch at (cash-only) Don Pedro Carnitas . Tacos al pastor (pork, onion and pineapple) are the reason to come here and they taste like they came straight from the streets of Mexico City.

Go to a game at Wrigley Field

The ballpark itself is a historical icon. It’s the second-oldest park in the U.S. (behind only Boston’s Fenway Park). It feels like nothing has changed since the park opened in 1914. Check out the old-school scoreboard. If you don’t want to go to a game or can’t get tickets, you can take a tour of the ballpark to learn more about its history. Be prepared for lots of bragging about the 2016 World Series win.

After the game, hop over to Clark Street Dogs for a classic Chicago hot dog. Don’t forget to get the chili cheese fries!

See a show at Buddy Guy’s Legends

Blues music is one of the few great American art forms. Buddy Guy is the master of Chicago blues. And Chicago is maybe the only city left in the country where you can see an incredible blues band any night of the week in a small club at a reasonable price.

Put it all together at Buddy Guy’s own blues club, right in the heart of the Loop. The music history practically drips from the walls. And you’re pretty much guaranteed to see an impressive show that punches way above its $20-a-ticket weight. It’s the perfect way to close out your 3 days in Chicago.

Extra days: 3 days in Chicago Itinerary

Have more time in your 3 days in Chicago itinerary? Consider checking out these places too.

Museum of Science and Industry

This museum is the largest of its kind in the U.S. You can see a German World War II boat or get a sense of what it’s like to live through a tornado. The museum would be especially good if you’re visiting with kids.

Museum of Contemporary Art

With an ever-changing set of temporary exhibitions, you never really know what you’re going to get at this museum. It’s good for modern art lovers but sometimes verges on just being weird.

Go to the Beach

Chicago’s lakeside location means it has easy access to a number of great beaches. If it’s warm enough when you visit, try one of the beaches in Lincoln Park. The park also houses a zoo and museums.

You definitely won’t get bored with 3 days in Chicago. Don’t overlook this midwestern gem!

Where to stay in Chicago

$ hi chicago hostel.

This is a great option for budget travelers visiting Chicago. Perfectly located just 3 minutes from the nearest subway stop and walking distance to Millenium Park, Grant Park, and Willis Tower. The modern dorm rooms are segregated by sex with shared bathrooms. For a small upgrade fee, you can get your own private room. Breakfast is included and there is a game room, computer, and communal kitchen for guests.

Book Now | Compare Prices for Later | Read Trip Advisor Reviews

$$ LondonHouse Chicago

Overlooking the Chicago River, this amazing hotel located in a high rise building is the perfect place to spend your 3 days in Chicago. Located at the start of the Magnificent Mile, LondonHouse Chicago offers modern chic rooms with full amenities. Some rooms have floor to ceiling windows overlooking the river. Don’t forget to check out the lobby bar or rooftop restaurant with views of the river.

$$$ Langham Chicago

This is a supreme choice for luxury and the perfect place to spend your 3 days in Chicago in style. Located in a tower with views of Lake Michigan this hotel is conveniently located close to all the hotspots in downtown Chicago including Millennium Park. The rooms have floor to ceiling windows with amazing views, some with waterfront views. Enjoy the indoor pool, spa, and health club on site.

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The Ultimate Chicago Bucket List | Chicago Travel Blog

Looking for bucket list things to do in Chicago? These are the best attractions and foods to eat for your Chicago bucket list whether visiting for a long weekend or only spending a day in Chicago .

Chicago Bucket List

Take an Architecture River Cruise

Chicago has amazing architecture and the best way enjoy it is by going on an architecture river cruise .

Take a Lake Cruise

skyline from lake cruise in Chicago bucket list summer

If you enjoy being on the water, a lake cruise is also a fun activity. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views. Summer is the best season for a lake cruise as the cool breeze on the water is refreshing on a hot day. If your time is short, you can do a combination river and lake cruise .

Hang Out on the Riverwalk

The Chicago Riverwalk is a pedestrial walkway along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. It is one of the best spots in Chicago for boat and people watching especially in the summer.

There are also restaurants , bars, shops and spots to sit and relax along the way. You can see a map of attractions on the Riverwalk here .

If you are on the Riverwalk at night, check out Art on theMART , a 30-minute program of digital art projections shown twice nightly across the river-façade of the Merchandise Mart. Spectators can watch the show from the jetty section of the Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Go Kayaking in the River

Kayaking in the Chicago River is a fun and active way to explore the city. There are several companies that offer kayaking tours in Chicago including Urban Kayaks, Kayak Chicago and Wateriders .

Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.

Ride the Large Ferris Wheel at Navy Pier

ferris wheel at Navy Pier Chicago bucketlist

Navy Pier is a not to missed attraction especially if you are visiting Chicago with kids. Navy Pier is full of fun things to do including a large Ferris wheel ( click here to purchase a fast pass ticket and skip the long line), rides and games , restaurants, shops and the Chicago Children’s Museum . Visiting Navy Pier is free, although you have to pay for the attractions.

Navy Pier puts on a free fireworks show on Wednesday and Saturday nights in the summer .

Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises.

Watch Free Fireworks at Night

As mentioned above, Navy Pier puts on a fireworks show every Wednesday night and Saturday night from Memorial Day weekend through Labor Day weekend. While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars.

Another great option for watching the fireworks is a fireworks lake or river cruise which will stop on the water for passengers to enjoy the show.

Stand on the Ledge at Willis Tower

The Willis Tower (formerly known as the Sears Tower and what many locals still call it) used to be the tallest building in the world from 1974 until 1998. You can enjoy great views from The Skydeck , its observatory on the 103rd floor of the Willis Tower (233 S Wacker Dr). For the best instagram photos head to The Ledge , glass balconies extending four feet outside the 103rd floor.

Tip: The Skydeck Chicago gets crowded especially on weekends. For fewer crowds visit right after it opens during midweek. (Click here to buy a skip the line ticket if you want to avoid long lines).

Enjoy Skyline Views from 360 CHICAGO Observation Deck

View this post on Instagram A post shared by 360 CHICAGO Observation Deck (@360chicago) on Feb 12, 2020 at 1:07pm PST

360 CHICAGO (formerly John Hancock Observatory) on the 94th floor of the 875 North Michigan Avenue (the building formerly known as the John Hancock Center) is another observatory with great Chicago skyline views . It gets crowded especially on weekends (but is usually less crowded than the Skydeck). (Click here to buy a skip the line ticket ).

The highlight is TILT an enclosed moving platform that tilts you out over Michigan Avenue. You can also experience TILT, an enclosed moving platform that tilts you outward over Michigan Avenue for unique, downward facing views.

See Cloud Gate (The Bean)

The Bean needs to be on your Chicago bucket list

If you have seen photos of Chicago, chances are you have seen photos of Cloud Gate (which most people call The Bean), the iconic mirrored sculpture in Millennium Park. The Bean is a must see attraction is one of the top photo spots in Chicago .

Listen to Free Music in Millennium Park

A great Chicago activity in the summer is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.

The annual Grant Park Music Festival is the only free outdoor classical-music concert series in the US. It features the Grant Park Symphony Orchestra and Grant Park Chorus along with guest performers and conductors.

The Millennium Park Summer Music Series features a wide variety of genre-defying music from established and emerging artists.

Watch the Water Displays at Buckingham Fountain

Buckingham Fountain in Chicago bucket list attraction

Buckingham Fountain , a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world.

When the water is turned on (usually May to October), it produces a major water display for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display.

Shop (or Window Shop) on the Magnificent Mile

Join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the 360 Observation Deck , the historic Chicago Water Tower and the Tribune Tower.

Visit the Art Institute of Chicago

The Art Institute of Chicago bucket list winter

Chicago has many great museums which are worth visiting. The Art Institute of Chicago , conveniently located right next to Millennium Park, is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world. In addition to its large permanent collection of art from around the world, you can see rotating exhibits. (Click here to buy a skip the line ticket if you want to avoid long lines).

Visit the Museum Campus

view from Adler Planetarium Skyline Walk

Tip: If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.

Visit the Museum of Science and Industry

cherry blossoms in front of Museum of Science and Industry in Chicago

The Museum of Science and Industry in Hyde Park is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits.

If the weather allows and you have extra time in Hyde Park, you might want to check neighboring Jackson Park . This park has cherry blossom trees in the spring and it also has a free Japanese garden.

Promontory Point is about a half mile away and has great skyline views of Chicago.

Explore the Lakefront Trail

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. In the summer and especially on weekends, the lakefront is packed with locals and visitors walking, running and riding bikes. Walking or biking all or part of the trail is a great way to see Chicago skyline, people watch and get some exercise. Here is a map of the trail as well as its access points.

Visit North Avenue Beach

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan. Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions.

Chicago skyline view from North Avenue beach

North Avenue Beach is a busy and popular beach and is located close to Lincoln Park. Even if you are not a beach lover, North Avenue Beach is worth visiting just for the amazing skyline views.

Enjoy the Views from a Rooftop Restaurant

View this post on Instagram A post shared by LondonHouse Chicago (@lhchicago) on Jan 31, 2020 at 7:17pm PST

Chicago has several rooftop bars and restaurants with amazing views of Chicago. These rooftops have bucket list worthy views:

LH ON 22 (85 East Wacker Drive) offers great views of the Chicago River.

Cindy’s (12 S Michigan Ave), a restaurant and bar on the rooftop of the Chicago Athletic Association Hotel, offers panoramic worthy views of Millennium Park and Lake Michigan.

The J. Parker (1816 N Clark St) on the rooftop of the Hotel Lincoln, has great views of Lincoln Park.

Watch a Baseball Game at Wrigley Field

Whether a fan of the Cubs, baseball in general or just a lively atmosphere, a day at historic Wrigley Field is a must for locals and tourists alike. You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere while drinking and eating.

You can find the Cubs’ schedule here .

If you cannot find tickets, you can watch a game from Wrigley View Rooftop .

You can also sign up for tours of the stadium for a behind-the-scenes look.

See a Show at the Chicago Theatre

Walk The 606

The 606 is Chicago’s version of The Highline in NYC , an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square. It is a bit off the beaten tourist path but it great place to walk, run or bike. There are several access points so you can get off the trail to explore the various neighborhoods.

Have a Chicago-Style Hot Dog

Chicago style hot dog from Portillos chicago bucket list food and restaurants

Try a Chicago-style hot dog – one of foods that Chicago is most famous for . The classic version of the Chicago dog is an all-beef hot dog served on a poppy seed bun and topped with yellow mustard, pickle, relish, sliced tomato, onions, sport peppers and celery salt. Ketchup is not allowed. You can find hot dog stands all over Chicago Portillos is a popular spot and convenient as it has outposts all over Chicago.

If you are not visiting Chicago soon, you can order Chicago style hot dogs online here and enjoy them from home.

Try Deep Dish Pizza

Chicago is famous for Chicago-style deep-dish pizza . The main difference between deep-dish pizza and most other forms of pizza is that the crust is very deep, creating a very thick pizza that resembles a pie more than a flatbread.

There is a lot of debate which restaurant in Chicago serves the best deep dish pizza but you can’t go wrong with either Lou Malnati’s or Giordano’s , two of the most popular pizza places with several locations in downtown Chicago. If you do eat at one of these keep in mind that they are usually busy especially on weekends and in the summer (during peak times you will often see people waiting outside on the sidewalk).

Most locals prefer Pequods in the Lincoln Park neighborhood of Chicago which is said to have the best deep dish pizza in Chicago and is famous for its caramelized crust.

Try an Italian Beef Sandwich

Although not as well known as deep dish pizza and Chicago style hot dogs, Italian beef is another dish Chicago is famous for . Al’s Italian Beef is the best and most famous place in Chicago to try an Italian beef sandwich. Another good spot is Portillos if you are there for a Chicago hot dog.

These things are the top things to do, see and eat in Chicago that need to be on your bucket list.

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

Most Instagrammable Places in Chicago
Best Free Things to Do in Chicago

Need more bucket list inspiration? You might enjoy our other travel bucket lists:

Best Places to Visit in the Midwest for Your Bucket List
USA Travel Bucket List: 100+ Best Places to Visit in the United States
Best Road Trips in the USA For Your Bucket List

BEST Chicago Themed Gifts for the Chicago Lover in Your Life

savvyglobetrotter

Chicago Travel Guide

Last Updated: April 15, 2024

Best known as the “Windy City” because the local politicians blow hot air, Chicago is one of my favorite cities in the entire United States — especially in the summer when the weather is perfect.

Because the winter is harsh here, the city comes alive in the spring and summer as residents buzz about after being confined inside. There’s not one person I know who doesn’t say, “You can’t get better than Chicago in the summer.”

Chicago’s biggest draws include its green space, the most famous being Grant and Millennium Park, home to the iconic Chicago Bean sculpture (officially known as Cloud Gate). The city also boasts world-class food, fun nightlife, lots of activities, outgoing people, and an uplifting atmosphere. There’s a lot to do here for people of any budget or travel style.

This travel guide to Chicago can help you plan a fun and affordable trip without breaking the bank!

Things to See and Do
Typical Costs
Suggested Budget
Money-Saving Tips
Where to Stay
How to Get Around
How to Stay Safe
Best Places to Book Your Trip
Related Blogs on Chicago

Top 5 Things to See and Do in Chicago

The huge, reflective chrome bean with people surrounding and tall buildings behind it in Chicago, USA.

1. Relax in Grant and Millennium Park

Located downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. People play chess here when the weather is nice and during the summer there are a lot of free concerts. Grant Park stretches along Chicago’s waterfront and is the larger park, while Millennium Park is the subsection where the famous “Chicago Bean” sculpture is located. Officially titled “Cloud Gate,” this iconic work of public art is a must-see while visiting Chicago. Starting at noon on the 1st and 3rd Saturdays April-November, the Chicago Cultural Center hosts walking tours focusing on the art of Millennium Park.

