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Top Chicago Architecture Tours

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35 Chicago Architecture Tours

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90-min Chicago River Architecture TourDay Cruises

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90-min Chicago River Architecture Tour

star-5
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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Booked by 5,703 travellers
  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$39.00 
From  
US$39.00 
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  • 1 hour 30 minutes
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  • Free Cancellation

Chicago Architecture River CruiseDay Cruises

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Chicago Architecture River Cruise

star-5
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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Booked by 104,534 travellers
  • 1 hour
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  • Free Cancellation
From  
US$41.44 
From  
US$41.44 
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  • 1 hour
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  • Free Cancellation

Chicago in a Day: Food, History and Architecture Combo TourHalf-day Tours

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

star-5
An excellent choice for first-time visitors, this tour provides a comprehensive overview of the city and hits on both classic attractions and little-known sites. Beginning at the Chicago Theatre, work your way to the Chicago Pedway, an elaborate network of underground tunnels used by locals and commuters. Stroll the Chicago Riverwalk and the Magnificent Mile, then embark on a food tour to taste some of the city’s famous foods.
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Booked by 248 travellers
Small group
  • 5 hours
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  • Free Cancellation
From  
US$102.30 
From  
US$102.30 
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  • 5 hours
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  • Free Cancellation

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Chicago City Minibus Tour with Optional Architecture River CruiseBus Tours

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Chicago City Minibus Tour with Optional Architecture River Cruise

star-4.5
Explore Chicago's iconic landmarks on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore downtown and Northside 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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Booked by 3,422 travellers
Small group
  • 2 to 4 hours
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  • Free Cancellation
From  
US$39.45 
From  
US$39.45 
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  • 2 to 4 hours
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  • Free Cancellation

Loop Interior Architecture Walking Tour with PedwayArchitecture Tours

Loop Interior Architecture Walking Tour with Pedway

star-5
Venture inside renowned Chicago landmarks, elegant lobbies, and underground corridors on this walking tour. Your expert guide will share insights about interior architectural features of this design-rich city—from mosaic domes to the sprawling Chicago Pedway System—bringing the details of the Windy City into vivid focus. Stop to admire Chase Tower, the Marshall Field and Company Building, the Chicago Cultural Center, and more.
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Booked by 2,657 travellers
Small group
  • 2 hours
From  
US$29.00 
From  
US$29.00 
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  • 2 hours

Chicago Lake and River Architecture TourDay Cruises

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Chicago Lake and River Architecture Tour

star-4.5
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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Booked by 2,034 travellers
  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$39.00 
From  
US$39.00 
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  • 1 hour 30 minutes
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  • Free Cancellation

45-min Chicago River Architecture TourDay Cruises

45-min Chicago River Architecture Tour

star-5
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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Booked by 425 travellers
  • 45 minutes
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  • Free Cancellation
From  
US$23.00 
From  
US$23.00 
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  • 45 minutes
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  • Free Cancellation

Historic Chicago Walking Bar TourArchitecture Tours

Historic Chicago Walking Bar Tour

star-4.5
Explore downtown Chicago on a pub crawl with an educational twist! Your expert guide shares entertaining facts about the history of jazz, theater, social clubs, and the Prohibition era in the Windy City as you take in historic buildings and architecture. Use iPads to view historic photos and videos that accompany your guide’s stories as you stop in both famous and hidden bars for drinks and appetizers. A short walk allows plenty of time to see Chicago’s famous architecture and pubs on this tour – great for visitors and locals alike!
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Booked by 740 travellers
Small group
  • 2 hours 30 minutes
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  • Free Cancellation
From  
US$39.00 
From  
US$39.00 
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  • 2 hours 30 minutes
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  • Free Cancellation

VIP: Architectural River Cruise and Chicago Helicopter TourLuxury Tours

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VIP: Architectural River Cruise and Chicago Helicopter Tour

star-4.5
Experience Chicago from the air and the water on this two-part tour that features a river cruise and a helicopter ride above the city. First, take a cruise down the Chicago River to learn about the architectural history of the town. Then, board a state-of-the-art helicopter and fly above the skyline. Both tours are fully narrated and pass landmarks including Navy Pier, Wrigley Field, Soldier Field, the John Hancock Center, Willis Tower, and more.
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Booked by 309 travellers
Small group
  • 15 minutes to 1 hour 30 minutes
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  • Free Cancellation
From  
US$195.00 
From  
US$195.00 
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  • 15 minutes to 1 hour 30 minutes
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  • Free Cancellation

Chicago Architectural River CruiseDay Cruises

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Chicago Architectural River Cruise

star-4.5
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.
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Booked by 7,527 travellers
  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$49.28 
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US$49.28 
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  • 1 hour 30 minutes
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  • Free Cancellation

