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The 17 best architecture tours of Chicago

Discover Art Deco skyscrapers, modern marvels and Frank Lloyd Wright–designed homes on these architecture tours of Chicago

Even if you're a longtime local, there's something special about taking in the city's architecture on foot or from the water with the help of an expert. From glass and steel castles to ornate Art Deco buildings to street art and cultural landmarks in our neighborhoods, there's a reason these tours are among the best attractions in Chicago . Nerd out over the design, engineering and construction behind the most beautiful buildings in Chicago on guided walks, bus rides and boat tours . First-time visitors will be happy to know that these architecture tours double as sightseeing walks of the best Chicago attractions —you might even be able to snap a few Instagrams along the way. Here's a few of our favorite tours that are equally engaging for tourists and Chicago lifers. 

RECOMMENDED: Check out the full guide to the best Chicago tours

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Architecture tours of Chicago

Chicago Architecture Foundation River Cruise

For a comprehensive overview of Chicago’s skyline, there’s no better vantage point than aboard Chicago's First Lady. You’ll spy more than 50 architecturally significant buildings, from the Wrigley Building to newcomers like the St. Regis. An expert guide will give you the lowdown on Chicago’s rise from the Great Fire of 1871, the advent of balloon-frame construction and other crucial moments in the city’s history. Choose to cruise by day or watch the city light up with an evening option.  $52

Shoreline Sightseeing Architecture River Tour

You're certainly not short on great options to see Chicago's stunning architecture from the river. On Shoreline Sightseeing's signature 75-minute tour, you'll observe more than 40 landmarks, including Tribune Tower and Marina City. A knowledgeable guide shares the stories behind the architects, engineers, movers and shakers that gave us the nickname "City of the Big Shoulders." $43-47

Chicago's Original Architecture River Tour

Travel the Chicago River in style with a bartender, an entertaining tour guide and killer views as you explore the city's architecture on all three main branches of the Chicago river. A 45-minute version is also available. $42

Must-See Chicago

Want to check out Chicago's architecture but short on time? Try this 90-minute "Greatest Hits" walking tour from the Chicago Architecture Foundation, which offers an informative, fast-paced introduction to key landmarks. The tour includes stops at more than a dozen buildings, including the Chicago Theatre, Aqua Tower, Willis (Sears) Tower, the Wrigley Building and the Art Institute of Chicago. Make sure to bring something to take notes! $30

One of the coolest aspects of Chicago architecture is that it's always evolving, with new landmarks continuing to shape our skyline. This 90-minute tour from the Chicago Architecture Foundation is all about what's new in Chicago, taking guests to buildings like 462 N. Park and the St. Regis and discussing their impact on the city's changing built environment and economy. $30

Frank Lloyd Wright Trust Bus Tours

These tours, led by experts dedicated to preserving and educating about the work of Chicagoland's most famous architect, are definitely not cheap, but a must for Frank Lloyd Wright superfans. (Frankenstans?) The "Wright Around Chicago" includes stops at the gorgeous Rookery Building and Wright's home and studio in Oak Park, while the "Wright Along the Lake" tour includes a visit to the exquisite 1915 Emil Bach House. Oh, and lunch and a prosecco toast are included. $195

Free Tours By Foot's Architecture Tour

If you're traveling on a budget, you can still get an excellent overview of Chicago's architecture thanks to Free Tours By Foot's pay-what-you-can two-hour walking tours. These volunteer-led tours take you to key landmarks like Cloud Gate, Marina City, the Leo Burnett Building and works by Frank Lloyd Wright, Louis Sullivan and Mies van der Rohe. 

Chicago Walking Tour: Art Deco Skyscrapers

Take a trip back to the Roaring Twenties with this tour, which takes you through the history of many iconic Chicago buildings. Choose from the Loop route, which includes One North LaSalle and the towering Board of Trade, or the Riverfront route for the gold-topped Carbide and Carbon building and the Holabird and Root-designed 333 N. Wacker Drive. Admire the geometric shapes, vibrant colors and sophisticated elegance that Art Deco construction is so well known for on these two-hour walking tours. $30

Chicago Mahogany Tours

Although these tours (which are created and by civic historian and TikTok star Shermann "Dilla" Thomas) aren't exclusively architecture-focused, the built environment plays a huge role in their explorations of the history, contributions and legacies of South Side neighborhoods like Roseland and Back of the Yards. And from Bronzeville's beautiful boulevards to Pullman's historic workers' homes, there's plenty for architecture buffs to explore on these important tours. 

Chicago For Chicagoans

Live in Chicago and feel like you've done all the downtown-centric architecture tours? Maybe it's time to give Chicago for Chicagoans a go. The tours, developed for locals by locals, are designed to build community and give Chicago natives a stronger appreciation for their neighborhoods and neighbors. Enjoy walking tours and fun scavenger hunts of Albany Park, Chinatown, Pilsen, Beverly and more—and the tours frequently end at local restaurants if all that walking works up an appetite.

