Runs and Places

Run Where I Live: Chicago

Chicago - The Bean

I was recently invited to participate in the Run Where I Live Series, which is a set of blog posts about the best local running routes and resources in a given city written by the people who live there.  Having grown up in the Chicago area, I hope this post does my city proud-

Chicago is one of the best cities in the world to be a runner.  I know that’s a pretty bold statement to make, but I feel comfortable making it based on my experience.  I’ve lived in the Chicago area since I was about 4 years old, but before then, I lived just outside of L.A., Denver and New York City.  Obviously I was pretty young at the time, but I’ve been back to visit those places a number of times over the years.  I’ve also traveled to do races in 33 US states, three countries, and two continents and I’ve done an extensive amount of domestic and international travel for the various jobs I’ve held over the years as well.  I know that I’m biased, but I can honestly say that while there have been different things that I’ve enjoyed about every city I’ve been to, I’ve yet to visit another city that compares to Chicago overall.

Chicago Running Stats

As a runner, I love the wide variety of places to run in the city and suburbs, which include urban, rural, and natural settings.  I also love that there are plenty of different races to choose from with their own themes and convenient locations.  The terrain around the city is also nice and flat (although you can still find some hills if you want to).  Lastly, the running community in Chicago is nothing short of amazing.

Where to Run

The obvious choice for a great place to run in Chicago is the Lakefront Trail.  This 18 mile long paved trail runs between Lake Michigan and Lake Shore Drive, just to the East of Downtown Chicago.  It runs the entire length of the city and offers beautiful views of the Chicago skyline on one side and Lake Michigan on the other.  It also passes by some of the most scenic areas of Chicago, including:

  • The Museum of Science and Industry
  • The Burnham Park Bird Sanctuary
  • McCormick Place
  • Soldier Field
  • The Museum Campus
  • Grant Park
  • Buckingham Fountain
  • Maggie Daley Park
  • Monroe Harbor
  • Navy Pier
  • Oak Street Beach
  • North Avenue Beach
  • Belmont Harbor
  • Montrose Harbor
  • The Gold Coast Historic District

The trail is flat, well maintained, and has markers every half mile.  As an added bonus, during the summer months, a number of volunteers from local running clubs and shops set up tables alongside the trail and hand out cups of water to the runners and cyclists who pass by.

Chicago Skyline from the Lakefront Path

Other Options

If there’s one downside to the Lakefront Path, it’s that it gets crowded when the weather is nice.  Go for a run on a nice cool spring morning and you may find yourself doing a little bit of weaving to avoid all of the other people on the trail.  So, if you’re looking for something that’s a little more quiet, you’ll still have plenty of options.  These are just a few:

The 606 is an old railroad line in the Logan Square neighborhood that was recently converted into a running and biking trail.  It includes sculptures, flowering trees, easy access to parks and an observatory where runners can stop and watch the sunset over the Chicago Skyline.

The Fox River Trail is a 43 mile long paved trail that runs alongside the Fox River through three different counties in Chicago’s western suburbs.  It features views of numerous points of interest including nature preserves, Frank Lloyd Wright homes and windmills.  If you run through Batavia, you’ll see the former sanitarium where Mary Todd Lincoln was confined.  The trail is also the site of the Fox Valley Marathon.

The Old Plank Road Trail is a 22 mile stretch of trail in Chicago’s south suburbs.  It’s surrounded by hundred-plus year old trees, nature preserves and easy access to parks and golf courses.  The trail is also home to the Frankfort Half Marathon.

The North Branch Trail starts at the intersection of Caldwell and Devon on the Northwest Side of Chicago.  It stretches 17 miles alongside the Chicago River to the Chicago Botanical Gardens.  The trail was recently extended to connect to the Green Bay Trail, which stretches all the way into Wisconsin.

Chicago - Alternate Running Trail Options

Where to Shop

Whether you’re looking for massive corporate owned sporting goods stores or small independent running shops, there’s no shortage of places to buy running gear in Chicago.  Here are some of the best ones:

Michigan Avenue is home to the Nike Store, which features five floors of Nike shoes and accessories, the Garmin store, which sells GPS equipment and accessories.  It’s also home to Lulumon and Under Armour stores along with several others.

Chicago Skyline at Sunset

Fleet Feet Sports is a national chain that offers personalized service from experts.  Fleet Feet has six locations in the Chicago Area: South Loop, Oak Park, Old Town, Lincoln Square, Elmhurst, and Schererville, Indiana.

Universal Sole in Lakeview and Live Grit in the West Loop sponsor a number of running events around Chicago.  They also have helpful staff who use a scientific method to help runners find the right shoes.

