• Museum of Contemporary Art - Nestled in the Gold Coast, the Museum of Contemporary Art is a hidden gem that showcases Chicago’s innovative artistic spirit. During the Chicago Bike Tour through the iconic Lakefront Neighborhoods, participants will pass by this modern cultural center, surrounded by historic mansions and tree-lined streets. The juxtaposition of cutting-edge art and classic Chicago elegance is striking.

On this Bicycle Tour in Chicago, guides explain how the MCA has elevated the city’s status in the global art scene by hosting provocative exhibits and avant-garde artists in the Midwest. It serves as a reminder that Chicago is not only about its history but also about its ongoing transformation.

Among the most enriching activities in Chicago, visiting the Museum of Contemporary Art by bike allows participants to experience the intersection of creativity, architecture, and neighborhood charm in a memorable Lakefront ride.

• Gold Coast - The Gold Coast epitomizes Chicago’s elegance. On the Chicago Bike Tour through the stunning Lakefront Neighborhoods, participants will glide past grand mansions, historic brownstones, and tree-lined streets that echo tales of old-money ambition and architectural brilliance. Insiders know this neighborhood rose from the ashes of the Great Chicago Fire, becoming home to the city’s most influential families.

During this immersive Bicycle Tour in Chicago, guides reveal how industrial magnates and cultural leaders shaped this lakeside enclave, all while participants enjoy the lake breezes just a few blocks away. It’s refined, serene, and steeped in history.

Among the most captivating activities in Chicago, exploring the Gold Coast by bike offers a unique blend of prestige, preservation, and proximity to the water—an unforgettable highlight of the Lakefront adventure.

• The Magnificent Mile - The Magnificent Mile is where Chicago showcases its confidence. On the Chicago Bike Tour through the iconic Lakefront Neighborhoods, participants will ride past legendary storefronts, historic hotels, and architectural landmarks that define the city’s commercial heart. Insiders know this stretch of Michigan Avenue was once lined with mansions before evolving into one of the world’s most famous shopping corridors.

On this engaging Bicycle Tour in Chicago, guides share how the Mag Mile became a symbol of Chicago’s resilience and global influence. It’s more than just retail—it’s about reinvention.

Among the essential activities in Chicago, experiencing The Magnificent Mile by bike provides a perspective beyond the storefronts, connecting luxury, history, and lakefront energy in one unforgettable ride.

• Lincoln Park Zoo - Lincoln Park Zoo is where nature, history, and skyline views converge in the heart of the city. On the Chicago Bike Tour through the beautiful Lakefront Neighborhoods, participants will ride past one of the oldest free zoos in the country, surrounded by green space and just steps from Lake Michigan. Insiders know the zoo dates back to 1868 and reflects Chicago’s long-standing commitment to public access and conservation.

On this refreshing Bicycle Tour in Chicago, participants will learn how Lincoln Park transformed from cemetery grounds after the Great Chicago Fire into one of the city’s most cherished outdoor spaces.

Among the most memorable activities in Chicago, experiencing Lincoln Park Zoo by bike combines wildlife, lake breezes, and neighborhood charm into one vibrant Lakefront adventure.

• St Michael Catholic Church in Old Town - St. Michael’s Church in Old Town stands as one of Chicago’s quiet symbols of resilience. On the Chicago Bike Tour through the historic Lakefront Neighborhoods, participants will visit this 1852 landmark that famously survived the Great Chicago Fire—one of the few structures left standing when much of the city was reduced to ashes. Insiders know its towering steeple once served as a navigation point for ships on Lake Michigan.

On this immersive Bicycle Tour in Chicago, guides share how Old Town rebuilt around this church, preserving its character while the rest of the city modernized.

Among the most meaningful activities in Chicago, visiting St. Michael’s by bike connects participants to the city’s grit, faith, and rebirth—all woven into a scenic Lakefront ride through Chicago’s most charming neighborhoods.

• North Avenue Beach - North Avenue Beach is where Chicago’s skyline and lakefront lifestyle meet. On the Chicago Bike Tour through the vibrant Lakefront Neighborhoods, participants will ride along the water with sweeping city views rising dramatically behind the sand. Insiders know this beach offers one of the most photographed skyline angles in the city—especially when looking south toward downtown.

On this refreshing Bicycle Tour in Chicago, participants will hear how the lakefront was preserved “forever open, clear, and free,” providing Chicagoans with unmatched public access to nature in the heart of a major city. It’s active, social, and unmistakably Chicago.

Among the most energizing activities in Chicago, experiencing North Avenue Beach by bike blends fresh air, panoramic views, and neighborhood charm into one unforgettable Lakefront adventure.

• Lakefront Trail - The Lakefront Bicycle Trail is Chicago’s ultimate outdoor runway. On the Chicago Bike Tour through the breathtaking Lakefront Neighborhoods, participants will cruise this iconic path with Lake Michigan on one side and the skyline towering on the other. Insiders know this 18-mile stretch is where locals run, ride, and reset—especially at sunrise when the city feels wide open and alive.

On this immersive Bicycle Tour in Chicago, guides share how the lakefront was intentionally protected for public use, shaping Chicago’s identity as a city that values access to nature. It’s smooth, scenic, and endlessly photogenic.

Among the most unforgettable activities in Chicago, riding the Lakefront Trail by bike offers freedom, perspective, and fresh air—an essential highlight of this dynamic Lakefront adventure.

