Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In

Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In

Brands

World Marathon Majors

A Runner’s Guide to Chicago: The World Major Marathon Cities

Chicago running offers world-class scenery and variety, including extensive waterfront trails, beautiful parks, and great neighborhoods. Here's your guide to running in the Windy City.

Get access to everything we publish when you sign up for Outside+.

This is an unprecedented autumn in the history of running. Over the course of seven weeks this fall, five of the six World Marathon Majors are being held. All eyes will focus on Berlin, London, Chicago, Boston, and New York. In honor of this marathon-palooza, Great Runs is partnering with PodiumRunner on a series of running guides for each of these cities: A bit about their running culture, details on the best places to run, and marathon course highlights. Each guide will be published the week of that city’s marathon.

Chicago: Sunday, October 10

Runners racing during the 2019 Bank of America Chicago Marathon in October, 2019.
Runners racing during the 2019 Bank of America Chicago Marathon in October, 2019 in Chicago, Illinois. (Photo: Quinn Harris/Getty Images)

There might be fewer eyes on the Chicago Marathon this year, with attention — and elite runners — favoring the time-shifted Boston Marathon, which is occurring the following day. But Chicago nevertheless deserves its due, as both a great city to visit and one with a fantastic running culture. One thing visitors will immediately notice about Chicago is that everything’s done on a grand scale. Compared to other cities world-wide, the streets are wider and the blocks are longer, the buildings are taller, the architecture is bigger. The food and culture scene is similarly world-class. 

Like other great running cities, Chicago offers wonderful and varied scenery, including extensive waterfront trails, beautiful parks, and great neighborhoods. One unique feature of Chicago-area running is the hundreds of miles of trails in its large network of Forest Preserves. 

Here are some of our favorite places in Chicago for running.

Chicago Lakefront

Chicago’s lakefront path extends 18 miles north and south, with spectacular views much of the way. (Photo: 101 Degrees West)

This 18-mile trail along Lake Michigan is one of the most spectacular urban runs in the country. Great views of the lake, the city skyline, and key sights such as Navy Pier and Museum Campus. The path is especially festive in good weather (so much so it can feel crowded). Recent improvements include separate paths for pedestrians and cyclists. In winter, with a cold wind blowing off the water, the Lakefront path can be… invigorating.

Central Chicago Parks

The hazy, autumn Chicago skyline under a cloudy sky appears beyond Lincoln Park Lagoon, leaving a reflection in the water.
Chicago’s Lincoln Park (Photo: Getty Images)

You can create a long, traffic-free scenic loop that combines historic Grant Park with the newer Millennium Park. Also, make sure to include Lincoln Park as part when you head north on the Lakefront Trail.

Chicago Riverwalk & Loop

Jackson Boulevard Bridge Crossing Chicago River.
The Chicago Riverwalk provides a lovely jog along a picturesque river. (Photo: Getty Images)

The Riverwalk takes you past the incomparable architecture lining the Chicago river, passing below the city’s classic drawbridge. Combine the Riverwalk path with our map of the Chicago Loop for a great ‘runseeing’ tour of Chicago’s fantastic architecture!

Hyde Park Area

View of the Lake Michigan promenade in Hyde Park with the downtown Chicago skyline in the distance.
View of the Lake Michigan promenade in Hyde Park with the downtown Chicago skyline in the distance. (Photo: Getty Images)

At the southern end of the Lakefront Path, one can put together a fabulous run combining Jackson Park and Promontory Point. Then, take the famous Midway Pleasance, which connects to the scenic University of Chicago campus and Washington Park.

The 606 Trail

City path in the spring, the Chicago 606.
Bloomingdale Trail, a.k.a. the 606, is an elevated pedestrian trail that travels through the Bucktown and Humboldt Park neighborhoods on Chicago’s northwest side. (Photo: Getty Images)

Chicago’s answer to New York’s High Line is the latest addition to the city’s running scene. Lined with urban greenery, the 606 is a new elevated trail built along a former rail line in Chicago’s west side with separate pedestrian and bike paths. It also includes intriguing public art and charming landscaping. Also known as the Bloomingdale Trail, it runs 2.7 miles, from Walsh Park at the I-90, west to N. Ridgeway Ave. An out and back along the trail is 5.4 miles. You can also combine with Humboldt Park, which has 2 miles of green trails around a couple of ponds.

North Shore Beauty

Follow all or part of the North Shore Classic Half Marathon course, which features some of the gorgeous, tree-lined streets made famous by film director John Hughes (Ferris Bueller’s Day Off, The Breakfast Club).

Great Chicago Neighborhoods for Running

Create your own route in some of Chicago’s attractive residential neighborhoods, along tree-lined streets past historic homes. Some of our favorites are on the north shore and northwest of the city: Highland Park, Fort Sheridian, Glencoe, Winnetka, and Buffalo Grove. West of the city, we love running around Oak Park and Riverside.

Forest Preserves & Multi-Use Paths

Paved trail in wooded area,
Suburbs of Chicago feature a collection of trails winding through forest preserves. (Photo: Getty Images)

Greater Chicago covers a huge geographic area. The suburbs feature a large collection of trails in Forest Preserves, as well as an extensive network of multi-use paths. Here are some of our favorites, organized by geographic area.

Destination Run: Indiana Dunes National Park

View of Lake Michigan over the dunes at Indiana Dunes National Park.
View of Lake Michigan over the dunes at Indiana Dunes National Park. (Photo: Getty Images)

Located only an hour from Chicago and also accessible via public transportation, Indiana Dunes National Park and adjacent Indiana Dunes State Park feature some wonderful running options through a variety of terrain, including spectacular dunescapes, marshlands, forests, and many miles of beachfront along Lake Michigan.

The Marathon Course

Map of the Chicago Marathon course.
Map of the Chicago Marathon course. (Photo: Google Maps)

The Chicago Marathon course is flat and fast. Four world records have been set over the years! Runners will enjoy exploring 29 neighborhoods in the course of 26.2 miles. The race begins in Grant Park and, after a few ups and downs, heads uptown for seven miles through the Lincoln Park, Wrigleyville, and Fort Sheridian neighborhoods, then doubles back to head south at mile eight, but along different streets. At the halfway mark, runners cross the Chicago River, turning west through West Loop and Greektown toward the United Center, and then south through Little Italy and Chinatown. The final two miles are, fittingly, along Michigan Ave., with the finish line back in Grant Park. 

About the Author 

Mark Lowenstein is Chief Running Officer of Great Runs, the ultimate guide to the best places to run in destinations worldwide. He can be reached at mark.lowenstein@greatruns.com.