Chicago Walking Tour: Modern Architecture

If you prefer sleek metal and glass designs to ornate Gothic architecture, you’ll want to book a spot on this two-hour walking tour of the city’s most famous modern buildings. Peep minimalist designs from Ludwig Mies van der Rohe, admire the Beaux-Arts beauty of the Harold Washington Library and ogle the chic contemporary look of One South Dearborn, among others. $30

White City Revisited

The announcement that the World’s Columbian Exhibition of 1893 would be held in Chicago spurred an explosion of new construction. Beaux-Arts buildings sprung up all over Jackson Park and the South Side—so many sparkly new buildings, in fact, that the area earned the nickname “White City.” More than 125 years later, visitors can still see the architectural impact of the fair on the city. This tour includes a visit to Jackson Park's Garden of the Phoenix and the Skylanding sculpture by Yoko Ono. $30

Private Chicago Architecture Tour

Don’t want to share your tour guide with a group? Reserve a private tour to spend an entire afternoon exploring the city’s most impressive buildings. You’ll stop at everything from Willis Tower to Gothic facades on the Magnificent Mile to Frank Lloyd Wright homes in Oak Park. Did we mention you’ll be chauffeured from stop to stop in a luxury town car or SUV, too? $930.60

Women in Chicago Architecture

As in so many industries, women’s contributions to the world of architecture have only recently begun to get their moment in the sun. Discover some of the female architects leaving their mark on Chicago’s skyline on this 45-minute virtual tour led by an expert from the Chicago Architecture Foundation, featuring sites like the Aqua Tower and Equitable Building. Who built the world? Girls! $8 for the public, free for members

Brick of Chicago

What's so exciting about brick? Common brick built much of Chicago, and this tour, created by local teacher Will Quam, takes you around neighborhoods like Logan Square, Hyde Park and Bronzeville to show how the built environment created our interesting and beautiful city. After marveling at churches and greystones and Gilded Age mansions, you'll find yourself taking a second, more appreciative look at the world around you. $12–19

Historic Austin

This 2-hour neighborhood-centric Chicago Architecture Foundation tour takes you through historic Midway Park, shows you works by prominent local architects including Frederick Schock, William Drummond and Dwight Perkins and gives you an opportunity to marvel at the neighborhood's grand Queen Anne and Prairie homes. During the tour, you'll also hear from Austin residents about their efforts to revitalize the neighborhood following decades of disinvestment and racist housing practices.

Walk Pilsen

Explore the cultural influence and impact of the many immigrant groups who have called Pilsen home and the intersection of art and architecture on this tour from the Chicago Architecture Foundation. On this two-hour tour, you'll visit residential, commercial, residential and cultural sites, from the 18th Street Pink Line station's murals to the Sokols, century-old Czech athletic clubs. $30

Looking for more Chicago tours?

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To get the best views of Chicago's picturesque urban sprawl, you need to take a helicopter tour.

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Chicago architecture tours and cruises

From Gothic Revival survivors of the Great Chicago Fire to the birth and evolution of the modern skyscraper, the Chicago skyline is a mesmerizing homage to legendary architects and groundbreaking styles. And the best way to dive into it all is on a Chicago architecture tour.

Here’s an overview of some of the city’s amazing architecture tours, from in-depth walking tours to boat cruises along the Chicago River or Lake Michigan shoreline.

In this article

Chicago architecture boat tours, chicago architecture walking tours, chicago architecture bus tours.

Chicago Architecture Center River Cruise A top-rated architecture experience, this relaxing boat cruise aboard Chicago’s First Lady is known for its expert tour guides who share the stories behind more than 50 significant buildings.

Chicago Fireboat Tours Come aboard a real Chicago fireboat and cruise the same waterways where the historic ship once fought fires. The expert guides will highlight architecture, history, and the boat itself as you sail from Lake Michigan onto the Chicago River.

Wendella Tours and Cruises Choose your own adventure on Wendella’s architecture tours. This long-running cruise company offers lake and river excursions, with shorter and more in-depth options.

Mercury, Chicago’s Skyline Cruiseline Admire the city’s stunning skyline on this informative boat tour that covers both Lake Michigan and the Chicago River. The live narration covers the city’s rich history while pointing out architectural icons along the way.

Shoreline Sightseeing Company Discover the city and its iconic skyline from the water on these guided tours. Choose between exploring all three branches of the Chicago River or sailing down the Lake Michigan shoreline.

Tall Ship Windy You’re in for a truly unique experience aboard this 148-foot, traditional four-masted schooner, where you’ll sail Chicago’s scenic lakeshore and learn about the history of the city and its world-famous architecture.

City Cruises Admire dramatic riverfront views while enjoying an elegant meal aboard this all-glass vessel, where your brunch or lunch is accompanied by informative narration and picture-perfect views.

Inside Chicago Walking Tours Hear about the hidden details and real stories of Chicago’s legendary architecture on an Inside Chicago Walking Tour. These in-depth tours take you inside some of the city’s most fascinating buildings, from Art Deco masterpieces to famous movie locations.

Free Tours by Foot The name says it all. These budget-friendly excursions use a “pay-what-you-can” model. Their architecture-themed tour takes you along the Chicago Riverwalk and throughout the Loop and Millennium Park.

Tours With Mike Led by an award-winning guide, Tours With Mike offers a unique perspective on the city’s architecture. One popular route is the Ugly Buildings tour, an “educational roast” of some of Chicago’s lesser-known spots.

Chicago Greeter For the architecture junkie who’s also on a budget, the free Chicago Greeter program pairs you with a local who’ll highlight either downtown or in your pick of the city’s neighborhoods. If you don’t get a chance to register in advance, look into an on-the-spot InstaGreeter  walk instead.

MetroWalkz Self-Guided Walking Tours Explore Chicago at your own pace with a free, self-guided walking tour. Just select one of MetroWalkz’s digital, mobile-friendly tours, showcasing several unique areas of the city. Their Loop Architecture Tour will give you a good overview of Chicago’s downtown.