2. Stroll down the Magnificent Mile

Often nicknamed “Mag Mile,” this stretch along Michigan Avenue from the Chicago River to Oak Street is known for its upscale designer boutiques. In fact, rent here is the 3rd highest in the US (after Fifth Avenue in New York City and Rodeo Drive in Beverley Hills). Even if you don’t want to blow your budget on some expensive threads, it’s still an experience to stroll down the avenue and take in the sights, and the people, and enjoy the view of the Chicago River. There are several landmarks and attractions along the avenue too, including the 360 Chicago observation deck for expansive views over the city.

3. Experience St. Patrick’s Day

Next to Ireland , Chicago is the best place to be on March 17th. To honor its large Irish-American population, the city dyes its river green, hosts a huge parade, and parties until the sun comes up (complete with copious amounts of green beer). The tradition began in 1843 when the city’s first Irish parade was held, but it wasn’t until 1962 that the dyeing of the Chicago River started, at the suggestion of a local plumber’s union. This union is still responsible for the green river each year, though they won’t divulge their secrets on the dye used (it’s environmentally friendly, though). Take a river cruise on the emerald waters or snap a pic from the sidelines and enjoy. This is one of the biggest days of the year here!

4. Have fun at Navy Pier

This 3,300-foot-long (1,010 meters) pier on the shoreline of Lake Michigan started off as a shipping pier but has also been a prison for draft dodgers during World War II, a Naval training center, and a temporary university campus. Since 1995, it has reopened to the public in its current form, and become sort of like a carnival in a city. It’s Chicago’s second-most visited tourist attraction (after The Bean) and contains some rides, a Ferris wheel, lots of restaurants, a Shakespeare theater, boat tours, a large number of beer gardens, mini-golf, and more! It’s a good place to have some silly fun (especially if you have kids).

5. Try deep dish pizza

Chicago developed the deep-dish pizza, as well as the stuffed crust pizza, and no trip is complete without trying both. The deep-dish pizza was invented in 1943 by Pizzeria Uno, which is now a national restaurant chain. For something more local, Chicagoans swear by Lou Malnati’s. Personally, I’m not usually a huge fan of deep dish but I was impressed by theirs! If you really want to indulge, hop on a pizza tour offered by Chicago Pizza Tours, where you’ll get to sample all the varieties of pizza on offer in this city. Tours start at $59 USD.

Other Things to See and Do in Chicago

1. visit the oriental institute museum.

The Oriental Institute (OI) of the University of Chicago is a leading research center for the ancient Middle East. Their museum is home to a huge archaeological collection of objects from the Near East, including ancient Egypt, Israel, Syria, Turkey, Iraq, and Iran. Established in 1919, the museum has all kinds of artifacts, photographs, historical records, and even a giant 17-foot-tall statue of King Tut that weighs over six tons! Suggested admission is $10 USD.

2. See the Chicago Cultural Center

The former site of the Chicago Public Library, this historic landmark is known for its exquisite Tiffany mosaics, especially in its performance venue Preston Bradley Hall. Its rooms were inspired by the Acropolis of Athens , the Palazzo Ducale in Venice , and the Palazzo in Florence . It has changing art exhibits, events, performances, and free guided tours of the historic building (Thursdays and Fridays at 1:15pm). Check the website to see what events and performances are available during your visit. It’s free to visit.

3. Get Shown Around By a Local

Chicago has a local greeter program, which offers free walking tours of various neighborhoods from a knowledgeable local. This is a great opportunity to see more of the city while learning about it directly from an expert local guide who can answer all your questions. You can sign up at chicagogreeter.com (you need to do it at least 10 days in advance). I highly, highly, highly recommend doing this!

4. Stop by the City History Museum

This museum provides a solid overview of the history of Chicago, with an in-depth focus on the Great Chicago Fire in 1871 that burned down most of the city (the fire killed 300 people and left 100,000 people homeless. Abraham Lincoln’s final draft of the Emancipation Proclamation was lost in the fire too). The museum has 22 million items, including President Lincoln’s deathbed and the clothing he and his wife wore when he was assassinated. The rotating exhibitions highlight different events and cultural groups that contributed to the city’s history, like the Polish immigrants that came to the city starting in the mid-1800s and the way art was used to influence societal change during the 1960s and 1970s. Admission is $19 USD.

5. See the Cubs play

Locals are incredibly passionate about their baseball team. Get in the spirit and head out to a game at the Cubs’ home stadium, Wrigley Field. Even if you don’t know a lot about baseball, it’s still super fun. It gets really intense when the Cubs play Chicago’s other team, the White Sox. The season goes from March-November and tickets usually start around $15 USD for the upper deck and go up from there.

6. See Robie House

This Frank Lloyd Wright masterpiece, completed in 1909, is a premier example of his Prairie School design. From the overhanging roofline to the expansive interior, the home design balances simplicity with perfectly placed details. The choices of each element, like the limestone incorporated into the exterior and the iridescent glass of the windows, was done with intention to bring a feeling of expansive natural landscapes. Wright helped make Chicago architecture famous and this house is one of his best-known buildings. Today, the house is located on the University of Chicago campus and is listed as a UNESCO World Heritage site along with 8 other of Wright’s most emblematic works. Admission starts at $20 USD, which includes a guided tour of the interior.

7. Visit the Art Institute of Chicago

This is Chicago’s most famous museum, and in fact one of the oldest and largest art museums in the world. From photography to architecture to textiles, it houses a collection that includes works by Eva Hesse, David Hockney, and Ellsworth Kelly. This is where you can see the Hartwell Memorial Window designed for Tiffany Studios more than a century ago and a famous Vincent Van Gogh painting, The Bedroom. You’ll also find a 12th-century statue of the Buddha and 16th century German armor made for jousting. Founded in 1879, the museum has over 300,000 items in its permanent collection and hosts upwards of 30 special exhibits each year. Admission is $32 USD.

8. Take a food tour

Get to know the city through its culinary scene, from deep-dish pizza to microbreweries to Chinatown’s best restaurants. Get Your Guide offers a huge assortment of tours depending on your culinary interests. Usually, they involve some educational element. You can combine your love of food with architecture, history, or kayaking. Others focus on certain items, like donuts, or specific neighborhoods, like the culturally diverse Westside. There’s even a tour that combines traditional Chicago staples dishes with gangsters like Al Capone. Tours start from $55 USD and go up from there.

9. View some war-inspired art

The National Veterans Art Museum (formerly The National Vietnam Veterans Art Museum) is a great yet seldom-visited museum. It features over 2,500 works of art created by Vietnam war veterans and, more recently, veterans from Iraq and Afghanistan. The entrance has 58,226 dog tags hanging from the ceiling, representing the soldiers who died in Vietnam. It’s a stark, somber reminder of our overly-romanticized notion of war. Admission is free, though donations are welcomed.

10. Get acquainted with nature

Established in 1857, The Peggy Notebaert Nature Museum is a beautiful institution with roof-top gardens and plenty of information about the ecosystems surrounding Chicago. The “butterfly haven” is the most interesting — it’s an enclosed space with over 200 species of butterflies, a waterfall, and garden paths. There’s an exhibit about the natural wetlands of Illinois and the endangered species that live there and a resource center focused on sustainability. Outside the building you’ll find the Deb Lahey Nature Trails where you can walk through and learn about plant life native to the area. They also organize dozens of educational programs for both kids and adults. This museum is open daily and it costs $17 USD.

11. Catch an improv show

Chicago is the birthplace of improv comedy and a visit to the city wouldn’t be complete without catching a show. There are tons of companies here — many of which have given birth to comedy greats like Tina Fey, Amy Poehler, Stephen Colbert, Mike Myers, Steve Carell, Eugene Levy, Bill Murray, and a ton of others. Second City is the most popular venue/troupe. Tickets start at around $25 USD. The iO Theater has been a hotspot for comedy and improv in Chicago for decades, has four stages, and continues to put on shows five nights a week. Tickets here star around $23. The Laugh Factory, ComedySportz, and Zanies are just a few of the other popular venues in the city.

12. Go to the beach

When most people think of Lake Michigan, they don’t imagine sand, waves, and water as far as the eye can see — but it’s there! Downtown Chicago runs right next to the shore and offers a little piece of nature in a city of skyscrapers. North Avenue Beach is one of the most popular because of its location just north of downtown. You can even rent SUPs, kayaks, and jet skis there. Loyola Beach is a little further north and is much quieter, if you want to get away from the crowds. 31st Street Beach is at the edge of Burnham Park, south of downtown, and another place to find rentals for water activities. 57th Street Beach, Montrose Beach, and Ohio Street Beach are other most popular choices.

13. See the Willis Tower

The Willis Tower (formally the Sears Tower) held the title of the world’s tallest building for 25 years. Currently, it’s the third-tallest building in the US and the 23rd tallest in the world. Standing at 1,450 feet (110 stories) tall, visitors can take the elevator to the SkyDeck (the highest observation deck in the United States) for panoramic views over Chicago. For those who don’t mind heights, the SkyDeck’s Ledge is a glass box extending over 4 feet over the city, offering heart-pounding views of the urban landscape below. Admission is $32 USD.

14. Explore the Field Museum of Natural History

This museum was built for the World’s Columbian Exposition of 1893 to house its impressive biological and anthropological collections. Built in the Neoclassical style, the museum has 24 million objects, including exhibits on everything from mummies to meteorites, and more. Some sections focus on specific peoples, like the Maori of New Zealand. Others highlight flora and fauna, such as birds native to North America, and plant life from around the world. 3D movies are a fun way to learn more about interesting topics, like dinosaurs that once lived in Antarctica. There’s also a library with over 275,000 books. Admission starts at $30 USD. The expansive garden of native plants outside the museum is free to visit.

15. Stroll the Chicago Riverwalk

Do like the locals do and hang out on the south bank of the Chicago River, where you can walk the Chicago Riverwalk from Lake Shore Drive to Lake Street (it’s a little over a mile). Grab a glass of wine at the Riverwalk Wine Garden by City Winery and enjoy some people-watching. It’s a gorgeous place for a stroll in the summer! At night, you can see the projections of Art on theMART, the largest permanent digital art exhibition in the world.

16. Visit the Adler Planetarium

This was the first planetarium in the United States. It boasts immersive theater programs, rotating exhibitions, and other fun events (including lectures). You can virtually experience the depths of powerful black holes and the heights of Voyager 1, the farthest manmade object from Earth. There are also awesome special events, like Adler After Dark which lets you explore the planetarium while enjoying drinks and live entertainment. Admission starts at $19 USD.

17. Take a bike tour

To explore the city’s main sights and cover a lot of ground, take a bike tour. Bobby’s Bike Hike uses expert local guides so you learn a ton about the city. They offer food tours, neighborhood tours, and tours of Chicago’s main attractions, all by bike. The Lakefront Neighborhoods tour is a good way to get familiar with the city and its layout. The Bikes, Brews, & Bites tour combines gives you a chance to sample a few iconic Chicago dishes and learn the history behind them while exploring and enjoying local craft beers along the way. It’s a fun way to explore and you get to see a lot too! Tours start at $46 USD.

18. Float on the Chicago River

Getting out on the river is a great way to see the city from a different perspective. Paddle around in a kayak from Urban Kayaks, bike your way through the water on a Cycleboat (it’s also BYOB!), take an architecture boat tour, or go traditional and take a dinner cruise. Prices vary greatly depending on what you choose, but expect to pay at least $45 USD to get out on the water.

Chicago Travel Costs

Large avenue with median in the middle and tall buildings in Chicago, USA.

Hostel prices – During peak season, a bed in a 4-6-bed dorm costs about $50-70 USD and $35-65USD in the off-season. For a room with eight beds or more, expect to pay around $45-60 USD in peak season and $30 – 45 USD off-peak.

A basic private room starts at $136 USD during peak season and goes up from there. Prices drop to around about $70-120 USD in the off-season. Free Wi-Fi is standard and most hostels have self-catering facilities. Some hostels also offer free breakfast and a few have a bar/restaurant on premises.

Budget hotel prices – Budget two-star hotels start at $110 USD per night in peak season. In the off-season, prices drop to around $85 USD. Expect basic amenities like free Wi-Fi, AC, TV, and a coffee/tea maker.

There are also lots of Airbnb options in Chicago. A private room starts at $40 USD per night while an entire home/apartment averages $130 USD per night. Expect to pay double (or more) if you don’t book in advance.

Food – Chicago has lots of fast food and street food options. The city is famous for deep dish pizza, Italian beef sandwiches, and Chicago dogs, which are simple hot dogs dressed with mustard, hot peppers, tomato slices, green relish, and a pickle spear. Another dish to try in the city is a jibarito sandwich, which was created by Puerto Rican immigrants. It’s typically thin-sliced steak, tomato, lettuce, cheese, and mayonnaise between a “bun” of smashed and fried plantains.

You can get a huge hot dog, a chili dog, or a few tacos for under $5 USD, or a sandwich for under $10 USD. A personal deep dish pizza starts at about $13 USD (Lou Malnati’s Pizzeria is the best place to order it). Fast food (think McDonald’s) is around $11 USD for a combo meal.

You can eat at an inexpensive casual restaurant with table service for around $25 USD. For a three-course meal with a drink, expect to pay closer to $55 USD.

Chinese food is around $9-13 USD and you can find Thai food for around $13-15 USD. Beer is $7 USD, a cocktail is $11-15 USD, and a glass of wine is $10 -12 USD. In terms of non-alcoholic drinks, a latte/cappuccino is $5 USD while bottled water is $2.50 USD.

If you cook your own food, expect to pay around $50-60 USD per week for basic staples like pasta, rice, vegetables, and some meat. There are plenty of grocery stores around, even close to the downtown area. Mariano’s is known for high quality and low prices.

Backpacking Chicago Suggested Budgets

If you’re backpacking Chicago, expect to spend about $80 USD per day. This budget covers a hostel dorm, using public transportation, cooking your own food, and free attractions like walking tours, the parks, and the beaches. If you plan on drinking, add $20 USD to your daily budget.

A mid-range budget of about $240 USD includes staying in a private accommodation, eating out for most meals, enjoying a couple of drinks, taking the occasional taxi, and doing some paid activities like museum visits or a bike tour.

On a “luxury” budget of about $430 USD or more per day, you can stay in a hotel, eat out anywhere you want, drink as much as you’d like, take more taxis or rent a car, and do more paid activities. After that, the sky is the limit!

