Chicago Lakefront Neighborhoods Bicycle Tour

Walking & Biking Tours in Chicago

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Tour description provided by Viator

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 by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more! Bobby’s now offers over a dozen specialized tours, but The Lakefront Neighborhoods ride is what started it all. Join one of Bobby’s expert guides on this 3-hour romp through Chicago’s beautiful North Side neighborhoods. See the ever-rising skyscrapers of Streeterville, the luxe residential property of the Gold Coast, the cozy artists’ village of Old Town, and the rolling greenery of Lincoln Park. You’ll finish off with a cruise down the Lakefront Trail, one of the most popular waterfront bike paths in the nation. This leisure-paced journey is sure to make memories that’ll last a lifetime!
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.

What’s included

  • Bicycle
  • Helmet
  • Local tour guide

What’s not included

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