8 Best Bike Trails in Chicago

Best Bike Trails In Chicago featured image

Are you on the hunt for the perfect path to pedal through in the Windy City? Chicago offers an expansive network of bike trails that cater to all levels of cyclists.

When it comes to the Best Bike Trails in Chicago, this comprehensive guide has got you covered, from lakeside routes with skyline views to tranquil woodland escapes.

If you're passionate about cycling and looking to explore Chicago from a different vantage point, we've rounded up the top trails you won't want to miss.

Ready to clip in and ride? Keep reading to discover your next favorite biking adventure in Chicago.

The 8 Best Bike Trails in Chicago

1. Lakefront Trail

Stretching for at least 18.5 miles, this trail is not  for biking alone as it is partially shared with people who want to take a walk, jog or skateboard, making it multi-purpose.

If you ride along this area, you will meet people with scooters, skateboards, skate shoes, and pedestrians.

The trail connects the city's four largest lakefront parks, Lincoln Park, Grant Park, Burnham Park, and Jackson Park, as well as several beaches and recreational facilities.

Lakefront Trail

Undoubtedly, one of Chicago's most well-known and beautiful cycling routes is the Lakefront Trail.

Stunning views of the lake, the city skyline, and many parks may be seen from this walk.

Bikers in perfect harmony may enjoy Chicago's natural beauty and urban activity, from the busy Navy Pier to the peaceful Promontory Point.

This trail offers the opportunity to enjoy some of the best the city has to offer, so as you ride down this trail, be sure to stop and take a moment to breathe in the fresh air and enjoy the view along the way.

2. The 606 - Bloomingdale Trail

the 606 trail chicago

Photo via wikipedia

Another exciting spot for bike lovers is the 606, located at 1805 N Ridgeway Avenue, Chicago, IL 60647, stretching 6.7 miles and serving as a multi-purpose recreational facility.

This walkway runs east to Elston Avenue, giving a link across Ashland Avenue and under the freeway and train lines, and goes by the name Bloomingdale Trail, which is also its alternate name.

This path receives its name from its location's zip code.

Once an elevated railway, this scenic bike trail now winds through Logan Square, Humboldt Park, and West Town.

If those areas sound familiar, you'll want to explore this path. It offers great views, exciting thrills, and the chance to meet like-minded people. 

For those looking to immerse themselves in Chicago's creative scene fully, this 2.7-mile route is a great option. It is decorated with artwork and combines urban aesthetics and green areas.

3. Cal-Sag Trail

Cal-Sag Trail

Photo via enjoyillinois.com

Stretching over 26 miles, this trail connects the Chicago south land from Indiana and the Chicago Lakefront to Lemont, Illinois and the I&M Canal Trail.

The Cal-Sag Trail provides insights into the area's history, cultural heritage, and natural beauty.

You'll see markers and signage about the region's industrial background, especially its connections to commerce and transportation. 

These historical components give the voyage depth and provide an understanding of how the environment has changed through time.

The Cal-Sag Trail is a well-kept secret that offers a chance to disconnect from the bustle of the city and get back in touch with nature.

This path provides an entirely immersive experience that enables riders to learn about the fascinating history and intense feeling of community beyond Chicago's metropolitan limits.

Therefore, the Cal-Sag Trail offers a fascinating excursion that unveils a less-known aspect of the Windy City, whether you're looking for solitude, a fresh viewpoint, or an adventure off the usual road.

If you need more information about this particular trail, check this website, calsagtrail.org, for updates about the path.

4. Unearthing the Major Taylor Trail

Major Taylor Trail

Photo via Belt Magazine

Delve into an extraordinary cycling experience in Chicago's Far South Side with the Major Taylor Trail.

Spanning 7.6 miles, this cycling pathway is more than just an exercise route—it's a tribute to a historic icon, Marshall "Major" Taylor.

As a path-breaker in both cycling and racial equality, Taylor set multiple world records during the late 19th century, becoming a symbol of determination and resilience.

