Lakefront Neighborhoods Bike Tour

  • 3 Hours1:30pm Weekdays, 10:30am Weekends
  • Ages from 1+
  • Level: Ridiculously Easy
  • Length: 7 mi/11 km
  • Electric Bike Upgrade $29.99

Bike Along the Lakefront Trail & Local Neighborhoods

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’s Included

  • Bike and helmet

What to Bring

  • Wear comfortable clothing/shoes (Closed-toed shoes preferred)
  • Bring a camera, there’s plenty of views and picture opportunities!

Important Info

  • Must be able to ride a bike (Child equipment available for kids)
  • We tour rain or shine. We do provide ponchos if it is announced to rain.

Departure Locations

  • Bobby’s Bike Hike Headquarters (540 N. Lake Shore Drive)

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.



Extra Information

Named for Captain George Wellington Streeter, Streeterville is the bustling downtown district east of Michigan Avenue, north of the Chicago RIver. Streeterville is home to such beloved landmarks as the John Hancock Center and the Museum of Contemporary Art.

Opened in 1967, The Museum of Contemporary Art, or MCA, is home to one of the largest collections of post-WWII visual art in the world.

The Gold Coast neighborhood is world-famous for its upscale dining and shopping, and high-end real estate, located just north of the Chicago Loop.

The original Playboy Mansion was located on State Street in Chicago’s legendary Gold Coast neighborhood. Purchased by Hugh Hefner in 1959, the mansion still boasts a basement pool and swim-up bar.

Lincoln Park is Chicago’s largest municipal park, covering 5 miles of the Lake Michigan waterfront, and 1200 acres of land. It is home to numerous bike and walking paths, sports fields, playscapes, and one of America’s largest free zoos.

Old Town is one of Chicago’s most historic North Side neighborhoods. Beloved by beatniks in the 1950s and 60s, and hippies in the 70s, Old Town is now a quiet, tree-line arts district.

Located in the heart of Old Town, stunning St. Michael’s Church is one of less than a dozen buildings to have survived the Great Chicago Fire of 1871.

The Lincoln Park Zoo is free for all to enjoy and is home to hundreds of beautiful animals from all over the world including lions, tigers, penguins, reptiles, gorillas, and camels.

North Avenue Beach is one of the Windy City’s most popular public beaches. It features white sand, kayak and jet-ski rentals, bars, restaurants, and the clear, freshwater of the great Lake Michigan.

The sprawling Lakefront Trail is an 18-mile, paved bike and walking path that straddles the shore of Lake Michigan, and connects the Windy City’s north and south side neighborhoods.

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