Updated November 17, 2022
With tons of green spaces and picturesque waterways, Chicago is a fantastic city for runners. Running in Chicago is a great way to explore the city, especially during the warmer months of the year. You can run around the Windy City for miles and miles, passing near the Chicago River, trailing along Lake Michigan, or jogging through one of the many parks in the city.
Not sure which trail to hit next? Here’s a list of 12 of the best places to go running in Chicago and the surrounding areas, including paved trails, parks, and nature preserves.
Top Places to Go Running in Chicago
1. Lakefront Trail
- Location: Lake Michigan
- Route Length: Up to 18 miles
- Trail Type: Paved
The Lakefront Trail is arguably Chicago’s most popular running route. Located on the shores of Lake Michigan, the Lakefront Trail is composed on 18 miles of paved trails that are shared with runners, dog walkers, and bikers. On evenings and weekends, the Lakefront Trail is usually packed with people, making it an especially great place to go if you’re running alone or enjoy being around the masses.
Along the Lakefront Trail, there are tons of sandy beach hangout areas, cute waterfront restaurants and bars, and graffiti-lined underpasses. You’ll also have the opportunity to pass by the iconic Navy Pier, Monroe Harbor, North Avenue Beach, and the Museum District.
The best time to enjoy the Lakefront Trail is at sunrise, when the sun hangs low over the water and you can catch the coolest, crispest summer air in Chicago. It’s also considerably less crowded during this time of day.
2. The Riverwalk
- Location: The Loop
- Route Length: 3.4 miles
- Trail Type: Paved
Chicago’s Riverwalk may very well be the heart of the city. Located along the Chicago River, this buzzing boardwalk is full of people at practically all times of day, and is home to many of the city’s coolest views. It’s also a fabulous place to go running in Chicago, as you’ll catch views of some of the city’s most unique architecture.
A run on the 3.4-mile trail on the Riverwalk is best done in the mornings, when the boardwalk isn’t so full of bar-hoppers and large groups. At this time of day, you’ll get more uninterrupted running time and spend less energy dodging other people.
While on the trail, you can see views of the river, the city’s unique buildings, and watch people kayaking along the Chicago River or passing by on boat tours.
3. Grant Park & Millennium Park
- Location: The Loop
- Route Length: 3-5 miles
- Trail Type: Paved
When you close your eyes and think of Chicago, Grant Park probably comes to mind. Home to giant green spaces, Lollapalooza, and the famed Cloud Gate, it’s one of the most epic places to go running in Chicago. And, with various trails winding through the park, there are options to create a route of up to 5 miles in the area.
The reason why we love Grant Park for running is because it’s a great way to see many Chicago icons from a unique perspective. While running, you can soak in several of the city’s best sights – think Navy Pier, the skyline, and the Museum District – all while getting your morning miles in.
4. Magnificent Mile
- Location: The Loop
- Route Length: 1-2 miles
- Trail Type: Urban/paved
The Magnificent Mile is Chicago’s “5th Avenue,” filled with some of the city’s best hotels, shops, and entertainment options. During certain times of day, it can also be an excellent place for running in Chicago, giving you access to the downtown environment during your morning run.
As with many of our recommendations, the Magnificent Mile is best for running in the early morning, before the rush hour crowds begin to flow through the streets. Another thing to keep in mind about this area is that there are several intersections with stop lights, meaning you won’t have many opportunities to run uninterrupted unless you veer off into Millennium Park or the Lakefront Trail.
5. Milwaukee Avenue
- Location: North Side
- Route Length: Varies
- Trail Type: Urban/paved
For those craving a longer urban run, Milwaukee Avenue is one of the coolest Chicago running spots. Yes, you’ll have to deal with the minor annoyance of stoplights and sidewalks, but in exchange, you’ll have the opportunity to pass through some of Chicago’s most interesting neighborhoods and explore a completely different side of the city.
