With all the parks and green spaces scattered throughout the city, Chicago really is a runner’s paradise, offering a variety of long-distance trails that combine urban landscapes with pockets of nature. Whether you're looking for stunning views of Lake Michigan, peaceful forest preserves or a mix of both, these 5-miles-and-up running routes accessible within a few miles of our luxury Chicago apartments will keep you motivated and energized through all your training. 

Where to go on 5+ mile runs around Chicago

Chicago Lakefront Trail

One of the most iconic routes is the Chicago Lakefront Trail, a paved path that stretches for 18 miles along the scenic shoreline of Lake Michigan. 

Starting at Hollywood Avenue on the north side and extending to 71st Street in the south, this trail offers unbeatable views of the Chicago skyline, sandy beaches and endless water. Along the way, you’ll pass by major landmarks like Navy Pier, Soldier Field and Grant Park, making it perfect for runners who enjoy sightseeing as much as running. The Lakefront Trail is ideal for those who enjoy a bustling atmosphere, as it’s a popular spot for joggers, cyclists and beachgoers alike.

Lincoln Park Trail

Heading a little more towards nature, the Lincoln Park Trail provides a scenic 5-mile running route that stretches over 7 miles when incorporating loops within the park. 

Located along the north side of the city, this trail meanders through Lincoln Park’s lush gardens, past the Lincoln Park Zoo and around North Pond, offering runners plenty of fauna and flora to look at, including migratory and backyard birds and the occasional turtle basking in the sun. The path is a mix of paved and dirt surfaces, providing a peaceful escape without leaving the city. Runners can enjoy views of the lake as well as the rich greenery that characterizes this historic park.

Bloomingdale Trail (The 606)

For a more urban experience, the Bloomingdale Trail, also known as The 606, is a 2.7-mile (one-way) elevated trail that runs through the city’s northwest neighborhoods of Logan Square, Wicker Park and Bucktown. While the trail itself is just under three miles, adding a loop through surrounding parks and neighborhoods can easily extend your run to well over 5 miles.

The 606 offers a unique vantage point as you pass over streets and through art installations, with plenty of murals, gardens and local architecture to admire. It’s a vibrant trail that blends city life with a touch of greenery, perfect for those who enjoy a more artistic, scenic and energetic environment.

IDNR Burnham Greenway Trail

For those who prefer to venture a bit farther south, the IDNR Burnham Greenway Trail offers just over 9 miles of uninterrupted running through Chicago’s southeast side. This trail is part of the larger Grand Illinois Trail system and takes you through natural wetlands and forests right along the Indiana-Illinois border.

The Burnham Greenway is mostly paved and offers a quieter, more serene running experience compared to some of the busier city trails. Runners might spot deer, waterfowl and other wildlife, making this route an excellent option for nature lovers.

Wolf Lake Memorial Trail

Just over the border from the IDNR Burnham Greenway Trail, the Wolf Lake Memorial Trail is a 5.5-mile path that loops around Wolf Lake in the Whiting neighborhood. This lesser-known gem provides runners with serene views of the lake and surrounding wetlands while winding through wooded areas, marshes and across small bridges. The trail is a combination of paved and gravel paths and is a great route for those seeking solitude and a break from the urban hustle, as well as the chance to encounter local wildlife like herons, egrets and the occasional bald eagle.

Salt Creek Greenway Trail

Further west, the Salt Creek Greenway Trail offers a picturesque route that spans nearly 14 miles through suburban forest preserves, not to mention connecting to a web of other trails within the various woods along the way. 

This trail features a variety of scenic settings to include shaded woodlands, open meadows, riverside sections and more. Wildlife sightings from deer to hawks to butterflies and more are common here, and the path is predominantly paved, with some sections of gravel, making it suitable for a variety of running styles.

Des Plaines River Trail

The Des Plaines River Trail offers another excellent escape into scenic solitude, with over 31 miles of mixed terrain running alongside the scenic Des Plaines River. 

Located primarily in Lake and Cook Counties, this trail offers plenty of variety, from dense woodlands to scenic river views. Runners are known to have spotted wildlife like deer, foxes, and a variety of bird species, so the longer drive out of town certainly makes it worth the while. The soft dirt and gravel paths are easy on the joints, making this an excellent choice for long-distance runners looking for a more forgiving surface to vary their training regimen. 

Illinois Prairie Path

The Illinois Prairie Path is a favorite for those who want to escape a little deeper into nature. 

This trail stretches for over 60 miles across multiple branches, starting in Maywood and extending well into DuPage County. Its wide gravel paths take you through wooded areas, open fields and suburban neighborhoods — there’s plenty to see all along the way. The Prairie Path is well-known for its wildflower displays in the warmer months and offers runners a peaceful, quiet experience, far removed from the city’s noise. The flat terrain also makes it ideal for long-distance and endurance training!

I&M Canal Trail

Finally, the I&M Canal Trail provides a historical backdrop for long runs. This trail follows the Illinois & Michigan Canal for over 60 miles, with a section running from the southwestern suburbs of Chicago to LaSalle. While not entirely within the city limits, the trail offers a unique blend of natural beauty and industrial history, as it passes through forest preserves, wetlands and remnants of the canal’s old infrastructure. The gravel paths are quiet and secluded, offering runners the opportunity to enjoy some solitude while appreciating the area’s rich heritage. If you’re into long-distance or ultra-running, then this trail is the one for you!

Whether you’re looking for a scenic lakefront run, an urban adventure or a peaceful escape into nature, these trails around Chicago offer something for every runner. With such a diverse range of options, exploring the city’s long-distance routes is a great way to get outside, meet your training goals and enjoy it all the while!

Have fun!

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Featured photo by Jenny Hill on Unsplash