Exploring the Best Bike Trails Chicago Has to Offer

Pedal Through the Windy City’s Most Scenic and Thrilling Paths

Chicago may be known for its towering skyline, deep-dish pizza, and historic sports teams, but for cycling enthusiasts, it also offers some of the most rewarding bike rides in the Midwest. From 

lakeside stretches to forested paths and urban greenways, bike trails in Chicago offer a wide range of experiences for riders of all levels. Whether you’re a seasoned cyclist looking for a long-distance challenge or a casual rider wanting a scenic afternoon ride, the city’s trail network won’t disappoint. And for a fresh perspective after your ride, hop on Chicago’s Best 90-Minute Architecture Boat Tour—it’s a relaxing way to take in the city’s stunning skyline from the water.

The Iconic Lakefront Trail

Let’s start with the obvious choice—Chicago’s Lakefront Trail. Stretching for 18 miles along Lake Michigan, this trail is a favorite among locals and tourists alike. It provides unbeatable views of the city skyline, beaches, and waterfront parks. The route connects neighborhoods from Edgewater to Hyde Park and passes by many of Chicago’s most famous landmarks like Navy Pier, Grant Park, and the Museum Campus.

It’s perfect for both recreational riders and commuters, with separate lanes for cyclists and pedestrians in many areas. On weekends, expect a lively, bustling atmosphere. For a more peaceful ride, early mornings are ideal.

The 606 (Bloomingdale Trail)

Once an abandoned rail line, The 606 is now one of the coolest urban bike rides Chicago has to offer. This 2.7-mile elevated trail winds through several northwest side neighborhoods, including Logan Square, Wicker Park, and Humboldt Park. The trail is lined with native landscaping and public art installations, offering a unique blend of urban adventure and cultural engagement.

Because of its elevation and well-maintained surface, it’s great for a quick ride without traffic interference. It’s also a local favorite for jogging and family strolls, so cyclists should be mindful of pedestrian traffic.

North Branch Trail

For those wanting a longer, more immersive nature ride, the North Branch Trail is ideal. Stretching about 20 miles, this trail runs from Gompers Park in the city all the way up to the Chicago Botanic Garden in Glencoe. You’ll ride through forest preserves, alongside the Chicago River, and past picnic areas and wildlife habitats.

It’s one of the best bike trails Chicago has to offer for riders seeking to escape the urban rush without traveling too far. Pack a lunch and make a day of it—especially in spring or early fall when the leaves are changing.

Major Taylor Trail

Named after Marshall “Major” Taylor, the first African-American cycling champion, this trail spans approximately 8.1 miles through the city’s South Side. It runs through the Dan Ryan Woods and other green spaces, offering a more relaxed and community-driven biking experience.

It’s less trafficked than the Lakefront or The 606, making it a good choice for those looking for a quieter, reflective ride. Along the way, you’ll also encounter educational signage about Major Taylor and the history of the area.

Burnham Greenway

For a more industrial-meets-nature ride, the Burnham Greenway starts near the city and heads southeast through historic neighborhoods and eventually into the South Suburbs. It’s a trail in progress, but the existing segments offer peaceful riding and a peek into parts of Chicago often overlooked by tourists.

While not as popular as other routes, it offers valuable connectivity to other trail systems and is particularly attractive for cyclists looking to avoid busy roads.

Palos Trail System

Though technically just outside Chicago in the Cook County Forest Preserves, the Palos Trail System deserves a mention for anyone looking for a more rugged biking experience. This extensive system of over 50 miles of trails includes both paved paths and challenging mountain biking terrain. It’s a hotspot for adventure cyclists and those training for endurance rides.

Make sure to check the trail conditions before heading out, especially after rain, as some trails can become muddy or closed temporarily.

Tips for Biking in Chicago

• Safety First: Always wear a helmet and obey traffic laws when sharing roads with vehicles.
• Watch the Weather: Chicago weather can change quickly—pack a lightweight rain jacket just in case.
• Hydrate and Fuel Up: Especially on longer trails, make sure to bring water and a snack.
• Bike Rentals: Don’t own a bike? No problem. Divvy Bikes, Chicago’s bike-share system, is available throughout the city with hundreds of stations.
• Maintenance Matters: Make sure your tires are inflated and your brakes are working before hitting the trails.

Ride with a View: Private Architecture Boat Tour Chicago

If you want to mix up your outdoor experience, consider giving your legs a break and hopping aboard one of the city’s iconic boat tours. The Chicago’s Best 90-Minute Architecture Boat Tour offers an unmatched view of the city’s architectural landmarks from the water. It’s a fantastic way to wind down after a long ride or to learn more about the buildings you whizzed past on your bike.

This tour covers all branches of the Chicago River and features knowledgeable guides who explain the city’s architectural evolution. It’s especially magical in the golden hour light, so consider booking a late afternoon cruise.

Chicago offers an impressive variety of trails that cater to every level of cyclist. Whether you’re riding along the lake, through forest preserves, or down elevated urban railways, there’s a path that fits your style and pace. With routes like the Lakefront Trail, The 606, and the North Branch Trail, bike rides in Chicago are more than just exercise—they’re a way to explore the city’s diverse neighborhoods, history, and natural beauty.

So grab your helmet, hop on your bike, and discover why bike trails in Chicago are among the best in the country.