• Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
    Likely to Sell Out

    Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

    Taste all of Chicago’s classic eats on this 4 1/2 hour guided bicycle tour! Join the expert tour guides of Bobby’s Bike Hike, America’s longest-running...
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     4 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $89
    Details
    from
    $89
    Details
  • Bike Tour of Chicago's Lakefront Neighborhoods
    Likely to Sell Out

    Bike Tour of Chicago's Lakefront Neighborhoods

    This is the tour that made Bobby famous! Bobby’s Bike Hike is America’s longest-running city bicycle tour company, and has been repeatedly recognized for excellence...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $54.99
    Details
    from
    $54.99
    Details
  • Chicago's Ultimate City Bike Tour
    Likely to Sell Out

    Chicago's Ultimate City Bike Tour

    Get acquainted with Chicago’s most iconic landmarks on this riotous guided bicycle tour! Join the expert guides of Bobby’s Bike Hike, America’s longest-running city bicycle...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $54.99
    Details
    from
    $54.99
    Details
  • Chicago's West Side Foodie Ride Bike Tour

    Chicago's West Side Foodie Ride Bike Tour

    Take a detour off the beaten path, and explore the flavors of Chicago’s vibrant West Side with Bobbys's Bike Hike, America's longest running city bike...
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     4 hours  Free Cancellation  Instant Confirmation
    from
    $89
    Details
    from
    $89
    Details
  • Chicago Lakefront Electric Bike Tour
    Likely to Sell Out

    Chicago Lakefront Electric Bike Tour

    9

    This tour takes you along the Lakefront bike path. Which you'll be able to experience the beautiful nature that surrounds the city skyscrapers. You will...
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     45 to 60 minutes  Free Cancellation  Instant Confirmation
    from
    $69.34
    Details
    from
    $69.34
    Details
  • Chicago Family Food & Bike Tour with Top Attractions

    Chicago Family Food & Bike Tour with Top Attractions

    This tour is perfect for the entire family, put on by Bobby’s Bike Hike, whose food tours in just the past year have ranked as...
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     4 hours  Free Cancellation  Instant Confirmation
    from
    $79
    Details
    from
    $79
    Details
  • Chicago Lincoln Park Bike Adventure
    Likely to Sell Out

    Chicago Lincoln Park Bike Adventure

    7

    Enjoy the car-free lakefront trail and explore Chicago’s beaches, parks, lagoons, and gorgeous Lincoln Park Zoo (free admission). This tour offers a diverse mix of...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $49
    Details
    from
    $49
    Details
  • Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

    Fun Chicago Bike Tour with Pizza, Hot Dogs, Cupcakes and Beer

    1

    Take an adventurous half-day journey through the most interesting Chicago neighborhoods with a friendly private guide and see the city from a new perspective riding...
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     4 hours  Free Cancellation  Instant Confirmation
    from
    $179
    Details
    from
    $179
    Details
  • The Chicago E-Bike Tour

    The Chicago E-Bike Tour

    3

    Discover the unique flavor of our Absolutely Chicago E-Bike Tour. Experience the city's rich history, stunning architecture, and breathtaking views as you pedal along on...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $87.69
    Details
    from
    $87.69
    Details
  • Fright Hike: Chicago Halloween Bike Tour

    Fright Hike: Chicago Halloween Bike Tour

    7

    Come get spooked on Bobby’s Fright Hike! Bobby’s Bike Hike is America’s longest running city bicycle company, and this is Chicago’s premiere Halloween ghost tour....
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $54.99
    Details
    from
    $54.99
    Details
  • Bike Tour in Chicago

    Bike Tour in Chicago

    New To The Site!

    Take a spin through the Windy City on a bike tour and discover the most remarkable and world-famous sights. Hit the streets like a local...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $129
    Details
    from
    $129
    Details
  • Unforgettable Small Group Biking Tours from Chicago to Milwaukee

    Unforgettable Small Group Biking Tours from Chicago to Milwaukee

    New To The Site!

    Our tours have varying difficulty levels to accommodate different skill levels. We take every safety precaution available to prioritize your well-being. Our routes that take...
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     1 day 10 hours  Free Cancellation  Instant Confirmation
    from
    $349
    Details
    from
    $349
    Details
  • Small Group Bike Tours From Chicago to Lake Geneva

    Small Group Bike Tours From Chicago to Lake Geneva

    New To The Site!

    The route to Lake Geneva follows the incredible coastline of Lake Michigan and eventually into the rolling green hills of Wisconsin. Your group will stop...
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     2 days  Free Cancellation  Instant Confirmation
    from
    $449
    Details
    from
    $449
    Details
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Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Chicago Bike & Mountain Bike Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best Chicago Bike & Mountain Bike Tours are:

Q: What are the best kid-friendly options for Chicago Bike & Mountain Bike Tours Activities?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly Chicago Bike & Mountain Bike Tours are:

View all kid-friendly Activities

Q: Which Chicago Bike & Mountain Bike Tours have Instant Confirmation?

A: Chicago Bike & Mountain Bike Tours with Instant Confirmation include:

View all Activities with Instant Confirmation

Q: Which Chicago Bike & Mountain Bike Tours have Free Cancellation?

A: Chicago Bike & Mountain Bike Tours with Free Cancellation (in most cases up to 24 hours in advance of your activity date, check the specific activity page) include:

View all Activities with Free Cancellation

Q: Got any more Chicago trip ideas?

A: We sure do. Check out our curated lists of hand-picked Chicago Activities.

View all Chicago Trip Ideas

Q: What are the most popular styles of Tours and Activities in Chicago?

A: Based on our sales data over the past year, the most popular styles of tours and activities in Chicago are:

View all tour styles in Chicago