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Chicago Architecture Guide

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Chicago Architecture Guide
Chicago is famous for its architecture, especially its towering skyscrapers, and you can see it all on an architecture tour. Because building design evolved as the city grew, there’s plenty to learn about the storied history—here’s where to start.

Willis Tower — once the tallest building in the world
Formerly known as the Sears Tower, this downtown skyscraper stands 108 stories high, making it the second tallest building in the US. The 103rd-floor Skydeck offers spectacular views, and a step out onto the Ledge lets you look straight down to the street below. Make it a stop on a hop-on hop-off bus tour or book VIP access for breakfast, lunch, or dinner at the Skydeck. It’s also visible from most river and downtown walking tours.

John Hancock Center — offering the best views of Lake Michigan
The fourth-tallest building in the city, the John Hancock Center features a 94th-floor observatory and a 95th-floor restaurant, as well as the best views of Lake Michigan in the city. Don’t miss TILT—an enclosed glass platform that tilts guests out over Michigan Avenue from the 94th floor. Stop off at the center during a bus tour or see it from above on a helicopter tour of the city. 

Marina City — Chicago’s “corn cob towers”
Shaped like two corn cobs standing tall along the Chicago River, the Marina City towers were once the tallest residential buildings in the world. Today, they’re home to a mix of commercial and residential uses, including a hotel, bowling alley, several restaurants, and the House of Blues concert hall. View Marina City from an architecture boat cruise or a kayaking tour on the Chicago River.

Tribune Tower — neo-Gothic design on Michigan Avenue
Overlooking the Chicago River, the Tribune Tower features dozens of stones and bricks from historically significant sites all over the world, including fragments from the Berlin Wall, the Parthenon, the Great Wall of China, and Angkor Wat. View the tower on an architecture boat cruise or a walking tour of historic skyscrapers.

Wrigley Building — lighting up the Magnificent Mile
Across the street from Tribune Tower, the Wrigley Building was the first major office building north of the Chicago River. Check it out from the river below or by joining a walking tour of historic skyscrapers.

Chicago Cultural Center — stunning stained-glass domes
The Italian Renaissance-inspired interior of the Chicago Cultural Center (which formerly hosted the city’s central library) features gorgeous stained-glass domes, colorful mosaic floors, and walls made of green, white, and pink marble. Take a walking tour of the Loop focused on interior architecture or Tiffany glass.
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Chicago Architecture River CruiseDay Cruises

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Chicago Architecture River Cruise

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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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  • 1 hour
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  • Free Cancellation
From  
US$41.44 
From  
US$41.44 
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  • 1 hour
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago Helicopter TourLuxury Tours

Chicago Helicopter Tour

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On a daytime helicopter tour over Chicago, enjoy views of the city's famed architecture and other sights from the air. Fly over Willis Tower (the old Sears Tower), Wrigley Field, Lincoln Park, and more while a pilot provides commentary about the city as you go.
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  • 12 to 15 minutes
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  • Free Cancellation
From  
US$154.99 
Price varies by group size
From  
US$154.99 
Price varies by group size
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  • 12 to 15 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Loop Interior Architecture Walking Tour with PedwayArchitecture Tours

Loop Interior Architecture Walking Tour with Pedway

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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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  • 2 hours
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US$29.00 
From  
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  • 2 hours

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Private Chicago City Sights Helicopter TourPrivate Sightseeing Tours

Private Chicago City Sights Helicopter Tour

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You and a guest will soar above Chicago’s skyscapers, shoreline and iconic sights on a private, 15-minute helicopter tour of the city. Communicate with your personal pilot through a two-way headset, and personalize your flight to your interests. Capture extraordinary aerial images of the city scape as you fly past Lincoln Park and Lake Michigan, then spot Willis Tower, the John Hancock Building and the gleaming Trump Tower. Bank high above Millennium Park and enjoy views of the Windy City from the comfort of a climate-controlled private helicopter. Tour route is subject to change.
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  • 30 minutes
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  • Free Cancellation
From  
US$408.00 
From  
US$408.00 
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  • 30 minutes
  • Reserve Now & Pay Later
  • Free Cancellation

Chicago Helicopter Tour Nighttime ExperienceCity Packages

Chicago Helicopter Tour Nighttime Experience

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Soar above the city lights of Chicago on a 15-minute nighttime helicopter ride with live narration by experienced pilots. Enjoy birds-eye views of downtown landmarks, then bank past Navy Pier to Lincoln Park and Uptown. Hear about the history of the city as you take in unforgettable views of downtown’s bristling skyscrapers, and see Willis Tower, Millennium Park and Soldier Field. This unique experience offers a once in a lifetime view of the Second City at its most stunning.
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  • 12 to 15 minutes
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  • Free Cancellation
From  
US$169.99 
From  
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  • 12 to 15 minutes
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  • Free Cancellation

Chicago Walking Tour: Modern ArchitectureArchitecture Tours

Chicago Walking Tour: Modern Architecture

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Embark on a walking tour of Chicago's more-recent architecture heritage with a 2-hour stroll highlighting the city's modern, postmodern, and international structures. Especially known for its architectural originality, Chi-town boasts everything from the elegant metal and glass tower of One South Dearborn to the Harold Washington Library, with its Beaux-Arts inspired exterior. Your guide will highlight these and other unique buildings, relaying background on their individual histories and construction en route.
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  • 1 hour 45 minutes
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  • Free Cancellation
From  
US$26.00 
From  
US$26.00 
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  • 1 hour 45 minutes
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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

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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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  • 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


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