Chicago's Ultimate City Bike Tour of Downtown Attractions
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Discover Chicago’s most famous landmarks on this lively guided city bike tour! Led by the friendly experts at Bobby’s Bike Hike, the longest-running city bicycle tour company in America, you'll spend 3 hours exploring the heart of downtown Chicago at a relaxed pace.
Cycle past iconic sights like Millennium Park, the Chicago Riverwalk, Lakefront, Museum Campus, and Navy Pier. Get up close to landmarks such as Cloud Gate (the “Bean”), Buckingham Fountain, Soldier Field, and the Pritzker Pavilion. Whether you're visiting for the first time or a seasoned local, this tour offers fresh perspectives and insider stories that bring Chicago’s vibrant history and architecture to life.
All equipment is included, so you just need to bring your curiosity. Make memories on two wheels that you'll cherish forever—experience Chicago like never before!
Frequently asked questions
How long is the bike tour?
The tour lasts approximately 3 hours, covering many of Chicago’s top downtown attractions.
What’s included in the tour?
Bikes, helmets, child equipment, and all gear are provided. Guides share insider tips, history, and hidden gems along the route.
Is the tour suitable for all ages and fitness levels?
Yes. The tour is suitable for all physical fitness levels and is designed to be enjoyable for everyone, from infants to adults.
Are there any additional costs?
A suggested guide gratuity of $10 per person is appreciated (cash, Venmo, or PayPal). Food and drinks are not included.
Where do I meet for the tour?
Meet at 540 N. Lake Shore Drive (entrance on Ohio Street). Arrive 15 minutes early and walk through the driveway tunnel to the starting point.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 3 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Named Top 20 Tour in the World by TripAdvisor—see why guests rave about Bobby’s Bike Hike!
- Bikes, helmets, child equipment, and all gear included
- Fun, local guides share insider tips, history, food, & hidden gems
- See Chicago’s top downtown attractions & architecture on a scenic, culture-rich ride
Not included
- $10 per person suggested guide gratuity (cash, Venmo, PayPal)
- Food and drinks
Itinerary
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Stop 1
Millennium Park is where modern Chicago shines. Glide into this iconic space to see bold architecture, public art, and skyline views. Learn how the park was built over active rail lines and became a symbol of Chicago’s creativity and reinvention. Highlights include the Jay Pritzker Pavilion and interactive art installations.
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Stop 2
Buckingham Fountain is a Chicago icon. Ride into Grant Park to see this grand Beaux-Arts masterpiece, especially stunning when the central jet shoots skyward on the hour. It symbolizes Lake Michigan and the city’s water connection, offering a cinematic backdrop of the skyline.
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Stop 3
The Lakefront Bike Trail offers a front-row seat to Chicago’s lakefront lifestyle. Cruise along this 18-mile stretch with Lake Michigan on one side and the skyline on the other, soaking in the summer energy—runners, beachgoers, sailboats, and breezes included.
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Stop 4
Museum Campus is a water-surrounded peninsula home to the Field Museum, Shedd Aquarium, and Adler Planetarium. It’s a hub of culture and stunning skyline views, with a panoramic perspective of Chicago’s evolution from industrial land to cultural landmark.
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Stop 5
Navy Pier is Chicago’s lively waterfront hub. See the Centennial Wheel and learn about its history from shipping facility to entertainment destination. Feel the city’s energy and enjoy views of the skyline and lakefront.
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Stop 6
Northerly Island offers a peaceful escape with prairie landscapes, skyline views, and Lake Michigan. Once an airfield, now a nature preserve, it’s a quiet spot to experience Chicago’s natural beauty and sustainability efforts.
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Stop 7
Soldier Field stands as a symbol of Chicago’s sports and resilience. Ride past this historic stadium, home to the Bears, and admire its blend of old and new architecture overlooking the lake and city skyline.
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Stop 8
The Chicago Riverwalk showcases the city’s architectural story. Ride above the river, observing historic bridges, boat tours, and skyscrapers, and learn how the river’s reversal transformed Chicago’s urban landscape.
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Stop 9
The Chicago Theatre is a downtown icon. See its neon marquee on State Street and learn about its history as a key entertainment venue that helped define Chicago’s cultural scene.
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Stop 10
Shedd Aquarium is a beloved cultural and scientific institution. Ride into Museum Campus to see this Beaux-Arts marvel with breathtaking skyline views, connecting visitors to Chicago’s commitment to discovery and education.
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Stop 11
Grant Park is Chicago’s front yard. Pedal through this expansive green space, known for festivals and celebrations, and learn about its history of preservation and community importance.
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Stop 12
The Field Museum is a symbol of Chicago’s global reach. Ride into Museum Campus to explore this neoclassical museum, with views of the skyline and water, and learn about its history since the 1893 World’s Fair.
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Stop 13
12th Street Beach is a hidden gem. Pass by this tranquil stretch of sand near Museum Campus, where calm waters and skyline views create a peaceful retreat from the city’s hustle.
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Stop 14
Cloud Gate, aka 'The Bean,' is a must-see. Experience this mirrored sculpture reflecting the city’s skyline from multiple angles, capturing Chicago’s modern artistic spirit.
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Stop 15
Jay Pritzker Pavilion is a standout in Millennium Park. Admire Gehry’s stainless-steel design and its role as a premier outdoor concert venue that shapes Chicago’s cultural scene.
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Stop 16
Crown Fountain is a playful public art piece. Watch the faces of Chicagoans projected on twin towers spit water into the pool below, celebrating community and diversity.
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Stop 17
Adler Planetarium crowns the Museum Campus. Look back toward downtown for a stunning skyline view and learn about Chicago’s pioneering role in astronomy and science education.
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Stop 18
Daley Plaza is the civic heart of Chicago. See the modernist architecture and Picasso sculpture, and learn how this space has hosted protests, markets, and celebrations over the years.
Meeting point & pickup
Meet at the starting point
Arrive at 540 N. Lake Shore Drive (entrance on Ohio Street). Walk through the driveway tunnel to join your tour. Please arrive 15 minutes early to get ready.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day in advance
- No refund if cancelled within 24 hours
- Tour may be canceled due to bad weather or insufficient bookings
Instant confirmation
Your booking is confirmed immediately after checkout.
From $59.00 per person
- Free cancellation
- Secure checkout with our booking partner