Chicago Travel Guide: Money-Saving Tips

Chicago is an expensive city, especially when it comes to attractions and accommodation. But, like any major city, there are always pockets of affordability if you know where to look. Here are some ways to save money in Chicago:

Get the Chicago City Pass – There are two different sightseeing passes available for Chicago. The CityPASS lets you choose either three or five attractions from a list of nine. Prices range from $102 USD to $139 USD. Go City passes offer more flexibility with entrance to more than twenty-five attractions. The All-Inclusive pass gives you entrance to an unlimited number of attractions. Prices for this pass range from $124 USD for a one-day pass to $234 for a five-day pass. The Explorer Pass gives you entrance into a specific number of attractions from the list. Prices range from $84 USD for a two-attraction pass to $189 for a seven-attraction pass. The Explorer passes are valid for sixty days. These passes are worth it if you are going to see a lot of attractions. Do the math before you get them though!
Redeem hotel points – Be sure to sign up for hotel credit cards and use those points when you travel. There’s nothing better than free accommodation and most cards come with at least 1-2 nights free. This post can help you get started with the basics so you can start earning points today and have plenty for your trip.
Stay with a local – Couchsurfing is the best way to save money on accommodation in Chicago. You’ll not only get a free place to stay but you get to connect with a local who can share their insider tips. It’s perfect for budget travelers who want to make connections.
Look for the happy hours – The Ultimate Happy Hours website lists all the happy hour drink and food specials around Chicago. It’s updated with new info frequently!
Go on a free walking tour – This is a great way to learn the history behind the places you are seeing and avoid missing any must-see stops. Free Chicago Walking Tours has several interesting walking tours that can show you the main sights. Just be sure to tip your guide at the end!
Bring a water bottle – The tap water here is safe to drink so bring a reusable water bottle to save money and reduce your plastic use. LifeStraw is my go-to brand as their bottles have built in filters to ensure your water is always clean and safe.

Where to Stay in Chicago

Accommodations are expensive in Chicago. However, there are a lot of hostels (with private rooms too) and budget hotels that can help keep your costs down. Here are my recommended places to stay in Chicago:

Found Chicago River North
Chicago Getaway Hostel
Parthenon Hostel
Freehand Chicago

For more hostel suggestions, be sure to check out my complete list of the best hostels in Chicago!

How to Get Around Chicago

Elevated train going through tall buildings in Chicago, USA.

Public Transportation – The Chicago Transit Authority operates the L Train (elevated subway train) and the bus system. Their website has a complete list of routes and planning tools. The L Train costs $2.50 USD per journey, which is automatically deducted from your Ventra card (a rechargeable card that you can buy at any L station). The Ventra card itself costs $5 USD, but that amount gets refunded when you register the card.

The train from the airport costs $5 USD. You can also take a city bus, which is $2.25 USD.

There are also passes available, including a one-day pass for $5 USD, a 3-day pass for $15 USD, and a 7-day pass for $20 USD.

Water Taxis – Water taxis are a fun way to get around some parts of Chicago. A one-way ticket between two docks costs between $6USD. You can get an all-day pass with unlimited trips for $10. If you’ll be staying in the city longer, a 10-ride pass is available for $25.

Bicycle – Chicago is incredibly bike-friendly. Divvy is the city’s bike-sharing program. There are 5,800 Divvy bikes and you can get an unlimited day pass for $18.10 USD (for rides up to three hours each). You can also pay $1 USD to unlock a bike and then prices start at $0.18 USD per minute of your ride, depending on whether you take a bike or scooter. You can purchase these passes at station kiosks or via the app.

Taxis – Taxis are expensive here! Everything is meter-based starting at $3.25 USD and then $2.25 USD per mile. Skip the taxis if you can.

Ridesharing – Uber and Lyft are way cheaper than taxis and are the best way to get around a city if you don’t want to take a bus or pay for a taxi. I would definitely take them late at night over the bus too.

When to Go to Chicago

Spring (April to the end of May) and fall (September to the end of October) are both excellent times to visit Chicago, thanks to pleasant temperatures and fewer crowds.

Fall is especially nice, with daily temperatures averaging 60-70°F (15-21°C). You need to pack a sweater for this time of year, but tourist attractions are less crowded and hotel/hostel rooms are cheaper. The parks around the city are full of trees so it’s a great time to see the leaves changing. Chicago also has unique Halloween celebrations like Fall Fest and the Night of 1,000 Jack-o-Lanterns.

Summer (June-August) is peak season in Chicago. It’s hot, with temperatures reaching the mid-80s°F (high 20s°C), and tourist crowds are at their highest. Although it’s nice to take advantage of the weather, keep in mind that prices increase for accommodations and vacancies are low. August can be rainy, so pack a light rain jacket. This is the best time of year for attending outdoor events like the Millenium Park Summer Music Series.

Spring is a good time to visit as well. Temperatures average between 47-70°F (8-21°C), so you’ll want to pack layers. Outdoor activities begin to pick up and you can enjoy time on the river or a day watching a baseball game. There are flower shows and it’s cherry blossom season in the city as well.

Avoid visiting in winter unless you don’t mind some super cold days! The wind can be sharp during the winter months in Chicago. High temperatures average between 31-37°F (-1-3°C), but can feel much colder with the wind. If you want to do a lot of museum hopping or sightseeing indoors, you can save a lot of money on accommodations.

How to Stay Safe in Chicago

Although Chicago gets a bad reputation for crime and violence, it’s still a safe place to backpack and travel. Violent attacks tend to be confined to certain areas (especially where drug and gang violence are a problem) and rarely impact visitors. As a traveler, you’re likely to stick to the Loop, Wicker Park, Bucktown, and the Old Town, all of which are very safe.

Avoid Chicago’s South Side unless you want to see a White Sox game (the L Train stops right outside the stadium).

You might encounter petty crime, like theft, around famous tourist landmarks. Keep an eye on your belongings at all times, especially while taking public transportation.

If you’re approached by strangers asking for money or directions, use caution. This may be an attempt to draw you into an unwanted situation. Give brief, firm answers and move away to an area with more people.

At some attractions, like the Art Institute or the Field Museum, you may get approached by scammers who claim they can give you a cheaper tour inside. Avoid these “guides” as it’s all a scam. Read this post on common travel scams to avoid .

Solo female travelers should generally feel safe here but the standard precautions apply (never leave your drink unattended at the bar, never walk home alone intoxicated, etc.). For more specific tips, visit one of the numerous solo female travel blogs. They’ll be able to provide better tips than I can.

If you experience an emergency, dial 911 for assistance.

Always trust your gut instinct. Make copies of your personal documents, including your passport and ID.

The most important piece of advice I can offer is to purchase good travel insurance. Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. You can use the widget below to find the policy right for you:

Chicago Travel Guide: The Best Booking Resources

These are my favorite companies to use when I travel. They consistently have the best deals, offer world-class customer service and great value, and overall, are better than their competitors. They are the companies I use the most and are always the starting point in my search for travel deals.

Skyscanner – Skyscanner is my favorite flight search engine. They search small websites and budget airlines that larger search sites tend to miss. They are hands down the number one place to start.
Hostelworld – This is the best hostel accommodation site out there with the largest inventory, best search interface, and widest availability.
Booking.com – The best all around booking site that constantly provides the cheapest and lowest rates. They have the widest selection of budget accommodation. In all my tests, they’ve always had the cheapest rates out of all the booking websites.
Get Your Guide – Get Your Guide is a huge online marketplace for tours and excursions. They have tons of tour options available in cities all around the world, including everything from cooking classes, walking tours, street art lessons, and more!
SafetyWing – Safety Wing offers convenient and affordable plans tailored to digital nomads and long-term travelers. They have cheap monthly plans, great customer service, and an easy-to-use claims process that makes it perfect for those on the road.
LifeStraw – My go-to company for reusable water bottles with built-in filters so you can ensure your drinking water is always clean and safe.
Unbound Merino – They make lightweight, durable, easy-to-clean travel clothing.
Top Travel Credit Cards – Points are the best way to cut down travel expenses. Here’s my favorite point earning credit cards so you can get free travel!

Chicago Travel Guide: Related Articles

Want more info? Check out all the articles I’ve written on United States travel and continue planning your trip:

How to Experience Milwaukee Like a Local

The 7 Best Hotels in New York City

The 7 Best Hotels in Miami

Where to Stay in Miami: The Best Neighborhoods for Your Visit

How to Spend 24 Hours in Raleigh, North Carolina

The 6 Best Hotels in Austin

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Traveling to Chicago for the First Time: 13 Tips & Tricks

By Author Jurga

Posted on Last updated: September 8, 2023

Traveling to Chicago for the First Time: 13 Tips & Tricks

Are you traveling to Chicago, Illinois, for the first time and looking for some travel tips for a more memorable and enjoyable visit? In this guide, we share our top tips and useful info for visiting Chicago.

Big city life, cool unique neighborhoods, fantastic food, lakefront fun, and Midwest charm – these are just a few things that await you when visiting the Windy City.

But how to make the most of your visit , see the musts, but also get a bit off the beaten path and simply enjoy the best that Chicago has to offer without getting overwhelmed?

In this guide, we share our top tips that will help you to make the most of your first visit to Chicago. Find out!

These are our top tips for visiting Chicago:

1. Stay in the Heart of the City

If you are traveling to Chicago for the first time, you’re likely planning to see all the main tourist landmarks. For sightseeing, we recommend staying right in the heart of downtown so you will be near all the action. Chicago is a very walkable city, with many attractions close to each other, and the best way to enjoy your trip is to stay as close as possible to the main sights.

A good thing about Chicago is that it has lodging for every budget and every style, from 5-star luxurious hotels to eclectic private rentals in a cool neighborhood.

Where to stay: The Loop is one of the top areas to stay in because it’s where Chicago’s most popular tourist attractions are located. If you do your research and make your reservation right, you should be able to walk or take a short Uber ride to most of the top spots in the city.

Go od to know: The Loop is the 1.79-mile elevated train (called the “L”) that “loops” around the Chicago downtown area. Chicagoans use the term “The Loop” to refer to Chicago’s entire downtown area.

Here are some of the best-rated hotels in this area, for all budgets:

$$$$$ The Langham
$$$$ Hyatt Regency
$$$ Hyatt Place – The Loop (great price/location/quality)
$$ La Quinta by Wyndham
$ Congress Plaza Hotel (a very popular hotel on a lower budget)

Personal favorites: The one thing I highly recommend is finding a room at a boutique hotel like The Blackstone for a much more unique experience than staying at a big hotel chain.

Another one of my favorites is the Chicago classic hotel, the Palmer House (Hilton hotel). Staying at the Palmer House during the holidays is a special experience, don’t miss it! The Palmer House is also within walking distance to Millennium Park, Maggie Daley Park, Cloud Gate (the Bean), and the Art Institute.

Shoppers should stay near the Magnificent Mile while foodies and art lovers will love the River North area, just a few blocks away. This Hilton Garden Inn is well-located for these areas.

TIP: Using the map below, you can also compare hotels and short-term apartment rentals in Chicago city center. Simply insert your travel dates and group size, and you’ll see what’s available for your stay. Check it out!

2. Avoid Bank Holidays & School Breaks

Chicago is a very popular city break destination in the US attracting over 50 million visitors each year.

The busiest times to visit Chicago are, of course, during school breaks and US bank holiday weekends. So if you can, try to avoid these peak periods for fewer crowds and better prices.

Summer life in Chicago is extra special and you are going to want to see this gorgeous city during the warmer months. The winters can be gloomy and grey, so the city really feels like it comes to life when the seasons change.

Now that we told you to avoid the peak times, it would be unfair not to mention that the summer season is popular for a good reason . Even though busy and hot, Chicago is beautiful in summer!

Chicago’s summer festival scene is like no other with various events, such as Lollapalooza, Taste of Chicago, Venetian Night, and the Air and Water Show to name a few. There is always something cool to do! The outdoor dining and rooftop bars in areas like River North & Riverwalk are also a huge part of Chicago’s summer fun.

The nicest time to visit Chicago is April-May and mid-September-October when the weather is pleasant and it’s not as busy as in the peak summer months and not as cold as in the winter. On the other hand, Chicago has so much to offer that you can have the most enjoyable visit at any time of the year. You just have to plan well and adjust your itinerary to the season.

3. Book in Advance

One of the biggest mistakes you can make when visiting any popular destination is not to plan your visit in advance, especially if you are traveling during the busy season. Chicago is no exception.

Starting with accommodations and ending with Chicago attractions – booking in advance means more choice, better prices, and less time wasted queuing. After all, you want to make the most of your trip to Chicago and not spend your precious time standing in line or have to stay at a hotel far from everything because the best options are either too expensive or aren’t available anymore.

Sometimes, tickets for the main attractions are cheaper if booked online at least a day in advance. Not to mention that some activities can sell out. In addition, by booking in advance, you can read customer reviews, compare different options, and avoid disappointment.

If you want to go see a show or a sports game in Chicago, book your tickets well in advance. Sometimes, you can book last-minute as well, but not for the most popular shows/games, not to mention that you usually get the worst seats when booking last minute.

TIP: For skip-the-line tickets to popular Chicago attractions and the most popular tours, we recommend checking the GetYourGuide website . We book all our tickets/ tours via them when we travel – the prices are good, you can read real customer reviews, and easily find the best tour. Furthermore, they have the most flexible cancelation policy and their customer service is amazing. Viator is also a good option and has a big selection of tours and tickets.

Good to know: The most popular tour in Chicago is the Chicago River Architecture Cruise . No visit to Chicago would be complete without doing this.

4. Take Advantage of Different Transportation Options

Chicago has a plethora of options when it comes to public transportation : CTA buses, the L, and the Metra (suburban train) to name a few.

If it’s raining or cold, you can also use the Chicago Pedway , the city’s pedestrian walkway system of underground tunnels and overhead bridges. It’s a great way to easily get around the city center.

If the weather is gorgeous and you are looking for a fun way to explore Chicago check out the city’s bike-share program at various locations all over town. Riding your bike down Lake Michigan and taking in the gorgeous Chicago skyline is always so much fun. Biking is also a great way to cover bigger distances and see more of the city in a shorter time. See also bike tours and rentals for more ideas.

