On this small-group Windy City bike tour, you won't just pedal past the lakefront neighborhoods of Chicago's North Side—you'll see more of the city than you could if exploring on your own. Follow a local guide along quiet streets, city parks, and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. As you go, glimpse offbeat attractions like the Playboy Mansion, Oprah’s penthouse, and the Victorian houses of Old Town.
This small-group tour keeps your sightseeing personal
Visit many lakefront highlights, all in a single trip
Spot local landmarks you’d miss if traveling alone
Bikes and helmets are provided for your ease and safety
What To Expect
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.
• Admission Ticket Free
St Michael Catholic Church in Old Town
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 187
• Admission Ticket Free
The Magnificent Mile
The Magnificent Mile is Chicago’s premier commercial district, home to upscale shops, cool restaurants and hotels, and Michigan Avenue.
• Admission Ticket Free
Lincoln Park Zoo
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.
15 minutes • Admission Ticket Free
Lake Michigan
One of the five Great Lakes and a beautiful Chicago staple.
15 minutes • Admission Ticket Free
North Avenue Beach
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.
15 minutes • Admission Ticket Free
Lakefront Trail
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.
20 minutes • Admission Ticket Free
Gold Coast
Enjoy the oppulent mansions along Chicago’s lakefront
10 minutes • Admission Ticket Free
Old Town
Enjoy Chicago’s beautiful neighborhood just north of downtown. Old Town survived the Great Chicago Fire of 1871
5 minutes • Admission Ticket Free
Lincoln Park
Gorgeous neighborhood on the north coast of Chicago
10 minutes • Admission Ticket Free
Lakefront Trail
Enjoy the most gorgeous section the 20 mile Lakefront Bike Trail
10 minutes • Admission Ticket Free
Highlight
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.
Not wheelchair accessible
Storage for larger bags/items available for free
Please note: children must be strong, capable riders and be able to bike for 9 miles
Near public transportation
Infant seats available
Most travelers can participate
TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
Operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough guests to meet requirements. In the event of this occurring, you will be offered an alternative or full refund.
This tour/activity will have a maximum of 15 travelers
Include
Bicycle
Helmet
Local tour guide
Exclude
Food and drinks
$10 per person suggested guide gratuity. (via Cash, Venmo and PayPal)