25 Chicago Must-Do Races to fill your 2020 Race Calendar

25 Chicago Must-Do Races to fill your 2020 Race Calendar

Chicago is a great place to run and it has many unique and fun races. Whether you live in or near The Windy City or have a reason to travel here, do mark your calendar for some of these must-do races. I haven’t done all of them (yet), but the ones I haven’t done come highly recommended by numerous sources in the Chicago running community. Wishing you happy miles…enjoy!

F^3 Lake Half Marathon (January)
Location: Soldier Field
Distance: Half Marathon
2020 Date: Saturday January 25, Race Start: 10:00 AM
Link to Information & Registration: https://f3running.com/ 
Why run it? In my advanced age I have shied away from racing in the winter months (in cold climates), but I’m thinking if I ever do this one, it will be for bragging rights. It’s Chicago after all and if you’re not running on the lakefront in January can you call yourself a real Chicago runner? One of the Fs in F^3 stands for freezing…the others? I’ll let you use your imagination. But it’s epic. Or so I’ve heard.

Miles per Hour (February)
Location: McCormick Place
Distance: How far you can run in an hour?
2020 Date: Sunday, February 16, 8:00 AM
Link to Registration: https://www.milesperhourrun.com/
Why run it? This is the inaugural year for this event and it’s unique – and it’s indoors! While this is not the first race to take place inside McCormick Place, Chicago Area Runners Association in partnership with the Chicago Auto Show to put a fun spin on it. It’s a 2.4 mile course with no finish line. The goal is to see how far you can run in an hour. There are team challenges as well. Certainly worth checking out. I’m already registered.

Shamrock Shuffle (March)
Location: Grant Park
Distance: 8k
2020 Date: Sunday, March 22, 8:30 AM
Link to Registration: https://www.shamrockshuffle.com/register-for-2020/8krun/
Why run it? This race is kind of the kick off to the spring racing season in Chicago. With over 20,000 finishers anyone who’s anyone in the Chicago racing community is likely to be part of this event. 8k (or just shy of 5 miles) is manageable, but it has the energy of the marathon. For more on why, read my review here.


CARA Lakefront 10 Miler (April)
Location: Montrose Beach
Distance: 10 Miles & 5k
2020 Date: Saturday, April 18, 9:00 AM (8:30 AM for 5k)
Link to Information & Registration: https://www.caralakefront10.com/
Why run it? There are limited races of this distance and the course for this is north of the city (while Soldier Field 10 run south). This is one of the first longer races of the spring and registering now will (hopefully) keep you motivated and training during the winter.

Ravenswood 5k (April)
Location: Ravenswood; Corner of Wilson and Hermitage Avenues
Distance: 5k
2020 Date: Sunday, April 26, 8:00 AM
Link to Information & Registration: https://www.ravenswoodrun.com
Why run it? Ravenswood is a pretty neighborhood northwest of downtown and the 5k course provides a nice tour. It has the feel of a local community 5k, but is organized by Chicago race giant RAM Racing and sponsored by Fleet Feet. It’s family friendly and easily accessible by public transportation. For more on why, read my review here.

Race to Wrigley (April)
Location: Wrigley Field
Distance: 5k
2020 Date: To Be Announced (2019 date was Saturday, April 27)
Link to Information & Registration: https://www.race-cubs.com
Why run it? Going into its 15th year, this race explores another Chicago neighborhood – Wrigleyville/Lakeview. The course circles iconic Wrigley Field, home of the Cubs, and passes right under the famed marque sign (photo op!). It’s also family friendly and easily accessible by public transportation.

Cinco de Miler (May)
Location: Montrose Harbor
Distance: 5 Miles
2020 Date: Saturday, May 2, 8:30 AM
Link to Information & Registration: https://www.cincodemiler.com
Why run it? The course is beautiful and the post-race party – ah, fiesta! – is out of this world! It’s another well-organized RAM Racing event which starts and finishes adjacent to Montrose Beach. For more information on why, read my review here.


