Discover the architectural soul of Chicago on a thoughtfully curated half-day city tour. Travel through the city’s most influential districts, from historic riverfront landmarks to groundbreaking modern skyscrapers. Explore the Loop’s civic, financial, and architectural core, admire world-renowned towers, and experience Chicago’s most celebrated public spaces. This small-group tour offers a comprehensive introduction to Chicago’s skyline, history, and urban design, concluding with a panoramic skyline view before returning guests to the original pickup point. Ideal for first-time visitors and architecture enthusiasts alike.
Explore Chicago’s iconic riverfront skyscrapers and historic bridges
See legendary architecture including Willis Tower and Marina City
Discover the heart of Chicago’s financial, civic, and architectural power
Pass by Millennium Park and spend time at Cloud Gate (The Bean)
Enjoy a panoramic Chicago skyline view, included for all guests
You will be dropped off at your pick-up location.
Pick up time selection: 9:00am or 2:00pm
The tour lasts approximately 4-5 hours. Return time may vary depending on the itinerary, traffic, and weather conditions.
Same as pick-up locations
Itinerary: Michigan Avenue & Chicago River: (20 mins) - Tribune Tower – Wrigley Building – DuSable Bridge Chicago Riverside Skyscraper Experimental Zone: Trump Tower (Pass by) - 330 North Wabash (Pass by) (formerly IBM Building / Langham Hotel) - Marina City (Corn Cob Towers) (Pass by) Chicago School & Loop Core Area: The MART (Merchandise Mart) (3 mins) - Civic Opera House (Pass by) - The CME Group Building(Pass by) - Willis Tower (formerly Sears Tower) (10 mins) Financial Order and Urban Power: Chicago Board of Trade (CBOT) (Pass by) - Federal Reserve Bank of Chicago (Pass by) Public Spaces · Road Culture · Urban Symbols: Historic Route 66 Begin Sign and Art Institute of Chicago (10 mins) - Millennium Park (Pass by)- Cloud Gate (The Bean) (30 mins) Chicago City Skyline (10 mins)
Michigan Avenue & Chicago River: Begin along Chicago’s most famous boulevard and riverfront, where the city’s architectural identity was shaped. See the Tribune Tower, Wrigley Building, and cross the DuSable Bridge for classic skyline views
Tribune Tower: A neo-Gothic landmark famous for embedding stones from historic sites worldwide, symbolizing Chicago’s global ambition.
330 North Wabash: Designed by Mies van der Rohe, this minimalist tower exemplifies Chicago’s influence on modern international architecture.
Marina City: Instantly recognizable for its “corn cob” shape, these twin towers pioneered mixed-use urban living.
Merchandise Mart: Once the world’s largest building by floor area, it remains a global hub for design and commerce.
Civic Opera House: An Art Deco landmark blending culture and business, reflecting Chicago’s commitment to the arts.
CME Group Building: Home to the world’s largest derivatives marketplace, symbolizing Chicago’s global financial influence.
Willis Tower: Once the tallest building in the world, this engineering marvel remains a defining symbol of Chicago.
Chicago Board of Trade Building: An Art Deco masterpiece highlighting Chicago’s historic role in commodities trading.
Federal Reserve Bank of Chicago: A powerful symbol of Chicago’s role in national monetary policy.
Historic Route 66 Begin Sign: Celebrates Chicago’s place in American road culture and cross-country travel history. Art Institute of Chicago (Exterior): One of the world’s premier art museums anchoring the city’s cultural scene.
Millennium Park: A modern public space blending art, architecture, and community design.
Cloud Gate: Known as “The Bean,” this reflective sculpture invites visitors to interact with the city’s skyline.
Chicago Skyline View: The tour concludes with a panoramic view uniting historic towers and modern icons
Show 9 more
For a full refund, cancel at least 24 hours before the scheduled departure time.
Show more
You can cancel up to 24 hours in advance of the experience for a full refund.
Your guide to the flawless travel experience