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Top Chicago Architecture Tours

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Lake Michigan is cool, but most people say Chicago’s crown jewel is its architecture. The city has countless ways for you to immerse yourself in the subject. Take an architecture-themed river cruise or walk to see the buildings that make the Windy City so iconic. Some tours even venture through the Pedway, Chicago’s underground pedestrian tunnels. Alternatively, ride the “L”—elevated train—with a guide to learn about famous architects like Frank Lloyd Wright or board a double-decker bus to take in the historic structures. Chicago architecture tours will leave you with a profound appreciation for design.

63 results

Best Seller
Chicago River 45-Minute Architecture Tour from Magnificent Mile
4.7
(1,948)

Chicago River 45-Minute Architecture Tour from Magnificent Mile

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.
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  • 45 minutes
  • Free Cancellation
from
$28
Chicago Architecture River Cruise
4.8
(14,063)

Chicago Architecture River Cruise

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this 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'll cover multiple branches of the Chicago River, and will learn insider facts and stories you'd otherwise miss.
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  • 1 hour
  • Free Cancellation
from
$49
Original Chicago Architecture Interiors Tour: Dazzling Interiors
5.0
(1,014)

Original Chicago Architecture Interiors Tour: Dazzling Interiors

See the overlooked highlights of Chicago’s Loop district with a walking tour that takes in the best of the bustling, vibrant neighborhood’s inside spaces. Get behind the façades to explore stunningly designed interiors as you follow a specially designed route with an experienced guide. Learn about the city’s architecture, art and history while visiting a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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  • 2 hours
  • Free Cancellation
from
$30
Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
3.9
(1,955)

Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour by Open-Top Bus

Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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  • 2 hours
  • Free Cancellation
from
$50
Likely to Sell Out
Chicago Lake and River Architecture Tour
4.7
(2,012)

Chicago Lake and River Architecture Tour

Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$45
Chicago Architecture Center River Cruise aboard Chicago's First Lady
4.9
(3,381)

Chicago Architecture Center River Cruise aboard Chicago's First Lady

Enjoy a quintessential Chicago experience when you go on an architecture-themed river tour. Pick from multiple convenient start times, and board your vessel—the Lady Liberty—directly from the Chicago Riverwalk. Your trained docent guides will give you a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and you can spy landmarks like the Marina City towers and Navy Pier from the water’s edge.
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  • 1 hour 30 minutes
from
$56
Likely to Sell Out
Chicago Fireworks Dinner Cruise with Buffet
3.8
(77)

Chicago Fireworks Dinner Cruise with Buffet

Enjoy a memorable, one-of-a-kind night out on Lake Michigan aboard this combination dinner, dancing, and sightseeing cruise. Make your own way to Navy Pier, and set off as the evening begins. You can admire views of Chicago’s picture-perfect skyline as the sun starts to set. While on board, take advantage of the all-you-can-eat buffet dinner, drinks to purchase, a DJ-helmed soundtrack, and even a fireworks display (weather permitting).
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  • 3 hours
from
$194
Chicago in a Day: Food, History and Architecture Walking Tour
4.9
(934)

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

An excellent choice for first-time visitors, this four-in-one tour provides a comprehensive introduction to the city's top landmarks, history, culinary highlights, and shows the legacy left behind by the Prohibition Era. With just a small group for company, you'll set off on foot to discover Chicago architectural icons and visit highlights like the Chicago Riverwalk, Millennium Park, and more. In between, enjoy generous tastings of beloved dishes from deep-dish pizza to Italian beef sandwiches and beyond.
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  • 5 hours
  • Free Cancellation
from
$101
Likely to Sell Out
Chicago River 90-Minute Architecture Tour
4.7
(7,197)

Chicago River 90-Minute Architecture Tour

Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$45
360 CHICAGO Observation Deck Admission
3.9
(955)

360 CHICAGO Observation Deck Admission

Tower above the Windy City’s world-famous skyline with admission to 360 Chicago. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.
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  • 1 to 4 hours
  • Free Cancellation
from
$30
Chicago City Tour with Architecture River Cruise Option
4.8
(647)

Chicago City Tour with Architecture River Cruise Option

Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods. You have a chance to get out and 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.
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  • 2 to 4 hours
  • Free Cancellation
from
$48
Chicago Gourmet Dinner Cruise on Lake Michigan
3.6
(342)

Chicago Gourmet Dinner Cruise on Lake Michigan

Enjoy an evening out in style in Chicago on a gourmet dinner cruise with Chicago’s stunning skyline as your backdrop. Sit down for a 3-course dinner, made with fresh seasonal ingredients and prepared by a chef. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis Tower and Navy Pier, and musical entertainment provided by the onboard DJ.
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  • 2 hours 30 minutes
from
$139
Chicago Architecture Tour: Underground Pedway and the Loop
4.9
(230)

Chicago Architecture Tour: Underground Pedway and the Loop

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.
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  • 2 hours
  • Free Cancellation
from
$35
Likely to Sell Out
Chicago River Architecture Tour with Small Boat Upgrade Option
4.8
(817)

Chicago River Architecture Tour with Small Boat Upgrade Option

Chicago is known internationally for its architectural diversity and dynamism—and this in-depth tour will introduce you to many of the city’s best-known and most influential landmarks. Meet at the pier right off Lake Shore Drive, hop aboard your boat, and set off. You’ll spy highlights ranging from Chicago’s skyscrapers and bustling Navy Pier to the famous “Bean” sculpture—and will learn about the different architectural movements that shaped the city. Upgrade your experience to a small boat with a maximum of 60 people, or choose the combo tour option which includes a 90-minute sightseeing tour of Chicago's architecture by minibus.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$49
Chicago Walking Tour: Historic Treasures of Chicago
4.9
(336)