If you’re looking for a fun way to explore the Chicago Riverwalk, Michigan Avenue, or the West Loop area, you can also buy a ticket for the Chicago Water Taxi . This cool mode of transportation connects several Chicago neighborhoods AND they do have restrooms on board.

And, of course, there are hop-on-hop-off buses , segway tours , and so many other fun ways to explore Chicago without having to walk all day.

Airport transfers: The easiest way to get to and from both O’Hare and Midway airports to the downtown area is by rapid trains on CTA . They run 24 hours a day, seven days a week. It will take you about 45 minutes to get from O’Hare to downtown on the CTA Blue Line. And it will take you about 25 minutes from Midway to downtown on the CTA Orange Line. You can also book private transfers online if you prefer not to take public transport, but of course, it will be more expensive.

5. Take Advantage of City Passes

If you are visiting Chicago for the first time, you’ll likely want to see at least some of the main tourist attractions. Sometimes, it makes sense to look into getting a City Pass instead of booking separate tickets for each of them.

There are two best options when it comes to attraction passes in Chicago: Chicago Explorer Pass and the more popular option – Chicago: Go City All-Inclusive Pass. They both cover the same main attractions, but in a different way:

Chicago Explorer Pass allows you to see 3, 4, 5, or 6 attractions of your choice within 2 months from its first activation.
Chicago: Go City All-Inclusive Pass allows you to see as many attractions as you want within a certain period (the number of days purchased). You can get this pass for 1, 2, 3, or 5 days. It’s ideal for those who want to see as much as possible in a short time and can save you up to 45% on the attraction tickets.

Also worth mentioning is the Chicago CityPASS . This pass gives you free entrance to 5 of the main Chicago Attractions over 9 consecutive days. However, it has a rather limited selection of attractions you can choose from. But if those are the ones that you want to see, then it’s a great value as well.

TIP: Be sure to see which attractions are included before deciding if these passes are worth it for you. And if you get a pass, make the most of it! It can be of great value if you use it right.

6. Enjoy FREE Chicago Attractions

A city trip can quickly become quite expensive – there are just so many sights and attractions that you want to see. The good news is that you can also enjoy some of the nicest places in Chicago free of charge.

Here are just a few suggestions of free things to do in Chicago:

Millennium Park, Grant Park, Maggie Daley Park.
Lakefront Trail, parks, and beaches.
Chicago Riverwalk.
Lincoln Park Conservatory and Lincoln Park Zoo.

There are also many free museums in Chicago and some museums offer free museum days. So be sure to do some research before you go and take advantage of it.

7. Foresee Enough Time and Don’t Try to See Everything

If you are traveling to Chicago for the first time, you are probably wondering how much time you need in the city. Chicago is huge and there is no way to see everything in just a few days… So don’t come here thinking that you can see it all in just one or two days.

That being said, you can see most of the main sights in Chicago in 2 days and this makes Chicago a nice weekend-break destination as well. However, this will just be enough time to get a feel of what Chicago is truly about.

If you want to explore a bit deeper, spend some time at the museums, explore some local neighborhoods, etc., we recommend at least 3-4 days in Chicago.

Also, don’t try to see ‘everything’ in Chicago. This is simply not possible and will leave you tired and frustrated. Plan to visit just 2-4 bigger attractions every day and leave some time to experience the food (maybe even go on a food tour ), take a boat trip on Lake Michigan , or get a bit off the beaten path… You’ll have a much more enjoyable trip this way!

View from 360 Chicago observation deck at John Hancock building

8. Spend Time on the Water

One of the best things about visiting Chicago is getting to experience the waterfront fun. Both Lake Michigan and the Chicago River offer so many fun activities and it’s well worth your time.

Chicago has some of the most spectacular architecture in the world. As already mentioned, one of the most popular things to do in Chicago is to take an architecture boat tour down the Chicago River.

Take a bike ride or walk down Lakefront Trail and soak in the lakefront breezes and panoramic views. Hit the beaches (Oak Street Beach and North Avenue are my favorites) for a relaxing day in the sun. Also be sure to take a ride on the giant Centennial Wheel at Navy Pier to see the city from a different perspective.

There are also many companies offering all kinds of boat tours on Lake Michigan, or sometimes a combination of both – the lake and the river. From scenic cruises, lunch- or dinner cruises, to romantic sunset cruises and so much more… It will be hard to choose, but you also can’t go wrong – it’s always worth it.

Lake Michigan and Chicago Skyline at sunset

9. Explore Local Neighborhoods

If you have more than just 2-3 days in Chicago, get out of the city to explore some of the cool neighborhoods beyond the downtown Chicago Loop area! Each neighborhood has its own unique personality.

Explore Chinatown, Greek Town, or Little Italy to feel like you have been transported across the world. Each of these towns has a unique cultural heritage, and – of course – some great restaurants with authentic delicious food from all corners of the world.

TIP: If you want to feel like you’re living in a scene from the old Chicago Al Capone mob days, be sure to check out the iconic Rosebud Restaurant in Little Italy. It has been around for over 40 years and is a celebrity hot spot! Be sure to try their signature Rosebud Meat Lasagna or Chicken Parmesan.

Ping Tom Memorial Park in Chicago Chinatown

10. See a Sports Game

Chicago is one of the top sports cities in the U.S. and Chicagoans take their teams very seriously. No matter what time of year you are visiting you will have the opportunity to paint your face, buy a logo hat, and start cheering for your Windy City favorite!

Here are just a few suggestions:

April – September: Baseball. Check out the Chicago Cubs or the Chicago White Sox .
October – April: Basketball or Hockey. Check out the Chicago Bulls and take a selfie with the towering statue of legendary Bulls star Michael Jordan right outside of the United Center. Hockey fans, check out the Chicago Blackhawks or Chicago Wolves .

TIP: Here, you can see what’s scheduled and find tickets for local sports games .

11. Don’t Miss the Museum Campus

Museum Campus is one of the best things to do in Chicago for anyone that loves to learn. You could spend several days exploring the 57-acre park located in Grant Park right alongside Lake Michigan. But even if you only have half a day, it’s well worth checking it out!

The Museum Campus consists of the Field Museum of Natural History , Adler Planetarium , and Shedd Aquarium all side by side right next to Soldiers Field . The museums are easily walkable along very pedestrian-friendly walkways.

TIP: About 6 miles south of the Museum Campus is another favorite, the Museum of Science and Industry . You could easily spend an entire day here!

Good to know: All these museums are included in the Chicago Go City All-Inn Pass – ideal if you want to just quickly check out a few of them on the same day. Otherwise – if you are on a longer visit – Chicago CityPASS offers a better value because it remains valid for 9 consecutive days, allowing you to spend more time at each museum.

Man With Fish sculpture at Shedd Aquarium in Chicago

12. Wear Layers & Comfortable Shoes

There are some theories as to why Chicago is called the Windy City, and just one of them is the weather. However, it’s often very windy in Chicago indeed, especially at Lake Michigan.

The Lakefront area can sometimes be 10 degrees cooler than other parts of the city. So, no matter what time of the year you visit Chicago, it is wise to wear several layers so that you can adjust and stay comfortable during your visit.

Also, comfortable shoes are a must when visiting Chicago! You’re going to be doing a ton of walking so make sure your feet are prepared for all the mileage.

We also recommend taking a reusable water bottle with you.

13. Eat Like a Local

There are three things that every traveler must experience while they are visiting Chicago. These three things are the most iconic Chicago foods that are Windy City classics:

Chicago Style Hot-Dog . This is an all-beef dog with a poppyseed bun, relish, mustard, tomatoes, and onions. Do NOT ask for ketchup on your Chicago dog, everyone will know you are from out of town. Portillo’s Hot Dogs and ADB (America’s Dog and Burger) serve some of the best Chicago hot dogs! The most convenient ADB location is at the Navy Pier food court.
Deep-Dish Pizza . This saucy thick-crust pizza is one of a kind, and one of the foods you must try in Chicago. Some of the best places for this include Lou Malnati’s, Giordano’s, or Ginos East and you can’t go wrong with either of them.
Italian Beef Sandwich . This is Chicago’s version of Philly’s Cheesesteak (see our guide to Philadelphia for more info). Be sure to get your sandwich “dipped” in the special juice that makes this sandwich a favorite of the locals. Hit up Johnnie’s Beef or Al’s to get some of the best Italian Beef in town.

TIP: Malört (wormwood-based digestif liquor) might be one of the worst-tasting liquors around, but it’s legendary in Chicago. The shot of Malört has become quite a cult classic in Chicago and somewhat of a rite of passage. So give it a try, if you dare!

Chicago Travel FAQ

The best time to visit Chicago is anytime but winter. Winters can be brutal with freezing cold temperatures and lots of snow. Summers are fantastic in Chicago and the best time to enjoy the lake and outdoor fun. For the best weather and fewer crowds, visit Chicago in April – May or September – October.

While there is so much to see and do in Chicago, if your time in Chicago is really limited, don’t miss the architecture river cruise , lakefront, and Willis Tower (formerly known as Sears Tower), the 3rd-tallest building in the Western Hemisphere.

Chicago is famous for its architecture, skyscrapers, Lake Michigan, great sports teams, deep-dish pizza, and fantastic midwestern locals who passionately love their city. It’s also world-known for the green-dyed Chicago River on St. Patrick’s Day.

While there are some areas of Chicago that may not feel safe, visiting the main tourist attractions in the city center, you shouldn’t worry too much. Still, you should always be cautious and it never harms to do some research, especially if you are traveling alone or at night.

Ideally, you plan at least 3-4 days in Chicago, but you’ll be able to see many of the ‘musts’ in 2 days as well. You will never run out of things to do in Chicago, so if you have the time, we recommend staying for a week. This will allow you enough time to see all the main sights, explore the museums, and get a bit off the beaten path as well.

Yes, Chicago is always worth a trip – no matter how little time you have. If you have just 1 day, focus on the downtown area: do a river cruise , spend some time at Millennium Park and Grant Park, and visit Willis Tower Skydeck and potentially also 360 Chicago Observation Deck .

READ ALSO: How to see the best of Chicago in 2 days

You may also like our guides to 1 day in New York , 2 days in New York , and 1 day in Philadelphia . Even on short visits, you can cover a lot of ground and see much more than you think – check it out!

If going southwest, you may like to check our San Diego itinerary suggestions as well as LA itinerary for 3 days .

If you found this post useful, don’t forget to bookmark it and share it with your friends. Are you on Pinterest? Pin these images!

Traveling to Chicago for the first time - tips and info for your visit

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Thursday 9th of March 2023

How to come there

Friday 10th of March 2023

? How to travel to Chicago? Like anywhere else - depending on where you travel from - by plane, by car...

Thursday 7th of October 2021

Hi Jurga, we are visiting Chicago for 3 (full) days. Do you recommend one of the city passes and if so which one? Thx

Friday 8th of October 2021

Hi Charles, it really depends on what you are planning to see and do exactly, but if you are planning to do a lot of sightseeing and visit many places that require a ticket, then I think the Go City All-Inclusive Pass makes the most sense for you. You can get it for 3 days as well, which is a very good value, better than for the shorter durations (it always is with these passes - the longer you stay, the cheaper it is per day).

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Chicago travel blog — the fullest chicago travel guide blog for a great budget trip for first-timers.

Chicago is the third largest US city after New York and Los Angeles. The name of Chicago city derived from a Native American word that means “stinky onion”. It is also known as the “Windy City” which is famous for its fascinating attractions and unique, modern architecture with many high-rise buildings. However, no one knows the exact origin of this name. Just know that most people believe it comes from winds blowing from Lake Michigan into the city. This city is also famous for many spectacular churches and cathedrals with the world’s tallest bell towers and many museums. This is considered an expensive tourist destination in America when it comes to admission fees to attractions, traveling and accommodation, but that doesn’t mean you need a lot of money to travel to this beautiful city of Chicago. So, what to do and how to plan a budget perfect trip to Chicago for the first-time? Let’s check out our Chicago travel blog (Chicago blog) with the fullest Chicago travel guide blog (Chicago travel guide, Chicago tourist guide, Chicago visitor guide, Chicago IL travel guide, Chicago IL visitor guide) from how to get, best time to come, where to stay, best places to visit and top things to do to find out the answer!

Chicago trip blog — The fullest Chicago travel guide blog on my trip to Chicago
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Today, Chicago is an cosmopolitan city with a wide variety of different ethnicities, beliefs, cultures, cuisine, parks and shopping malls. If you love shopping, the brand stores on the Magnificent Mile street are the shopping places for you. And if you love special, stunning architecture? Chicago has a lot of skyscrapers to admire with modern architectural styles mixed with the traditional styles of buildings such as Willis Tower, Aqua Tower, Tribune Tower, 875 North Michigan Avenue (formerly known as John Hancock Center) and Chicago Water Tower.

If it’s shopping you want, go to the “Magnificent Mile” a trendy section of Michigan Avenue.

Chicago travel blog: An overview of the city of Chicago

Chicago is a large and bustling city located in the state of Illinois, USA, right next to the large lake of Michigan. With an area of 606.1 square kilometers (Chicago Metropolitan Area is 28.120 km²) and a population of more than 2.6 million people (the current metropolitan area population in 2021 more than 9.5 million people). Chicago is currently the third largest city in the United States and also the largest city in the State of Illinois and the Midwestern United States. After the civil war in 1812, the residential areas were relocated to the outskirts of the city until the 1830s people gradually returned to resettle in Chicago. Since that time, the city of Chicago has played an important role in American history.

Chicago is a modern, thrive and developed city located in the southwestern part of Lake Michigan was founded in 1837. In 1871, the city was burned mostly by the Great Chicago Fire. More than 300 people were killed, 18.000 buildings were destroyed and more than a third of the city’s residents became homeless. One of the main reasons causing this great fire is that the architecture of the city is mostly by wood and the streets are very small and narrow. From this massive disaster, the city government had to set a series of extremely strict fire safety rules including the construction of buildings, thereby it has been changing the traditional architecture of the city.