Chicago Spring Half/10k (May)
Location: Maggie Daley Park
Distance: Half Marathon & 10k
2020 Date: Sunday, May 17, 7:00 AM (7:45 AM for 10k)
Link to Information & Registration: https://www.chicagospringhalf.com
Why run it? It’s a great time of year for Half Marathon – or a 10k if you’re not ready to go the full distance. There is a great post-race HOT breakfast and spring market! It’s also the first half of the Chicagoland Half Marathon Series. Runners completing the Half here and the Half on September 27th, are awarded a 3rd finisher’s medal. For more on why, read my review here.

Soldier Field 10 (May)
Location: Soldier Field
Distance: 10 Miles
2020 Date: Saturday, May 23, 7:00 AM
Link to Information & Registration: https://www.soldierfield10.com
Why run it? I can’t think of a better way to spend Memorial Day weekend in Chicago than at the Soldier Field 10. Race organizers do a wonderful job recognizing the sacrifices of our service men and women and for the close to 7,000 participants, it’s a chance to run one of the Runner’s World Top 35 Iconic Races and finish on the 50 yard line of one of the NFL’s most iconic stadiums.

Humboldt Mile (June)
Location: Humboldt Park
Distance: 1 Mile
2020 Date: To Be Announced (2019 date was Saturday, June 1)
Link to Information & Registration: https://www.hftd.org/thehumboldtmile-register
Why run it? Presented by local running crew Three Run Two for the benefit of Hope for the Day, raising awareness about mental health and suicide prevention. Aside from my personal connection to Three Run Two and the mission of HFTD, mile races are rare. The Humboldt Park course is also rare.

Run for the Zoo (June)
Location: Lincoln Park Zoo
Distance: 5k & 10k
2020 Date: Sunday, June 7, 7:30 AM (8:15 AM for 10k; 9:00 AM for Kid’s Safari Stampede
Link to Information & Registration: https://www.lpzoo.org/run-zoo
Why run it? Do you get to see animals? Yes! Is it family friendly? One of the friendliest! I love the Lincoln Park Zoo and this race is fun! The course goes right through animal exhibits and beautiful spring gardens all in bloom. For more on why, read my review here.


Proud to Run 5k/10k/Half (June)
Location: Montrose Harbor
Distance: 5k, 10k & Half Marathon
2020 Date: To Be Announced (2019 date was Saturday, June 29)
Link to Information & Registration: http://frontrunnerschicago.com/proud-to-run-chicago/
Why run it? Chicago does PRIDE well and this race is just one of the many events in which to take part. It offers a variety of distances for novice and experienced runners and from everything I’ve heard, this 38-year-old event does not disappoint.

Chinatown 5k (July)
Location: Chinatown Square on Archer Ave
Distance: 5k
2020 Date: To Be Announced (2019 date was Saturday, July 13)
Link to Information & Registration: http://chinatown5k.wixsite.com/cc5k/race-info
Why run it? Chinatown marks the 20-mile mark on the marathon course, often the site of “the wall” for many runners. If you’re one of those runners who need to make peace with Chinatown, or simply don’t want to run 20 miles to get there, this 5k is for you. It explores another one of Chicago’s special neighborhoods and there’s lots for participants to do, see, and eat after the race.

Chicago Rock N Roll 5k/Half (July)
Location: Grant Park
Distance: 5k & Half Marathon
2020 Date: Saturday, July 18, 7:30 AM (5k) & Sunday, July 19, 6:30 AM (Half)
Link to Registration: https://www.runrocknroll.com/Events/Chicago
Why run it? Chicago is just one of the stops for the Rock N Roll international race series, but is pretty great as a stand alone event too. Voted one of the Top 20 Half Marathons by BibRave, its a nice mix of city streets and lakefront. For more on why, read my review here.