Big Bus Chicago : These hop-on, hop-off bus tours are a great way to explore Chicago’s architecture at your own pace. The route cruises by all the city’s top landmarks. Hop on to hear pre-recorded commentary, hop off to get out and explore on your own.

Chicago Mahogany Tours : Immerse yourself in Chicago’s neighborhoods, from Bronzeville to Pullman, on these bus tours that touch on everything from architecture to culture, with an emphasis on Black history.

Chicago Architecture Center : These in-depth bus tours, led by seasoned guides, cover a wider variety of topics, like historic houses of worship, the Chicago World’s Fair, Gothic-style architecture, and beyond.

From this article

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Rookery building.

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Chicago Detours

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Inside Chicago Walking Tours

eVisitorGuide and MetroWalkz Tours

The Magnificent Mile

Special Event Venues

360 chicago observation deck.

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Mercury, Chicago’s Skyline Cruiseline

Shoreline Sightseeing Company

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Art Deco: Landmark Lobbies

Step out of the cold and into the lobbies of three Art Deco skyscrapers whose lavish materials and modern ornament epitomized the prosperity and optimism of the Roaring ‘20s.

All of the buildings on this 1-hour tour are located within 1½ blocks of the Chicago Architecture Center. The shorter walking distance allows for longer viewing time inside the faithfully restored lobbies of three landmark Art Deco buildings and, for comparison, one neo-classical building. Offered only in January and February, this tour offers less exposure to the elements and more exposure to the glamour and history of some of Chicago’s best Art Deco buildings.

• Many tours sell out. To guarantee your space advance reservations are strongly recommended.
• The tour includes two optional views from balconies that are reached by stairs. 

Photos From This Tour

Upcoming Art Deco: Landmark Lobbies Tours

Friday jan 3.

• 2:30pm Buy Tickets

Saturday Jan 4

• 11:00am Buy Tickets

Friday Jan 10

Saturday jan 11, friday jan 17, saturday jan 18.

Chicago Walking Tour: Historic Treasures of Chicago

• Walking tour of Chicago Architecture
• Narration by a professional and certified guide
• Admission to the Galleries of the Chicago Architecture Center
• Entry/Admission - Chicago
• Hotel pick-up or drop-off
• Storage for luggage or strollers
• Entry/Admission - Wrigley Building
• Entry/Admission - Carbide and Carbon Building
• Chicago Architecture Center, 111 E Wacker Dr, Chicago, IL 60601, USA Meet at the Chicago Architecture Center at 111 E Wacker Drive, Chicago, IL, 60601
• Chicago Cultural Center, 78 E Washington St, Chicago, IL 60602, USA The tour will end in the Chicago Cultural Center. The docent will return to the Chicago Architecture Center and participants are welcome to accompany the docent back to the CAC.
• Wheelchair accessible
• Stroller accessible
• Service animals allowed
• Near public transportation
• Transportation is wheelchair accessible
• Surfaces are wheelchair accessible
• Confirmation will be received at time of booking
• No heart problems or other serious medical conditions
• Most travelers can participate
• Access to building interiors featured on this tour may be subject to change, due to weekend and holiday schedules or unforeseen closures.
• Pets are not allowed.
• This tour/activity will have a maximum of 15 travelers
• For a full refund, cancel at least 24 hours in advance of the start date of the experience.
• Chicago Cultural Center
• Chicago Architecture Center
• Wrigley Building
• Reliance Building
• Carbide and Carbon Building

Similar experiences

• You'll start at Chicago Architecture Center 111 E Wacker Dr, Chicago, IL 60601, USA Meet at the Chicago Architecture Center at 111 E Wacker Drive, Chicago, IL, 60601 See address & details
• 1 Chicago Architecture Center Stop: 5 minutes - Admission included See details
• 2 Wrigley Building Stop: 5 minutes - Admission excluded See details
• 3 Palmer House Hilton Historic Lobby Stop: 10 minutes See details
• 4 Carbide and Carbon Building Stop: 5 minutes - Admission excluded See details
• 5 Reliance Building Stop: 5 minutes See details
• 6 Chicago Cultural Center Stop: 10 minutes See details
• You'll end at Chicago Cultural Center 78 E Washington St, Chicago, IL 60602, USA The tour will end in the Chicago Cultural Center. The docent will return to the Chicago Architecture Center and participants are welcome to accompany the docent back to the CAC. See address & details

