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The 17 Best Bike Rides in Chicago

For those seeking an exhilarating way to explore the beautiful city of Chicago, bike rides offer the perfect combination of exercise, adventure, and sightseeing. With a plethora of scenic routes and trails to choose from, biking enthusiasts can pedal their way through the vibrant neighborhoods, picturesque parks, and iconic landmarks that the Windy City has to offer.

Whether you are a seasoned cyclist looking for a challenging ride or a casual rider in search of a leisurely route, Chicago has something for everyone. From lakefront paths to urban explorations, there are endless possibilities to suit your biking preferences and skill level.

Get ready to grab your helmet, hop on your bike, and embark on an unforgettable journey through the vibrant streets and picturesque landscapes of Chicago with our curated list of the Best Bike Rides in Chicago.

How this ranking works

This guide does not try to list everyone. It is our pick of bike rides in Chicago, built on each business's public reputation and on how central this service is to what it does.

Some businesses pay for a fuller profile or a featured position. It is only open to those that have already passed our selection, and it is always marked.

Top 3Full rankingMapTips for choosing

Our 17 local picks compared

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours#1
What sets it apart
  • An absolutely fantastic tour with knowledgeable and engaging guides.

  • Delicious food experiences at top-notch restaurants.

  • Great historical insights and city exploration during the tours.

  • Highly recommended for both locals and visitors alike.

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours

4.91,036 reviews
540 N Lake Shore Dr, Chicago, IL 60611, United States

Bobby's Bike Hike - Chicago Bike, Walking & Food Tours is a top-notch tour operator located in Chicago, offering a variety of exciting tours to explore the city. With a remarkable rating of 4.9, based on 1036 reviews, it's clear that customers have had outstanding experiences with this business.

Some key points from customer reviews include:

The business offers accessible options for wheelchair users to ensure everyone can enjoy the tours. With passionate guides like Jeff and Greg leading the way, customers can expect a memorable and enriching experience exploring the vibrant city of Chicago.

Lakefront Trail - Fullerton - 2400 N, Chicago#2
What sets it apart
  • A beautiful and well-kept trail with stunning views and multiple activity options.

  • Great place to watch the sunrise or sunset, with clean facilities and picturesque surroundings.

  • Perfect for outdoor enthusiasts looking to enjoy biking, walking, or running along the lakefront.

  • Customers appreciate the relaxing and serene ambiance of the area, making it an enjoyable experience for all.

Lakefront Trail - Fullerton - 2400 N

4.9260 reviews
Lakefront Trl, Chicago, IL 60614, United States

Lakefront Trail - Fullerton - 2400 N offers a stunning and well-kept trail for visitors to enjoy. With options for birdwatching, cycling, hiking, jogging, and walking, this picturesque area provides a total of 13.5 miles along the lakefront. Customers rave about the beautiful views and serene atmosphere, making it an ideal spot to catch the sunrise or sunset. The trail also features bike lanes and is praised for being clean and well-maintained.

Customer reviews highlight:

The 606, Chicago#3
What sets it apart
  • Absolutely love this trail! Perfect for biking, walking, and running. Plenty of bench spots to relax and enjoy the sun.

  • A safe, beautifully landscaped trail ideal for walks and bike rides regardless of the season.

  • Great place for various activities like exercising, walking your dogs, or simply taking a stroll through different neighborhoods.

  • Beautiful elevated park with easy access points, perfect for joggers, walkers, bikers, and dog owners.

The 606

4.81,762 reviews
1805 N Ridgeway Ave, Chicago, IL 60647, United States

The 606 is a popular hiking area located in Chicago, offering a variety of activities such as cycling, hiking, jogging, and walking on a point-to-point trail. Visitors also have access to skateboarding areas and dog parks, making it an ideal destination for individuals and families alike.

Customer reviews rave about the trail, mentioning key points such as:

With a high rating of 4.8, The 606 is praised by visitors for its well-maintained trails, beautiful scenery, and diverse amenities, making it a must-visit destination for outdoor enthusiasts in Chicago.

Bobby's Bike Hike - Miami Bike, Walking & Food Tours, Chicago#4
What sets it apart
  • Knowledgeable and friendly guides who provide interesting insights

  • Great selection of tours catering to different interests

  • Well-organized and enjoyable experiences for all participants

Bobby's Bike Hike - Miami Bike, Walking & Food Tours

5.086 reviews
nan

Bobby's Bike Hike - Miami Bike, Walking & Food Tours is a renowned tour operator in Miami that offers a unique and exciting way to explore the city. Whether you prefer biking, walking, or indulging in delicious food tours, they have something for everyone.

