Top Chicago Architecture Tours - page 3

Downtown Chicago Guided Walking Tour Semi-Private 12ppl Max

2 hours 30 minutesFree Cancellation

(1)

from $52

Explore Chicago's iconic skyline on this enlightening Riverwalk architectural tour. Experience the rich tapestry of history and innovation as "you get your steps in" along the scenic Riverwalk, revealing the stories behind the city’s most celebrated structures. Expert guides will share insights into the work of renowned architects like Mies van der Rohe and Jeanne Gang, showcasing the stunning interplay of glass, steel, and water. Ideal for architecture enthusiasts and first-time visitors alike, this tour offers a unique perspective on the Windy City’s vibrant culture and architectural beauty. - Discover Chicago’s architectural evolution from Art Deco to modern designs - Guided insights from experts on legendary architects and their masterpieces - Enjoy a scenic stroll along the picturesque Riverwalk - Perfect for both architecture lovers and those new to Chicago

Chicago Riverwalk Architecture Walking Tour and Discover Skyline

Chicago Riverwalk Architecture Walking Tour and Discover Skyline

1 hour 30 minutesFree Cancellation

from $49

Chicago Architecture, Art and History Tour - Off The Beaten Path

This short but sweet and unique adventure will take you on a 2-hour walking tour by the interiors of the most iconic buildings of Chicago downtown. Dive into the extravaganza of splendid hidden gems of the city as you explore the details that no mainstream tours can offer. The itinerary is thoroughly designed by a professional local guide who knows every corner of the Chicago skyscrapers. • Get beyond the famous facades to experience the surprising interiors of the neighborhood • Follow your local guide to discover what’s hidden from most of the tourists • Be provided with fun and surprising facts about the destinations • The tour is interesting for the Chi guests as well as for the residents.

Chicago Architecture, Art and History Tour - Off The Beaten Path

2 hoursFree Cancellation

3.5

from $95

Likely to Sell Out

Workers Cottages of Oldtown Triangle Walking Tour

Leave behind Chicago’s buzz and see the Windy City as it used to be, some 150 years ago. The Oldtown Triangle—one of the most beloved ‘hoods in the city—survived the Great Chicago Fire of 1871, and it still stands today as a beacon to history. With your guide at the helm, you’ll witness fantastic architecture, national landmarks, and hear stories of the city’s often wild past.

Workers Cottages of Oldtown Triangle Walking Tour

1 hour 45 minutesFree Cancellation

Dive into the center of the architectural boom of the roaring 1920s and take a chance to enjoy the grand facades of the Art Deco skyscrapers on this guided walking tour. Go back in history while admiring one of the epicenters of the style’s birth. Immerse yourself into the life of the Windy City between World War I and World War II, the time when the design evolved and turned into neo archaic Mesoamerican grandeur, which can’t leave anyone indifferent. Be delighted with the variety of decorations and geometrical shapes which distinguish Art-Deco from Neoclassicism. Uncover the stories behind the famous Loop district of Chicago. Delve into the atmosphere of the 1920s as you listen to more insights and facts from your enthusiastic local guide. Overview the history and pay attention to the details you wouldn’t notice without a tour. Grab the chance to get inside famous buildings and revel in the Art Deco interiors.

(53)

from $45

Chicago Art Deco Architecture Tour - History of the Jazz Age

History of the Jazz Age at Chicago Art Deco Architecture Tour

1 hour 30 minutesFree Cancellation

3.5

from $67

Private 2-Hour Walking Tour: Chicago Loop Interior Architecture

Chicago is renowned for its architecture—and this immersive walking tour offers the perfect way to discover its highlights. Pick from a wide range of start times, meet your private guide right in the Loop, and set off on foot. In between seeing renowned landmarks like the Chicago Cultural Center, public art by Picasso, and other heritage buildings, you’ll learn all about the city’s history.

Private 2-Hour Walking Tour: Chicago Loop Interior Architecture

2 hours

from $315

Enjoy an immersive way to discover Chicago's more recent architectural heritage with this small-group walking tour. Led by your architectural expert guide, you'll discover many of the Windy City's modern, postmodern, and other newer structures, including works by architects like Mies van der Rohe, Bertrand Goldberg, and beyond. As you go, your guide will point out the buildings many visitors overlook, and share stories from their history you wouldn't otherwise hear.