Bloomingdale Trail Run 5k/8k (July)
Location: Walsh Park
Distance: 5k or 8k
2020 Date: To Be Announced (2019 date was Saturday, July 27)
Link to Information & Registration: https://www.the606.org/events/bloomingdale-trail-run/
Why run it? The Bloomingdale trail is the famed elevated 606 rail line converted to a pedestrian and bike path beginning in 2004. Participants in this event will get great views of the cities northwest side neighborhoods of Bucktown, Wicker Park, Humboldt Park and Logan Square.

BTN Big 10 5k/10k (August)
Location: Grant Park
Distance: 5k & 10k
2020 Date: To Be Announced (2019 date was Sunday, August 11)
Link to Information & Registration: https://btnbig10k.com
Why run it? Team spirit and friendly rivalries are what this college football kick-off classic is all about. Participants choose a participant shirt of one of the Big 10 schools. And yes, my New Jersey readers, that includes Rutgers! The 5k and 10k are followed by a Tailgate party complete with mascots and cheerleaders.

Run Mag Mile (September)
Location: Grant Park
Distance: 5k & 10k
2020 Date: Saturday, September 12, 7:00 AM
Link to Information & Registration: https://www.runmagmile.com
Why run it? This is the only race that runs up and down Chicago’s famous Michigan Avenue. The 10k has an additional loop along the lakefront – and a finisher’s medal!

Chicago Half Marathon/5k (September)
Location: Jackson Park
Distance: 5k & Half Marathon
2020 Date: Sunday, September 27, 7:00 AM (7:45 AM for 5k)
Link to Registration: https://www.chicagohalfmarathon.com
Why run it? This is a south side race and gives runners a different perspective of Lakeshore Drive. It is also the 2nd Half of the Chicagoland Half Marathon series and the extra medal is ridiculously large. For more on why, read my review here.

Bucktown 5k (October)
Location: Bucktown; Burr Elementary School Grounds
Distance: 5k
2020 Date: Sunday, October 4, 8:30 AM
Link to Information & Registration: https://www.bucktown5k.com
Why run it? Like Ravenswood 5k in the spring, this race offers another tour through another one of Chicago’s pretty neighborhoods. There is also always great swag from sweatshirts to sweatpants to blankets. No ordinary tee shirts at this race!


International 5k/Chicago Marathon (October)
Location: Daley Plaza (5k); Grant Park (Marathon)
Distance: 5k & Full Marathon
2020 Date: Saturday, October 10, 7:30 AM (5k); Sunday October 11, 7:30 AM (Marathon)
Link to Information & Registration: https://www.chicagomarathon.com
Why run it? The Chicago Marathon is awesome! Read about my 2019 experience here. Registration is now open for 2020 and there are (almost) 11 months to train for it. But if you”re not up for the full 26.2, there’s a 5k on Saturday that will put you in the middle of all the festivities. That’s my plan for next year.

Pumpkins in the Park 5k (October)
Location: Lincoln Park
Distance: 5k
2020 Date: Saturday, October 24, time TBA
Link to Information & Registration: https://www.pumpkins5k.com
Why run it? On the flip side of Run for the Zoo, this is a family-friendly fall event that takes advantage of the lovely gardens around the zoo and Lincoln Park. Consumes are optional.

Carrera de los Muertos 5k (Oct/Nov)
Location: Pilsen
Distance: 5k
2020 Date: To Be Announced (2019 date was Saturday, November 2)
Link to Inforamtion & Registration: http://unoraceofthedead.org
Why run it? Pilsen is another one of Chicago’s wonderful neighborhoods. They were the most energetic and spirited neighborhood I passed through on the marathon, but to be part of it, you only have to come out for the Race of the Dead. Watch THIS VIDEO if you still need convincing.