• Lake Michigan - Lake Michigan is not just a backdrop—it’s Chicago’s defining feature. On the Chicago Bike Tour through the stunning Lakefront Neighborhoods, participants will ride alongside one of the largest freshwater lakes in the world, with open blue water stretching to the horizon. Insiders know that on clear days, it feels more like an ocean than a lake—complete with sailboats, beaches, and that unmistakable Midwest breeze.

On this unforgettable Bicycle Tour in Chicago, guides share how the lake shaped the city’s growth, trade, and identity—and why its shoreline remains “forever open, clear, and free.”

Among the most iconic activities in Chicago, experiencing Lake Michigan by bike blends skyline views, fresh air, and waterfront energy into one powerful, perspective-shifting Lakefront adventure.

• Old Town - Old Town is where Chicago’s past still thrives on every block. On the Chicago Bike Tour through the charming Lakefront Neighborhoods, participants will pedal along cobblestone-style streets lined with Victorian-era homes that survived the Great Chicago Fire. Insiders know this neighborhood became a haven for artists, comedians, and counterculture thinkers in the 1960s—shaping Chicago’s creative spirit.

On this engaging Bicycle Tour in Chicago, guides reveal how Old Town balances historic preservation with modern energy, from iconic churches to tucked-away gardens.

Among the most authentic activities in Chicago, exploring Old Town by bike offers character, resilience, and story—an unforgettable highlight of this scenic Lakefront adventure.

• Lincoln Park - Lincoln Park is where elegance, green space, and lakefront living converge. On the Chicago Bike Tour through the picturesque Lakefront Neighborhoods, participants will ride past historic brownstones, shaded streets, and one of the largest urban parks in the country. Insiders know Lincoln Park was once the site of the city cemetery before being transformed into a vibrant public oasis after the Great Chicago Fire.

On this immersive Bicycle Tour in Chicago, guides share how the neighborhood blends architectural charm, cultural institutions, and easy access to Lake Michigan. It’s refined yet relaxed—classic Chicago.

Among the most rewarding activities in Chicago, exploring Lincoln Park by bike offers fresh air, fascinating history, and a true local feel woven into this unforgettable Lakefront adventure.

• Streeterville - Streeterville is where ambition meets the lake. On the Chicago Bike Tour through the dynamic Lakefront Neighborhoods, participants will ride through this high-rise enclave built on reclaimed land from the Great Chicago Fire era. Insiders know this area was once a literal sandbar—transformed into one of the city’s most valuable and scenic neighborhoods.

On this Bicycle Tour in Chicago, participants will glide past modern towers, tucked-away marinas, and sweeping Lake Michigan views while hearing how Streeterville evolved from shipping chaos to luxury living. It’s a powerful example of Chicago’s constant reinvention.

Among the most fascinating activities in Chicago, exploring Streeterville by bike offers skyline drama, lake breezes, and a front-row seat to the city’s bold architectural story—all woven seamlessly into this unforgettable Lakefront ride.

• Lincoln Monument Gardens - The Standing Lincoln Statue in Lincoln Park is a quiet yet powerful tribute to leadership and legacy. On the Chicago Bike Tour through the scenic Lakefront Neighborhoods, participants will ride to this striking sculpture of Abraham Lincoln—long before he became president—capturing him as a thoughtful, rising statesman. Insiders know this statue predates the more famous Lincoln Memorial in D.C., giving Chicago its own early tribute to the 16th president.

On this enriching Bicycle Tour in Chicago, guides share how Lincoln’s Illinois roots shaped his path—and why this statue reflects the city’s deep connection to his story.

Among the most meaningful activities in Chicago, visiting the Standing Lincoln Statue by bike blends history, art, and lakeside beauty into one inspiring Lakefront adventure.

• Local tour guide
• Bicycle
• Helmet

• Food and drinks
• $10 per person suggested guide gratuity. (via Cash, Venmo and PayPal)

Bobby’s Bike Hike, a celebrated and long-standing American city bicycle tour company, is the tour that catapulted Bobby to fame. It has repeatedly received recognition from renowned platforms such as National Geographic, USA Today, The Associated Press, Conde Nast Traveler, among others! Bobby now offers a range of over a dozen specialized tours, with The Lakefront Neighborhoods ride being the one that set the ball rolling. Embark on a 3-hour adventure with one of Bobby’s experienced guides through the stunning neighborhoods of Chicago’s North Side. Take in sights of Streeterville’s ever-growing skyline, Gold Coast’s high-end residential properties, the artistic enclave of Old Town, and the verdant landscapes of Lincoln Park. The tour culminates in a leisurely ride down the Lakefront Trail, one of the nation’s most loved shoreline bike paths. This relaxed adventure is certain to create long-lasting memories! The tour sets off from 540 N. Lake Shore Drive, Chicago.

• This Chicago Bicycle 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.
• Storage for larger bags/items available for free
• Please note: children must be strong, capable riders and be able to bike for 9 miles
• TripAdvisor rated Bobby’s Bike Hike its highest-level Traveler’s Choice Award each year since 2002.
• Chicago Bike Tour operates rain or shine, please dress appropriately. If extreme weather forces cancellation there will be options to change tours or refund.
• Minimum numbers apply for the bike tour of Chicago. 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.

For a full refund, cancel at least 24 hours before the scheduled departure time.