Top Chicago Architecture Tours

Chicago River 90-Minute Architecture Tour

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

(10 600)

from US$45

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16 695)

from US$39

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

Join us in the daytime or evening for City lights and breathtaking views

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

(3 449)

from US$28

Chicago Architecture Center River Cruise aboard First Lady

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

(6 630)

from US$57

Chicago River 90-Minute Architecture Boat Tour

4.8

(1 830)

from US$37

Chicago Lake and River Architecture Tour

This tour cruises the Chicago River and Lake Michigan.

Maximize your Chicago sightseeing on a river cruise—and travel aboard a unique historical vessel, which other tours don’t offer—on this one-of-a-kind excursion. Pick from different departure times and board a classic Chicago fireboat, which served the city’s fire department from 1937 to 1981. As you sail Lake Michigan and the Chicago River, view architectural highlights including the Wrigley Building and Chicago Lighthouse, and chart the boat’s firefighting history via the on-board displays and commentary.

(2 396)

from US$45

Historical and Architectural Chicago Fireboat River & Lake Cruise

Historical and Architectural Chicago Fireboat River & Lake Cruise

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

(414)

from US$47

Chicago Architectural River Cruise

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

(842)

from US$50

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Original Chicago Architecture Interiors Tour: Dazzling Interiors

(1 743)

Chicago Architecture and True Crime History Tour

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

(525)

Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a trip down the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to in-depth commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Museum Campus, and other top sights.

Chicago Architecture Tour and Speedboat Ride and Lake Michigan

Chicago Seadog River & Lake Architectural Tour

1 hour 15 minutesFree Cancellation

4.5

(280)

from US$42

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

4.3

(1 877)

from US$44

Total Chicago: From Architecture to Food

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

Chicago in a Day Walking Tour: Food, History & Architecture

4 hours 30 minutesFree Cancellation

Price varies by group size

(1 331)

from US$101

Get a fresher perspective on the Windy City—and a traffic-free one—with this Chicago River architecture cruise. As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch, listening to onboard narration about the city's architecture and history along the way. Unlike your standard walking tour, you can expect comfort, great food, and endless photo opportunities.

City Cruises Chicago: River Architectural Lunch Cruise

City Cruises Chicago: River Architectural Lunch Cruise

Explore the hidden side of Downtown Chicago—and see sights that even many locals miss—on a small-group walking tour of the Pedway (an underground network of tunnels that connects Chicago buildings) and the vibrant Loop. Ideal for architecture fans, this tour includes insider stories and landmarks you wouldn't spot on your own—plus a chance to see Windy City icons like the Picasso Statue and Millennium Park.

4.3

(43)

from US$74

Chicago Architecture Tour: Underground Pedway and the Loop

Chicago Architecture Tour: Underground Pedway and the Loop

(524)

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour

3.9

(2 350)

from US$49

(61)

Explore the architectural genius of Frank Lloyd Wright on a private, fully personalized tour in Chicago, home to the world’s largest collection of his buildings. Travel in comfort with your English-speaking driver, who shares insights into Wright’s life, ideas, and influence on modern architecture. Begin at the Frank Lloyd Wright Home & Studio, where he lived and developed many revolutionary designs. Continue through the Oak Park to admire beautifully preserved Prairie School homes and early residential works. Visit Unity Temple, one of Wright’s most celebrated modern religious buildings, then return toward Chicago to see The Rookery Building with its grand lobby and intricate design. Conclude at Robie House, a masterpiece of Prairie School architecture showcasing Wright’s signature horizontal lines and integration with the landscape. This flexible experience offers architecture enthusiasts a relaxed way to explore Wright’s legacy and the evolution of modern American design.

Frank Lloyd Wright Oak Park Architecture Tour from Chicago

Frank Lloyd Wright Oak Park Architecture Tour from Chicago

5 hoursFree Cancellation

4.0

(4)

from US$223

Price varies by group size

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

The Chicago River, as seen from our stop on wacky Wacker Drive

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

4.8

(731)

from US$50

Chicago Walking Tour: Historic Treasures of Chicago

Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue, State Street, and the vibrant Loop area. Revisit the heyday of the skyscraper and visit stunning, art deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.

Chicago Walking Tour: Historic Treasures of Chicago

(435)

Discover one of Chicago’s top architectural marvels when you explore Frank Lloyd Wright’s UNESCO-listed Frederick C. Robie House, located right on the University of Chicago’s campus. Considered a masterpiece of Prairie School architecture, the building is famed for its cantilevered roof and rich wood details. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.