Hot Chocolate 15k/5k (November)
Location: Grant Park
Distance: 15k & 5k
2020 Date: Sunday, November 8, 7:00 AM
Link to Inforamtion & Registration: https://www.hotchocolate15k.com/chicago
Why run it? Chocolate. Do you need more? Read my review from last week. I’m already registered for 2020.

Happy Holidays Bonus Races

Lincoln Park Turkey Trot 5k/8k (Nov)
Location: Lincoln Park
Distance: 5k & 8k
2020 Date: Thursday, November 28, 9:00 AM
Link to Information & Registration: https://www.turkeytrotchicago.co

Grant Park Turkey Trot 5k/10k (Nov)
Location: Grant Park
Distance: 5k & 10k
2020 Date: Thursday, November 28, 9:00 AM
Link to Information & Registration: https://allcommunityevents.com/grantparkturkeytrot

Why Run it? Read about why you should run a Turkey Trot HERE. And there’s still time to register for one this year!

Santa Hustle 5k (Dec)
Location: Soldier Field
Distance: 5k
2020 Date: Saturday, December 7, 9:00 AM
Link to Information & Registration: https://santahustle.com/chicago/ 
Why run it? If your goal is to run a race every month, why not make December’s a holiday themed? This 5k amenities include a hoodie, Santa hat & beard and finisher’s medal! And yes, there’s still time to sign up for 2019.

On the Radar…New Races in 2020

Chicago 26.2 (April)
Location: Grant Park
Distance: Full Marathon
2020 Date: Sunday, April 5, 7:30 AM
Link to Information & Registration: https://runmfg.com/index.php/events/chicago262
Why run it? Looking for another marathon in Chicago? Looking to run a spring marathon? Want to be part of the inaugural event? Then you have a good reason or two to give this a try. This event is so new that there is no corse map available yet, although it’s planned for the Lakefront, making it very different from the Bank of America Chicago Marathon in the fall. The race organizers also put on the Chicago 10k in August which didn’t make my list above.

Chicago 13.1 (June)
Location: Union Park
Distance: Half Marathon
2020 Date: Sunday, June 7, 2020, 7:30 AM
Link to Information & Registration: https://www.chicago13point1.com
Why run it? This half will put runners in Chicago’s westside neighborhoods which will be a very different experience from all of the other races listed above. The sponsor – Bank of America – and organizers are the same folks that bring us the Shamrock Shuffle and Chicago Marathon, so I have a lot of confidence that this event will be done right. I’m already signed up!


My 2019 race calendar will be a wrap after Thanksgiving weekend. The first race on the 2020 calendar is a destination race in Southern California in early February (more on that to come). I will be back in Chicago to see how many Miles per Hour I can run on February 16 inside at McCormick Place. Then let’s see how many of these races we can do together. Joining me?

Race Review: Hot Chocolate 15k/5k (Chicago)

Race Review: Hot Chocolate 15k/5k (Chicago)

I ran the Hot Chocolate 15k in Chicago last Sunday. It was awesome! There was also a 5k and between both events there were over 32,000 finishers making it one of Chicago’s biggest races. Sponsored by Allstate, Hot Chocolate has become one of those kind of iconic races that everyone does. With Shamrock Shuffle which opens the Chicago race season in March, it serves as as a bookend to the season in November.

Hot Chocolate Chicago is part of the bigger Allstate Hot Chocolate 15k/5k brand that is billed as “America’s Sweetest Race.” It involves 24 races across the U.S.

This was my first year running the Chicago event (I have not done any of the others) and I will certainly be back. Aside from some logistical issues getting into our B corral it was a well run event. The congestion getting to the corral from bag check honestly could have been avoided if we had gotten there earlier. It was a 7am start though, and with temps hovering around freezing, we just didn’t want to be waiting around longer that we had to, nor did we want to get up any earlier. Our bad.