• nelatt 0 contributions 5.0 of 5 bubbles Best education experience during our tour Amazing tour of beautiful buildings and spectacular interiors Paul our guide was very knowledgeable and provided pertinent details and history Read more Written April 30, 2024
• valeriek1212 0 contributions 5.0 of 5 bubbles Tour the new in the old: a surprising gem Old post office with Lorie. Very comprehensive, knowledgeable. Learned a lot in 90 min. Saw how the old building has been reworked and repurposed. Read more Written April 29, 2024
• BertholdGreen 0 contributions 5.0 of 5 bubbles Chicago's architectural origin Our guide, Wayne, led us in a short loop of the area around the Architecture Centre. He described the origin of Chicago from Fort Dearborn (brass plaques in the ground at Columbus / Walker Drive), how the river flow was reversed, how the city was raised to avoid flooding, and how the Great Fire of 1871 was the impetus for architects to experiment with architectural innovation as the city was rebuilt. We viewed buildings in chronological order, from early skyscrapers to new supertall high rises. Wayne gave us an insightful, interesting, and informative tour. Read more Written April 28, 2024
• Anna R 0 contributions 5.0 of 5 bubbles Architecture Boat Tour - Fantastic!!! The architecture boat tour was fantastic! Alison our guide was very knowledgeable and charming - we learned so much! My teenage son (17) loved it too. Read more Written April 27, 2024
• A9896VLjs 0 contributions 5.0 of 5 bubbles So revealing Our docent was so informed and passionate. We saw south Streeterville from an architectural and historical perspective. Read more Written April 24, 2024
• Damon H 0 contributions 5.0 of 5 bubbles Excellent tour Tom was a very informative and friendly guide who provided lots of interesting stories about the development of architecture in Chicago. Highly recommend. Read more Written April 24, 2024
• B7673GLjesperh 0 contributions 4.0 of 5 bubbles Interesting and effective tour Our guide, Matt, was great. He told the stories and the facts with both knowledge and humor. I liked the higher pace which made us see much of the loop. Read more Written April 21, 2024
• 618herbr 0 contributions 5.0 of 5 bubbles Walking Tour: a walk through time with Robert the tour guide All the staff were friendly and helpful. Our walking tour guide Robert was awesome! He provided the basic facts along with stories about the life’s of the buildings we visited. He kept the tour interesting by exhibiting enthusiasm and a love of the history of the bulidlings. Read more Written April 21, 2024
• U19PGrichardt 0 contributions 5.0 of 5 bubbles Good way to learn Chicago’s history Great way to learn Chicago’s history. I have known Chicago’s history but the way this tour showed it to me was fascinating. Our tour guide Rene was very good explaining how from the very origins Chicago got the first settlers and how was discovered. From the Chicago great fire and the way they re built the city. How Chicago became a city and grew so fast due being the busiest trading port in the world. He showed us pretty cool architecture through the years and how it has evolved since then including all the new latest additions to the city. We saw some cool Art Deco buildings like the Motor club ,and contemporary styles like the St Regis. I really enjoyed this tour and I definitely will recommend it to everyone who is visiting or live in Chicago! Read more Written April 21, 2024
• markgM3560FM 0 contributions 5.0 of 5 bubbles Fulton-Randolph Markets - Newly Appreciated We toured the Fulton-Randolph Market neighborhood tour with Lynne, who enlightened us with her broad knowledge of the historic/transformed/transforming elements of this Chicago neighborhood. As with so many CAC tours, we left with a deeper appreciation for an area we frequent quite often such that we look forward to future walks unattached to a restaurant destination. Highly recommended! Read more Written April 21, 2024
• R C 0 contributions 5.0 of 5 bubbles OLD POST OFFICE TOUR I took the architecture tour for the Old Post Office with John S. This past week and I must have to say I was fascinated with the beauty of this building. Learned how important and busy was the post office back in the day in Chicago! Also it was very cool seeing how the building has been readapted and reused for a new purpose, specially after being abandoned for many years! We saw the pretty interior and how they have changed the inside of it. Also we visited the rooftop and seeing the green roof they have to be environmental friendly. He showed us all around and took us through the history and beauty of this building. I definitely will recommend this tour to my family and friends who live in Chicago! Read more Written April 18, 2024
• Lahdeedahleigh 0 contributions 5.0 of 5 bubbles Walk through history Chicago's architecture is abundantly interesting and varied. Our guide, Chris P, offered historical perspectives at each stop. Read more Written April 18, 2024
• Rhonda C 0 contributions 5.0 of 5 bubbles Marshall Fields on State Delta’s tour of the former Marshall Fields building on State Street was fantastic! We learned so much about about this building and its history. Highly recommended! Read more Written April 15, 2024
• Compass56399755148 0 contributions 5.0 of 5 bubbles Great tour! Must to while in Chicago Second time taking a walking tour with the Chicago Architecture Centre. Loved it every time. Definitely worth it to do the walking tour as details are much easier to absorb and the flow with the guide is closer. Will likely do it again! Read more Written April 14, 2024
• richardwG7724RL 0 contributions 4.0 of 5 bubbles Great way to connect to Chicago. Quentin was very knowledgeable, accessible and entertaining. So much history! Someone needs to test the audio sets; mine was terrible. Consider using potentiometer cleaner spray on the volume knobs, lt could help to avoid replacing a lot of them. Read more Written April 14, 2024

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Chicago Walking Tours

See our Calendar Below for All Tours, as well as Things to Do & Travel Tips

Featured tours.

Architecture Tour

Architecture tour highlights.

Haunted History

Haunted history highlights.

Loop and Millennium Park

Loop and millennium park highlights.

Riverwalk and History Tour

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Lincoln Park & Blues

Lincoln park & blues highlights.

Winter Riverwalk

Winter riverwalk highlights.

Free Tours by Foot is pleased to present the best pay-what-you-like guided Chicago walking tours. 

These interesting and informative sightseeing city tours will take you through many of the Windy City's most famous neighborhoods.

Everyone should be permitted to take a guided tour for a price they feel it was worth or what they could afford – even free!  

Pay-what-you-like tours are tours for every budget.  

• Walking Tours
• Architecture Tours
• Tourist Discount Passes
• Chicago Travel Tips

CHICAGO WALKING TOURS

We provide a platform for local, freelance tour guides to lead walking tours as well as ghost and architecture tours at no upfront cost, so that you may enjoy a worry-free quality sightseeing experience.

Walking tours are our forte, and we offer a number of daily and weekly pay-what-you-like walking tours of Chicago as well as completely free self-guided options.