Chicago is also known for its main rail line connecting the Western and the Eastern of the US, Chicago is home to the largest meat packaging industry in the United States. Beef is shipped from Texas and surrounding areas here and is processed, packaged and shipped around the world.

Chicago travel blog: When to visit?

The best time to visit Chicago is in April and May, when summer is yet to come and less tourists. If you want to participate in prominent festivals of the city such as the Chicago Pride Parade and the Chicago Blues Festival , you should plan your trip in June to August.

best time to visit chicago Image by: chicago travel blog.

The fall begins from September to October is a suitable time for nature exploration trips, hiking. From November to March is the time to take part in the exciting winter activities.

Chicago blog: How to get to Chicago?

Chicago is located in the Midwestern of the US and it owns 2 international airports, O’Hare Airport (ORD) and Midway Airport (MDW) . From Vietnam, if you want to flying to this city, you can easily buy air tickets from airlines such as Korean Air, China Airlines, Cathay Pacific, American Airlines, … Fares usually ranging from $525 to $1.200 depending on the time of travel and airline.

Getting to the city center

From O’Hare Airport to the city: The airport is about 18.1 mi from city center. You can take the Blue Line ‘L’ train is the easiest way to get from O’Hare Airport to city center which takes about 21 minutes and costs $5/way. You can take the Blue Line at Terminals 1, 2, and 3 by just following the signs at the airport that say “CTA Trains” or “Trains to the City.” See more here.

From Midway Airport to the city: The airport is about 11.6 mi from city center. You should take the Orange Line train from Midway (on the southwest side of Chicago) to city center via elevated tracks. All routes from the Midway Airport station will go to the downtown Loop. The traveling time to city center from Midway is 20-25 minutes and costs $2.50/trip or less. See more here.

You also take taxi or rent a car or using Uber or Lyft service to get to downtown Chicago. Details fares you can see the table below.

Chicago travel guide blog: Transportation in Chicago

For trips to explore the city of Chicago, you should choose the means of the Elevated train “L” (Chicago “L”) operated by Chicago Transit Authority (CTA) which serving the city of Chicago 24/24 service with 102.8 mi (165.4 km) with 8 lines, is the 4th largest rapid transit system in the US and some of its surrounding suburbs; taxi; water taxi or Uber, Lyft. For a unique and cost-effective experience, walking or using a bicycle is also a good choice. Even so, the city of Chicago is very crowded so it will be difficult to find a parking space, so be aware of this matter.

Buses have always been one of the most used types of public transport in Chicago. It is not only convenient and also very cheap. Even Chicago also has a bus system that specializes in serving people with disabilities.

This is a very unique type of transportation in Chicago. The perfect combination of sightseeing and transportation, these water taxis will help you get to the many popular tourist attractions of the city at a low cost of traveling.

Alternatively, if you want to leisurely getting around, breathing in the fresh air of Chicago with short distances, you can use the Divvy bike sharing system or walking.

In addition, you can also use technology ride-hailing service such as Uber and Lyft , which is very convenient and affordable, a bit more expensive than buses, but much cheaper than taxis.

Chicago travel blog: Where to go and what to do?

Millennium park.

This is a famous park built on an area of 24.5 acres (99.000 m2). This park currently owns a large music stage and is equipped with modern sound and light systems with a capacity of up to 11.000 people. In addition, visiting the Millennium Park, you also have the opportunity to admire many unique and impressive sculptures.

Located in the heart of the city, this large park offers a lot of green space and is where a lot of talented chess players who can defeat any chess player from elsewhere. Millenium Park also has a beautiful outdoor restaurant, a large and modern musical stage with two towering glass structures that make up the famous Crown Fountain. The park opens all-year round and this is one of my favorite spots in Chicago.

Address: 201 E Randolph St, Chicago, IL 60602, United States Opened: July 16, 2004 Access: Millennium Station (Washington/Wabash and South Shore Line)

Cloud Gate (The “Bean”)

Cloud Gate is considered the most signature symbol of the city of Chicago and is a highlight in the architecture of Millennium Park. The Cloud Gate was designed by British Indian sculptor Anish Kapoor, inspired by liquid mercury crystal drops. The construction is made of stainless steel weighing 110 tons, 11 meters high, 20 meters long and 13 meters wide. From the outside, the Cloud Gate is like a giant bean that reflects the sky and the skyline of the city of Chicago, so it is also known as “The Bean”.

Navy Pier, formerly a US navy base, has now become a tourist dock with many restaurants, bars, theaters, parks and souvenir shops. It also holds the record for being the world’s longest pier. Navy Pier can be said to be the most bustling entertainment hub of the city. When coming here, visitors can strolling on the busy streets, watching interesting circus performances at Pepsi Skyline stage, enjoy lunch and experience the city of Chicago by taking a sightseeing boat tour along Chicago river or sit on the giant ferris wheel while watching the tranquil of Lake Michigan.

Navy Pier Centennial Wheel Chicago

Opening hours from 10am to midnight depending on the season and especially without entrance tickets, only admissions to access a few special spots.

Address: 600 E Grand Ave, Chicago, IL 60611, United States Area: 14 ha Year built: 1916 Hours: 10AM–12AM

The Art Institute of Chicago

Located in Chicago’s Grant Park, was founded in 1879 and it owns one of the most impressive art collections in the United States, the Art Institute of Chicago is a must-visit place of the city. There are more than 300,000 works from all over the world and many art exhibitions are held every year which giving you a meaningful tour.

Address: 111 S Michigan Ave, Chicago, IL 60603, United States Hours:11AM–6PM/Tuesday; Wednesday: Closed

One of the Chicago’s most popular tourist attractions is its museums. Some of the interesting museums include: Art Institute of Chicago , Field Museum , Museum of Science and Industry , Chicago History Museum … These are large-scale museums with lots of valuable workarts and entrance tickets are quite expensive. However, these museums often offer free days of visit and coupons, so as long as you plan in detail, free admission is not impossible at all.

Shedd Aquarium

Although it was built in 1930, the indoor public aquarium Shedd Aquarium is still considered one of the largest aquariums in the world. The aquarium will give you a very detailed view of marine life. The aquariums here are extremely huge and the explanations and descriptions are also very detailed. There are more than 32,000 marine species living here including about 1500 species of fish, large and rare species such as whales, white dolphins, sea lions, …

Address: 1200 S Lake Shore Dr, Chicago, IL 60605, United States Hours: 9AM–5PM Total volume of tanks: 5 million US gallons (19,000 m3) Admission fee is 39.95 USD / adult and 29.95 / child under 11 years old.

Chicago Water Tower

This is a beautiful water tower designed by William Boyington with a height of up to 115m and was built in 1869. The water tower of Chicago is not only beautiful but also considered one of the two oldest water towers in the United States. In addition to playing an important role in providing water source for the entire city, the Chicago Water Tower is also a popular tourist spot.

In 1872, a great fire broke out and destroyed all the structures surrounding this water tower, only it remained. Currently, this place is also a museum as a name City Gallery in the Historic Water Tower which displaying many unique works of famous photographers and artists around the world.

Address: 806 Michigan Ave, Chicago, IL 60611, United States Hours: 10AM–7PM Architectural style: Gothic Revival architecture

Willis Tower

Having came Chicago without visiting the Willis Tower is a biggest regret. With a height of up to 442, 527 m to tip, Willis Tower held the record for the tallest tower in the world for 25 years. And to this day, it is still considered the tallest steel structure in America.

Willis Tower (Former name: Sears Tower (1973–2009)) has 110 storey and possesses a very unique architecture covered in a prominent black appearance, dominating the sky of Chicago. Standing at its skydeck, you can panoramic view of the beautiful city of Chicago from above. The best time to visit this tower is at night when the whole city starts to light up creating a very sparkling, fanciful scene.

Located on the 103rd floor of the Willis Tower, Skydeck Chicago offers guests a great view of the city. Therefore, this is a prominent tourist attraction, attracting more than 2 million visitors each year.

Address: 233 S Wacker Dr, Chicago, IL 60606, United States Construction started: 1970 Skydeck ticket price: Adult – Ages 12 and up: $26.00-$30.00/Youth – Ages 3 to 11: $14.00-$18.00/Children under 3 are FREE!

Chicago CityPASS

To save your money when visit Chicago attractions, you should buy Chicago CityPASS is an all-inclusive pass. With this pass you can freely access and skip-the-line of many attractions such as the Shedd Aquarium, the Field Museum, and Skydeck Chicago. Moreover, it will grant you a choice to be able to access the Adler Planetarium or the Art Institute of Chicago. You’ll also be able to select an admission to freely visit the Museum of Science and Industry or the 360 Chicago Observation Deck.

You can also refer Go Chicago – All Inclusive Pass and Go Chicago – Explorer Pass with a lot of privileges even better Chicago CityPASS.

Frederick C. Robie House

This masterpiece was designed by Frank Lloyd Wright and completed in 1909 and is a prime example of the Prairie School design school. Wright contributed to the shaping of Chicago’s architectural style and this place became one of the most famous works in Chicago.

Address: 5757 S Woodlawn Ave, Chicago, IL 60637, United States Opened: 1909 Hours: 10AM–3PM/Tuesday, Wednesday: Closed Admission: 18 USD / adult, discounts for students, the elderly, soldiers and children.

Lake Michigan

The famous Chicago tourist attraction not to be missed is the beautiful Lake Michigan that is considered the air conditioner of the city. It helps to keep lakeside neighborhoods warmer in winter and cool in summer. Michigan is one of the North America’s Five Great Lakes ( Superior, Michigan, Huron, Erie and Ontario) is a precious freshwater resource from melting ice and no algae. Especially if you come to the Wind City in August, visitors will be witnessed the spectacular performances of jets above the blue lake.

Movable Bridges

It is also one of the many features and will make visitors delightful when coming to Chicago. There were 56 movable bridges in the past, but due to the city’s development they were gradually being replaced, so up to now, there are only about 38 remains.

Chicago is famous for its many stunning churches with unique architectural styles. Chicago can be considered as home to the churches with the tallest bell towers in the world. Even there is a bell tower up to 180m high and it is the tallest bell tower in the world. Chicago’s cathedrals are very beautiful, notably St. Josaphat Parish , St Adalbert’s Catholic Church, and especially St. Mary of the Angels . If there are churches built in the style of Byzantin, it is not difficult to find Ukrainian or Icelandic churches such as St. Nicholas Ukrainian Catholic Cathedral.

Grant Park and the Buckingham Fountain

Also known as Chicago’s front yard, Grant Park is a huge park covering an area of up to 129 ha, loved by locals and tourists. At the center of the park is the Buckingham fountain – one of the largest fountains in the world.

Buckingham Fountain which opened in 1927 in Beaux-Arts architecture, Historicism architectural styles was built in 1927 and inspired by the Latona fountain at the Palace of Versailles in France. This fountain has a total of 193 jets, every 20 minutes, these jets begin to push water gradually higher, the highest water column can be up to 46m. Buckingham fountain only operates from April to October, in winter months, it will be decorated with colorful lights.

Address: 301 S Columbus Dr, Chicago, IL 60605, United States

Magnificent Mile Avenue

Chicago has a special street called the “Magnificent Mile” that connects the north part of the city to near Lake Michigan which is very wide and beautiful. On this avenue there are more than 450 stores, supermarkets, high-rise buildings… selling everything from household appliances to fashion.

This shopping street has long been considered one of the symbols of Chicago. This is the most shopping and entertainment place in Chicago with hundreds of luxury stores such as Nike, Apple, Disney, Tommy, Gucci, Hermes, … Not only that, you can also enjoy many delicious dishes in luxury restaurants along the Magnificent Mile Avenue.

In addition, the avenue is also home to the Museum Of Contemporary Art Chicago, world-class 5-star hotels, first-class bars and pubs along with many famous media and press centers for visitors to explore.

Chicago River

Admiring the architecture along the Chicago River is the fun thing to do in Chicago. However, the boat tour price is not cheap, the fare per person for a cruise trip is about $20, but you can completely apply the tip to save money by taking a water taxi which running from Michigan Avenue to Chinatown. Traveling by water taxi not only saves you money but it also free offer the opportunity to see famous buildings along the banks of Chicago river and visit best restaurants in Chicago.

Lincoln Park Zoo

Nestled in lagoons and mature (old-growth) forests, the Lincoln Park Zoo is one of America’s most exciting stops. It offers a close-up view of the world-class wildlife. Moreover, the zoo is also an interesting weekend stop with a quiet space, bring you temporarily away from the hustle and bustle of urban life.

Established in 1868 the Lincoln Zoo is one of the oldest zoos in the United States. The place is sought-after for recreational, educational and conservation activities. Here, you will find the slogan “Lincoln Zoo is everyone’s zoo” and is open daily with a free admission.

Lincoln Park Private Photo Shoot and Walking Tour in Chicago

Chicago featuring zoo animals and land animals as well as a couple

Address: 2001 N Clark St, Chicago, IL 60614, United States Hours: 10AM–5PM

Chicago blog: What and where to eat?

The city of Chicago is famous for many famous restaurants, of course the cost of eating is also not cheap at all, the price of a meal at these restaurants is about $85 to more than $150 / meal. You can absolutely enjoy the delicious and famous dishes from the top chefs prepared right at the restaurants with prices ranging from $10 – $20 per dish.

Here are some signature dishes you should try.

Chicago-style Stuffed Pizza

Chicago stuffed pizza is one of Chicago’s famous dishes and you can easily find it anywhere in the city whether it’s a sidewalk eaterie or at restaurants. It is prepared following several different styles that developed in Chicago. The most famous version is the deep-dish pizza. The pan in which it is baked gives the pizza its characteristically high edge which provides ample space for large amounts of cheese and a chunky tomato sauce.

Some famous places where you can taste it such as:

Burt’s Place (8541 Ferris Ave, Morton Grove, IL 60053)
Bartoli’s (1955 W Addison St, Chicago, IL 60613)
The Art of Pizza (3033 N Ashland Ave, Chicago, IL 60657)
Pequod’s (2207 N Clybourn Ave, Chicago, IL 60614)
Milly’s Pizza in the Pan (1801 N Spaulding Ave, Chicago, IL 60647)

Jibarito Sandwiches

The jibarito is a Puerto Rican staple of Chicago cuisine, is a sandwich made with flattened, fried green plantains instead of bread, garlic-flavored mayonnaise, and a filling that typically includes meat, cheese, lettuce and tomato and may have a few copycats out there.

