If you’re looking for the best places to run in Chicago, local runner Allison Yates, founder of Read and Run Chicago, offers her expert insight. Whether you want to hit beautiful lakefront paths or get away from the bustle of the city and run on scenic trails, Chicago has endless options for runners.

Exploring the Best Places to Run in Chicago

By Allison Yates, Chicago runner and writer

With over 22 miles of coastline, wide boulevards, and lots of great mural-spotting opportunities, there are countless places in Chicago to get some miles and enjoy yourself along the way. As the founder of the running event organization Read & Run Chicago, my work has taken me far north, far south, and even outside the city.

Read & Run Chicago hosts running tours inspired by books. This means that our running routes–which are built by stories, as we say–feature all areas of the city, as locations depend on where the story takes place. Each one of the places featured below has history. I’ve included some hints at history and invite you to continue the learning journey while you run.

As with all cities, running in Chicago calls for some basic safety tips. Map out your route ahead of your run, or better yet, run with a local for an unforgettable experience. Check out our running safety tips for more ways to stay safe on the run.

Whether you’re looking for some speed, hoping to feel camaraderie with other runners, or simply want some fresh air and nice views, these are the best spots for pounding the pavement (or trails!) in Chicago.

Running the Lakefront Trail

Spanning Lake Michigan for 18.5 miles and traversing 13 Chicago neighborhoods, the city’s Lakefront Trail is the ultimate spot for runners and one of the best places to run in Chicago. Fully paved, flat, split into running/walking and biking paths – and not to mention stunning – this path is perfect for long runs, speed work, and leisurely runs to catch skyline views (stop at Promontory Point, Oak Street Beach, North Avenue Beach’s pier, and near Diversey Harbor’s Chevron sculpture for a few good photo opportunities), and many, many chances for the absolute thrill of jumping in the lake in the middle of a run.

Though heavily trafficked in some areas (mostly concentrated between the North Avenue Beach and Museum Campus access points, and especially around the premiere tourist destination Navy Pier), you’ll still find many peaceful corners and tucked-away nature spots. While the 18.5-mile paved path is the official Lakefront Trail, you’ll find many connected and offshoot trails, primarily around the North Side harbors, Grant Park, and Jackson Park.

During weekend mornings, especially throughout the summer, you’ll see packs of dozens of running clubs and marathon training groups. If you want to avoid crowds, head out as early as possible. There are also public water fountains, but they only run from late summer until early fall. Bring your own hydration, especially if you’re out for a long run!

Given the wide range of possible routes to run the Lakefront Trail, it’s impossible to list all of them here. If you need a starting point, here are a few of my favorite ways to experience the trail:

Millennium Park to Promontory Point (~7 miles one way, ~14 round trip): Starting at either the Loop’s Millennium Park or Hyde Park’s Promontory Point, this long-run route is ideal for running through the city’s most famous tourist spots in the Museum Campus, soaking in the best native plants of the region along Burnham Nature Sanctuary and enjoying quieter and less obstructed lake views. Stop in Promontory Point for a quick dip (I prefer the rocks on the north side of the field house), and then either run or bike back to Millennium Park using one of the city’s Divvy shared bikes.
Oak Street Beach to Theater on the Lake (~3.5 miles roundtrip): You’ll see North Siders come alive in the summer evenings along this route. Intramural beach volleyball leagues, friends and families picnicking at sunset, children splashing at the beach, and of course, runners and cyclists, are all common sightings on this stretch. Savor the city views as you run back south from Theater on the Lake.
Belmont Harbor to Montrose Dunes Nature Area (~5 miles roundtrip): You’ll get the best of the North Side harbors, city views, and nature preserves on this (minimum) five-mile route. Enter through the Belmont Harbor access point and head north along the path. You can stay on the paved path or head to the crushed gravel path along the lake just after the Bill Jarvis Migratory Bird Sanctuary until you reach Montrose Harbor. Keep following the shoreline as you wrap around to the Montrose Point Bird Sanctuary and on the other side of the point, the Dunes Nature Area. As the names suggest, this area is ideal for bird enthusiasts and nature lovers. For a little extra mileage, take the ~.5-miles of nature trails within the sanctuary for a chance to see some.