Best of Chicago: History & Culture Tour with Chocolate and PopcornLuxury Tours

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Best of Chicago: History & Culture Tour with Chocolate and Popcorn

star-5
The Windy City is known for its spectacular architecture and eclectic food scene. Experience both on this tour through the downtown that combines sights with nibbles. Take in famous landmarks like the Wrigley Building, Tribune Tower, and Cloud Gate on foot and with the scenic L train or water taxi along the Chicago River. Taste popcorn and chocolate from two beloved city eateries during the tour.
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Booked by 29 travellers
Small group
  • 2 hours 30 minutes
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  • Free Cancellation
From  
US$50.63 
From  
US$50.63 
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  • 2 hours 30 minutes
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  • Free Cancellation

Chicago City Minibus TourBus Tours

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Chicago City Minibus Tour

star-5
NOTE: WE ARE ONLY OPERATING PRIVATE TOURS UNTIL AT LEAST EARLY MAY, DUE TO COVID 19. Enjoy Chicago’s famous sights and fabulous views on this award-winning small-group sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its many attractions. The small-group atmosphere with maximum of 12 people ensures a more personal experience. 
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Booked by 14 travellers
Small group
  • 2 hours
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  • Free Cancellation
From  
US$39.45 
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  • 2 hours
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  • Free Cancellation

Chicago Architecture Fireworks CruiseNight Cruises

Chicago Architecture Fireworks Cruise

star-4.5
Take advantage of a rare chance to experience Chicago’s illuminated skyline beneath a fantastic fireworks display. This summer evening cruise (available on selected nights), takes you past more than 40 significant works of architecture like the Wrigley Building, Chicago Tribune Tower, John Hancock Center, and more. Your expert guide shares each building’s story, and the cruise concludes with a stunning view of the fireworks from Navy Pier.
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Booked by 1,846 travellers
  • 1 hour 30 minutes
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  • Free Cancellation
From  
US$45.40 
From  
US$45.40 
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  • 1 hour 30 minutes
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  • Free Cancellation

Land and River Architecture Tour of Chicago's Scenic North SideHalf-day Tours

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Land and River Architecture Tour of Chicago's Scenic North Side

star-4.5
Discover Chicago’s iconic architectural gems from every angle on a 3.5-hour tour of the North Side. Divided between land and water, the comprehensive tour enables you to cover a huge area of the city without getting worn out. Travel comfortably by coach or trolley to Fort Dearborn, Wrigley Building, and more. Afterwards, see the Windy City's famous skyscrapers, bridges, and historical sites on a 90-minute cruise down Chicago River.
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Booked by 25 travellers
  • 3 hours 30 minutes
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  • Free Cancellation
From  
US$76.95 
From  
US$76.95 
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  • 3 hours 30 minutes
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  • Free Cancellation

Frank Lloyd Wright Robie House Architecture Tours

Frank Lloyd Wright Robie House

The Frederick C. Robie House on the University of Chicago campus is considered one of the most important buildings in the history of American architecture. This Prairie style masterpiece is now a UNESCO World Heritage Site on the 20th Century Architecture of Frank Lloyd Wright List. Discover the residence Wright described as “a cornerstone of modern architecture” on guided tours that take in both the exterior and interior of the building. Inspired by the expansive landscape of the Midwest prairie, Wright’s Robie House is the most famous of the architect’s groundbreaking Prairie houses. Public tours are available Thursday - Monday. The museum is closed Tuesday and Wednesday. Save when you book directly at Visit to learn more.
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Booked by 5 travellers
Small group
  • 1 hour
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  • Free Cancellation
From  
US$24.00 
From  
US$24.00 
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  • 1 hour
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  • Free Cancellation

Lake Michigan and Chicago River Architecture Cruise by SpeedboatJet Boats & Speed Boats

Lake Michigan and Chicago River Architecture Cruise by Speedboat

star-4.5
Discover Chicago's world-renowned architecture during this sightseeing cruise. Board a comfortable riverboat for a cruise on the Chicago River, viewing landmarks like the Willis Tower and the Tribune Tower while listening to engaging commentary from your guide. Then board a speedboat for an exciting ride up the shore of Lake Michigan for views of Grant Park, the Chicago Harbor, and the Museum Campus.
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Booked by 3,526 travellers
  • 1 hour 15 minutes
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  • Free Cancellation
From  
US$49.82 
From  
US$49.82 
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  • 1 hour 15 minutes
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  • Free Cancellation