Some best places to eat jibarito:

El Picosito Jibaro (3216 W Lawrence Ave, Chicago, IL 60625)
La Cocina Boricua De La Familia Galarza (2420 W Fullerton Ave, Chicago, IL 60647)
Casa Yari (3268 W Fullerton Ave, Chicago, IL 60647)
Jibaritos y Mas (3400 W Fullerton Ave, Chicago, IL 60647)
The Jibarito Stop (1646 W. 18th St, Chicago, IL 60608)

Chicago-style hot dog

This dish is known as the “tycoon of street food” in Chicago because of its popularity. The hot dog is placed in the steamed bun, topping with yellow mustard, chopped onions, sweet green pickle relish, onion, tomato wedges, a dill pickle spear, pickle spear, sport peppers, … and a dash of celery salt.

Chicago also has a bustling nightlife with countless of bars, pubs opening through the night, the perfect places to sip a cocktail, beer or wine and witnessing a vibrant nightlife of the city. If you want to try the signature Chicago drink, call Chicago Fizz Cocktail is a classic and stylish cocktail which is made from rum, ruby port, egg white and soda to create a delicious drink. Or try The Chicago Cocktail is a brandy-based mixed drink probably named for the city of Chicago and is made from spirits and champagne (Lemon wedge, superfine sugar; Brandy; Fresh lemon juice; Orange curacao; Maraschino liqueur).

Chicago travel blog: Where to stay?

If you have a tight budget when traveling to this expensive city, you should not rent hotels in central areas or on Magnificent Mile avenue because the room rates is very high. To rent cheap hotels, you should stay in Lakeview, Lincoln Park and Bucktown neighbourhoods or hotels near Michigan Avenue or rent hotels far from the city center, the price is cheaper. However, it is advisable to rent hotels near main roads to conveniently travel to tourist attractions which located around city center.

Below we recommend more best cheap, budget, mid-range and upscale hotels with good ratings and reviews you can refer to.

The Langham, Chicago , a top rated 5-star hotel with room rates from $449/night (Check rates on Agoda.com or Booking.com ).
Sofitel Chicago Magnificent Mile , a top rated 5-star hotel with room rates from $188/night (Check rates on Agoda.com or Booking.com ).
Hilton Chicago/Magnificent Mile Suites , a top rated 5-star hotel with room rates from $143/night (Check rates on Agoda.com or Booking.com ).
Radisson Blu Aqua Hotel , a top rated 4-star hotel with room rates from $161/night (Check rates on Agoda.com or Booking.com ).
The Talbott Hotel , a top rated 4-star hotel with room rates from $161/night (Check rates on Agoda.com or Booking.com ).

Some best day tours, trips, activities and transfer services, tickets in, from and to Chicago you can refer to

Go Chicago – All Inclusive Pass
Go Chicago – Explorer Pass
360 Chicago Observation Deck Ticket
Chicago Broadway Show Ticket in New York
Chicago Big Bus Hop-On Hop-Off Tours (Open-Top)
Chicago Segway Tours
The North Of Chicago Tour
Best of Chicago Grand Tour with River Cruise/Chicago Style Pizza Combo
Shared Chicago Airports (ORD/MDW) Transfers for Chicago

Are you looking for more top things to do in Chicago: Tours, activities, attractions and other things? Let’s check it out here . And My Chicago trip blog — The fullest Chicago travel guide blog on my trip to Chicago.

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A Chicago Family Vacation – 4 Day Itinerary

June 13, 2019

Chicago is a huge and diverse city to visit. From incredible food, architecture, and lots of world-class attractions and museums – it is perfect for a family trip. We decided to spend Payton’s 10th birthday celebrations in the state of Illinois, road-tripping to Alton and Grafton and exploring the Great Rivers and Routes along the way. The last stop was a Chicago family vacation we had been dreaming about. Here is our 4 day itinerary to give you some ideas for your own trip!

Disclaimer: We were hosted by Choose Chicago, and most of the activities and restaurants featured below. However, as always, all opinions are my own.

Payton and John - A Chicago Family Vacation

Accommodation in Chicago

Our favourite hotel in Chicago is Loews ( 455 N Park Dr ). We just cannot say enough good things about this hotel. Perfect location, helpful staff, amazing views of Navy Pier and Lake Michigan, excellent dining options in ETA and Streeterville Social rooftop restaurant, and so much more. Loews Chicago is kid friendly, pet friendly, and perfect for a Chicago family vacation.

4 Days in Chicago

Day 1: architecture river cruise + riverwalk + the bean, shoreline sightseeing architecture cruise.

Chicago is famous for its architecture, and this cruise allows you to learn more and admire the beauty of it all. The tour lasts about 75 minutes and features over 40 Chicago landmarks. It is definitely a great way to begin your Chicago adventure and orientate yourself. Shoreline Sightseeing also offers Classic Lake Tours and Fireworks Tours (during the summer); leaving from either Navy Pier or Michigan Avenue. The boat was comfortable, and the guide was knowledgeable. The snack bar was perfect for kids and adults alike.

Shoreline Sightseeing - A Chicago Family Vacation

The Riverwalk in Chicago is one of the most well-developed and beautiful urban trails we have seen. Allowing you to take in the sights, along this path and riverside boardwalk. It’s the scenic route to connect lots of parts of the city center!

No visit to Chicago is complete without a visit to The Bean right? It’s real name is ‘ Cloud Gate ‘, and it was designed by British artist, Anish Kapoor.

Payton enjoying Cloud Gate - A Chicago Family Vacation

Dining on Day 1: SafeHouse Chicago

Looking for a unique dining experience? SafeHouse Chicago combines fun, theater and immersive dining. A spy museum, an escape room, an awesome dinner, a scavenger hunt, a magician, and more. All rolled into one fantastic evening that far exceeded our expectations of themed dining. Become an undercover spy for an evening at SafeHouse Chicago !

SafeHouse Chicago dining - A Chicago Family Vacation

Day 2: The Field Museum + Chicago Food Planet + 360 Observation Deck

The field museum.

Upon entry you can’t help but notice the vastness and beauty of this museum. Immediately you come face-to-face with the largest dinosaur that ever lived. The Titanosaur is the biggest dinosaur that scientists have discovered to date and is one of the first things that you see on the main floor as you enter. This touchable cast reaches 122 feet across and 28 feet tall at the head and truly conveys the sheer size of the biggest animal to ever live.

At The Field Museum you can also see Sue the Tyrannosaurus Rex. This T-Rex is named after Sue Hendrickson, an American explorer and fossil collector who discovered the remains. SUE is the most complete T-Rex fossil skeleton to be discovered and sits here at Field Museum, 90% complete.

You can also learn about the Tsavo man-eaters – the lions that hunted railway workers in Africa at the end of the 19th century. Upon returning home, we the fictional movie The Ghost and the Darkness , which recounts this story too!

Thanks to our Chicago City Pass, we had access to lots of museums and attractions in Chicago. Is the City Pass is right for you ?

Chicago Food Planet

Fancy learning about the Chicago food scene? We headed over to Navy Pier to visit Chicago Food Planet for a decadent lunch. We got to try our first ever Chicago style hot dog, deep dish pizza, and more!

If you’re looking for additional Chicago tour companies during your Chicago family vacation, check out this comprehensive guide: 24+ Best Chicago Tours !

Chicago style hot dog - A Chicago Family Vacation

TILT at the 360 Chicago Observation Deck

Located 1,000 feet above the Magnificent Mile in the iconic John Hancock Building, 360 Chicago Observation Deck offers breathtaking views of the city skyline and Lake Michigan. 360 Chicago is also the home of TILT – an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th floor! Would you dare to Tilt?

Payton loved it and looks much more relaxed in this video than John does. Cameras and videos are not allowed during TILT, but being visiting media, I was allowed to video them during their experience. Of course, as soon a they were done, I had to put the camera away and try it myself. It’s certainly not for those afraid of heights – but feels very safe.

Chicago 360 Observation Deck - A Chicago Family Vacation

Happy Hour at Signature 95

After our daring adventure of tilting out over Michigan Avenue, I needed a drink! We headed to Signature 95, located on the 95th and 96th floor of the same building, for a refreshment.

View this post on Instagram Happy hour over 1,000 ft above the streets of Chicago @signatureroom95 @choosechicago #happyhour #ouradventures #familytravel #chicagoriver #enjoyillinois #travelblogger #winetravels #chicago #windycity #chicagoskyline #midwestmoment #chicagoriver #chicagoeats #signatureroom #theviews #traveltribe A post shared by Endless Family Travels (@endlessfamilytravels) on May 9, 2019 at 2:51pm PDT

TIP: Here we were able to relax and unwind while taking in the breathtaking views of the city and Lake Michigan. I must mention to the ladies, if you visit the lounge, you MUST visit the restroom during your time there (even if you don’t have to actually use it). Some of the most amazing views of the city below are from the huge windows in the lady’s restroom.

Dining on Day 2: Texas de Brazil

If you’ve never been to a Brazilian steakhouse, then you must try it at Texas de Brazil. This chain was founded as a family-owned business in 1998 in Addison, Texas; and is now the largest Brazilian-American steakhouse brand. Each location offers a lively ambiance and rodizio-style dining, and has an expansive salad area, an open grill kitchen, and an award-winning wine cellar.

This unique dining experience can be controlled by using a token on your table which signals to the servers whether you want more food. Hungry for more, turn the token over to green. Getting full and want to slow it down, turn the token to red. Control the pace of your own dining experience, and try lots of delicious Brazilian barbecue!

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Day 3: Shedd Aquarium + Adler Planetarium + Lakefront Trail

These two fantastic attractions are located along the Lakefront Trail, within walking distance of each other on the beautiful Lake Michigan. The Field Museum is also in this area.

Shedd Aquarium

Shedd Aquarium is included with the Chicago City Pass , and you get priority entry – which saves so much time. We have visited multiple aquariums around the country and feel that all of them have something unique to offer. This aquarium opened in May of 1930 and was, for some time, the largest aquarium in the world with 5,000,000 US gallons of water. It also contains 32,000 animals – wow!

I could fill this entire feature with pictures from the Shedd Aquarium – it has so many beautiful displays. We arrived at 9am just as they opened and began exploring. The aquatic presentation is included with admission and is a must during your visit, but arrive early because seats fill up quickly!

Adler Planetarium

During our recent space studies, Payton had learned about early space travel and some of the first astronauts. The displays at the Adler Planetarium really brought all of that knowledge to life. This museum is really large and requires a significant amount of time to fully explore. So I recommend the whole afternoon on Day 3 to really see it all. We enjoyed the exhibits and also the hands on activities that Payton could take part in.

Lakefront Trail

The walkway connecting the aquarium and the planetarium is worth stopping to admire too. Some of the most amazing views of the Chicago skyline can be seen from here in my opinion. Not to mention the expansive Lake Michigan. Most of my photos of Payton explain why Chicago was named the ‘ Windy City ‘!

Payton in the Windy City - A Chicago Family Vacation

Dining on Day 3: Steak 48

Sometimes Yelp really does come through for you. This is how we discovered Steak 48 . It managed to exceed the already great reviews in our estimation. First of all, the place is huge with tons of seating – perfect for when you are traveling with family. Second, the food is just outstanding. I ordered the bone-in filet (a first for me) with an egg. It was so tender that there was no need for a steak knife.

For our dessert connoisseur daughter, a chocolate sundae with cookies and creme popcorn! Very original and delicious according to Payton.

Day 4: SkyDeck + Museum of Science and Industry + A Show!

Day 4 begins at Willis Tower, known to the locals as the Sears Tower…

The Ledge at the Skydeck

Would you dare step outside of the tallest building in the Western Hemisphere, on nothing but glass? At 1,353 feet in the air, the Ledge’s glass boxes extend 4.3 feet from the SkyDeck and provides an amazing view of the city. That first step can be unnerving, but Payton never hesitated and made the most of every second of her time on the Ledge!

View this post on Instagram Would you step out on the ledge @skydeckchicago with only glass separating you from the streets of Chicago 1,353 feet below? Payton didn’t just step out, she lived the moment to the max as she always does! No fear in this one, our adrenaline junkie! @skydeckchicago @citypass @choosechicago @john.biggers.37 #chicago #chicagoskyline #chicagoriver #ouradventures #familytravel #travelblogger #skydeckchicago #skydeckledgechicago #whattodoinchicago #ouradventures #nofear #adrenalinejunkie #adrenalinerush #citypasschicago #midwestmoment #enjoyillinois A post shared by Endless Family Travels (@endlessfamilytravels) on May 11, 2019 at 10:27am PDT

Museum of Science and Industry

The Museum of Science and Industry is about 8-10 miles from the other attractions, but well worth the drive.

One of the most interesting exhibits we explored was the U-505 Submarine. Highlighting the 75th anniversary of the capture of this German submarine. I was not even aware that the submarine was housed here until we arrived.

They offer tours of the U-505 Submarine, but you must book ahead

U-505 Submarine at Museum of Science and Industry, Chicago

Blue Man Group

If you have never seen Blue Man Group before then you should definitely check them out while you’re in Chicago. We have seen them in Las Vegas, but the group in Chicago has added some twists to make it original. We enjoyed the show greatly and Payton was still laughing hours after it ended.

The show lasts for 90 minutes, with no intermission and includes members of the audience in many scenes. Add the Blue Man Group show at the Briar Street Theater to your Chicago family vacation.

Blue Man Group - A Chicago Family Vacation

Dining on Day 4: ETA or Streeterville Social at Loews

If, like us, you are exhausted after your 4 days in Chicago with the kids, then I recommend the laidback atmosphere and great food from the restaurants at Loews. The Streeterville Social rooftop bar is worth a visit for its views alone!

Top Tip: The starting point of the Historic Route 66 is in Chicago, at the intersection of Jackson Boulevard and Michigan Avenue!

Historic Route 66 starting point - A Chicago Family Vacation

Let us help you plan your Chicago family vacation, with our full service Travel Agency !

