Chicago Lakefront Neighborhoods Bicycle Tour

Bobby's Chicago Bike Hike

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What You'll Get

The trip begins at the Bobby’s Bike Hike headquarters. This is where you’ll meet your fun-loving, enthusiastic guide and your ready-to-ride Bobby’s bicycle. After an introduction to Chicago’s epic history, your group will head out into the beautiful downtown district of Streeterville.

Named for Captain George Wellington Streeter, Streeterville is home to many of Chicago’s most beloved institutions including the Museum of Contemporary Art and the John Hancock Center. The tour will then roll past the Magnificent Mile shopping strip into the historic Gold Coast neighborhood.

The Gold Coast has been Chicago’s highest rent district since the 1870s and is home to some of the most beautiful Victorian homes in the United States. One particularly interesting piece of property in the area is the building that housed the original Playboy Mansion, complete with a pool and swim-up bar.

From there your guide will lead you into leafy Lincoln Park, the city’s largest municipal green space. Check out a few of the countless bike paths, sports fields, walking trails, and works of public art that this 1200-acre park has to offer!

Old Town is up next, the neighborhood that inspired the creation of this tour where you can get up close and personal with the local culture experience. Its quiet, tree-lined streets are rarely traversed by bus tours, despite the rich history that the area boasts. Here you’ll get a peek at the stunning spire of St. Michael’s church, one of very few buildings that survived the Great Chicago Fire. From there the tour travels back into Lincoln Park to see the world-famous (and free!) Lincoln Park Zoo, before heading east all the way to the clear-blue shores of Lake Michigan.

You’ll get to experience the beaches that define this sandy, summer-loving town up close and personal. North Avenue and Oak Street beaches can be packed with up to 300,000 Chicagoans on a warm Saturday in July! As the group rides back down south along the beautiful, paved Lakefront Trail, you’ll see why Chicago has been repeatedly chosen as America’s greatest city for bikers.

The tour concludes back at the Bobby’s Bike Hike Streeterville HQ, after three hours and eight miles of history, sightseeing, and two-wheeled fun.

Additional Information

  • Confirmation will be received at time of booking
  • This tour is appropriate for all ages and fitness levels. Professional guides blend quality information, group interaction, and most of all, fun, to create an unforgettable Chicago experience. Bikes are provided. Child bikes, seats and tagalongs are available.
  • Storage for larger bags/items available for free
  • Please note: children must be strong, capable riders and be able to bike for 9 miles
  • Bicycle
  • Helmet
  • Local tour guide

  • Food and drinks
  • Gratuity for guide (15-20% suggested, Venmo and PayPal available)

3 hours

Return Details
Returns to original departure point

Voucher Info
You can present either a paper or an electronic voucher for this activity.

The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Bobby's Chicago Bike Hike in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon.

This offer is not eligible for promo codes.

The Fine Print

  • Voucher valid only for date and time listed; may not be exchanged or redeemed for other dates.
  • Purchaser name and phone number must be provided at checkout; this information will be shared with Viator and the tour operator for purposes of order fulfillment.
  • Groupon promo codes may not be used for this offer. Groupon voucher Terms of Sale and Extraordinary Event Policy do not apply.
  • See Viator voucher terms under "Viator Vouchers" here.
  • Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Offer is not eligible for our promo codes or other discounts.

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