You could browse the tours that we have by clicking the links below, by scrolling our public calendar (also below) or it just might be best to go directly to our  booking page . 

There’s no cost to book our walking tours. 

We have roughly 1000 reviews with a rating of  5 out of 5 stars and with 97% of reviewers rating us as very good or excellent.

We are so well-reviewed, yet TripAdvisor seems to hide us from you (probably because they can’t sell our tours for commission).   Read the reviews  for yourself.  

Our premiere Chicago walking tours are great day or night and serve as introductions to the city, Chicago history and cover the many of the main tourist attractions.   

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Our Regularly Scheduled Tours

• The Birth of the Skyscraper:  Architecture Tour is a great way to discover and appreciate the incredible landscape of buildings in Chicago and it ends in Grant Park near the famed Buckingham Fountain.
• The  Riverwalk and Chicago History Tour follows the path of the Chicago River and focuses on the history of Chicago, the Chicago Flag, and the beautiful buildings that line the river.
• North Loop and Millennium Park Tour , which covers a great portion of Chicago’s downtown Loop neighborhood, public art, and ends in Millennium Park.
• Our  Chicago Ghost Tour -Haunting History is for folks who love haunting history and creepy tales of the dark side of the White City.
• On The Magnificent Mile Tour , you will discover fun Chicago facts like the history of deep dish pizza while exploring our most popular downtown area.

Weekly Tours

• Our  Gold Coast Tour  meanders through the history of high society where you will be introduced to the glamorous residential neighborhood built around Lakeshore Drive.
• Explore Lincoln Park on our Lincoln Park and Gangster Tour to appreciate a unique neighborhood scattered with hidden history including tales of Chicago Gangsters.
• We also offer a West Loop tour which combines great storytelling for history buffs with great photo ops for those more in the “sightseeing” mood! 
• Get out of downtown and check out the Chicago Street Art on our Wicker Park Culture & Street Art tour.

Winter Tours

We offer tours year-round, even in Chicago's winter, but we take into account the need to be seasonably appropriate for walking tours. Check out our special Winter offers:

• In the winter, we offer a Pedway Tour that explores the indoor tunnels and paths to discover Chicago architecture and arts in a warmer way.
• There is also a  Winter Loop option where we will spend about half of the time outdoors looking up at the skyscrapers and the other half will be spent inside exquisite public buildings and lobbies.
• Our Winter Architecture Tour explores the unique landscape of buildings in the downtown area while also popping into many lovely lobbies for warmth!  This tour is abbreviated and adjusted for our Chicago winters.

En Español:

• Tour del North Loop y Millennium Park
• El Tour Chicago Riverwalk
• Audio Tours

CHICAGO ARCHITECTURE TOURS

Many of our pay-what-you-like walking tours are architecture tours or architectural points are a large part of them.

These tours include:

• The Birth of the Skyscraper
• North Loop and Millennium Park Tour
• Riverwalk and Chicago History Tour
• The Magnificent Mile Tour
• West Loop Tour

In addition to our walking tours, there are other walking tour companies that offer excellent architecture tours.

Another popular option is to take an architectural boat cruise . There are even architectural tours by bus as well as Segway.

If you are on a budget or would just like to take things at your own pace, then consider one of our self-guided walks .

OTHER TOURS

In addition to walking tours, Chicago has bus, bike & boat tours. Read all about them...

• What is the Best Chicago Architecture Tour?
• Chicago Boat Tours Compared
• Hop on Hop off Chicago | Big Bus Tours vs. City Sightseeing Tours
• Chicago Ghost Tours | Haunted Tours in the Windy City
• Chicago Segway Tours
• Chicago Bike Rentals and Tours

PRIVATE TOURS

We also offer our guiding services for private groups, families, or school groups where we can guide you in the Loop, the South Side and anywhere else in Chicago.

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Travels & Treasures

9 Great Chicago Architecture Tours

If you’re looking for the best Chicago architecture tours, you’ve found them here! As a local who has explored these tours on weekends, during staycations, or while showing visiting friends around Chicago, I can honestly say that this list shares the most unique and fun experiences.

The city has great options including the best architectural boat tours, helicopter tours, walking tours, and more.

If you have limited hours, take the Hop On/Hop Off bus tour in Chicago or visit the top Chicago attractions to get the most out of a short amount of time. Real all about this in this roundup post!

Table of Contents

Best Chicago Architecture Tours

Chicago architecture cruise.

If you love touring on water, then this cruise is for you. I’ve taken this cruise several times while showing friends the city and they loved it too.

On this cruise, you will ride the Chicago River and see the city’s famous architecture. You’ll see the impressive flat skyline including over 40 famous buildings such as Navy Pier, the Wrigley Building, and the John Hancock Building with audio narratives. The tour covers all three branches of the Chicago River.

Navy Pier Centennial Wheel Regular & Express

This is one of my favorite ways to see the city and the Chicago skyline. You circle only once, but the ride is super slow, and you’ll have some great photo ops when you get to the top.

Navy Pier is among the most visited destinations in the world. It offers beautiful views from the wheel, and it’s a must-do when in the area! Located right on the pier, you have spectacular views of the city’s skyline, architecture, and waterfront.

45-Minute Private Helicopter Flight

I was scheduled to go on this flight but it was canceled due to bad weather. At least they are good at following safety protocol. Too bad that I missed this amazing experience by helicopter. From what I hear, you will get the best views of touring Chicago architecture, and the experience of flying amongst the clouds. 

