Lakefront Neighborhoods Bike Tour

Bike Along the Lakefront Trail & Local Neighborhoods

What's Priceless?

This journey offers the fun of exploring Chicago by bike and includes a special bonus for Mastercard users: a free rental locker.

This ‘live like a local’ Chicago bike tour experience is what made Bobby’s famous, taking you off the tourist route and into the quiet neighborhood streets, city parks, and sunny beaches of the city’s North Side. This three-hour guided bike tour will give you a generous glimpse at how Chicagoans enjoy their beautiful city via bike.

Rated the ‘Best Chicago Sightseeing Tour of 2021′ by TripAdvisor, ‘Most Organized Bike Ride of Chicago’ by the Chicago Reader, and ‘Best Chicago Tour’ by Citysearch, you can bet this tour is one of the best, if not the best family-friendly Chicago bike tour along the Lakefront Trail and local neighborhoods.

What to Expect
Depart from Bobby’s Bike Hike Headquarters

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.

Head Towards Lincoln Park and Old Town

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.

Cruise Towards Lake Michigan, Past North Avenue and Oak Street Beaches

From there the Chicago bike 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!

Cruise Back to Headquarters on the Lakefront Trail

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