Chicago Walking Tour: Modern Architecture

1 hour 30 minutesFree Cancellation

4.8

(66)

from $35

Logan Square Walking Tour Experience

1 hour 20 minutesFree Cancellation

from $35

Likely to Sell Out

Exclusive Downtown Chicago Guided Walking Tour 12ppl Max

What do the artists Picasso, Chagall, Miro, and Kapoor all have in common? Incredible public art hiding in plain sight amidst world famous architecture. Tour Chicago in a small group perfect for busy sidewalks and get up close to monumental art! Join one of our expert guides on this unique and exclusive 2.5 hour guided walking tour of Downtown Chicago. Highlights Include: Edward Kemeys’s “Lions” Juame Plensa’s “Crown Fountain” Anish Kapoor’s “Cloud Gate” (The Bean) Eduardo Kobra’s “Muddy Waters” Pablo Picasso’s “Untitled” Joan Miro’s “Chicago” Alexander Calder’s “Flamingo” Marc Chagall’s “Four Seasons” Louis Comfort Tiffany Art Glass Creation Augustus St. Gaudens “Abraham Lincoln” Marcel Francois Loyau “Clarence Buckingham Fountain”

Exclusive Downtown Chicago Guided Walking Tour 12ppl Max

2 hours 30 minutesFree Cancellation

from $52

It would take days to visit all of Chicago’s famous sights, but who has that kind of time? Cover the highlights of the Windy City during this private half-day walking tour. From the Magnificent Mile to Millennium Park, you’ll tick off top attractions while your guide fills you in on Chicago’s history. Finally, enjoy panoramic views overlooking the city from Hancock Tower’s Observation Deck—admission tickets included.

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

Welcome to Chicago: Private Half-Day Tour with 360 Observation Deck

3 hoursFree Cancellation

(3)

from $240

Explore the surprising beauty and history of the Windy City with this combo tour of Chicago’s Millennium Park and Riverwalk! Snap a picture by the famous Cloud Gate sculpture and get away from the hustle and bustle in the city’s most iconic park. Then, stroll along the picturesque riverside, admire Chicago’s totally unique architecture, and learn the fascinating stories behind the city’s skyline. This combo is the easiest, best way to get to know this complex city! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Special Offer

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

Chicago Riverwalk & Millennium Park Self-Guided Audio Tour Bundle

1 to 2 hoursFree Cancellation

Special Offer

Explore the sights and skyscrapers of Chicago’s spectacular Riverwalk on this private, self-led smartphone walking tour. Upon booking, download the app and receive a password to access your tour; once it’s on your phone, it is valid for an entire year. Set off at a time that works best for you: see highlights like the Merchandise Mart, Wrigley Building, Vietnam Veterans Memorial, and much more.

Chicago Riverwalk Self-Guided Walking Tour

1 to 2 hoursFree Cancellation

Step into the birthplace of the modern skyscraper on this immersive walking tour through Chicago’s historic Loop. Discover the stories, innovations, and hidden details behind the buildings that shaped the modern city. What makes this experience unique: • Small-group tour for a more personal experience • Story-driven guiding that brings Chicago’s architecture to life • Focus on early skyscrapers and hidden architectural details • Visit iconic landmarks in the historic Loop • One complimentary copy of my book, Chicago Beyond the Bean, is included per booking.

Chicago Early Skyscraper Walking Tour in the Loop

2 hoursFree Cancellation

from $39

Special Offer

Haunted Chicago: Lincoln Park Ghost Escape Game

Enjoy a flexible way to explore Chicago—and combine your sightseeing with a fun-filled scavenger hunt game—with this two-in-one smartphone excursion. Upon booking, receive access to the game on your smartphone, and set off at a time that works best for you. In between admiring highlights like the Chicago History Museum, Standing Lincoln Monument, and Lincoln Park Zoo, you’ll solve clues and participate in challenges.

Haunted Chicago: Lincoln Park Ghost Escape Game

2 hoursFree Cancellation

4.0

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from

Chicago Architecture and True Crime Tour: Fourth of July Edition

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Carol_H, Jun 2026

Guide Gus's Ghostly Gallivant

We had a fantastic time on the Chicago Architecture and True Crime Walking Tour! Our guide, Gus, was an outstanding storyteller—knowledgeable, engaging, and genuinely entertaining from start to finish. He blended fascinating architectural history with gripping true crime stories, making the tour both informative and fun. His enthusiasm and sense of humor kept everyone interested, and we came away with a much deeper appreciation for Chicago's history. I highly recommend this tour, especially if you're lucky enough to have Gus as your guide!