Running Away Multisport is quickly making a name for itself as the organizer of national races like the Hot Chocolate 5K/15K and Cinco De Miler.  However, it started out as an independent running store in Chicago’s Lincoln Park neighborhood.  RAM’s Lincoln Park and Deerfield locations cater to triathletes as well and offer a huge selection of shoes, bikes, and wetsuits along with excellent service.

Chicago - Monroe Harbor

Where to Eat

Want to fuel up the night before a race or go out and grab a beer after a run?  There are thousands of choices for places to eat in and around Chicago.  Below are a few of my favorites:

Chicagoans may not always agree on where the best place is to get pizza in the city, but the truth is that you really can’t go wrong with any of them.  Check out Lou Malnati’s, Gino’s East, or Pizzeria Uno (the original one on Ohio Street, not the fake chain knockoff with a similar name that’s headquartered in Boston) in the city.  If you’re out in the suburbs, stop by Nino’s in Alsip, Louisa’s in Crestwood, Beggar’s in Blue Island, or Vito and Nick’s in Ashburn.

Chicago - Flamingo Sculpture

Portillo’s, Superdawg and Gene and Jude’s, are just a few of the many options to get Chicago Style Hot Dogs.

Twisted Spoke, Leadbelly and The Bad Apple are some places for great burgers.

Johnnie’s, Luke’s and Al’s are where you’ll want to stop if you’re looking for an Italian Beef Sandwich.  Make sure you order it hot, sweet and dipped….

Chicago - Art Institute Lion

If you’re looking for other ethnic restaurants, check out Estrella Negra (Mexican / Day of the Dead Theme), Greek Islands, Italian Village, The Berghoff (German) or Carnivale.

Also make sure to check out Saucy Porka which is an Asian / Latin fusion restaurant that started out as a food truck but quickly moved to a brick and mortar location in Chicago’s financial district to accommodate the massive crowds of people who flock there to eat on a daily basis.  It’s not uncommon to see lines of people stretching out the door down to the end of the block at lunchtime.  Saucy Porka offers menu items like Bao Tacos, Chorizo Egg Rolls, Puerto Rican Rice with Edamame.

If you’d like some vegetarian options, check out Native Foods Cafe, Mana Food Bar, and Blind Faith Cafe.

Lastly, there are dozens of microbreweries around the city.  If you want a post run beer, these are some of the best: Haymarket, Half Acre, Revolution Brewing.

Chicago Running Groups or Clubs

With close to 9000 members, the Chicago Area Runner’s Association (CARA) is the largest running group in the Midwest and third largest in the United States.  CARA sponsors a number of races around Chicago, and gives members access to training clinics, group runs, and discounts on local races.

There are a number of other clubs available in and around Chicago as well, including Fleet Feet Sports, 3Run2, and the Lincoln Park Pacers.  There’s also a community specifically for Chicago Runners who have their own blogs.

Shamrock Shuffle Start Line - Chicago

Best Races in Chicago

This was a tough one.  There are literally thousands of races in Chicago throughout the year.  A quick search on for Chicago races in July alone yielded 17 pages of results.  Runners can easily find multiple races to do every weekend and even on most weekdays.  So I put together a list of different distances and tried to pick a race or two for each one.  Besides the races I listed below, there are a number of other great ones in and around Chicago too though.  I just didn’t have room to list them all:


The Chicago Lakefront 50/50 is an ultra marathon along Chicago’s lakefront in the fall.  The scenery is beautiful and runners have a choice of 50K or 50 mile distances.


I would be remiss if I didn’t mention Chicago Marathon here.  This race brings close to 50,000 runners from all over the world to Chicago every fall.  It has a flat, fast course that goes through 30 different Chicago neighborhoods and has amazing crowd support.  It’s also one of the World Marathon Majors.  If you only travel to Chicago for one race during your entire life, this should be it.

Chicago Marathon Medals

Half Marathon

I couldn’t decide between the Chicago Half Marathon and the Chicago Spring Half.  The Chicago Half Marathon starts near the University of Chicago campus on the south side of the city and runs up Lake Shore Drive towards the loop.  The Chicago Spring Half starts on the north side of the city and heads south along the lakefront.  You can’t go wrong with either of these two races.  Also, one is in the spring and the other is in the fall, so it’s easy to do both of them.

10 Mile

The Soldier Field 10 is held on Memorial Day weekend as a salute to the troops.  The race has an out and back course that starts in front of Soldier Field and heads south along the lakefront for five miles before turning around and heading back north.  Runners get great views of the Chicago skyline during the second half of the course and get to finish on the 50 yard line at Soldier Field.