4 Day Itinerary for a Chicago Family Vacation

4 days in Chicago, the Windy City , is enough to get a really good taste of this huge city. The city center is very walkable, and visitor-friendly. If you are visiting for any less than 4 days, that I recommend you definitely do a river tour, and get to one of the museums or Art Institute . As well as enjoy the marvellous street art and riverwalk – the city really is beautifully designed. A 4 day Chicago family vacation could be perfect for you and your loved ones – what do you think?

Have you visited Chicago? If so, what did you enjoy the most?

Endless Family Travels is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com.

24 thoughts on “A Chicago Family Vacation – 4 Day Itinerary”

sounds like the perfect trip to Chicago – we visit there often and always have a wonderful time!

What an unforgettable birthday celebration! Looks like a blast!

It has been many years since I visited Chicago. I enjoyed the musical LES MISÉRABLES.

That dessert looks amazing! Chicago is such a fun trip!

What a fun family adventure! Love those tilting images!

Hooray for the Architecture tour!

The only time I’ve been to Illinois was for boot camp! I hope I get to go back one day to explore more than a military base. 😑

Oh this makes me miss Chicago!! Such a fun city. I can’t wait to see the newly remodeled parts of Navy Pier!

oh i remember it well. fun to see the photos

I had no idea RT 66 start there! Looks like a wonderful trip!

You guys were in my backyard. We lived in the neighborhood behind the Bean. Miss & love Chi. Glad you guys had a blast.

What a fun vacation! When I get to Chicago, I will use these ideas!

Your daughter has amazing energy and I love her adventurous spirit!

Sounds like a great trip. Chicago is an amazing city!

I’ve never been! It looks so fun. I will have to check it out for sure.

Your hotel looks amazing! Love Chicago! Your daughter will remember this for trip forever.

Many years ago we did a river boat tour of Chicago, such an awesome way to see the city! My sister lives there now, these are some great ideas for when we go to visit her!

That SafeHouse sounds like a mix of all the overpriced touristy things I want to do when I travel–but rolled into one! I’ll definitely keep that in mind!

Wow! Chicago never fails to deliver! Going on a tour is the best idea especially if the place is as big as Chicago. Looks like you and the family had an amazing time!

The pictures were really awesome!

I love Chicago. I’ll usually take a train ride up there. Science and Industry is my favorite museum. One thing if you go by the Chicago Tribune, they have iconic artifacts on the wall.

Thanks for the info! We will definitely be back and will have to check this out!

Great post, reminded me of when we went to Chicago quite a few years ago now!

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CHICAGO - JULY 01: Children check out the view from the Ledge, a new glass cube that juts out from the 103rd floor Skydeck of the Sears Tower, during a media preview July 1, 2009 in Chicago, Illinois. The 1,353 foot high observatory will open to the public tomorrow. (Photo by Scott Olson/Getty Images)

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Chicago beach named among the best in the US by Travel and Leisure

CHICAGO - A Chicago beach has been recognized as one of the best beaches in the United States by Travel and Leisure, joining the ranks of popular beaches in Hawaii, Florida and California.

The 25 Best Beaches in the USA list, published earlier this month, names 25 of the best beaches in the country, listing Oak Street Beach in Chicago among the best in the nation.

The publication describes Oak Street Beach as: "Usually, you have to leave urban areas to find the best shorelines, but this Midwestern metropolis is one of the few exceptions. The impressive Chicago skyline serves as the backdrop for this popular beach, located on the shores of Lake Michigan. Lounge chairs, umbrellas, and cabanas are available for rent, and there's a variety of food from local vendors. Bikers, joggers, walkers, and roller-skaters abound on the paved path surrounding the beach. Relax in the sun, people-watch, or get in on a volleyball game or chess match — the choice is yours."

CHICAGO, ILLINOIS - JUNE 03: A lifeguard keeps watch over beachgoers at Oak Street Beach on June 03, 2021 in Chicago, Illinois. (Photo by Scott Olson/Getty Images)

The other beaches on the list:

Poipu Beach, Kauai, Hawaii
Ocean City, Maryland
Coronado Beach, San Diego, California
Pope Beach, Lake Tahoe, California
Clearwater Beach, Florida
Harris Beach, Oregon
Glass Beach, Port Townsend, Washington
Oak Street Beach, Chicago, Illinois
Carlsmith Beach, Hilo, Hawaii
Wrightsville Beach, North Carolina
Grand Haven State Park, Michigan
Santa Monica Beach, California
Medano Creek, Great Sand Dunes National Park, Colorado
North Beach, Tybee Island, Georgia
Good Harbor Beach, Gloucester, Massachusetts
Rockaway Beach, Queens, New York
Crystal Lake State Park, Baron, Vermont
Gulf Shores Public Beach, Alabama
Asbury Park Beach, New Jersey
Carmel Beach, Carmel-by-the-Sea, California
Coligny Beach Park, Hilton Head, South Carolina
Alki Beach, Seattle, Washington
Ocean Beach Park, New London, Connecticut
Coney Island Beach, Brooklyn, New York

Travel and Leisure does not reveal its methodology, but does say "Different criteria define the perfect beach for different people, such as the quality of the sand, the waves (or lack thereof), level of seclusion, public transportation and accessible parking, whether there's a boardwalk, activities, and even the amount of shade. Some beaches are found next to crystalline lakes, while others are beneath the peaks of majestic mountain ranges. Some are surf havens with stellar waves, while others cater to families with calm waters and things to do right on the sand."

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The Guilty Pleasures of the Chicago Athletic Association

The 1-Key Chicago Athletic Association has had an illustrious and sometimes sordid history that dates back to 1893, when it wasn’t quite a hotel. A lot has changed since then, but the ghosts of the past are never far away.

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As the Chicago World’s Fair entertained millions in 1893, a man by the name of H.H. Holmes was supposedly luring revelers to his nearby hotel. Just three miles west of the famous expo, torture rooms on the building’s second floor included chutes down to acid vats, or so the story goes. It’s said that the investigation uncovered gas chambers and a dissection table, even a crematorium to dispose of bodies (after Holmes removed the skeletons and sold them to unknowing medical labs). The press later called it the “Murder Castle.” The infamous hotel was immortalized in Erik Larson’s 2003 smash bestseller, The Devil in the White City . This is not that hotel. The Chicago Athletic Association opened in 1893, it too with an eye fixed on the World’s Fair. However, the intent of this stately building was to show the world that Chicago was more than just a meatpacking and crime town (much nobler goals than those of Mr. Holmes). On the outside, limestone columns and criss-crossed arches brought a European class to Michigan Avenue. Inside, the marble staircases and mosaic-tiled interiors were just as impressive. The only hitch was that hardly anyone was allowed in.

From 1893 to 2007, the Chicago Athletic Association was a private member’s club, right in the heart of downtown. The earliest members of this dark, opulent refuge spanned from quirky athletic royalty — the first pro football player or Olympian-turned-Tarzan actor Johnny Weismuller — to Chicago’s most iconic names. Field. Wrigley. McCormick. During prohibition, the iconic Venetian Gothic exterior would shield illicit saloons. Today, sitting in the dimly lit, grandly columned drawing room dotted with bookshelves and fireplaces, an old-fashioned balanced on the armrest of a leather chair, it’s easy to imagine you’re back in those earliest days. With one radical distinction. What was for a hundred years the pinnacle of social exclusivity now wants everyone inside. After nearly a decade out of use, a heroic renovation reopened the CAA as a hotel in 2015, letting in a little more light (literally and figuratively) without sacrificing the original cloistered, clubby feel. It’s among the city’s most impressive and vibrant hotels, and home too to some of downtown’s favorite restaurants and bars. Designed specifically to appeal to everyone. The facade and the public spaces now are as glamorous as the day it first opened. The club had closed in 2007, and a hundred years of ad hoc design decisions by club members had left it somewhat disjointed besides. New ownership recruited top Midwestern experts in marble and iron to pore over archival photos and original blueprints and restore the building to its roots. In the rooms, hotel designers Roman & Williams provided a decidedly more contemporary feel, with crisp spaces that reference the building’s sporting history via homages to turn of the century gymnasiums. Distinctive caged light fixtures hang from high ceilings. The criss-cross backs on the desks mimic old-timey stretching walls. Racquet leather wraps around the legs of the nightstands.

What’s the point of references like these — ones you might miss if you don’t look closely enough? You don’t need to know the history to feel it. Whether you’re conscious of it or not, all these little touches are Chicago. Ask general manager Patrick Hatton what kind of guests choose to stay at CAA and he tells you it’s simply people who “love the city… people who want to feel like they’re experiencing Chicago history while they’re in Chicago.” On your keycard is an image of Johnny Weismuller. In a glass display is an ode to William Wrigley — who, as a member when he bought the Cubs in 1915, adopted the CAA logo for the team. It’s a logo you see all over the hotel, and Cubs fans will instantly recognize the similarity. They still don’t know everything that happened here, which was kind of the point. But clubs like the Chicago Athletic Association were the precursors to professional sports, where amateur club members faced those of other cities in serious competition. The first man to ever earn a paycheck for playing football — William “Pudge” Heffelfinger — once belonged to CAA. The Pittsburgh Athletic Club paid him as a ringer in their match against Allegheny. Wholesome sporting and ambitious architecture notwithstanding, throughout the century the Chicago Athletic Association participated in its fair share of that enduring “crime town” reputation. During restoration, construction found a prohibition-era bar hidden behind the drywall. Now it’s the hotel’s popular microbar, the Milk Room, so named for the secretly spiked refreshments served in the speakeasies. Sit down and you might overhear a tour guide, stopping in the entrance to whisper to their group about Al Capone. The Cherry Circle Room is the foodie location — and among the only public spaces in the building not restored based on the original architectural specs. Instead, it stands much as it did at midcentury, when the men of the club walled in its windows and installed soundproof booths to go with a discreet entrance leading up from the street. “I’ll let you do the math on who they might have been entertaining,” comments Hatton. On the roof, the modern restaurant Cindy’s is the only brand-new space in the building, and it’s where you’ll find one of the best views in the city, a soaring look at Millennium Park stretching out to the lake. Reservations are essentially mandatory for the above, but the Shake Shack and coffee shop on the first floor offer more affordable, available options. The Game Room, by the drawing room that sees work-from-home warriors posted up with their laptops, draws flocks of after-work professionals to its shuffleboard and foosball tables.

Rooms and suites retain the stately feel of the drawing room, but the Roman & Williams design ensures they don’t feel quite as old-fashioned. Sixteen rooms, like the popular Millennium Junior Suites, face the park, drenched in sun. Suites are spacious with living areas, and the “Holy Cow” suites display a multiple-room grandiosity worthy of the Harry Caray catchphrase. The other two hundred or so, spread between the Michigan Ave building and the Madison Street annex, are downtown rooms, with views typical of city hotels making the most of their space. But despite the clever references by Roman and Williams, and the branded bathrobes that make you feel like a 19th-century boxer, this place isn’t really about the rooms. “When we reopened the club, it was very important for us not to have any membership elements whatsoever,” says Hatton. “When we say we opened the doors to the public for the very first time, we wanted to truly open the doors to the public. There are no membership elements to anything we do here.” “It was so exclusive before. Now it’s one hundred percent inclusive.” Even if you don’t get a room. “There’s so much for you to do in the rest of the hotel,” as Hatton puts it. “Come hang out with us.” Book the Chicago Athletic Association on the MICHELIN Guide →

In 2024, the MICHELIN Guide is announcing the first ever MICHELIN Keys — a brand new distinction that recognizes the most outstanding hotels across the world. The Chicago Athletic Association is a One Key hotel in the United States. Find our selection team’s official take, here .

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Travel | Ed Perkins on Travel: Solo travel – difficult…

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Travel | ed perkins on travel: solo travel – difficult but improving.

Travel is geared mainly to serve customers as couples. But for a variety of reasons, lots of travelers are not in a coupled relationship. In my case, I’m a widower; others include the never married, the divorced or separated, and even couples with diverse interests. Over the years, the travel business has given short shrift to these travelers, but suppliers have recently taken a closer look at what they see as a big potential source of business.

For years, some tour operators and cruise lines have been positioning themselves as “singles travel” specialists, but mostly their approach has been to match up singles into couples. True solo travel is different—true solo travelers do not what to share accommodations with strangers or even with friends who they might want to consider. They want sole occupancy of whatever arrangement they make.

If you’re traveled at all, you’ve seen that a lot of pricing is based on “per person, double occupancy,” or PPDO:

Most modern hotel rooms are designed to accommodate at least two people with two single, double, or queen beds; hotels charge the same rate for either one or two occupants.

Similarly, the vast majority of cruise cabins are set up to accommodate up to four people – two comfortably in separate small beds, combinable into a double, and two more uncomfortably in pull-down bunk beds.

Railroads charge each traveler the same for basic rail fare, but for compartments on overnight trains such as Amtrak’s long-distance trains, the price is the same for one as for two.

Although not promoted as such, rental cars are de facto PPDO: Adding a second passenger (or more) adds nothing to the daily or weekly rent.

Even with the prevalence of PPDO pricing, solo travelers have reasonable options:

Hotels. Although most new or recent hotels are designed for couples, small, older hotels in Europe often have single rooms designed for just one occupant, as do small Japanese business hotels. Daily rates are usually substantially less than but more than half the double-room rates. On my recent trips, I’ve found comfortable single rooms at small family-owned hotels in Brussels, Grindelwald, and Rothenburg ob der Tauber, as well as in Japan. But most of the time, I have to settle for the usual double rate.

Tours. Despite a growing number of self-styled “Solo” tour operators, most fall back on the formula that “we’ll match you with a suitable roommate, and we won’t charge extra if we can’t find one.” But if you really want accommodations by yourself, you pay a single supplement. What may be close to everybody’s favorite tour operator, Road Scholar ( roadscholar.org/); formerly Elderhostel but open to travelers of any age) posts a pull-down options menu that includes “solo travelers only” filter. The choices are limited, but they’re genuinely for solo travelers. Google “solo travel” to find other outfits worth a look.