The company has received 86 reviews with an outstanding 5.0 rating from satisfied customers. Here are some key points from their feedback:

Discover the beauty of Miami with Bobby's Bike Hike and create unforgettable memories while exploring the city in a fun and engaging way. Book your tour today!

Lakefront Trail - Grant Park, Chicago#5
What sets it apart
  • Excellent place to see the Chicago Skyline. Great walk.

  • Mind-blowing trail with million-dollar views. Stunning sights around sunset.

  • Quiet escape from the city with diverse scenery and landmarks along the way.

  • Perfect spot for a leisurely walk with beautiful city views and nearby attractions.

Lakefront Trail - Grant Park

4.8145 reviews

Open 24 hours

Lakefront Trl, Chicago, IL 60605, United States

Lakefront Trail - Grant Park offers a diverse array of activities for nature enthusiasts and outdoor lovers. From cycling to hiking, jogging, and walking, there is something for everyone to enjoy while taking in the scenic beauty of Lake Michigan. With amenities like picnic tables and a skateboarding area, visitors can make the most of their time outdoors.

Customers have praised the trail for its stunning views and peaceful ambiance. Some of the key points highlighted in reviews include:

Experience the beauty of Chicago's Lakefront Trail at their website and see why it is a must-visit destination for residents and visitors alike.

The Garden, Chicago#6
What sets it apart
  • Customers praise the park's diverse features, including dirt jumps and a pump track.

  • Visitors love the natural setting of the park, surrounded by trees and greenery.

  • Many riders appreciate the park's suitability for all types of riders, from beginners to more experienced bikers.

The Garden

4.877 reviews
3400 N Rockwell St, Chicago, IL 60618, United States

The Garden is a fantastic destination for biking enthusiasts in Chicago. Offering a variety of features such as a pump track, a quarter pipe, and large jumps, this park caters to riders of all levels. The park's natural surroundings provide a picturesque backdrop for a thrilling experience.

With a rating of 4.8 based on 77 reviews, The Garden is a highly recommended spot for anyone looking to enjoy biking in a beautiful outdoor setting.

3rd Coast Cycles, Chicago#7
What sets it apart
  • Excellent customer service

  • Convenient bicycle rental options

  • High-quality bicycle repair services

  • Knowledgeable staff

3rd Coast Cycles

4.8231 reviews
152 N DuSable Lake Shore Dr, Chicago, IL 60601, United States

3rd Coast Cycles is a dedicated bicycle store located in Chicago, IL. The business offers a range of services including kerbside pickup, delivery, in-store pick-up, in-store shopping, and same-day delivery. Customers can also enjoy activities such as bicycle hire and access amenities like Wi-Fi. The establishment is known for being LGBTQ+ friendly and a transgender safe space, making it a welcoming environment for all.

With a stellar rating of 4.8, based on 231 reviews, customers have praised 3rd Coast Cycles for:

Experience the top-notch services and friendly atmosphere at 3rd Coast Cycles for all your biking needs.

Lakefront Trail - Dusable Harbor - 150 N, Chicago#8
What sets it apart
  • Great place to train running and cycling. Perfect for long-distance activities.

  • Beautiful trail with stunning views of Lake Michigan and the Chicago skyline.

  • Well-maintained with separate tracks for pedestrians and cyclists.

  • Offers a relaxing and safe environment for various outdoor activities.

Lakefront Trail - Dusable Harbor - 150 N

4.651 reviews

Open 24 hours

Lakefront Trl, Chicago, IL 60601, United States

Lakefront Trail - Dusable Harbor - 150 N offers a stunning hiking area along Lake Michigan, providing a scenic route for visitors to enjoy. This trail is perfect for cycling, jogging, and walking, making it an ideal spot for outdoor enthusiasts. With amenities such as public toilets, it ensures convenience for all users.

Chicago Bike Adventures#9
What sets it apart
  • Knowledgeable and attentive guides who cater to the group's pace and interests

  • Customized tours that showcase the best of Chicago's neighborhoods, history, art, and culture

  • Safe and well-paced rides with plenty of stops to learn, enjoy, and take in the city

  • Exceptional customer service and attention to detail, making every tour a special and unforgettable experience

Chicago Bike Adventures

5.08 reviews
1300 N Ashland Ave, Chicago, IL 60622, United States

Chicago Bike Adventures is a premier tour operator in Chicago that offers unique and personalized bike tours for visitors to explore the city like never before. Their knowledgeable guides go above and beyond to create a memorable experience for each guest, tailoring the tours based on individual interests and preferences.

