Chicago Neighborhood Bike Tours: Streeterville, Gold Coast, Old Town and Beyond

A neighborhood tour trades the postcard route for streets with people on them. The tourist ride goes where the landmarks are. This one goes where Chicagoans live. The page below covers the tours that do it, and the ground they cover. For the full field, start at Bike Tours.

The pick: Lakefront Neighborhoods

Bobby’s Bike Hike runs the neighborhood tour. It lasts about three hours and covers 7 miles¹. Departures are 1:30 pm on weekdays and 10:30 am and 2:30 pm on weekends; the price starts at $49.99². The route leaves the tourist track for quiet neighborhood streets, city parks and the beaches of the North Side¹.

The ride starts and ends at 540 N. Lake Shore Drive¹. A bike and helmet are included¹. An e-bike upgrade costs $29.99¹. The tour runs rain or shine, with ponchos supplied when rain is announced¹.

The route, neighborhood by neighborhood

Streeterville. The group heads first into the downtown district of Streeterville¹, then rolls past the Magnificent Mile into the Gold Coast¹.

Gold Coast. The neighborhood grew in the wake of the Great Chicago Fire⁵. In 1882, the millionaire Potter Palmer moved here from Prairie Avenue⁵. It has been Chicago’s highest-rent district since the 1870s and holds some of the finest Victorian homes in the country¹. The building that housed the original Playboy Mansion stands in the district⁵.

Lincoln Park. The park is a 1,208-acre strip of lakefront and the city’s largest public park⁷. It stretches seven miles north from Grand Avenue⁷. The zoo is free and open year-round⁷. The park also holds the Conservatory, the Chicago History Museum and the Peggy Notebaert Nature Museum⁷.

Old Town. Its tree-lined streets are rarely used by bus tours¹. The neighborhood contains many of Chicago’s older, Victorian-era buildings, among them St. Michael’s Church, one of seven buildings to survive the Great Chicago Fire⁶. Many streets in the Old Town Triangle predate the fire and break from the city grid⁶.

The beaches. North Avenue and Oak Street beaches can hold up to 300,000 people on a warm Saturday in July¹. The group returns south along the Lakefront Trail¹. For the trail itself, read the Lakefront Trail guide.

The alternative: Lincoln Park Bike Adventure

Bike and Roll runs a three-hour Lincoln Park tour, departing at 10:30 AM daily³. Adults pay $65; ages 12 to 18 pay $45³. The top sights are the lakefront, Navy Pier, North Avenue Beach, Lincoln Park Zoo and the Conservatory³. Bike and Roll rates the riding as easy and kid-friendly³.

Four hours with food: neighborhoods by the plate

Two Bobby’s tours turn neighborhoods into a tasting. The Westside Foodie Ride runs four hours from $89.99, Friday to Sunday at noon, and traces the city’s immigrant history through food². The Family & Food tour runs four hours from $69.99 and covers North Side neighborhoods before heading south to downtown². The food bike tour guide has the details.

Beyond the city line: Pedal Oak Park

Oak Park holds the world’s largest collection of buildings designed by Frank Lloyd Wright⁴. The Frank Lloyd Wright Trust leads a two-hour ride past 21 Wright structures, among them the Home and Studio, the Heurtley House and the Cheney House⁴. It runs Saturdays and Sundays at 9:30 am, June through October⁴. Admission is $55, or $45 for Trust members⁴.

Groups are capped at 10, riders must be 12 or older, and the tour shows building exteriors only⁴. It starts at 951 Chicago Avenue in Oak Park⁴. Bring your own bike or use one supplied with the ticket⁴.

Choosing between them

• Visiting for the first time, with children: Bobby’s Lakefront Neighborhoods. All ages are welcome, with kids’ seats and tag-alongs¹.
• Short on streets, long on parkland: Bike and Roll’s Lincoln Park Bike Adventure³.
• Interested in architecture: Pedal Oak Park, ages 12 and up⁴.
• Hungry: one of the food tours².

Compare them against every other ride on the Chicago bike tours page, or see the lakefront bike tour guide.