Chicago Architecture Center River Cruise aboard First Lady

Leslie_Y, Jun 2026

The only architectural tour to consider

This is the only tour to consider when looking for an architectural boat tour. I accidentally booked on another company. On that day, the surroundings were not familiar and I fortunately was able to book on the first lady that day. Dr. Mark. (?) [a retired orthopedic surgeon] was our docent. I have lived in Chicago for over 70 years and last year was my first tour on the first lady. It certainly won’t be my last.

Chicago River 90-Minute Architecture Tour

Ashanay_G, Jun 2026

Accommodating & Amazing Views

This tour was very accommodating. We unfortunately missed the boat ride the first day and they were able to reschedule us for the next day no charge. Other than that the tour was worth the money. Would do it again. Drinks were good and viewes were nice.

Chicago Architecture River Cruise

CorazonC_N, Jun 2026

Excellent Cruise!

This was a "Deep Dive" Architecture Cruise and 1 1/2 hours. Guide was very well informed and narrated expert details on the architecture of buildings she pointed out as she was an Architect herself. This longer cruise showed us many more buildings plus allowed us to appreciate the history of Chicago via the buildings we saw and our guide's amazing narration. Well worth paying a bit more versus the regular priced river cruises.

Chicago Architectural River Cruise

Donald_L, Jun 2026

Excellent Adventure

We went in late afternoon, great time to see the city from the water. Tyler was an excellent guide and gave great insight into the history of the architecture and how it evolved over the last 100+ years. Best to sit top deck to take everything in but wear sunscreen. Refreshments were easily accessible and the staff were friendly beginning to end

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Guy_L, Jun 2026

Great historical tour!

Heath provided great insight on a number of historic buildings in the downtown area. The pace of the tour was perfect. His knowledge about the history of the buildings and the city is outstanding and I'd like to do it again if I get the chance. It's a great way to learn about the city for tourists, newcomers and long-time residents of the area. Well done, Heath!

Historical and Architectural Chicago Fireboat River & Lake Cruise

Karl_D, Jun 2026

Great trip the weather didn’t cooperate with.

Unfortunately, it was too windy for the Fireboat to navigate the waters. The staff on the boat were very pleasant and disappointed that we couldn’t leave the dock. We were refunded the entire cost. We are hopeful that we can return the summer to experience the tour.

Chicago River 90-Minute Architecture Boat Tour

Sophia_S, May 2026

THIS is the tour.

I have been on 4+ Chicago Architecture boat tours in my life and this one, with Hillary, was by FAR the best. She knows the city like the back of her hand (literally) and it was the quickest 90 min tour in the best way. Hillary deserves her own stand up comedy Netflix special. My whole family was so impressed and for the price, this was immaculate. I could not recommend this tour enough and if I would recommend a tour to a friend, this would be it! 1000/10!

Chicago Architecture Tour: Underground Pedway and the Loop

Marcellus_C, Apr 2026

Excellent tour with a lot of learning!

This was an excellent activity that gave us a history of the underground walkway, in addition to some of the historical buildings in Chicago. Henry was very knowledgeable--he was able to answer 95% of our questions (some of our questions did come out of left field!). Keep in mind - the tour starts across the street from City Hall and ends elsewhere. It wasn't a strenuous walk at all (one of us had knee issues--he didn't complain at all.) About the only "climbing" we did was on stairs exiting the underground pedway. Henry also gave us plenty of opportunities for bathroom breaks. My only regret was not eating a good breakfast before taking the 2+ hour walk. (P.s. Henry was an excellent guide for this because of his background in architectural/structural engineering.). I would take this tour again!

Chicago City Tour with Architecture River Cruise Option

Marty_R, Mar 2026

Wonderful tour with Alan!

Alan was a great tour guide - lots of fun information and entertained all of our questions. It was my 17 year old daughter’s first trip to Chicago, so I wanted her to get to see as much of the main parts of the city as possible, and we definitely hit all the ones I had on my list! The bus itself was clean and well cared for, and I like that it was smaller than the other buses because it made it much more personal. Alan also had great recommendations for places to go, where to eat, and was able to give ideas for spots that were of interest to us specifically. Highly recommended!