I have to say that I’m not a huge fan of the Hot Chocolate 15K…. but I’m definitely in the minority with that opinion.  The race attracts over 30,000 runners to Grant Park each November for a course that loops through the city and offers free hot chocolate to all finishers.

Quarter Marathon

What’s the difference between a quarter marathon and a 10K?  0.35 miles.  I almost left this one out because 6.55 miles is kind of a silly distance for a race, but the fact that there’s a race like this on the calendar really shows the wide variety of race distances that are available to runners in Chicago.  The Chicago Quarter Marathon brings runners on a 6.55 mile run along Chicago’s lakefront and offers nice Chicago themed finisher’s medals.


The BTN Big 10K offers school specific technical race shirts to runners along with a course that goes along the lakefront and ends with a massive tailgate party at Soldier Field to kick off College Football season.

5 Mile

Cinco De Miler is a five mile race held on the weekend before Cinco De Mayo each year.  The race runs along the Chicago Lakefront and finishes with a massive fiesta in the McCormick Place parking lot that includes Mexican food, beer, mariachi bands, and a mechanical bull.

Cinco De Miler - Chicago


This is another odd distance (4.97 miles), but with close to 40,000 runners annually, the Shamrock Shuffle is one of the most popular races in Chicago.  It’s held during the last weekend in March and is considered by many people to be the event that kicks off the running season in the city.  The Shamrock Shuffle starts and finishes in Grant Park and does a loop through downtown Chicago.  After crossing the finish line, runners celebrate with a big post-race party in front of Buckingham Fountain.


I can’t even begin to count the number of 5Ks available to runners in Chicago, but here are two local favorites: the Race of the Dead 5K is a Day of the Dead themed race that’s held in Chicago’s Pilsen neighborhood on the closest weekend to Day of the Dead (usually the first weekend in November, but the 2015 race happens to be on Halloween).  Runners dress in Day of the Dead makeup and costumes and some of the best Mexican restaurants in Chicago serve food and baked goods at the finish line.  The Race to Wrigley 5K runs through the Wrigleyville neighborhood on Chicago’s North Side every year in April to kick off baseball season.  The final leg of the race goes through the Wrigley Field concourse.

Wrigley Field - Chicago

Other Stuff

These last couple items aren’t necessarily directly related to running, but I did think they were important to mention:

Public transportation in Chicago is amazing.  There are trains, buses, water taxis, taxis, rickshaws, and services like Uber that will bring you anywhere you want to go in the city or suburbs.  This is important for runners because even though Chicago is a huge city, there’s no reason that someone can’t go for a run anywhere they want without having to go for a long drive to get there.  Every running trail and race that I mentioned earlier is accessible by at least one form of public transportation.

Lastly, Chicago may be a big city, but it’s still a Midwestern city.  This means that the people who live here have a reputation for being extremely friendly.  The lakefront trail may get crowded when the weather is nice, but if you go for a run on it, you’re guaranteed to get lots of hello’s and friendly waves from the people you see.  I’ve started conversations with strangers at the start and finish lines of races and had them become good friends.  No matter what level of runner you consider yourself to be, you won’t have any problem finding plenty of support from the Chicago running community.

I hope you enjoyed reading about running in Chicago…. the next stop is a post about Milwaukee, Wisconsin written by Laura at The Caffeinated Runner.  Check it out here:

If you’d like to see the full list of cities in this series, you can find them here.  Also, if you’d like to write a post about your own city and add it to the list, contact Danielle at

Chicago Skyline at NightCheck out my book Southern Fried Running on Amazon or subscribe to this blog today and get a free copy!


10 thoughts on “Run Where I Live: Chicago

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  3. Run Colby Run

    I don’t run TONS of 5ks, but I’m tempted to head out for the Day of the Dead one. Sugar skulls are my jam! That, and tacos. I love tacos. So if there are some at the finish, count me in. Same with the 5 Miler. Mexcian food and a mechanical bull PLUS running???? Another I’d be up for. Great post!!! 🙂

    1. Tom Leddy Post author

      Thanks!! If you decide to do either of those races, let me know. Sugar skulls and tacos rock… and they go especially good with beer!

  4. Danielle

    Such a fantastic post Tom, I feel like I could visit Chicago tomorrow and I’d be ready to go!

    Hopefully I’ll have the chance to visit (and hopefully run a race!) one day. Thanks so much for participating, I’m off to visit Laura now!

    1. Tom Leddy Post author

      Thanks Danielle! Hopefully you’ll make it out to Chicago sometime. If you do you’ll have to let me know!!

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