A run down Milwaukee Avenue will take you past Wicker Park, one of Chicago’s coolest residential areas, past the Flatiron Arts Building, and past lots of street art and local shops and cafes.
6. Hyde Park
- Location: Hyde Park
- Route Length: 5-7 miles
- Trail Type: Paved
Among the more unconventional Chicago running routes on our list takes you into south Chicago’s historic neighborhood of Hyde Park. Home to the University of Chicago, you’ll find Gothic architecture, tree-lined streets, and lots of historic townhomes as you run through the area.
A 5-mile run in Hyde Park will take you through the University of Chicago, Jackson Park, Promontory Point, and Washington Park, as well as past historic homes and Gothic-style buildings. It’s a fantastic contrast to the tall, shiny buildings and busy, crowded streets of the Downtown/Loop area of Chicago!
7. Lincoln Park
- Location: Lincoln Park
- Route Length: Up to 5.5 miles
- Trail Type: Gravel
Lincoln Park is one of the most beloved residential areas of Chicago, and in the middle of it lies a large, green park area that houses a picturesque lake and many trails that are perfect for running. The Lincoln Park Trail winds through the park’s wooded areas and us a wonderful, shady place for a run.
Within the park, you’ll find over 5 miles of runner-friendly trails. Along your run, you can admire the gorgeous Victorian architecture in the neighborhood, and you can pass by the zoo or the Lincoln Park Conservatory. Nearby, the Lincoln Park trails lead right to the North Avenue Beach stretch of the Lakefront Trail, perfect for extending your run and enjoying the cool, breezy lake air.
8. North Shore Channel Trail
- Location: North Chicago
- Route Length: 6.7 miles
- Trail Type: Paved
Located in the northern part of the city, the North Shore Channel Trail is a refreshing change from the Lakefront Trail for a long run in the city. The trail runs parallel to a quiet waterway called the North Shore Channel, and is lined with green spaces. Dotted with trees and bushes, it’s especially beautiful in the fall when the leaves begin to change colors.
Starting at Ronan Park, the North Shore Channel Trail is a quieter running route that spans almost exactly a half-marathon distance both ways. It’s great for distance training or simply running in a different scene.
9. The 606
- Location: Bloomingdale
- Route Length: 2.7 miles
- Trail Type: Paved
Another one of the most unique Chicago trails is the 606, an elevated trail that runs over former railroad tracks. Today, it’s been repurposed into an urban hiking, running, and biking trail. A run on the 606 will take you through green spaces, charming neighborhoods, and historic areas of Chicago.
The entire 606 trail spans 2.7 miles, beginning at Walsh Park and ending at North Ridgeway Ave. Additionally, there are multiple access points along the route where you can enter and exit at your leisure. Because it’s paved and mostly flat, it’s one of the best and most exciting places to go running in Chicago.
10. Humboldt Park
- Location: NW Chicago
- Route Length: 2+ miles
- Trail Type: Gravel
Humboldt Park is located in Wicker Park, one of Chicago’s most fun and quirky neighborhoods. It’s a beautiful, green park area that has several trails for runners, hikers, and bikers. In our opinion, a run here is best paired with brunch or a coffee in one of Wicker Park’s local cafes.
You can access Humboldt Park from the 606 trail for an extended run, or to explore even more of this lovely area of the city. There’s a loop trail around the park that’s short and sweet for a ~2 mile run around the area.
11. Busse Woods
- Location: NW Chicago
- Route Length: 8-mile loop
- Trail Type: Paved
With over 3,000 acres of woodlands, there’s no shortage of trails to run at Busse Woods. This forest and marsh area is home to lots of local wildlife and picturesque wooded areas, including an elk pasture. At under an hour from the city center, Busse Woods is a great area for running while immersing yourself in nature.
The most popular trail for runners and bikers is Busse Woods’ main 8-mile trail loop, which will take you around a large part of the park. With paved trails, you can enjoy road running while also enjoying the nature and wildlife viewing opportunities around you.
Running in Chicago: Additional Resources
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