Beginning in the lush landscapes of the Dan Ryan Woods at 81st Street, this remarkable trail is a seamless blend of nature and community.

It winds through a variety of scenic backdrops—from verdant forest preserves and quaint parks to vibrant neighborhoods.

You'll pedal your way south until you hit 95th Street, where on-street bike lanes take over temporarily, resuming its off-road charm at 105th Street.

As you make your way through the historic neighborhoods of West Pullman, Beverly, and Morgan Park, you'll sense the rich tapestry of Chicago’s cultural diversity and natural beauty.

The trail culminates at the breathtaking Whistler Woods Forest Preserve, adjacent to the Little Calumet River.

Whether you're a history buff, a cycling enthusiast, or just someone looking for a rejuvenating escape, the Major Taylor Trail offers an unparalleled adventure you won't soon forget.

5. North Branch Trail

North Branch Trail

Photo via Hotels.com

The North Branch Trail meanders beside the North Branch of the Chicago River as it extends from the Chicago Botanic Garden to the city's center.

This 20-mile track travels through parks, woodlands, and picturesque riverbanks while showcasing rural and urban scenery.

It's the perfect route for anybody looking for a serene ride with lots of picnics and birdwatching opportunities.

Please take a minute as you are riding down this track to appreciate the simplicity it gives with its wide variety of gorgeous vistas.

You may turn your bicycling experience into an activity using the ample green space the path provides.

Be alert as you pass by since this route has loops that cross through ecological areas with various local species; you never know what you could see along the way.

The urban landscape gradually reclaims its dominance as the trail approaches its southern terminus near Foster Avenue.

However, the serenity of the North Branch Trail lingers, leaving you with a sense of rejuvenation that only a communion with nature can provide.

In the heart of a bustling metropolis like Chicago, the North Branch Trail is a testament to the city's commitment to preserving and celebrating its natural heritage.

With its diverse landscapes, opportunities for wildlife observation, and moments of solitude, this trail beckons both locals and visitors to take a break from the urban frenzy and embark on a two-wheeled journey into the tranquility of nature.

So, saddle up, embark on the North Branch Trail, and let its beauty remind you that even amid a concrete jungle, pockets of serenity await those who seek them.

6. Burnham Greenway

Burnham Greenway

The closeness to Lake Calumet of the Burnham Greenway is one of its most alluring aspects.

The trail offers breathtaking views of this vast lake, which previously served as a vital conduit for moving raw materials and completed commodities.

Today, the lake provides a tranquil escape from the bustle of the city by reflecting the sky and the surrounding flora.

The Burnham Greenway on Chicago's south side offers a unique fusion of historical significance and natural serenity.

This 13-mile bike track, named after the great architect and urban planner Daniel Burnham, takes riders on an enthralling trip through districts that have seen the city's industrial development.

More than just a bike path, the Burnham Greenway represents civic involvement and resurgence.

Locals, environmentalists, and city planners have collaborated to develop this corridor into a location that honors the past and future of the city.

The route promotes outdoor activities, educational opportunities, and a revitalized understanding of the fine line that must be drawn between urban growth and environmental protection.

7. Des Plaines River Trail

Des Plaines River Trail

Fasten your helmet and gear up for an exhilarating 56-mile ride that will take you from the heart of Elmwood Park, Illinois, all the way to Russell, a quaint community teetering on the edge of the Wisconsin border.

Welcome to the Des Plaines River Trail, an odyssey that promises more than just pedal-pushing.

Following the graceful curves of its namesake, the Des Plaines River, this trail is a cornucopia of natural wonders and scenic beauty.

As you cycle through diverse terrains, you'll encounter forests so lush they seem to whisper secrets, parks that serve as green sanctuaries, and conservation areas where flora and fauna reign supreme.

Notable pit stops along this journey include the Gurnee Woods Forest Preserve, a treasure trove of biodiversity; Adler Memorial Park, a perfect pause for reflection; and the Ryerson Conservation Area, where nature takes the center stage.