Customers rave about their experiences with Chicago Bike Adventures, highlighting the following key points:

With a perfect rating of 5.0, it's no wonder why visitors love exploring Chicago with Chicago Bike Adventures. Book your tour today and get ready for an adventure like no other!

Lakefront Trail - Ohio Street Beach, Chicago#10
What sets it apart
  • Great for both long distance exercise and dynamic photo opportunities

  • Flat running area and a slanted biking path

  • Amazing lakeshore views, perfect for walking, running, biking, and more

  • Best views seen in a while

Lakefront Trail - Ohio Street Beach

4.711 reviews

Open 24 hours

600 N Lake Shore Dr, Chicago, IL 60611, United States

Lakefront Trail - Ohio Street Beach is a picturesque Hiking area located in Chicago, United States. The trail spans nearly 20 miles along Lake Michigan, providing separate lanes for walkers/runners and cyclists/skateboarders/rollerbladers, ensuring everyone can enjoy their preferred form of exercise safely. The trail is well-traveled, offering a safe and scenic route with stunning views of the downtown skyline and calm waters.

Wheel Fun Rentals, Chicago#11
What sets it apart
  • Rented a swan boat for an hour, found the price a bit high but enjoyed the experience

  • Staff were very nice and helpful, affordable prices for swan pedal boats

  • Had a wonderful visit, very friendly staff, and enjoyed the swan boat ride

  • Beautiful location, friendly and professional staff, amazing boats

Wheel Fun Rentals

4.232 reviews
Next to Boathouse Café, 1301 N Humboldt Dr, Chicago, IL 60622, United States

Wheel Fun Rentals is a premier bicycle rental service located in the heart of Chicago, IL. Visitors can enjoy a leisurely ride around the picturesque park on one of their high-quality bicycles. The friendly and experienced staff are always ready to assist customers with finding the perfect bike for their needs.

With a rating of 4.2 out of 5, it's clear that customers have had positive experiences at Wheel Fun Rentals.

Whether you're looking to explore the park on two wheels or take a relaxing boat ride on the pond, Wheel Fun Rentals has something for everyone. Plan your visit today and create unforgettable memories in this beautiful setting!

Bloomingdale Trail Park, Chicago#12
What sets it apart
  • Customers appreciate the incredible landscaping with native Illinois vegetation.

  • Visitors enjoy the variety of flowers and plants along the trail.

  • Many customers find the park dog-friendly with amenities suitable for pets.

  • The availability of benches, trash bins, and water fountains adds to the convenience of the park.

Bloomingdale Trail Park

4.71,137 reviews
1600 - 3700 W Bloomingdale Ave, Chicago, IL 60622, Chicago, IL 60647, United States

Bloomingdale Trail Park offers a picturesque hiking area in Chicago, IL. Visitors can enjoy a variety of outdoor activities such as cycling, jogging, and walking on the well-maintained trail. The park is dog-friendly, with designated areas for pets to roam. Customers have praised the park for its beautiful landscaping, easy accessibility, and family-friendly amenities.

Big Marsh Park, Chicago#13
What sets it apart
  • Beautiful marsh lands with surprising sculptures and art pieces along the trail.

  • Great place for hiking and biking, with bike rentals available.

  • Clean bathrooms, vending machines, and a welcoming atmosphere for families.

  • Wheelchair accessible paths, smooth paved trails, and wide eating areas for picnics.

Big Marsh Park

4.7429 reviews
11559 S Stony Is Ave, Chicago, IL 60617, United States

Big Marsh Park is a hidden gem in Chicago, offering a variety of activities for all ages. Visitors can enjoy hiking on the beautiful marsh lands, explore the unique sculptures and art pieces along the trails, and even engage in skateboarding at the designated area. The park is also kid-friendly, with options for birthday celebrations and safe hikes for children.

Customer reviews rave about the park's stunning scenery and well-maintained facilities. Here are some key points from recent visitors:

Whether you're looking for a peaceful nature walk or an exciting bike ride, Big Marsh Park is the perfect destination for outdoor enthusiasts of all kinds.