Willis Tower Skydeck and The Ledge

Having been on the Skydeck a couple of times, it never disappoints. What I didn’t like much was that there is a limited time that you have to stand in the box. But if there were no supervision, the line would be from the street.

But here, you will have some of the most breathtaking views of Lake Michigan. You’ll also see why home is to beautiful parks and cultural attractions such as the Adler Planetarium, Millenium Park, the Shedd Aquarium , and Grant Park.

Look north to see Chicago’s iconic skyscrapers and landmarks from Lincoln Park to the world-famous Wrigley Field.

Night Tour with Willis Tower Entry & Skyline Cruise

This tour is a wonderful way to spend the evening while touring in Chicago. You’ll immerse yourself in one of the tallest architectural buildings in Chicago along with a Chicago boat tour. 

Experience the Windy City’s most popular attractions on this overnight tour. Watch the night light show of Buckingham Fountain. Cruise along the Chicago skyline and climb to the top of the iconic Willis Tower.

Big Bus Panoramic Sunset Tour with Live Guide

If this is your first visit to this city, this is a great way to tour Chicago , Illinois and how it shines at night. There is so much to see on both sides of the bus since the architecture of Chicago is interesting.

Experience the stunning skyscrapers of Windy City that light up at night. Take a panoramic nighttime tour from the Magnificent Mile to Michigan Avenue past the Chicago Theater and Buckingham Fountain.

Chicago History, Culture, and Architecture Walking Tour

This is a great way to hear about Chicago’s history and architecture. Take a private stroll or share walks with family or friends for this architecture tour. You can see old and new architecture, try delicious local treats, see beautiful boats tour the river. 

I also recommend visiting the Jane Addams-Hull Ho use Museum for a firsthand experience of the artifacts and memorabilia that tell the story of this pivotal institution for social reform.

Chicago Architecture Center Exhibit Admission

The Chicago Architecture Center or CAC is located at the south end of Magnificent Rock near Michigan Walker Intersection. You’ll discover super-sized models of architecture from around the world.

The vouchers give you access to two floors of imaginative exhibitions at the city’s newest cultural venue.

Chicago Art Deco Skyscrapers Walking Tour

The luxurious materials and geometric decorations of Art Deco represent the opulence and optimism of the decadent 20s. Visit some of the city’s most beautiful architecture and learn about the history and characteristics of this modern decorative style.

Final Thoughts on the Best Chicago Architecture Tours

These are the best ways to tour Chicago architecture and see all the unmissable attractions. I’ve taken almost every single one of these tours, including ones not mentioned and found them worth the money.

I enjoyed seeing the towering skyscrapers and iconic landmarks. The tours offer a fascinating glimpse into the architectural history of the Chicago. Not to mention, it’s nice to play tourist in my own back yard.

As a visitor, be sure to plan your tour in advance and consider factors such as weather and time of day to make the most of your experience. Don’t forget your camera to capture the stunning views along the way.

Whether you’re an architecture enthusiast or simply looking to appreciate the city’s remarkable skyline, a Chicago architecture tour is a must-do activity. The buildings are inspiring structures, and some are a marvel of innovative designs that have shaped this iconic city.

Whether you go on water, in the air, or on foot , book your tour today and embark on a journey through Chicago’s architectural wonders.

Tanya, a travel writer and content creator who has lived in Chicago for over 30 years, is your go-to local expert for Chicago's hidden treasures. Tanya's deep knowledge of various cities and attractions is acquired through personal exploration, making her articles a treasure trove for travelers and families. She has visited 43 of the 50 United States, France, Italy, Spain, Portugal, and the UK.

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9 Great Chicago Architecture Tours

I f you're looking for the best Chicago architecture tours, you've found them here! As a local who has explored these tours on weekends, during staycations, or while showing visiting friends around Chicago, I can honestly say that this list shares the most unique and fun experiences.

The city has great options including the best architectural boat tours, helicopter tours, walking tours, and more.

If you have limited hours, take the Hop On/Hop Off bus tour in Chicago or visit the top Chicago attractions to get the most out of a short amount of time.

Architecture Tours You Should Try in Chicago

Chicago architecture cruise.

Check rates for Chicago Architecture Cruise

If you love touring on water, then this cruise is for you. I've taken this cruise several times while showing friends the city and they loved it too.

On this cruise, you will ride the Chicago River and see the city's famous architecture. You'll see the impressive flat skyline including over 40 famous buildings such as Navy Pier, the Wrigley Building, and the John Hancock Building with audio narratives. The tour covers all three branches of the Chicago River.

Navy Pier Centennial Wheel Regular & Express

Check rates at Navy Pier Centennial Wheel

This is one of my favorite ways to see the city and the Chicago skyline. You circle only once, but the ride is super slow, and you'll have some great photo ops when you get to the top.

Navy Pier is among the most visited destinations in the world. It offers beautiful views from the wheel, and it's a must-do when in the area! Located right on the pier, you have spectacular views of the city's skyline, architecture, and waterfront.

45-Minute Private Helicopter Flight

Check rates at 45-Minute Private Helicopter Flight

I was scheduled to go on this flight but it was canceled due to bad weather. At least they are good at following safety protocol. Too bad that I missed this amazing experience by helicopter. From what I hear, you will get the best views of touring Chicago architecture, and the experience of flying amongst the clouds. 