Frank Lloyd Wright Robie House Admission

Frank Lloyd Wright Robie House Admission

1 hourFree Cancellation

4.2

(149)

from US$27

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your interests guide you. Our expertly crafted audio experience unveils exclusive historical insights and hidden stories that even longtime residents don't know, transforming you from tourist to insider as you uncover the authentic soul of the Windy City. Unlike rigid group tours that rush you past remarkable details, you'll have the flexibility to choose which attractions captivate you most, creating a personalized journey that matches your curiosity and schedule perfectly. You'll experience the city as locals do – unhurried, authentic, and deeply connected to the stories that shaped this magnificent metropolis, all while enjoying a superior experience that combines the convenience of independence with the depth of expert knowledge.

Chicago Self-Guided Audio Tour

3 to 9 hours

3.9

(9)

from US$6

Chicago Architecture Walking Tour: What's New

There’s so much amazing architecture in Chicago but wandering around alone can leave you overwhelmed, and unsure of what you’re looking at. Check out some of Chicago's most important new buildings on an architecture walking tour. The tour is focused on the area around the Chicago Architecture Center (CAC), beside the Chicago River, so you don’t get overwhelmed exploring the whole city. Admission to the CAC’s galleries is also included.

Chicago Architecture Walking Tour: What's New

(90)

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.

Historic Homes and Cottages of Wicker Park Walking Tour

Historic Homes and Cottages of Wicker Park Walking Tour

1 hour 30 minutes

Chicago River 90-Minute Architecture Tour

(47)

from US$45

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Alia_M, Aug 2026

A must do

Highly recommend!!!! From check in to tour guide, seating, snacks beverages at the bar, friendly staff, to the outstanding views best photos up close it was all outstanding!!! We sat on the top and the tour guide was sooooo knowledgeable energetic kept us engaged the whole time!! He had great stories to go along with the architecture history and great personality loved the Chicago architecture history!! and just such a great vibe in the tour from the locals and tourists everyone shouting hi and happy 😊!! I would definitely do again!!

Chicago Lake and River Architecture Tour

FeleciaBritton, Aug 2026

Beautiful Tremendous Lake tour a must see

Excellent history lesson and beautiful scenery. Chicaho such a bountiful city and beautiful natural surroundings, the lake and the RIVER going throuth the city is very attractive. Great guide with a sense if humor always help. Priced right will always book again and again

Chicago Architecture River Cruise

Cleo_S, Aug 2026

Great Staff

The staff was lovely and the drinks were done perfectly, please don’t change the drinks. I honestly would do this ride just for the drinks lol. Only thing I would change are kids being allowed ha ha there should be an adults only option bc I couldn’t hear a thing over the extremely loud field trip.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

estefany_r, Aug 2026

Amazing experience & Amazing Tourist Guide

You will learn alot about chicago and have such a nice experience! I would totally recommend coming earlier to get good seating or you will end up going below to the enclosed section, arrived at 8:07 and the line was long even though the boat ride starts at 8:30!

Historical and Architectural Chicago Fireboat River & Lake Cruise

Ian_M, Jul 2026

Very informative and enjoyable tour

A very good tour, offering great value, and to travel on a fireboat made it more relevant. The guide was informative and funny too. Nice to stsrt outsifmde the city, trip around the harbour and go through the lock gates. Good information on architecture and buildings. A trip out to the lighthouse toward the end of tour was also an added bonus.

Chicago River 90-Minute Architecture Boat Tour

Julie_R, Jul 2026

Great tour, even between rain storms

The Chicago weather can be unpredictable and on a day with some of the weirdest weather, our tour went well with a break in the storm. Our guide was informative and charming as he pointed out the historical and significant buildings of Chicago. The whole tour was well worth braving the elements.

Chicago in a Day Walking Tour: Food, History & Architecture

Kimberly_L, Jul 2026

Rain or Shine

Our tour guide Dave was awesome. Our tour went through 3 seasons and a monsoon and he just kept going. Weather was crazy; you needed a fan when we started, by lunch it was dark, lightening and pouring rain and by the time it was over the weather had dropped 20 degrees. The food was very good.

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

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!

City Cruises Chicago: River Architectural Lunch Cruise

Shaterra_S, Aug 2025

Directions were poor but the cruise was very nice.

I can confirm that the instructions were awful. The pin that is in the reservation is for another parking lot. I recommend you follow the instructions that Viator gives you to start and then heed mine. The directions will take you to a parking lot on North Colombus Drive. If you stop there, you will miss your reservation. Make that right at the light on N Columbus Drive and go uphill. At the top of the hill, the NBC building should be on your right. If see a draw bridge, DO NOT CROSS IT. When you made it to the top of the hill, cross the street and make another right. You are standing at a parking lot again which is on your left now and facing ahead is the university of Chicago building. Right in front of the building there are some flags, that is where you will find stairs that will take you down to the Odyssey. Your destination will be immediately on your right. As for the cruise, the food was great. The portions were not small and the service was great. It was very informative, lively and a perfect time to spend the afternoon. Will return in the future for a dinner cruise.