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.
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  • 2 hours
  • Free Cancellation
from
$30
Chicago Walking Tour: Must-See Chicago
4.9
(83)

Chicago Walking Tour: Must-See Chicago

First-time visitors to Chicago seeking a quick overview of the city will enjoy this 90-minute small-group walking tour. Your guide will take you to some of Chicago’s most beautiful and interesting buildings, including the Tribune Tower, the Art Institute, the Willis Tower, and more. Learn about Chicago’s architecture, history, and culture while getting your bearings.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$30
Chicago City Tour: Elevated Architecture Tour with Train Ticket Included
4.8
(56)

Chicago City Tour: Elevated Architecture Tour with Train Ticket Included

Chicago’s “L,” or elevated train, is an icon of public transportation and a major feature of the Loop neighborhood. On this interactive tour, you’ll learn about the railway’s history while experiencing it as a rider. Meet your guide in the morning and set off with just a small group for company. As you ride between stops, you’ll also view Chicago icons like the Willis Tower, and will learn about the city’s architectural history.
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  • 2 hours
  • Free Cancellation
from
$36
Chicago Walking Tour: Art Deco Skyscrapers Loop
4.8
(130)

Chicago Walking Tour: Art Deco Skyscrapers Loop

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$30
Likely to Sell Out
Chicago: Culture and Architecture of the Prohibition Era
4.8
(79)

Chicago: Culture and Architecture of the Prohibition Era

Walk Chicago to see the legacy left behind by the Prohibition Era. See the gorgeous Chicago skyline and discover why this city's architecture is among the best in the world. Take in famous landmarks like the Chicago Riverwalk, Wrigley Building, Tribune Tower, Magnificent Mile, and many more, all while your guide shares insider tips and stories you'd miss on your own. Then, taste surprise local treats along the way.
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  • 2 hours 30 minutes
  • Free Cancellation
from
$50
Frank Lloyd Wright Robie House Admission
3.9
(95)

Frank Lloyd Wright Robie House Admission

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.
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  • 1 hour
  • Free Cancellation
from
$27
Chicago Walking Tour: The Magnificent Mile
4.8
(32)

Chicago Walking Tour: The Magnificent Mile

Learn all about the history beyond one of Chicago’s best-known thoroughfares—and spot numerous architectural icons as you go—on this small-group walking tour of the Magnificent Mile. Meet your guide at the Chicago Architecture Center and set off to soak up the street’s ambiance, and discover highlights like the Wrigley Building, John Hancock Center, and more. Entry to the Chicago Architecture Center is also included, so you can extend the experience.
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  • 1 hour 30 minutes
  • Free Cancellation
from
$30
Chicago Riverwalk Self-Guided Walking Tour
4.0
(5)

Chicago Riverwalk Self-Guided Walking Tour

Explore the sights and skyscrapers of Chicago’s spectacular Riverwalk—and enjoy the most budget-friendly and flexible sightseeing experience around—on this 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: you’ll see highlights like the Merchandise Mart, Wrigley Building, Vietnam Veterans Memorial, and much more.
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  • 1 to 2 hours
  • Free Cancellation
from
$15
Likely to Sell Out
Chicago River Architectural Lunch Cruise
4.2
(30)

Chicago River Architectural Lunch Cruise

Travel down the Chicago River on an architecture cruise aboard the "Odyssey." As you pass by some of Chicago's most notable buildings, you'll dine on a 3-course lunch with salad, a main course such as chicken, salmon, pasta, or short ribs, and a dessert such as cheesecake or sorbet. Listen to onboard narration about the city's architecture along the way.
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  • 2 hours
from
$105
Chicago Walking Tour: A Walk Through Time
4.9
(171)

Chicago Walking Tour: A Walk Through Time

Travel through architectural history on this express, small-group walking tour, which covers Chicago's most famous buildings in chronological order (and which is speedy enough to cater to the most time-pressed travelers). With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth commentary on Chicago's architectural history; you'll learn about each building, and will have plenty of chances to stop for photos.
... More
  • 1 hour 30 minutes
  • Free Cancellation
from
$30
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People Also Ask
Q:How much do architecture tours in Chicago cost?
A:

The typical architecture tour in Chicago is a 1.5-hour daytime river cruise, which costs around US$50 per person. Cruises that include lunch go for over US$100 while walking architecture tours are closer to US$30 a head.

Q:How long are Chicago architecture tours?
A:

Most Chicago architecture tours run for 1.5 hours, about the time it takes to cruise the Chicago River from Navy Pier, past the city’s famous riverside skyscrapers, and back. Some tours, accommodating families with young children and travelers on tight schedules, last closer to 45 minutes.

Q:What is included on Chicago architecture tours?
A:

Chicago architecture tours offer a crash course on the Windy City’s most recognizable buildings. While listening to an expert guide’s commentary about the city’s architectural history, you can take photos and, in some cases, enjoy complimentary drinks aboard your river cruise. Restrooms and luggage storage aren’t always included, so plan ahead.

Q:What do you see on a Chicago architecture tour?
A:

You’ll see Chicago’s greatest architectural feats, such as the undulating and award-winning Aqua building, the Tribune Tower’s ornate gothic revival facade, and the third tallest skyscraper in the Western Hemisphere, Willis Tower. Your guide will highlight Chicago landmarks like the “Bean” sculpture, Centennial Fountain, and Navy Pier.

Q:Why is Chicago famous for architecture?
A:

After the Great Chicago Fire of 1871 destroyed most of the city’s downtown, famed architects rebuilt the city’s skyline, giving rise to the world’s first skyscraper and, soon, one of the most architecturally diverse city centers on the globe. Art Deco, neoclassical, and Gothic revival structures stand next to sleek skyscrapers, reflecting the city’s uniquely varied design heritage.

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