2. Running Northerly Island

Even though the skyscrapers are a few minutes’ walk away from Northerly Island, running through the sparsely frequented shores of this man-made island feels like a faraway forest preserve. Though this land used to be a small airport called Meigs Field (it was destroyed in the middle of the night by Mayor Richard M. Daley in a notoriously Chicago-appropriate political move), it’s now an over 100-acre natural area.

Starting from the Loop’s Museum Campus, you can easily get in a 5K run by following the crushed gravel trail around the perimeter of the protected space. You’ll get to see over 150 native plant species and a pond as you hear the sounds of Lake Michigan crashing against the barrier rocks.

3. Running the Bloomingdale Trail and the 606

The 606 – the park that encompasses The Bloomingdale Trail and surrounding parks, so named for the first three digits of Chicagoans’ zip codes – is another one of the best places to run in Chicago. This straight, mostly flat (except for a very small incline around Damen Avenue that at times feels like a mountain) multi-use paved trail runs 2.7 miles from east to west. These conditions – along with the water fountains and two public-use bathrooms (the McCormick YMCA and this restroom at Western) – make the trail a great place for speed work or out-and-back repeats.

Though it's often referred to as Chicago’s answer to NYC’s High Line, the Windy City’s most famous rail-to-trail conversion is more focused on outdoor recreation and commuting than culture and commerce, though Chicago’s does feature murals and architecture recalling the area’s industrial past.

Traversing the Humboldt Park and Wicker Park/Bucktown neighborhoods and the start of the Lincoln Yards area, you can also make several stops off the trail for shopping and food and drink along the way. One must-see spot is Orkenoy, a brewery, and restaurant featuring Nordic-inspired food, housed in the Kimball Arts Center, a half mile from the west end access point. (One easy way to not miss it is to look for the huge “COFFEE + BEER” sign on the building – two things that seem tantalizing in the middle of a hard run!)

4. West Side Parks and Connecting Boulevards

West Siders have long known the merits of the city’s historic West Side parks, including Humboldt Park, Garfield Park, and Douglass Park, designed by Willian Le Baron Jenney in 1871 and revitalized by Jens Jensen in the early 1900s. These parks were executed by the West Park Commission, and in June 2022, the inaugural Bank of America Chicago 13.1 race route showcased the commission's wide boulevards, lush parks and manicured gardens, and historic sites to many Chicago-based runners who rarely venture from the Lakefront Trail.

Originally settled by Scandinavian, German, Jewish, and other European groups, these neighborhoods (of the same names as their parks) transitioned to predominantly African American or Latinx during the last half of the Great Migration. During this time, restrictive housing covenants were deemed unconstitutional, allowing African Americans more geographical mobility, and white flight ensued (or in the case of the Puerto Ricans, the famed Lincoln Park was gentrified and their families were pushed further west).

As a result, neighborhoods saw a mass exodus of long-standing residents and an influx of new ones, and through the tumult of the ensuing disinvestment in the following decades, each of these neighborhoods has a great spirit of resistance and activism. You’ll see Puerto Rican pride in Humboldt Park (which was also the stomping grounds of Puerto Rican independence movement supporters) and the old stomping grounds of Dr. Martin Luther King, Jr., who came to North Lawndale in 1965 to protest for more fair housing conditions.

Today, you’ll also see local running groups and activists like Peace Runners 773 fighting stereotypes and decades of injustice while building healthy communities.

For a great 13.1-mile long run, follow the 2022 half marathon’s course map, or see below for shorter route options. In all of the three parks below, tracing the perimeters will get more miles and though short, the crushed gravel and wood chip paths provide short but enjoyable respite from the pavement.

