Running
Top 10 running trails in Chicago: Discover the best routes
Explore Chicago’s top running trails to help you fast approach any finish line.
While Chicago may be best known for its sports, food, architecture, and museums, it’s also a hotspot for those who love city running.
“For me, the distance or the terrain or whatever doesn't matter," long-distance runner Florian Neuschwander shared with Red Bull. "The main thing is running!"
For those who simply appreciate being out as they run, the Windy City has no shortage of trail options. In Chicago, the terrain is often flat, but choosing one of the less common trails with hills can help you build more endurance. Below are the top running trails in Chicago so you can get your blood pumping and prepare for the Wings for Life World Run.
01
The Lakefront Trail
Participant during the Wings for Life World Run - App Run in Chicago 2021
© Drew Reynolds for Wings for Life World Run
At 18 miles long with barely any incline, Chicago’s Lakefront Trail is a great option for runners of all levels. You can run along solely a smaller portion of the trail, such as the part near Lincoln Park, for a milder run. You can also run the entire trail, which covers the whole of Chicago’s border with the Michigan River, for a sizable challenge.
As you run this trail, you’ll see stunning views of Chicago highlights, such as Buckingham Fountain and Oak Street Beach, and water for miles. No matter when you run this trail, you’ll likely encounter crowds of walkers, bikers, and other runners. Plus, there are plenty of opportunities to dip off the trail if you need a break or just want to explore the city.
02
Lincoln Park
Participant during the Wings for Life World Run - App Run in Chicago 2021
© Drew Reynolds for Wings for Life World Run
Within Lincoln Park’s 1,208 acres, paved trails will take you through highlights such as the Lincoln Park Zoo and the Benjamin Franklin Monument. Of particular note are the trails around the North Pond and South Pond, which couple gorgeous waterside views with easy terrain. The five-mile Lincoln Park Trail also makes for a reasonable intermediate-level run. Another option: Run south of South Pond, take the exit to the Lakefront Trail, and continue your Windy City running journey there.
03
The 606 Trail
The 2.7-mile Bloomingdale Trail, a.k.a. the 606 Trail, is a paved, flat pathway and an elevated former train track that opened in 2015. It starts just south of West Cortland Street on North Ridgeway Avenue, in the southwest corner of the Logan Square neighborhood. From there, it extends eastward to Walsh Park, in the northeast corner of the Wicker Park neighborhood.
When you run along the 606 Trail, you’ll see art installations and pass an observatory. You’ll likely see bikers, walkers, and other runners too since the 606 Trail is 10 feet wide, allowing for ample running space. This, alongside the unforgettable sights you’ll see along the way, make the 606 a top running trail in Chicago.
04
The Chicago Riverwalk
Participant during the Wings for Life World Run App Run in Chicago 2022
© Drew Reynolds for Wings for Life World Run
The eastmost point of the Chicago Riverwalk lies where the Chicago River meets Lake Michigan. From there, the walkway extends 1.3 miles westbound to West Wacker Drive and West Lake Street.
Running the walkway twice gives you half a mile more to run until you reach 5k, with beautiful riverfront views the whole time. Across the river, you’ll see Chicago landmarks such as the Wrigley Building and Merchandise Mart. You may fare best going at sunrise or sundown to avoid large crowds.
05
Burnham Greenway
This running trail is located all the way southeast in Chicago, in the Hegewisch neighborhood, next to the city’s border with Indiana. It spans 2.1 miles and primarily runs along Eggers Grove and the Wolf Lake Overlook. Since it’s far from downtown and runs through nature preserves, it’s an especially tranquil top running trail in Chicago. The hour-plus transit commute from the Loop may be worth it for the serenity of running alongside waterfowl and marshes.
06
Humboldt Park
As compared to bigger spaces like Grant Park and Lincoln Park, Humboldt is even grassier and greener. This 207-acre park is also home to a striking lagoon with running trails surrounding it. There’s a beach toward the north of the lagoon and a waterfall toward the south, adding to the park’s natural beauty. A two-mile loop spans the park, as do numerous gravel trails that offer more challenging running terrain.
07
Dan Ryan Woods
Picnic groves abound in the 257-acre Dan Ryan Woods, near the Gresham neighborhood, as do running opportunities. This forest preserve includes fitness stairs and a mile-long paved loop, plus access to the two-mile Major Taylor Trail.
On the lower-elevation east side of the loop, you may encounter oak trees along your run. On the higher-elevation west side, stunning hickory trees abound. Several runs around the loop will get your heartbeat up while exposing you to some of Chicago’s most stunning foliage.
08
Waterfall Glen Forest Preserve
Chicago is such a flat city that hilly runs exist almost exclusively in the city’s suburbs, such as at the Waterfall Glen Forest Preserve. Located in Lemont, Illinois, which is a half-hour drive from downtown Chicago, this park is home to a hilly 9.5-mile loop. On the southeast side of the loop lies Rocky Glen Waterfall, where the unforgettable sights and soothing sounds of falling water await.
09
North Branch Trail System
This series of trails starts near Chicago’s Lincoln Square neighborhood at the Irene C. Hernandez Family Picnic Area. From there, the 15.9-mile red trail extends up to the 4.4-mile black trail surrounding the Skokie Lagoons. These paths are paved, and the unpaved 7.9-mile yellow trail runs alongside the red trail’s top half. The trails are often flat, and memorable wildlife encounters from a distance are known to be common.
10
Palos Trail System
Located a half-hour drive from downtown Chicago, the Palos Trail System in Willow Springs, Illinois is among Cook County’s largest forest preserves. Most trails in this system are unpaved, such as the 9.2-mile yellow trail. This trail is of intermediate difficulty, with the 4.3-mile black trail being the park’s most challenging run. With five mile-plus paved trails and 11 mile-plus unpaved trails, your only limit in the Palos Trail System is how far you can run.
Running in and around the Windy City
The Wings for Life World Run is fast approaching, and exploring Chicago’s top running trails can help you fast approach the finish line. Parks in or near the Lake Michigan shoreline are home to views you’ll always keep with you and buzzing, energetic crowds. Trails outside the city offer more tranquility and nature to get you truly in the zone as you run. In Chicago, running is more than a sport — it’s a way to see the sights for yourself.