Bobby's Bike Hike

540 N Lake Shore Drive, Chicago, IL, United States
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  • 98%
    History Buffs

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  • Bobby's Bike Hike
    Betty N.
    Member of
    Local Culture
    Outdoor Enthusiasts
    + 5
    • Luxury Travelers
    • History Buffs
    • Nightlife Lovers
    • Trendsters
    • Art & Design Lovers
    5 Jul 13, 2013


    A few people realized that I practice law because I wanted to be Tom Hagen from The Godfather.

    So I have always been fascinated with mafia and the "underworld".

    This tour satisfied that fascination.

    Bicycle, helmet, and guide explaining the history of the outfit and how it has transformed over the years into what it is today.

    3.5 hours.

    Comfortable clothes.
    Sandals OK.

    Chicago's seedier side was unveiled on this ride through the Southside's most notorious areas, including the old Bridgeport neighborhood. We learned about the history of the Chicago Outfit as we rolled by famous mob hangouts and homes, Chicago's old red-light district, and Al Capone's old stomping grounds.

    Bridgeport, Chinatown, hidden Palmisano Park, old Italian Outfit hangouts (where we waved and said hello to the Italian men sitting out front), The old Levee District (Chicago's Red Light district), The McCormick Place, Prairie Ave District, Museum Campus and the Lakefront.

    Our tour guide, George, was terrific. Nice stops, directions, and explanations. We also had a nice pizza and Italian ice break along the way.

    Saturdays & Sundays


    3.5 hours


    Book online for 10% off.


    Recommended for:History Buffs
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  • Bobby's Bike Hike
    Jen Knoedl @GogobotChicago
    Member of
    Local Culture
    Outdoor Enthusiasts
    Budget Travelers
    + 10
    • Business Travelers
    • Family Travelers
    • Foodies
    • Wellness
    • LGBT
    • Vegetarian
    • Green Travelers
    • Students
    • Backpackers
    • Luxury Travelers
    5 Apr 04, 2013

    Riding a bike through the city is definitely one of the best ways to see it. If you are new to the city, entertaining visitors or just don't want to think too hard, having a guide tell you where to go might be just the thing. Friendly service and healthy entertainment makes this one of my favorite things to do in Chicago.

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  • Bobby's Bike Hike
    Devin Newmeyer
    5 Aug 13, 2013

    This was one of the best, well-organized tours that I have ever done. I definitely recommend!

    Was this review helpful?(1)


5.0 out of 5
3 member's reviews
71 people visited Bobby's Bike Hike


Bobby's Bike Hike provides signature guided bicycle tours and year-round walking tours of Chicago's lakefront, iconic downtown loop, and neighborhood attractions, all appropriate for every age and fitness level. Check out our brand-new, seasonal walking and food tours. Bobby tours Chicago in style with deluxe Schwinn Comfort bikes complete with cushy seats, fat tires, and annoying bells. The ... read more
hand-selected guides are chock full of historical information which is sure to inform and entertain you on your journey. The folks in the shop are friendly and helpful and they will take the time to teach you the ropes before sending you on your way.

Tours include the Lakefront Neighborhoods Tour which was voted Best Chicago Tour seven years in a row, the City Lights at Night Tour, which is a healthy way to explore Chicago at night, Bobby's 'Tike' Hike for families with younger riders, and the Bikes, Bites, & Brews Tour, which is a food sampling tour. If you want to learn about Chicago's seedier past, check out the Southside Chicago Mafia Tour. Or for a longer, more advanced ride check out the Tour de Chicago. There are also year-round walking and food tours, including the Chicago Favorites Food Tour, Public Art & Architecture Tour, and the Holiday Hike - Season Sampling Tour. All walking tours make use of Chicago's elaborately unique indoor pedway system in inclement weather.

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