5. Humboldt Park

Humboldt Park features a fieldhouse, lagoon, and sports fields connected by paved and unpaved multi-use trails and a vehicle road. For an easy, flat route, try this 2.1-mile loop around the lagoon. If you need a bit of elevation or hill repeats, head to the sledding hill on the northwest side of the park. You can also access this route from the 606’s Bloomingdale Trail.

6. Garfield Park

Similar to Humboldt Park, Garfield Park also features a pond, fieldhouse, and recreational space and an easy loop of around two miles. Make sure to admire the Gold Dome building – once the administrative headquarters of the West Park Commission, the series of three parks and interlinking boulevards – which is now the fieldhouse, and visit the Garfield Park Conservatory before leaving the area.

7. Douglass Park

Douglass Park, the last of the West Park Commission’s late 19th century is a series of ponds, green spaces, and recreational areas, split by Ogden Avenue, the start of the Historic Route 66. You can loop the park in around two and a half miles – here’s a great route for an example. A short jaunt from the park is the original Sears Tower, a 14-story neoclassical structure that once housed the warehouse for the Sears, Roebuck & Co. complex, the company that put catalogs on the map.

8. Hyde Park: Jackson Park, Midway Plaisance Park, and Washington Park

If you loved Erik Larson’s Devil in the White City, this area is for you. Hyde Park, home of the University of Chicago, also houses three interconnected green spaces you can run separately or together for extra miles.

Along the shores of Lake Michigan and accessible by the Lakefront Trail, Jackson Park was designed originally for the Chicago park and boulevard system (similar to the above West Side parks) and later remodeled for the 1893 World’s Columbian Exposition (the only remaining structure from the fair in Jackson Park is the Museum of Science and Industry). There are several shorter nature and paved trails of less than a mile that you can combine (and not get lost!) within this park. Otherwise, follow the Midway Plaisance Park a mile east past the University of Chicago campus until you connect with Washington Park, a sprawling green space of almost 400 acres (about half the size of Central Park) with flat trails and pavement.

9. Beverly

This far South Side neighborhood has many claims to fame. The most important one to runners? You can find the highest point in Chicago here. (“High” is relative, but when you need some incline, you’ll take what you can get! Think of this as an area to get gentle rolling hills).

Besides “elevation,” Beverly makes this list of best places to run in Chicago for its views – the architectural kind. If you’re out for a sightseeing or easy recovery run, you’ll have a lot to look at. Beverly boasts four historic districts that feature some of the city’s oldest homes and most unique architectural styles: the Ridge Historic District (feature Frank Lloyd Wright homes), Longwood Drive Historic District, Walter Burley Griffin Place Historic District, and the Beverly/Morgan Park Railroad Station Historic District.

If you want to run a 1.7-mile route featuring notable homes and Civil Rights history, check out this one from Read & Run Chicago’s 2021 tour of author Scott Smith’s essay about Beverly’s integration activism in the 1960s.

And if you happen to be in Chicago in May, the Beverly Area Planning Association hosts an annual Ridge Run, a much-celebrated 5K or 10K race that runs by incredible homes along Longwood Drive.

10. 312 RiverRun

The recently opened 312 RiverRun runs parallel to the North Branch of the Chicago River for around two miles, connecting Belmont Avenue to Montrose Avenue on Chicago’s Northwest Side. While mostly flat (with a small incline over the Riverview Bridge across Addison Avenue, which at 1,000 feet makes it the city’s longest pedestrian bridge!), this paved trail is the best way to get a 4-mile out-and-back run while experiencing one of the most natural areas of the once heavily polluted river. You’ll pass rowers and kayakers – and possibly see some wildlife – and be able to access Clark Park (with the Gang Studios-designed WMS Boathouse) and Horner Park, two wide green spaces perfect for clocking extra mileage.