The start and finish were on Columbus Drive similar to Shamrock Shuffle and the Marathon. The course then made a left staying on Lower Wacker until the 1 mile mark when we surfaced at Garvey Street. It wound around Lake, Clark and Van Buren and onto Michigan Avenue heading south. The 5k runners split off making the left on Roosevelt heading to the finish back on Columbus. 15k runners stayed straight basically picking up the blue line and following the Marathon course in the opposite direction until 31st Street where it stayed straight to Martin Luther King Jr. Drive and south to 35th Street.

It should be noted that in addition to water and Nuun, aid stations along the course also had chocolate. I passed on it in an effort to stay on pace, also knowing there was more of that – much more – expected at the finish. Some additional perks included a quality race-branded zip-up hoodie and free race photos.

Free race photos are great! I wish more races did it. This particular photo was a real keeper. I’m sure there will be never-ending creative captions for this one. Bring them on!

The course highlight for me was going over Lake Shore Drive via the bridge at W. 35th Street to the Lakefront Trail – first for me. From here the course was mostly Lakefront Trail. We stayed on the lake side of McCormick Place (I hate the service road/tunnel!), did a fly-by of Soldier Field and passed back under Lake Shore Drive at mile 9, just past the Museum Campus, heading back to the finish on Columbus. The 15k course might be the best mix of city streets and lakefront of any of the Chicago races I’ve done.



The real fun began at the finish line. There were finishers medals for both the 5k and 15k, with the 15k’s being a large replica of a chocolate bar. The post race party included, of course, hot chocolate, as well as some chocolate fondu and an assortment of fruit, pretzels and marshmallows for dipping. It was delicious! I really have to applaud the organizers for not going cheap here. The hot chocolate was really rich, not the watered down kind often served at events.

Yum! Photo Credit @flglchicago

The Allstate Hot Chocolate 15k/5k is organized by RAM Racing and the Chicago race was included as one of their “Run this Town” series events. In addition to our finishers medal for the day, we also received another medal for completing four races in the series. The other races we did for that achievement included Cinco de Miler (early May), Soldier Field 10 (Memorial Day weekend), and the Bucktown 5k (October).

The final race in the “Run this Town” series is the North Shore Turkey Trot. We’ll be doing that one too (no additional medal for being an overachiever) and then our 2019 racing season in Chicago really comes to a close.

Do mark your calendar for next year’s Hot Chocolate – November 8, 2020. Registration is open now! Click here. You can also feel good about supporting charity partner, Make-A-Wish.

Post-race party with Giant Marshmallow Man. Grant Park, Chicago, Illinois. November 2019.
How to run an airport runway

How to run an airport runway

This weekend was supposed to be the 22nd running of the Teterboro Airport 5k. I say supposed to because after many years of dealing with hot races (an airport runway in July is rarely cool), this year’s forecast exceeded anything that was safe and for the first time, the event was cancelled. Read more

Race Review: Race Against Hate

Race Review: Race Against Hate

I know four of my last six posts have been race reviews.  Can you stand another? Last weekend’s race was a great event for an even more important cause, so please bear with me another week.

We ran the 10k at the 20th Annual Ricky Birdsong Memorial Race Against Hate on Father’s Day. There were also 5k and Youth Mile and Half Mile races. Ricky Birdsong  was the men’s basketball coach for Northwestern, who, just about 20 years, ago was murdered by a white supremacist.  His killer went on a rampage that Independence Day weekend in 1999 that left 7 wounded and another dead. Read more

Race Review: The Bellin Run

Race Review: The Bellin Run

I still don’t totally understand the popularity of this race. The 42ndAnnual Bellin Run in Green Bay, Wisconsin last weekend had over 11,000 participants! It’s one of the largest fields for a 10k in the nation! The course was nice; rolling hills and winding streets through mostly residential parts of Green Bay and Allouez. In that regard it reminded me of the Ridgewood Run on Memorial Day in New Jersey. But the Ridgewood Run, while a big event, doesn’t have over 8600 finishers in the 10k. Read more