Bike and Roll Chicago - Millennium Park (34 S. Michigan Ave)#14
What sets it apart
  • Outstanding experience. Segway tours are a great way to explore the city, and the guide was knowledgeable and fun!

  • Helpful and friendly staff, especially when it comes to fixing issues like flat tires.

  • Great tour guides who are informative, kind, and make the experience enjoyable.

  • Easy online booking process with discounts available, plus a variety of rental options including tandem bikes for extra fun!

Bike and Roll Chicago - Millennium Park (34 S. Michigan Ave)

4.0110 reviews
34 S Michigan Ave, Chicago, IL 60603, United States

Bike and Roll Chicago - Millennium Park offers a fantastic bicycle rental service right in the heart of Chicago. With an impressive 4.0 rating from 110 reviews, it's clear that customers love this place. Some key points from their reviews include:

From their top-notch service to their convenient location, Bike and Roll Chicago - Millennium Park is a must-visit for anyone looking to explore the city on two wheels.

Chicago Riverview#15
What sets it apart
  • Great place for a picnic, kayaking, or enjoying a bit if nature in Chicago

  • Fun bike ride, walking, jogs, boats, canoeing, a lot of fun stuff going on here

  • Great views of the north branch and a nice escape from the noise and congestion of the NW side

  • Newly renovated to provide extended means for cycling or walk/run travel without interruption from Belmont through to Montrose streets

Chicago Riverview

4.930 reviews
N Branch Riverwalk, Chicago, IL 60618, United States

Chicago Riverview is a top destination for outdoor enthusiasts looking to enjoy nature in the heart of Chicago. With a stellar rating of 4.9, it's clear that visitors love this scenic hiking area. The accessibility features like Wheelchair-accessible entrance make it inclusive for all.

Customers rave about Chicago Riverview with comments like:

Whether you're into birdwatching, cycling, hiking, jogging, or just walking, Chicago Riverview has something for everyone. Don't miss out on this hidden gem in the bustling city of Chicago.

Bike and Roll Chicago#16
What sets it apart
  • Great Segway tour experience with a friendly and down-to-earth tour guide named Ivory. Highly recommend the Segway tour!

  • Navy Pier Segway tour was fun and informative, thanks to the awesome guide Ivory. Definitely recommend!

  • Easy booking process for a Segway tour with cool and relatable instructors. A fun time guaranteed!

  • Amazing Navy Pier Segway tour with patient and helpful guides. Highly recommended for first-timers!

Bike and Roll Chicago

3.853 reviews
700 E Grand Ave, Chicago, IL 60611, United States

Bike and Roll Chicago offers a fantastic experience for those looking to explore Chicago on wheels. Whether it's a bicycle rental for a leisurely ride along the lakefront or a thrilling Segway tour, they have something for everyone. The business prides itself on providing excellent customer service, as highlighted in the review summaries below:

With a rating of 3.8 stars and raving customer reviews, Bike and Roll Chicago is the go-to spot for a memorable biking or Segway adventure in the Windy City.

East Ohio Pedestrian/Bike pass through Tunnel to Jane Addams Memorial Park, Chicago#17
What sets it apart
  • This is a safe route, especially during early morning hours.

  • Watch out for potential flooding during bad weather.

  • Although graffiti is present, customers hope for its quick removal.

  • The tunnel serves as a great connection to the park and beach.

East Ohio Pedestrian/Bike pass through Tunnel to Jane Addams Memorial Park

4.25 reviews

Open 24 hours

E Ohio St, Chicago, IL 60611, United States

East Ohio Pedestrian/Bike pass through Tunnel to Jane Addams Memorial Park offers a convenient and safe way for individuals to access the park and Ohio Street beach. The tunnel, while not very long, provides a flat path that crosses a major highway, ensuring a secure passage. Customers have highlighted the following key points in their reviews:

With a 4.2-star rating, visitors appreciate the ease of accessibility this passageway provides.

The comparison in brief

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Map of Bike Rides in Chicago

Discover Chicago like never before with our comprehensive map of all the bike rides available in the city. Whether you're a casual rider looking to explore new neighborhoods or a seasoned cyclist seeking challenging routes, this map has something for everyone. Take advantage of the beautiful scenery and bike-friendly paths that make Chicago the perfect destination for cyclists.

Tips for choosing Bike Rides in Chicago

  1. Distance and difficulty level of each ride.
  2. Scenic views and attractions along the route.
  3. Amenities and facilities available for cyclists.
  4. Tips and recommendations from locals and experts.

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