Best Sightseeing on wheels in Chicago

Local Recommendations from our My Guide Chicago team

Experience the best of Chicago on a sightseeing tour in a unique and exciting way. Hop on a tour bus or bike and discover the city's top attractions.

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

Filter Sightseeing on wheels in Chicago

Chicago: Full-Day Guided City Tour by Bus

Discover the best of Chicago on a full-day city tour with a local guide. See the city's top sights, including Millennium Park and Michigan Avenue, and customize your experience with optional tickets.

$132.00

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Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour

4 Reviews

Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour

Thrills, gangsters, murder, and mayhem are all on the agenda on this fun but chilling nighttime Segway tour of Chicago. Guides become ghost hunters as you creep through the shadows to sites such as Haunted Fort Dearborn, Death Alley and so many more.

$77.70

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Chicago: Architecture River Cruise Skip-the-Ticket Line

4091 Reviews

Chicago: Architecture River Cruise Skip-the-Ticket Line

Cruise along the Chicago River on a boat tour and discover hidden architectural gems among the city’s renowned landmarks, with live narration.

$53.00

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Chicago: Architecture Boat Tour with Drinks

333 Reviews

Chicago: Architecture Boat Tour with Drinks

Experience the iconic scenery, skyscrapers, and architecture of Chicago on a guided boat cruise through the heart of the city. Pass by the Willis Tower, Wrigley Building, Tribune Tower, and more.

$39.00

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Chicago Architecture Experience by Train

14 Reviews

Chicago Architecture Experience by Train

Chicago is defined by its wild architecture, staples such as its famous deep dish pizza, and “The Bean” of Millennium Park. But how do you get from one attraction to another with ease?The Chicago “L”!

$49.00

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Best Seller

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

1036 Reviews

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Explore Chicago at your own pace with a Big Bus hop-on hop-off tour or sunset tour. See Chicago's landmarks including Willis Tower, Navy Pier, and Magnificent Mile from an open-top double-decker bus.

$49.50

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Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

72 Reviews

Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

Learn about the stories of gangsters, politicians, and more in the spaces where it happened on a bus or walking tour. Visit the speakeasies that made the famous, infamous.

$47.70

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Chicago: Westside Food Tasting Bike Tour with Guide

16 Reviews

Chicago: Westside Food Tasting Bike Tour with Guide

Eat around the world without leaving Chicago! Enjoy the city's best ethnic cuisines while biking through its most historic neighborhoods and along the gorgeous 606 and Lakefront trails.

$89.99

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Chicago: Gangsters and Ghosts Luxury Minibus Tour

9 Reviews

Chicago: Gangsters and Ghosts Luxury Minibus Tour

Discover Chicago's haunted past on a luxury Gangsters & Ghosts minibus. Explore notorious crime history & hear spine-chilling tales from expert guides about the ghosts that still haunt the streets.

$65.00

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Chicago: Guided Tour with Architecture River Cruise

20 Reviews

Chicago: Guided Tour with Architecture River Cruise

See the best of Chicago in just 1 day on this guided small group sightseeing tour. Visit iconic landmarks including Architecture River Cruise, Cloud Gate "the Bean", and Adler view point.

$254.00

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Chicago: The Devil In The White City Bus Tour

Dive into the dark history of Chicago with The Devil In The White City Bus Tour. Explore sites from Erik Larson’s bestselling book, including the infamous Murder Castle of H.H. Holmes

$59.00

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