Willis Tower Skydeck and The Ledge

Check rates for Willis Tower Skydeck and The Ledge

Having been on the Skydeck a couple of times, it never disappoints. What I didn't like much was that there is a limited time that you have to stand in the box. But if there were no supervision, the line would be from the street.

But here, you will have some of the most breathtaking views of Lake Michigan. You'll also see why home is to beautiful parks and cultural attractions such as the Adler Planetarium in Millennium and the Shedd Aquarium in Grant Park.

Look north to see Chicago's iconic skyscrapers and landmarks from Lincoln Park to the world-famous Wrigley Field.

Night Tour with Willis Tower Entry & Skyline Cruise

Check rates at Night Tour with Willis Tower Entry & Skyline Cruise

This tour is a wonderful way to spend the evening while touring in Chicago. You'll immerse yourself in one of the tallest architectural buildings in Chicago along with a Chicago boat tour. 

Experience the Windy City’s most popular attractions on this overnight tour. Watch the night light show of Buckingham Fountain. Cruise along the Chicago skyline and climb to the top of the iconic Willis Tower.

Big Bus Panoramic Sunset Tour with Live Guide

Check rates at Big Bus Open-Top Panoramic Night Tour

If this is your first visit to this city, this is a great way to tour Chicago , Illinois and how it shines at night. There is so much to see on both sides of the bus since the architecture of Chicago is interesting

Experience the stunning skyscrapers of Windy City that light up at night. Take a panoramic nighttime tour from the Magnificent Mile to Michigan Avenue past the Chicago Theater and Buckingham Fountain.

Chicago History, Culture, and Architecture Walking Tour

Check rates at Chicago History, Culture, and Architecture Walking Tour

This is a great way to hear about Chicago's history and architecture. Take a private stroll or share walks with family or friends for this architecture tour. You can see old and new architecture, try delicious local treats, see beautiful boats tour the river. 

Chicago Architecture Center Exhibit Admission

Check rates at Chicago Architecture Center Exhibit

The Chicago Architecture Center or CAC is located at the south end of Magnificent Rock near Michigan Walker Intersection. You'll discover super-sized models of architecture from around the world.

The vouchers give you access to two floors of imaginative exhibitions at the city's newest cultural venue.

Chicago Art Deco Skyscrapers Walking Tour

Check rates at Chicago Art Deco Skyscrapers Walking

The luxurious materials and geometric decorations of Art Deco represent the opulence and optimism of the decadent 20s. Visit some of the city's most beautiful architecture and learn about the history and characteristics of this modern decorative style.

Final Thoughts on the Best Chicago Architecture Tours

These are the best ways to tour Chicago architecture and see all the unmissable attractions. I've taken every single one of these tours, including ones not mentioned and found them worth the money.

I enjoyed seeing the towering skyscrapers and iconic landmarks. The tours offer a fascinating glimpse into the architectural history of the Chicago. Not to mention, it's nice to play tourist in my own back yard.

As a visitor, be sure to plan your tour in advance and consider factors such as weather and time of day to make the most of your experience. Don't forget your camera to capture the stunning views along the way.

Whether you're an architecture enthusiast or simply looking to appreciate the city's remarkable skyline, a Chicago architecture tour is a must-do activity. The buildings are inspiring structures and some are a marvel of innovative designs that have shaped this iconic city.

Whether you go on water, in the air, or on foot , book your tour today and embark on a journey through Chicago's architectural wonders.

Chicago River Boat Architecture Tours

Chicago River Tours | Fireworks Tours | Jazz/Cocktail Tours

River Boat Tours

Book your tour now, book by phone: (708) 488-6343, about the tours, chicago river boat architecture tours .

Welcome to Chicago River Boat Architecture Tours!  We’re proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Known for unique, daring, and historical architectural pursuits, it’s hard to cover all of the design and building treasures that make up the Windy City today. If you’re ready to learning more about the designs, people, and innovations behind these creations, throw on your captains hat and get ready to cruise along the Chicago River and see what architects from around the world travel to see in Chicago.

About The Chicago River Boat Architecture Tours

Chicago is known around the world for its architectural feats, both inside and outside of the buildings. From the 100-year-old Art Deco, Neo-Classical, and Gothic Towers, to some of the tallest modern-day skyscrapers, Chicago is where old meets futuristic architectural endeavors. It has something for everyone in a way that no other city replicates today.

Why Tour Chicago’s Architecture with Us?

We are born-and-raised Chicagoans ourselves, passionate about the community that we know and love. That passion and desire spills into all of our tours, drawing on personal experiences for curating a tour that just can’t be duplicated by a book or a movie. We want you to experience everything firsthand. Why tour with us?

• Expertise: All of our tour guides are either architects, architecture students, or architecture historians, making for an in-depth and personally rooted kind of touring experience that covers all of the discreet details.
• Variety: We offer a variety of uniquely different tours that cover everyone’s individual taste. We offer the Chicago River Boat Architecture Tour that takes you down the famous Chicago River; there are several different options such as Architecture, History, Cocktail Cruises and Firework Viewing Tours
• Flexibility : We want you to enjoy your Chicago River Boat touring experience, which is why we’re happy to talk with you and learn more about how our tours can accommodate you, your party, or your corporate outing. Our tours run daily, with availability always posted on our website here.