11. North Branch Trail System

Though the majority of the North Branch Trail system is technically outside the city limits, this system makes the list as it features nearly as many miles as the Lakefront Trail and is an inland (and often less frequented) alternative to the bustling Lake Michigan path. Starting in the Northwest Chicago neighborhood Albany Park (just further Northwest from the 312 River Run), the route runs north into the Chicago suburbs, parallel to the North Branch of the Chicago River through numerous forest preserves (including the Skokie Lagoons) until the Chicago Botanic Garden.

The 20 miles of paved, flat trails make this one of the best places to run in Chicago. The trails are ideal for long runs, while the small, single-track dirt trails in the surrounding forest preserves will put you in the thick of native plants and animals. The North Branch trail is also popular for cyclists, so runners should be careful to follow running safety rules and trail etiquette.

12. Riverwalk

Expect to run at a slower pace if you opt for these downtown Chicago River views, but the people-watching (and sightseeing) make this one of the best places to run in Chicago. The 1.25-mile paved Riverwalk puts runners in the heart of downtown (The Loop) and some of the city’s most celebrated architectural feats. In the summer, you’ll find Chicagoans enjoying happy hour at the bars lining the river or in the water kayaking or boating.

13. West Town/West Loop: Hubbard Street Murals and Kinzie Industrial Corridor

This wouldn’t be a blog for Runstreet if we didn’t highlight street art! The Hubbard Street Murals are an early 1970s project running for over 10 blocks along Hubbard Street near The West Loop, featuring protest art, culturally-affirming messages, and even some silly scenes with wacky animals. You can view historic and revamped community murals by starting from the intersection of Ogden and Hubbard and heading west.

A mile west of Ogden is the start of Kinzie Industrial Corridor, an industrial zone with ample room for running (particularly on the weekend) and a few warehouses and factories converted into breweries or coffee shops (try Metric for a quick caffeine boost mid-run). In my experience, it’s populated enough to feel safe while still giving you the space for speed (and views to occupy your mind on hard runs).

14. Pilsen: 16th Street Murals

And speaking of street art, you’ll find some of the best mural spotting in the city in Pilsen, making this one of the best places to run in Chicago for street art (also the location of the first Runstreet Daydream Art Run). Pilsen is the historic heart of Chicago’s Mexican-American community. Just South of The Hubbard Street murals, think of Hubbard Street as an appetizer for the big meal. Get ready to devour the art!

Mexican-Americans inspired by the Mexican Mural Movement brought the idea of murals to Chicago in the 1960s and originally focused on political movements and cultural pride. Wherever you run in Pilsen, the beauty and messages of the local and international artists will astonish and inspire you.

One of the best places to spot murals while running is along 16th Street for nearly two miles from Canal Street until Wolcott. You’ll view a series of murals that added color and heart to a gray railroad embankment and continue to be a space for self-expression and protest. For one option for how to experience the sights, check out this 1.8-mile route from a Read & Run Chicago event in January 2022.

15. 41st Street Pedestrian Bridge

Get your hill repeats here! Some Chicagoans love Cricket Hill at Montrose or the sledding hill at Soldier Field, but you can’t beat the architectural beauty and Lake Michigan views of the 41st Street Pedestrian Bridge, a 1,500-foot bridge linking the Bronzeville neighborhood with the Lakefront Trail. In the summer, you’ll also find local run clubs like 7onSundays training weekly here.

Hopefully, these varied and scenic trails give you inspiration to get out and enjoy the best places to run in Chicago. Tag @Runstreet on Instagram to share your picturesque runs and get cheered on in your workouts. Happy running to you!😊

Allison Yates is the founder and organizer of Read & Run Chicago. She works in education by day and spends her free time traveling, freelance writing, running, reading, and jumping in Lake Michigan (when it's not freezing!), among other hobbies.

15 Best Places to Run in Chicago: Tips from a Local