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Chicago Bike Tours: The Classic Lakefront Trail
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About the Tour
About the Tour
Chicago is a city built on reinvention, from the ashes of the Great Fire to the skyline that rose in its place. On this self-guided Chicago bike tour, you’ll explore the city the way locals love it: by bike, along the scenic Lakefront Trail and Chicago’s connected network of bike paths.
Starting near Navy Pier and the Bike Hub at Addams Memorial Park, this route takes you through Chicago’s most iconic landmarks, historic neighborhoods, and unforgettable skyline views. Ride beside Lake Michigan, through Museum Campus, across the Chicago River, and into the heart of the Loop while your audio guide brings the city’s stories to life.
This tour is designed for first-time visitors, casual riders, and travelers looking for a unique way to experience Chicago. Most of the route follows dedicated bike paths and bike lanes, allowing you to spend less time worrying about directions and more time enjoying the architecture, history, and hidden stories around you.
On this 60-minute cycling tour, you'll have a chance to:
- Ride the famous Chicago Lakefront Trail with incredible views of Lake Michigan and the skyline
- Visit the Shedd Aquarium, Adler Planetarium, and Field Museum in Museum Campus
- See Buckingham Fountain, one of the world’s largest fountains and a symbol of Grant Park
- Explore Millennium Park and Cloud Gate, better known as “The Bean”
- Pass the Chicago Theatre, State Street, and the historic heart of downtown
- Discover Union Station, the Chicago River, Willis Tower, and the city’s famous architecture
- Hear stories about Chicago’s Great Fire, innovation, transportation history, and the people who shaped the city
From historic landmarks to modern skyscrapers, every mile tells a story. Whether it’s your first time visiting Chicago or you’re looking to see the city from a new perspective, this self-guided bike tour lets you explore at your own pace with the freedom of riding like a local.
Grab a bike, put on your helmet, and get ready to experience Chicago — one landmark, one story, and one ride at a time.
Tour Producer
Tour Producer
Biking Chicago
Welcome to Biking Chicago, your local guide to exploring Chicago on two wheels. Our self-guided audio bike tours are designed for travelers who want the freedom to explore at their own pace while learning the stories that shaped one of America's greatest cities. Whether you're visiting Chicago for the first time or returning to see more, our tours combine local storytelling, historical insights, architecture, public art, and breathtaking skyline views into one unforgettable experience.
What makes our tours unique is that most of the route follows Chicago's extensive network of dedicated bike paths, protected bike lanes, and the world-famous Lakefront Trail. This allows riders of all experience levels to enjoy many of Chicago's top attractions while spending less time navigating busy city traffic and more time enjoying the ride.
If you're looking for one of the best things to do in Chicago, our self-guided bike tours offer a fun, affordable, and active way to experience the city. Simply rent a Divvy bike, follow the route, and let Chicago's history, lakefront, and skyline unfold around you.
Explore Chicago. Ride Chicago. Experience Chicago like a local.
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Preview Location
Preview Location
Location 10
Buckingham Fountain
Picture this: it’s 1927, the height of the roaring twenties. A woman philanthropist named Kate Buckingham, mourning her brother Claren...
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Major Landmarks
Major Landmarks
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Navy Pier
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Shedd Aquarium
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Field Museum
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Adler Planetarium
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Millennium Park
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Union Station Transit Center
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Daley Plaza
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Clarence F. Buckingham Memorial Fountain
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Grant Park
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Ogilvie Transportation Center
Getting There
Getting There
Route Overview
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Start location578-536 E Grand Ave, Chicago, IL 60611, USA
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Total distance14km
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Final locationN Streeter Dr, Chicago, IL 60611, USA
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Distance back to start location66.19m
Directions to Starting Point
Start your tour at the Divvy Bike Hub in Addams Memorial Park, located at the corner of E Grand avenue and E Ohio street. Across the street from Lake Point Tower Condominium.
Show Directions
Tips
Tips
Places to stop along the way
Take your time and enjoy the landmarks along the route. Recommended stops include:
• Navy Pier — famous for skyline views, fireworks, restaurants, and lakefront attractions.
• Monument of the Millennium Marker — See the Navy Pier Fireworks without a crowd.
• Museum Campus — visit the Shedd Aquarium, Field Museum, and Adler Planetarium.
• Buckingham Fountain — one of the largest fountains in the world and a Grant Park icon.
• Millennium Park — home of Cloud Gate “The Bean,” Jay Pritzker Pavilion, and Maggie Daley Park.
• Green 320— a perfect place for food, drinks, and to enjoy a park among skyscrapers.
• West Loop — one of Chicago’s best neighborhoods for restaurants, coffee shops, and nightlife.
• Northerly Island — A nature preserve near the Planetarium that is open if there is not a event.
For the best experience, plan extra time to stop, take photos, and enjoy Chicago at your own pace.
Best time of day
The best time to enjoy this Chicago bike tour is from spring through fall, especially between April and October when the weather is comfortable and the Lakefront Trail is at its best.
Morning rides offer fewer crowds, cooler temperatures, and beautiful sunrise views over Lake Michigan. Late afternoon and sunset rides provide some of the best skyline photos.
Avoid rush hour periods on weekdays, especially around 7:30–9:30 AM and 4:00–6:00 PM, when downtown streets and bike lanes can become busier.
The tour can be completed year-round, but winter riders should prepare for cold temperatures, strong lake winds, and possible icy conditions.
Precautions
This tour follows mostly dedicated bike paths, protected bike lanes, and the Chicago Lakefront Trail, but you are still riding in an active city environment. Always stay aware of pedestrians, runners, other cyclists, and changing traffic conditions.
A helmet is strongly recommended. Before starting, perform a quick ABC bike check: check the Air in your tires, test your Brakes, and make sure your Chain and gears are working properly.
Bring water, especially during summer, and dress for the weather. Chicago’s lakefront can feel much cooler and windier than the rest of the city.
Use your hand signals when turning and announce “on your left” when passing other riders.
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