Our Tours  

• Chicago River Boat Architecture Tour : When in Chicago, cruising down the Chicago River is  a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river.
• Chicago River Boat Cocktail Tour : Join us for this great Architecture Tour while sipping craft cocktails, beer or wine available for purchase at our bar on board!
• Lake Michigan Navy Pier Fireworks Cruise :  Fireworks, one of the Four Great Inventions of ancient China were invented in the 12th century. Chicago approved City-Wide Use of Fireworks on the 4th of July 1893,. Mayor of Chicago Patrick Eugene Prendergast issued a proclamation approving the use of fireworks to celebrate the World’s Colombian Exposition and to celebrate the nation’s 117th Independence Day. This fascination with fireworks, noise, and color continues today. The City of Chicago offers a fireworks show at Navy Pier on Saturday nights at 10:15 p.m. The Fireworks Cruise sails on both the Chicago River and Lake Michigan each Saturday at 8:30 pm.

Our Commitment to Your Touring Experience

We believe that tours should be entertaining, enlightening, informational, and perfectly organized, every single time. A tour shouldn’t feel laborious in any way; you should feel an effortless inclination to learn more about what we present at your fingertips. With our Chicago architectural tours, that’s exactly what we strive to provide, basing each tour from the perspective of an expert with the real-life example in the background.

If you’re thinking about booking a tour with us, know that our commitment to flexibility and accessible makes our Chicago Architecture Tours easy and convenient:

• 3 pm *Not Available Friday thru Sunday Summer Months*
• 6:30 pm (Jazz Band, Cocktail w/bar) *Sunday Only*
• 8 pm (Wednesdays)
• 8:30 pm (Saturdays)
• Seniors $48
• Youths $30 (7-12 years old)
• Children 6 and under Free

BOOK YOUR TOUR TODAY

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Chicago river boat cocktail tour.

Join us in the evening to sip cocktails while cruising the historic Chicago River! Get the same tour just with a cocktail in your hand! Premium bar on board with craft cocktails, wine and beer available for purchase. Drinks may be purchased individually with a credit card on the boat. Tour Information Pricing Adults $49… Continue reading Chicago River Boat Cocktail Tour

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Chicago river boat architectural tour.

Forming a length of 156 miles when combined, the Chicago River is a system of rivers and canals the characterize the infamous skyline of Chicago today. The river, running through the city, including the city center Chicago Loop, is evident of man made design and infrastructure when completed craftily. In 1887, the river was reversed… Continue reading Chicago River Boat Architectural Tour

Lake Michigan Navy Pier Fireworks Cruises (w/ Architecture Tour)

Enjoy your favorite drink while gazing Chicago’s magnificent architecture and finish your cruise with fabulous light show, at Navy Pier. Fireworks, one of the Four Great Inventions of ancient China were invented in the 12th century. Chicago approved City-Wide Use of Fireworks on the 4th of July 1893,. Mayor of Chicago Patrick Eugene Prendergast issued… Continue reading Lake Michigan Navy Pier Fireworks Cruises (w/ Architecture Tour)

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Winter Architecture Tours

• Chicago Architecture Center
• 111 E. Wacker Dr. Chicago 60601 USA
• (312) 922-3432
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Get the Inside Look Behind Chicago’s Architectural Icons on a Building Tour from the CAC!

Escape the cold temperatures and duck into one of the city’s renowned architectural wonders on a Chicago Architecture Center building tour. The CAC’s expertly trained docents are sure to keep you entertained with fascinating facts and behind-the-scenes secrets about each building's architectural past, present and future. And with a robust lineup of tours available, there’s something for everyone to enjoy. History buffs can step back in time on a tour of the Rookery, with exclusive access to famous spaces rarely open to visitors. Or marvel at the architectural details of the Reliance Building, an 1895 structure maintaining its original marble, mahogany doors and decorative wrought iron. Perhaps you’d prefer to look take in the city from new heights on a tour of the 100-story-tall 875 N. Michigan skyscraper.

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SPECTRUM BY MIRARI

875 N MICHIGAN AVE April 7, 2024 - May 6, 2024 The Magnificent Mile Association and SSA 76 invite you to experience the U.S. premiere of Spectrum by Mirari. This 4 week limited engagement experience is hosted by Hearn at 875 North Michigan Avenue.

From the Blog

Spectrum by mirari.

Experience a one of a kind fusion of light and sound at the plaza of 875 North Michigan Avenue. From April 7th to May 6th, immerse yourself in an interactive installation that delves deep into the phenomenon of communication. Read more

Announcing The Magnificent Mile™ Tulip

Chicago's springtime tradition blooms again! Every year, Michigan Avenue transforms into a vibrant floral spectacle with tens of thousands of tulips bursting into color in mid April to early May.

Open House Chicago: Explore Chicago's Architectural Wonders

Enjoy a lively day in Chicago starting with a one of a kind experience at Ed Debevic's. Then off to your Open House Chicago 2023 adventure. Savor a Halloween-themed afternoon tea at The Ritz-Carlton Chicago. Finally, end your day with some fun at Flight Club. 

Chicago Vintage Fest Mother's Day Pop-Up

Saturday, May 11th & Sunday, May 12th 12 – 6PM, Daily Pioneer Court, 401 North Michigan

This Weekend: Dash to The Altar™

In this season of love, celebrate  as  26 happy couples say “I do” on  October 7th at  The Wrigley Building  before the Chicago Marathon  on October 8th .  Keep reading  for what  your weekend in  the heart of Chicago  has in store .  

Kick-off the Fall Season In Style

Welcome to the vibrant Autumn season! Embrace the fall energy with a pumpkin cream nitro coffee from Beatrix. Sip on their new pumpkin cream nitro coffee while enjoying your choice of sweet or savory breakfast to start your day! Read more

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