No matter what kind of Windy City runner you are—a leisure runner, marathoner, or a visiting passerby with some spare time, there are several best places to run in Chicago that don’t involve four walls.
You can easily see the sights of Chicago without a car. It’s a destination filled with miles of scenic trails where you can enjoy a stroll or a brisk run with views of the lakefront, downtown architecture, attractions, art and nature. Whether you’re a dedicated runner or just looking for ways to work off that extra slice of deep-dish pizza, we’ve compiled a list of the best running trails in Chicago, including short, medium and long trails.
Short Trails (Less than 2 miles)
Short trails are perfect for running in Chicago during the midday slump or a fun family outing. You might break a sweat, but not bad enough that you can’t go back to the office after your lunch hour.
1. Chicago Riverwalk
Address: Lake Shore Drive to Lake Street
Trail length: 1.3 miles
The Chicago Riverwalk is a flat 1.3-mile paved path along the south side of the Chicago River downtown. Set amid some of the city’s architectural gems, it features public lawn space, dining options, fishing piers and boat docks. It’s perfect for a quick out-and-back jog, or you can connect to the Lakefront Trail for a longer outing.
2. Millennium Park
Address: 201 E. Randolph St.
Trail length: 0.7 miles
The second shortest of the Chicago running trails on our list, Millennium Park is small but mighty. The 24.5-acre park is one of the best parks in Chicago, thanks to its live shows, sculptures, monuments and other fun outdoor attractions like the Skydeck at Willis Tower. The trail is one of the top places to run in Chicago, whether on a midday stroll or a quick jog during your lunch break.
Millennium Park is part of Chicago’s larger Grant Park. You can visit the John G. Shedd Aquarium and Adler Planetarium, among other attractions nearby. While the trail is short, you can enjoy the surrounding nature and attractions all day.
3. South Shore Cultural Center
Address: 7059 S South Shore Dr.
Trail length: 1.1 miles
The South Shore Cultural Center totals just under 71 acres, and there’s a ton to do within this center. Walk along the 1.1-mile loop trail on South Shore Nature Sanctuary. Tee up and visit the 9-hole golf course, or visit one of the best beaches in Chicago to cool off on a hot day.
Inside the country club-like interior, you can visit the solarium or grab a bite to eat in the dining hall. If you want to try something new, park-goers can participate in dance, music, art and fitness classes. While you might visit for the short trail, you’ll likely stay for all the excitement!
4. Wicker Park
Address: 1425 N. Damen Ave.
Trail length: 0.3 miles
Wicker Park is the place to be if you’re looking for a quick jog around beautiful, well-tended gardens. This small but mighty park totals just under five acres and hosts a historic fountain, a dog-friendly area, a baseball field and basketball courts. While you can complete this trail rather quickly during a run, there’s plenty to do to fill your afternoon.
Mid-Length Trails (2 to 5 miles)
For more challenging Chicago running routes, these mid-length trails will get your blood pumping. Let these sights be your guide to Chicago, showing you all that the city has to offer.
5. Grant Park
Address: 337 E. Randolph St.
Trail length: 3-5 miles, depending on route taken
Grant Park, between busy Michigan Avenue and the lakeshore, spans a massive 313 acres in Chicago’s central business district in the Loop Community area. The trail length can vary—depending on your chosen paths, you can take a short, tree-lined diversion from the Lakefront Trail or a 3- to 5-mile route around the park.
The park itself includes notable attractions, including The Art Institute of Chicago and Buckingham Memorial Fountain, giving visitors plenty to do when they aren’t getting a move on. While resting from the sprint, stop to enjoy Chicago’s largest food and music festivals in this festive location.
6. Humboldt Park
Address: 1440 N. Humboldt Blvd.
Trail length: 2.7 miles
Take a break from the main tourist destination area along the lakefront and head to the Humboldt Park neighborhood, where you’ll find a beautiful 219-acre park of the same name. Explore the many well-maintained trails that wind through gardens and restored prairie, over bridges and past monuments and lagoons. A large hill offers a great view of the city skyline, making this a picture-perfect running spot.
7. Northerly Island
Address: 1521 S. Linn White Dr.
