Best Sightseeing on wheels in Central 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 Central Chicago

Chicago: Sunset Tour by Open-top Bus with Live Guide

42 Reviews

Chicago: Sunset Tour by Open-top Bus with Live Guide

Experience the Windy City’s dazzling skyscrapers lit up at night. Set off on a panoramic night tour from Navy Pier to the Magnificent Mile, passing by the Chicago Theatre and Buckingham Fountain.

$44.55

~~From $49.50~~

Chicago: Architecture River Cruise & Hop-on Hop-off Bus Tour

5 Reviews

Chicago: Architecture River Cruise & Hop-on Hop-off Bus Tour

Experience the best of Chicago's history and culture with a combination of a live-guided 75-minute architecture river cruise and a 2-day hop-on hop-off sightseeing tour by open-top bus.

$95.00

From

Chicago: Prohibition Speakeasies Bus Tour or Walking Tour

47 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

From

Best Seller

Chicago: Mob and Crime Bus Tour

619 Reviews

Chicago: Mob and Crime Bus Tour

Experience the dark side of the Windy City on a Crime and Mob Bus Tour that introduces you to Chicago’s history of crime. Escape into the city's underworld and learn about characters like Al Capone and John Dillinger.

$49.00

From

Chicago: Lakefront and Museum Campus Segway Tour

127 Reviews

Chicago: Lakefront and Museum Campus Segway Tour

Explore Chicago's picturesque Lakefront in a whole new way – on a Segway. Chicago's gorgeous lakefront, parks, and skyline are yours to roll through for a fun-filled tour.

$77.70

From

Chicago: City Minibus Tour with Optional Architecture Cruise

109 Reviews

Chicago: City Minibus Tour with Optional Architecture Cruise

Discover downtown Chicago, as well as some nearby neighborhoods on a minibus tour. Choose to add an architectural cruise of Chicago for the best way to see Chicago from both land and water.

$47.95

From

Best Seller

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

822 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

From

Chicago Crimes Night Tour

71 Reviews

Chicago Crimes Night Tour

Explore Chicago's criminal history on this 2-hour night time tour. Discover the history of Chicago’s most famous criminals, gangsters and mobsters, such as the famous Al Capone and John Dillinger.

$55.00

From

2 Hour Chicago Pier Fireworks & Evening Segway Tour

7 Reviews

2 Hour Chicago Pier Fireworks & Evening Segway Tour

Experience Chicago at night! See Buckingham Fountain's light show w/ the skyline backdrop. Ride along the lakefront to a secret spot for Navy Pier's fireworks display. An unforgettable evening awaits!

$78.48

From

Amazing Lakefront Segway Tour of Chicago

93 Reviews

Amazing Lakefront Segway Tour of Chicago

Glide around the Chicago lakefront on a Segway tour. Zip past the cascading fountains of Millenium Park, admire the city's towering skyline, and swoop through Grant Park’s manicured gardens.

$58.50

~~From $65.00~~

Chicago: 2-Day Hop-on Hop-off Tour & 360 CHICAGO Admission

3 Reviews

Chicago: 2-Day Hop-on Hop-off Tour & 360 CHICAGO Admission

See the Windy City from a unique open-top double decker and explore the city at your own pace. Then, soak in the famous skyline from 1,000-feet high at 360 CHICAGO Observation Deck.

$80.00

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