Cruise. For a long time, cruise lines ignored the solo traveler, relying instead on stiff single supplements for double cabins. But some of the newer liners feature cabins designed for one person. The good folks at Cruise Critic have compiled and posted a list ( cruisecritic.com/articles/which-ships-have-solo-cabins ) of cruise lines and cruise ships with true single cabins. Norwegian leads the pack in number of rooms and number of cabins per ships, but the other lines are catching up. Carnival, the biggest player, seems to be lagging the trend, but it does have a few on Cunard. Unfortunately, other than Cunard, no high-end lines yet make the list.

Trains. I don’t know any way to hack PPDO compartment prices on Amtrak, and Amtrak seldom puts them on sale. Sorry.

No Supplement Deals. Historically, tour operators and cruise lines have charged solo travelers the dreaded “single supplement” to occupy an accommodation designed for a couple. The supplement usually ranges from 50 percent more to double the PPDO rate. They’ve catered to solo travelers mainly through occasional “no single supplement” promotions, often for departures they believe are not likely to sell out – which means the best deals are last-minute deals. You can still find those.

(Send e-mail to Ed Perkins at [email protected]. Also, check out Ed’s new rail travel website at www.rail-guru.com.)

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Study ranks Chicago as most walkable city in America for tourists

W ith summer on the way and tourism ramping up in Chicago, a recent study shows that there is plenty of reason behind the appeal of traveling to the Windy City.

The study, conducted by Preply , analyzed major U.S. cities and measured how easy it was to navigate each city's most recognizable tourist landmarks on foot.

Compared to European cities that are known for being walkable, the expansive and car-dependent nature of many American cities makes it much more difficult to see what a city has to offer without a vehicle.

The study found that Chicago is the most walkable city for tourists in the U.S. by this metric, with it taking just 28 minutes to explore the city's most famous landmarks, including "The Bean" or "Cloud Gate" and the Magnificent Mile.

The brisk pace in Chicago is miles ahead of Orlando, which the study ranked as the least walkable city for American tourists.

According to Preply, it takes over 11 hours and 65,100 steps to cover Orlando's major landmarks on foot.

The only other cities where major landmarks can be seen within an hour on foot were Nashville and Dallas, taking 33 minutes and 41 minutes, respectively.

Rounding out the top five were Santa Fe and New Orleans, each requiring between 6,000 and 7,000 steps and less than an hour and 15 minutes to see the major attractions.

In addition to The Bean and the Magnificent Mile, Preply included Millennium Park itself, The Art Institute of Chicago and the Chicago Architecture Center as the spots that could be seen within 28 minutes of walking.

Outside of Chicago, Milwaukee was the lone U.S. city to crack the top 15, coming in at 15th at 2 hours and 35 minutes of walking and 14,280 steps.

You can see how other major American cities ranked along with more information about the study here.

Study ranks Chicago as most walkable city in America for tourists

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Day 3 - Afternoon. Once you come down from 360 Chicago in John Hancock building, you have plenty of options for lunch. Within a few blocks, you can find Cuban, Vietnamese, Mediterranean, and the Chicago staple of deep dish pizza. If you want a lunch with a view, consider eating at The Kennison.
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CHICAGO Itinerary • MUST READ! (2024) With incredible works of public art scattered all around the city and free access to many of its museums and art centers, Chicago is a cultural hub! It's also America's third-largest city and the birthplace of the modern skyscraper. This immense and beautiful city has a vibrant outdoor culture, with ...
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Join our travel affiliate program. Chicago is one of the most beautiful cities, with stunning architecture, delicious deep-dish pizza, a beautiful lake, and the only river in the world that flows backward. If you do not have a week to spend in the city, you can spend 4 days in Chicago exploring most of the must-see attractions. This guide has ...
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I have the inside scoop and, in this itinerary for Chicago, I'm going to detail exactly how you should spend your time on your trip. For short visits, I also wrote a 1 day Chicago itinerary. Disclosure: Travel Lemming is an independent reader-supported blog. You can support us by purchasing via the affiliate links on this page, which may earn ...
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You get to visit 7 of Chicago's best attractions like Shedd Aquarium, Skydeck Chicago, The Art Institute of Chicago, and 360 Chicago Observation Deck in the John Hancock Center Building. I would also recommend spending some time at Grant Park, the Chicago Cultural Center, Wrigley Field, Chicago Water Tower, and the Navy Pier.
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The Art Institute of Chicago. A rival to the best art museums in Paris and New York, the Art Institute of Chicago is the one must-visit museum when you have 3 days in Chicago. Most people come for the impressionist work, but there's plenty more here covering a huge span of art history. Tickets cost $25.
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Walk The 606. The 606 is Chicago's version of The Highline in NYC, an elevated trail goes through 2.7 miles of the city's northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square. It is a bit off the beaten tourist path but it great place to walk, run or bike.
25 Best Things To Do in Chicago in 2023
9. Explore The Lakefront Trail. Once you've got your fill of the city, one of the best things to do in Chicago to get some fresh air is to head to the lakefront. At 494 kilometers long and 190 kilometers wide, Lake Michigan is the largest of the Great Lakes and is actually the 6th largest freshwater lake on earth.
The Best Chicago 2-Day Itinerary
Architecture River Cruise Skip-the-Ticket Line. Duration: 1 - 75 hours. 5 (3772) Powered by GetYourGuide. Join our travel affiliate program. Chicago is an incredible city with stunning architecture, delicious deep-dish pizza, and a beautiful lake. Although it's one of the largest cities in the US, you can create an incredible Chicago 2-day ...
The ULTIMATE Chicago Bucket List
Walk The 606. The 606 is Chicago's version of The Highline in NYC, an elevated trail goes through 2.7 miles of the city's northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square. It is a bit off the beaten tourist path but it great place to walk, run or bike.
Chicago Budget Travel Guide (Updated 2024)
Chicago Travel Costs. Hostel prices - During peak season, a bed in a 4-6-bed dorm costs about $50-70 USD and $35-65USD in the off-season. For a room with eight beds or more, expect to pay around $45-60 USD in peak season and $30 - 45 USD off-peak.
Traveling to Chicago for the First Time: 13 Tips & Tricks
Chicago's skyscrapers. These are our top tips for visiting Chicago: 1. Stay in the Heart of the City. If you are traveling to Chicago for the first time, you're likely planning to see all the main tourist landmarks. For sightseeing, we recommend staying right in the heart of downtown so you will be near all the action.
Chicago travel blog
Chicago city skyline. | chicago travel blog Along the Chicago River | chicago blog The Cloud Gate (the "Bean") at Millennium Park, Chicago Today, Chicago is an cosmopolitan city with a wide variety of different ethnicities, beliefs, cultures, cuisine, parks and shopping malls.
First-Timer's Guide to Visiting Chicago
Pay a visit to one of the city's most famous public artworks, Cloud Gate, aka "The Bean.". Splash around in Crown Fountain, a shallow pool flanked by two 50-foot towers where the faces of Chicago locals spout water from pouting lips. Dine on the outdoor patio in the shadow of The Bean in the summer, or ice skate on the plaza in the winter.
Chicago Things to Do, Events, Restaurants, Hotels & Vacation Planning
Embark on a journey through Chicago's diverse tapestry of neighborhoods with this new neighborhood travel show. Learn more. Sundance Institute x Chicago ... See the city through the eyes of the people who know it best — Chicago locals. Read our blog for insider tips and guides. Blog, Museums, Tours & attractions 10 Chicago museum exhibits ...
How To Spend a Weekend in Chicago: 9 Must-Visit Attractions
2. View the Windy City's Skyline From Skydeck Chicago. Elevate your weekend in Chicago, quite literally, with a visit to Skydeck Chicago in the Willis Tower. Step onto The Ledge, a glass balcony extending four feet outside the 103rd floor, and experience breathtaking city views and beyond. It's a thrilling way to see Chicago's architectural ...
Home [travelsandtreasures.com]
Welcome to Travels & Treasures! This Chicago travel blog highlights the best city recommendations from a native Chicagoan. It also reveals authentic experiences of our family travels throughout US and European destinations. There is a reason why Travels & Treasures has been ranked a top Chicago Blog and Illinois Travel Website from 2020 to 2024!
A Chicago Family Vacation
4 Day Itinerary for a Chicago Family Vacation. 4 days in Chicago, the Windy City, is enough to get a really good taste of this huge city. The city center is very walkable, and visitor-friendly. If you are visiting for any less than 4 days, that I recommend you definitely do a river tour, and get to one of the museums or Art Institute.
Chicago city guide
Purchase our award-winning guidebooks. Get to the heart of Chicago with one of our in-depth, award-winning guidebooks, covering maps, itineraries, and expert guidance. Shop Our Guidebooks. 05 / Go Beyond.
Long Weekend in Chicago
The Devil in the White City is a book based on real characters and events associated with the 1893 Chicago World's Fair. Upton Sinclair's powerful novel The Jungle portrays Chicago immigrant life, poverty, and corruption in the meat-packing industry at the beginning of the 20th century.
Chicago Travel Blog
Lauren Monitz is a travel blogger specializing in Chicago travel, Chicago dining, Chicago restaurants and Chicago bars. ... Blog; Denver; Near & Far; Destinations; Travel Styles; Anything Goes; Work with Me; Contact; Menu Menu; 8 Totally Underrated Cities in the Midwest You Need to Visit March 10, 2021 / by Lo. The Best Road Trips from Chicago ...
Chicago Travel Blog
Chicago. Chicago is our home town. We were both born and raised in Chicago and have lived here most of our lives. Find our Chicago travel guides below. Chicago Travel Blog: Chicago is our hometown. Here you will find some of the best things for families to do in Chicago .
What Is Chicago Known for? 35 Things Chicagoans Love About Themselves
After interviewing travel experts and native Chicagoans, AZ Animals has compiled a list of the 35 things Chicago is known for and why its residents love the city so much. 1. Deep Dish Debate. Deep ...
Key Street: Michigan Ave. Leads to 7 Key Hotels in Chicago
On April 24, 2024, the MICHELIN Guide announced its very first Key hotels in the United States — a brand new distinction recognizing the most outstanding hotels in the country. We're thrilled to report that in Chicago, eight hotels earned at least One Key. Of those, half make their home in the kinds of historic buildings that give this city ...
Chicago beach named among the best in the US by Travel and Leisure
CHICAGO - A Chicago beach has been recognized as one of the best beaches in the United States by Travel and Leisure, joining the ranks of popular beaches in Hawaii, Florida and California.. The 25 ...
The Guilty Pleasures of the Chicago Athletic Association
From 1893 to 2007, the Chicago Athletic Association was a private member's club, right in the heart of downtown. The earliest members of this dark, opulent refuge spanned from quirky athletic royalty — the first pro football player or Olympian-turned-Tarzan actor Johnny Weismuller — to Chicago's most iconic names. Field. Wrigley. McCormick.
Ed Perkins on Travel: Solo travel
Solo traveler. By Ed Perkins. April 23, 2024 at 4:30 a.m. Travel is geared mainly to serve customers as couples. But for a variety of reasons, lots of travelers are not in a coupled relationship ...
Study ranks Chicago as most walkable city in America for tourists
The brisk pace in Chicago is miles ahead of Orlando, which the study ranked as the least walkable city for American tourists. According to Preply, it takes over 11 hours and 65,100 steps to cover ...

The Perfect 3 Days in Chicago Itinerary (2024 Edition)

When to Visit Chicago

Travel Tips for Visiting Chicago

Day 1 – Morning

Day 1 – Afternoon

Day 1 – Evening

Day 2 – Morning

Day 2 – Afternoon

Day 2 – Evening

Day 3 – Morning

Day 3 – Afternoon

Day 3 – Evening

Chicago Itinerary Travel Guide

Where to Stay in Chicago

Where to Eat and Drink in Chicago

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CHICAGO Itinerary • MUST READ! (2024)

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Best Time To Visit Chicago

Best Hostel in Chicago – Hi Chicago

Best Airbnb in Chicago – Modern loft for 2

Best Budget Hotel in Chicago – Best Western Grant Park Hotel

Day 1 / Stop 1 – The Art Institute of Chicago

Day 1 / Stop 2 – Garfield Park Conservatory

Day 1 / Stop 3 – Millennium Park & Cloud Gate

Day 1 / Stop 4 – The Field Museum

Day 1 / Stop 5 – Willis Tower Skydeck

Day 1 / Stop 6 – Comedy at Annoyance Theatre & Bar

Day 2 / Stop 1 – Grant Park and Buckingham Fountain

Day 2 / Stop 2 – Chicago Cultural Center

Day 2 / Stop 3 – Museum of Science and Industry

Day 2 / Stop 4 – Navy Pier

Day 2 / Stop 5 – Wrigley Field

Day 2 / Stop 6 – Magnificent Mile

Day 2 / Stop 7 – Jazz at Blue Chicago

Chicago River Cruise

Chicago Food tour

Richard H. Driehaus Museum

Mob and Crime Bus Tour

Watch a Football Game at Soldier Field

Don’t Forget Your Travel Insurance for Chicago

Chicago to New York City Day Trip by Air

Tour of SW Michigan Wine Country from Chicago

Chicago Grand City Tour & 360 Chicago Observation Deck

Detroit: The Rise, Fall & Renewal Walking Tour

Milwaukee Scavenger Hunt Adventure

How many days are enough in Chicago?

What should you include on a 3 day Chicago itinerary?

Where is the best place to stay for a weekend in Chicago?

What are the best day trips from Chicago?

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Chicago Itinerary: The Ultimate Travel Guide

5 Day Chicago Itinerary

Lunch at Cold Storage

Millennium Park

Cindy’s Rooftop

Architecture River Cruise

Blue Chicago Jazz Club

Girl and the Goat

Chicago Itinerary: Day 2

Duck Duck Goat

Museum of Contemporary Art

Petit Margeaux

Pequod’s

Chicago Itinerary: Day 3

The Highline Bar

Oak Street Beach

London House

Second City Comedy Show

Greek Islands

Chicago Itinerary: Day 4

Lincoln Park Zoo

3 Arts Club Café

Shopping at the Magnificent Mile

Chicago Itinerary: Day 5

Willis Tower Skydeck

Kayaking on the river