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Top Chicago Bike & Mountain Bike Tours

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13 Tours and Activities

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

Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this 4-hour bike tour through the windy city. You’ll cover about 13 miles (21 km), following an informative guide at a moderate pace through the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$72.99 USD
From  
$72.99 USD
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Chicago Lakefront Neighborhoods Bicycle Tour

Pedal past the lakefront neighborhoods of Chicago's North Side on this 3-hour bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$49.99 USD
From  
$49.99 USD
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Chicago's Electric Bikes at Night Tour

See Chicago light up at night with a 3-hour bicycle tour of the Windy City’s most iconic sights and neighborhoods. Follow your guide along a leisurely route, watch the Buckingham Fountain light show and take in evening views of Millennium Park and the Museum Campus. Pedal through downtown streets, capture unforgettable images of Chicago’s magnificent skyline then finish your tour in the heart of the city.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$55.99 USD
From  
$55.99 USD
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Chicago Lincoln Park Bike Adventure

Experience Chicago like never before on this guided, 3-hour bicycle tour. Ride the walking- and cycling-only Chicago Lakefront Trail to and through the city’s beautiful beaches, parks and lagoons. See the coast of Lake Michigan and the breathtaking Chicago skyline, plus bustling Navy Pier, popular North Avenue Beach, the 35-acre Lincoln Park Zoo and Conservatory and much more. The use of a bike and helmet is included.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$42.50 USD
From  
$42.50 USD
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Bikes, Bites, and Brews: Chicago's West Side Foodie Ride

Taste food from around the world on this 4-hour cycling tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Mexican tortas, French sweets, and Polish pierogis.
  • Duration: 4 hours
  • Free Cancellation
  • Duration: 4 hours
  • Free Cancellation
From  
$72.99 USD
From  
$72.99 USD
See Details

Chicago Bike Tour

Experience the top sights of the Windy City on a 3.5-hour guided bike tour. Traveling on two wheels allows you to skip the sluggish pace of city traffic and avoid the limitations of walking. Let your guide take care of narration and navigation as you ride through eight neighborhoods, including Lincoln Park and Old Town. Stop for photos as you pedal onwards to the city’s lakefront and beyond.
  • Duration: 3.5 to 4 hrs
  • Free Cancellation
  • Duration: 3.5 to 4 hrs
  • Free Cancellation
From  
$42.51 USD
From  
$42.51 USD
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Tike Hike: Chicago Family Bike Tour

Cruise through Chicago on this family-friendly bicycle tour catered to kids. Perfect for kids age 10 and under, this tour mixes fun games and contests in with educational stops at some of Chicago's iconic sights. Parents can ride along with their children on cruiser-style bikes during this safe, enjoyable 2-hour tour that covers an easy 4.5 miles (7 km).
  • Duration: 2 hours
  • Free Cancellation
  • Duration: 2 hours
  • Free Cancellation
From  
$44.99 USD
From  
$44.99 USD
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Chicago Bike Tour and Skydeck Admission

Enjoy two Chicago experiences at one price with this combo bike tour and admission to the Skydeck Chicago at Willis Tower. With a guide, you'll ride through eight neighborhoods and along the Lake Michigan waterfront to take in the city's attractions and scenery, listening to stories and history about Chicago as you go. Then visit the Skydeck for a 360-degree view from 1,353 feet (412 meters) in the air.
  • Duration: 3.5 to 4 hrs
  • Free Cancellation
  • Duration: 3.5 to 4 hrs
  • Free Cancellation
From  
$64.31 USD
From  
$64.31 USD
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Chicago's Greatest Hits Bicycle Tour

Explore Chicago’s most iconic sites with a 2.5-hour bike tour that explores Museum Campus, parks and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$44.99 USD
From  
$44.99 USD
See Details

Friendly Neighborhoods Bike Tour

See for yourself what makes Chicago such a great place to bike on this tour. You’ll leave the more touristy parts of the city behind as you make your way into the parks and neighborhoods of the locals. Visit the Gold Coast, Old Town, and Lincoln Park, cycle through the DePaul campus and stop at Wrigley Park plus more. You’ll get a look at stately architecture and lovely parks as you go.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$42.50 USD
From  
$42.50 USD
See Details

Fright Hike: Chicago Halloween Bike Tour

Pedal through Chicago’s scary heritage with a 3-hour Halloween bike tour that includes hauntings, tragedies and overflowing cemeteries. Experience the creepiest parts of the city as you follow your professional actor guides through the Halloween streets, and watch them bring Chicago’s ghosts to life. Learn about the infamous ‘Resurrection Mary,’ figure out why the Levee District is so famously haunted, and hear the story of H.H. Holmes, Chicago’s most notorious serial killer.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$64.00 USD
From  
$64.00 USD
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Chicago Sunset Bike Tour

The Second City takes on another life as the sun sets behind its iconic skyline. Our sunset bike tour will show you the best Chicago as it illuminates after dusk.
  • Duration: 3 hours
  • Free Cancellation
  • Duration: 3 hours
  • Free Cancellation
From  
$42.51 USD
From  
$42.51 USD
See Details

Bikes at Night Ride in Chicago

Ride a bicycle through Chicago's Museum Campus and take in the city sights during a 2.5-hour nighttime ride. View illuminated attractions and pedal along pathways to Buckingham Fountain to see its feast of lights. Finish your guided bike tour at Navy Pier and watch its legendary fireworks display reflected on Lake Michigan and the city skyline. Number of participants is limited to ensure a small-group experience.
  • Duration: 2 hours 30 minutes
  • Free Cancellation
  • Duration: 2 hours 30 minutes
  • Free Cancellation
From  
$42.50 USD
From  
$42.50 USD
See Details


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(888) 680-5731
(888) 680-5731