Trail length: 2 miles
Just southeast of Grant Park is Northerly Island, a man-made peninsula that formerly was an airstrip. The southern part of the peninsula is now a nature preserve featuring landscaped wildlife habitats, a lagoon and fabulous views of the city skyline.
Take the paved path through the nature preserve to see 150 different varieties of native plants, making this one of the best runs in Chicago for nature lovers. There is no artificial lighting to create a natural environment for the animals that inhabit the preserve, so you’ll want to explore this path during daylight hours.
8. The 606 (The Bloomingdale Trail)
Address: 1600-3700 W. Bloomingdale Ave.
Trail length: 2.7 mile
Not far from Humboldt Park is the Bloomingdale Trail, which is commonly known as the 606. You can run in the city — without the stoplights and traffic — on this 2.7-mile elevated path from Logan Square to Bucktown.
Formerly an abandoned rail line, it’s now a tree-lined, landscaped park offering separate pedestrian and bike paths, city views and public art. Be warned: This path leads past some of the city’s best dining spots, and with 12 access points along the way, you’ll be tempted to hop off and explore nearby restaurants.
9. Lincoln Park
Address: 500-5700 N. Lake Shore Dr.
Trail length: 5 miles
With an enormous space of 1,189 acres, Lincoln Park is a premier spot in Chi-town to visit and get your steps in. The city’s largest park boasts an easy-to-run five-mile loop that’s open all year and a host of other fun things for solo runners and families.
See the animals at the Lincoln Park Zoo, catch a show at the Theater on the Lake, or get in touch with nature at the Peggy Notebaert Nature Museum. And if you’re going on a run with littles, you can stop by any of the five playgrounds Lincoln Park offers. It’s no wonder why this park is a top budget-friendly trip in Chicago.
10. Jackson Park
Address: 6401 S. Stony Island Ave.
Trail length: 4.2 miles
Jackson Park spans an incredible 552 acres and is a must-see for any native Chicagoan or tourist, thanks to its vast activities. From a gymnasium to a golf course, a playground to tennis courts, Jackson Park offers something for everyone.
And the same is true for runners—if you’re looking for where to run in Chicago, this is the place. This park offers a beautiful running trail of over four miles of scenic nature, offering tranquility during your most strenuous workout. Since Chicago’s winters can make enjoying this nature-focused area difficult, expect to see larger crowds during the summer.
Long Trails (Over 5 miles)
These long trails are for those needing a challenging run through Chicago. Pack water and maybe a snack, bring your most comfortable shoes and get ready to run!
11. Chicago Lakefront Trail
Address: 5800 N. Sheridan Rd. to 7100 S. South Shore Dr
Trail length: 18 miles
The Chicago Lakefront Trail is an extravagant 18-mile paved trail along the shore of Lake Michigan. It offers great views of the lake and the Chicago skyline and passes several local parks and attractions.
It’s no wonder that this trail is one of the top things to do in Chicago; this location is popular with local runners, walkers, and bicyclists as well as tourists, so if your trip is in the summer, you may find it a bit crowded in the middle section near the museums. Distance markers every half mile help you track your progress, and there are plenty of water fountains and restrooms along the way.
12. Burnham Greenway
Address: E. 100th St. to US 6, just east of Torrence Ave
Trail length: 5.3 miles
Although the Burnham Greenway has two distinct trails—the north trail that runs 3.15 miles and the south trail that runs 2.1 miles—you can still enjoy a nice run through both in one afternoon. Fear not, long-distance runners—there are plans to both extend and connect both sides of this system, making it a whopping 11-mile trail.
On the north side of the trail, you can find playgrounds and access to biking, swimming and fishing. The south side features baseball fields, a playground and a skate park. This running trail is perfect for those looking for a nice long run with an opportunity to take breaks in between.
Run Towards Your Next Vacation With AAA
Chicago is beautiful to visit in any season to take in the sights and beauties of nature. What better way to do that than with a run? Windy City locals can frequent the best places to run in Chicago often, but out-of-towners can take advantage of AAA Travel services to book a hotel and visit Chi-town's sights and sounds first-hand. And if you’re not a Chicago native, your AAA Membership can help make your travel planning easy.