VIP: Chicago Helicopter Tour Plus 360 Chicago Observation DeckAttraction Tickets

VIP: Chicago Helicopter Tour Plus 360 Chicago Observation Deck

star-4
Travelers who like to get to know a city by seeing it from above will love this tour. View Chicago’s long coastline from the seat of a helicopter, then take your time spotting each individual landmark from the observation deck at 360 Chicago. There will be opportunities to take lots of impressive photos. Choose between a daytime or nighttime tours, for unforgettable views at any time of day.
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Booked by 157 travellers
Small group
  • 1 to 3 hours
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  • Free Cancellation
From  
US$175.00 
From  
US$175.00 
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  • 1 to 3 hours
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  • Free Cancellation

Chicago Land and River Architecture Tour: North and South ShoresDay Cruises

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Chicago Land and River Architecture Tour: North and South Shores

star-4.5
Whether you’re short on time or want to orient yourself to Chicago, a 3.5-hour land and river tour is the perfect option. The comprehensive itinerary takes you through both the North and South sides. Listen as your guide tells insider stories about the people who shaped the city. After the land tour, rest your feet and see the city from a unique vantage point during a 90-minute river cruise.
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Booked by 92 travellers
  • 3 hours 30 minutes
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  • Free Cancellation
From  
US$92.95 
From  
US$92.95 
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  • 3 hours 30 minutes
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  • Free Cancellation

Private Chicago Architecture TourHalf-day Tours

Private Chicago Architecture Tour

star-5
Ever since Chicago became the birthplace of the modern skyscraper, the city has been renowned for its architectural creativity and ingenuity. Led by an expert guide, explore some of the city’s most iconic buildings such as Sears Tower, The John Hancock Building, historic brownstones, and the homes of Oak Park designed by beloved architect Frank Lloyd Wright. You will be able to explore the insides of some locations on this completely customizable tour.
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Booked by 23 travellers
Private experience
  • 3 hours
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  • Free Cancellation
From  
US$660.00 
per group
From  
US$660.00 
per group
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  • 3 hours
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  • Free Cancellation

Odyssey Chicago River Architectural Lunch CruiseDay Cruises

Odyssey 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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Booked by 39 travellers
  • 2 hours
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  • Free Cancellation
From  
US$101.86 
From  
US$101.86 
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  • 2 hours
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  • Free Cancellation

Chicago Architecture Walking Tour: Dazzling Interiors of the LoopLuxury Tours

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Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

star-5
See the overlooked highlights of Chicago’s Loop district with a 2-hour 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 visitng a side of Chicago that’s beyond the tourist trail, and experience the Windy City with a local perspective.
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Booked by 335 travellers
  • 2 hours
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  • Free Cancellation
From  
US$30.00 
From  
US$30.00 
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  • 2 hours
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  • Free Cancellation

2 HR History of Chicago Architecture & Art Segway TourLuxury Tours

2 HR History of Chicago Architecture & Art Segway Tour

star-5
Explore the art and architectural highlights of Chicago on a Segway during this guided tour. This family-friendly tour takes visitors by the outdoor sculptures, landmark buildings, and iconic skyline of the city. Accompanied by educational and informative commentary, this city tour saves you from hours of walking and lets you see all of Chicago's top art and architectural attractions in one tour.
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Booked by 78 travellers
  • 2 hours
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  • Free Cancellation
From  
US$75.10 
From  
US$75.10 
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  • 2 hours
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  • Free Cancellation

Chicago Land and River Architecture Tour: Historic South SideDay Cruises

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Chicago Land and River Architecture Tour: Historic South Side

star-4
See the architecture of Chicago's South Side by both land and on a Chicago River boat tour. Traveling south of the Loop along Michigan Avenue and South Lake Shore Drive, you'll pass by sights such as the Art Institute of Chicago, University of Chicago, Jackson Park, the Museum of Science and Industry, Museum Campus, Buckingham Fountain, and former President Obama's home.
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Booked by 10 travellers
  • 3 hours 30 minutes
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  • Free Cancellation
From  
US$73.95 
From  
US$73.95 
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  • 3 hours 30 minutes
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  • Free Cancellation

Chicago Architecture TourArchitecture Tours

Chicago Architecture Tour

Surround yourself in the Windy City's architectural gems on a 2-hour walking tour. Follow your guide past noteworthy landmarks and lesser known gems. Then visit the Chicago Cultural Center, also known as The People’s Palace, and marvel at the Randolph Street entrance, Grand Army of the Republic Memorial, and more. Beginning at the Clark Street Bridge, the tour concludes next to Millennium Park where you can continue your day of sightseeing.
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Booked by 9 travellers
  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation
From  
US$25.00 
From  
US$25.00 
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  • 2 hours
  • Reserve Now & Pay Later
  • Free Cancellation


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