Best Jeep & 4WD Tours in Chicago

Local Recommendations from our My Guide Chicago team

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!

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Chicago: Private Architecture Tour - 3 or 6 Hours

5 Reviews

Chicago: Private Architecture Tour - 3 or 6 Hours

Discover a city known for its architectural creativity and ingenuity. Explore some of Chicago's most iconic buildings, with the option to visit Oak Park and the homes of Frank Lloyd Wright.

$780.00

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Chicago: Private 3-Hour Al Capone Gangster Tour

5 Reviews

Chicago: Private 3-Hour Al Capone Gangster Tour

Visit the notorious hangouts of John Dillinger, the Untouchables, and Al Capone with an expert historian as your guide. Chicago’s mob history has long been immortalized in popular media - embark on this Chicago gangster tour to learn the true story.

$880.00

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Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

6 Reviews

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Travel back in time to the 1920s, when Chicago was a Prohibition Era hub for lively speakeasies. Your guide, a young, local historian, will lead you through secret entrances to speakeasies once frequented by bank robbers and Chicago gangsters.

$950.00

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