Pack an extra water bottle or two, maybe even a picnic basket.

Whether you're a hardcore cyclist or someone who just wants to stretch their legs in the great outdoors, the Des Plaines River Trail is your passport to an unforgettable ride.

From its meandering waterway to its canopy of trees, it's not just a trail; it's a whole new world waiting to be explored.

8. Discover the Green Bay Trail

Green Bay Trail

Photo via enjoyillinois.com

Straddling the serene landscapes between Wilmette and Highland Park, the Green Bay Trail is an 8.9-mile path that provides an immersive North Shore experience.

If you find yourself in the vicinity of the iconic Bahá'í House of Worship, make the Green Bay Trail your next stop.

The adventure starts right in front of the Wilmette Village Hall, setting the stage for a unique blend of natural beauty and suburban charm.

Running parallel to the Metra's Union Pacific / North Line, this trail lets you experience a slice of everyday life in the Chicago area.

While most of the trail is smooth and paved, there's an intriguing stretch between Glencoe and Highland Park that features a crushed-stone surface, giving off a rustic, country feel.

What makes this trail more than just a pleasant bike ride or walk are its adjoining attractions. For music lovers, the trail offers a pathway to Ravinia Park, famed for its Ravinia Festival that hosts a range of musical performances each year.

Golf enthusiasts will delight in passing various country clubs that exude exclusivity and elegance.

If flora and fauna are more your style, a detour at County Line Road leads you straight to the Chicago Botanic Garden—a living encyclopedia of diverse plant species.

Tips for Cycling in Chicago: Navigating the Windy City on Two Wheels

Tips For Cycling In Chicago

Cycling in Chicago offers an exhilarating way to explore the city's diverse neighborhoods, scenic trails, and iconic landmarks.

But to fully enjoy the experience, it's crucial to prioritize safety and etiquette. So, whether you're a local or a tourist, here are some invaluable tips for cycling in the Windy City.

  • Choose a Bike Trail You're Comfortable With: Chicago offers a plethora of biking routes ranging from flat, paved trails to more rugged terrains. Choose a route that aligns with your comfort level and skillset.
  • Follow the Bike Route, and Don't Ride on Sidewalks: Bike lanes are specifically designed for cyclists. Riding on the sidewalk is not only hazardous but often illegal unless marked otherwise.
  • Avoid Headphones and Phones: Riding with headphones or using your phone can be a dangerous distraction, preventing you from hearing important audio cues from your surroundings.
  • Use Gestures for Communication: When turning or changing speed, hand signals are an effective way to communicate your intentions to both motorists and fellow cyclists.
  • Maintain a Safe Distance from Parked Cars: Always keep at least three feet away from parked cars to avoid the risk of getting "doored."
  • Conduct a Pre-Ride Check: Before hitting the trail, inspect your bike for any potential issues. Check the brakes, gears, and tire pressure to ensure a safe ride.
  • Ride With the Traffic: Always ride in the direction of traffic. Cycling against the flow is dangerous and generally against the law.
  • Be Cautious Around Pedestrians: Particularly on shared paths, always exercise extra caution where pedestrians are walking, yielding the right of way when necessary.

Wrap Up

Biking trails serve as havens of nostalgia, capturing the senses with beautiful vistas and open greenery. The fresh air fills your lungs as you pass by lakes and weave through parks. These trails aren't just for sightseeing, though.

They offer the perfect setting to mingle with like-minded cycling enthusiasts or to engage in a bonding experience with friends and family.

If you prefer solo adventures, there's nothing like the thrill and freedom of pedaling away, your heart pumping as the hustle and bustle of the windy city simply melt away.

So, if you ever find yourself in need of a boost and an energy-driven activity, why not pick up your bicycle from the garage or even rent one, whether you are a novice, a local, a visitor, or a professional, all are welcome to these scenic spots.