A Tale of Five Races: The Chicago Marathon Edition

Chicago is an October sort of city even in spring.
— Nelson Algren

As the Chicago Marathon approaches (happy race week to all who celebrate!), I thought a fitting topic would be my own personal experiences with the Chicago Marathon and highlight what makes it such a fun, fast, and challenging race.

As one of the seven world majors, the Chicago Marathon has steadily grown in popularity, especially in more recent years. While the city hosted running events as early as the 1920s, the Chicago course as it is known today was run in September 1977 and was known as the “Mayor Daley Marathon.” The first race in 1977 had just 4,800 runners, while the 2024 running of the same race had 50,000 participants.

Part of the massive appeal of the Chicago Marathon is the fact that it is a flat, fast course that winds through the Loop, the West Side, North Side, and South Side of the city, giving runners a 26.2 mile running tour of many of the more popular areas. It’s also a famously spectator-friendly course, as the loops out and back, especially in the back half of the race, allow for spectators to easily spot runners multiple times on the course.

Additionally, the logistics of this race are relatively easy compared to other World Majors. The race starts and ends at Grant Park, which is easily accessible by public transportation, walking if staying in one of the many hotels in the area, or a short drive. Whereas other races require multiple modes of transportation to just get to the start line, Chicago starts and ends in a hub of the city.

The biggest draw for me personally, along with most other runners, is the fact that the Chicago Marathon is an extremely flat and fast course. According to World Marathoner, “Chicago offers 243 feet (74 meters) up and 242 feet (73 meters) down. Minimal elevation changes, wide streets, and excellent organization make it one of the most popular courses among marathoners worldwide. Chicago is a place where you can focus on an even pace and fight for your best result.”

Flat course, good vibes, easy logistics? Sign me up. Which brings us to my own personal Chicago experiences: the good, the bad, the very good, and the very ugly. Welcome to what I’ll dub the “KJWC Chicago Chronicles.”

CHICAGO #1: 2015

Coming off the heels of the 2014 Boston Marathon and a few other smaller marathons, I was working full time as a fitness trainer and really putting time and effort into my marathon training. I was finally incorporating speed work and strength work, and was feeling ready to attempt my first Boston Qualifying time (sub 3:30 for my age group at that time, TBT). I showed up to my first Chicago Marathon ready to work. I had been training with a good friend of mine who was much faster than I was, and pushing the pace with her on training runs and having her as my guide on race day (she had already run Chicago once) was absolutely pivotal. I had the time of my life. I ended up qualifying for Boston that day for the first time, and was elated. The stars aligned, the weather was perfect, and we executed our race plan without a hitch. The flat course allowed me to PR by a whopping 11 minutes, and thus, my sights were set on 2016 and an even loftier goal. The road to sub-three was calling my name.

CHICAGO #2: 2016

The training period between 2015 and 2016 was filled with a lot of hard work. After nailing my first BQ and shaving a lot of time off my former PR in Chicago in 2015, I decided to hire a coach for my friend and I and we set our sights on breaking the elusive sub-three hour barrier. My friend Lauren had already broken this barrier, so having her there as my training partner through the grueling summer months is something I will forever be grateful for. I made running essentially my full-time job.

My coach had me doing 100-plus mile weeks fairly consistently through the entire cycle. I was hammering tempo runs, 1k repeats at the track, and was so hungry I was waking up in the middle of the night craving late-night sugar fixes like cupcakes and gummy bears.

As I have described in former blogs, I was running the most and running my fastest, but I was grinding and was miserable. Once I set that goal though, I was not about to give it up. I rolled into the Chicago Marathon in 2016 more anxious than I had ever been about a race before. I had pizza from Eataly after going to the expo, got minimal steps, and showed up at Grant Park at 5am on race day morning wearing very unsupportive shoes, shorts with no pockets, and my gels tucked into my sports bra and waistband (ouch).

But we absolutely did the damn thing.

For the first and only time in my personal racing career, the low elevation, the cheers from the crowds, and the ability to see my friends and family at four different points of the race carried us to the finish line. We breezed through the halfway point in 1:27, and finished the race with no stops with a personal best that still stands for me to this day: 2:58:08. This was one of the proudest moments not only in my running career, but in my life.

CHICAGO #3: 2019

Coming off the PR in 2016, it took a couple years for my feet to hit the pavement in Chicago again. I wanted to try (unsuccessfully) to PR on other courses and explore marathons in other cities. However, in 2019 I had finally convinced my then-fiancee Emily to run her first marathon, and I knew the vibes in Chicago would be on point for her. We signed up, and I committed to running a BQ-race and planned on circling back after and cheering her on at the finish line.

In July of that training cycle, however, the absolute worst thing to happen to a runner happened to me: injury. Prior to this race (knocks on wood), I had been pretty injury-free, at least directly tied to my running. However, the mileage finally caught up with me. I noticed a pain in the top and side of my foot that eventually went from annoying to excruciating; I could barely walk, let alone run, and my foot was swollen and hot to the touch. I went to a PT who suggested I may have an stress-related injury and to take a couple weeks off. I didn’t want to hear it, so went to another PT who sent me to get an MRI, which confirmed my worst fears. I had a stress reaction in my foot that without proper attention, would very quickly escalate to a stress fracture. I was put in a boot for six weeks and told not to run for up to ten weeks, which would bring me to one month before Chicago.

I was devastated but determined.

Cycling was approved as a form of cross training, so I hit the spin bikes hard and did a lot of strength training that did not put pressure on my foot, and the second I was cleared to run again, I did.

And I truly believe this was a sign from the universe that I needed to ease up on the mileage and pay more attention to cross training and strength work. And Chicago’s vibes delivered: I ran a 3:09 (!!), and was able to circle around and cheer Emily on as she crossed her first finish line with a huge smile on her face. Once again, a great day.

And, note to reader: DO NOT IGNORE PAIN! INCORPORATE CROSS TRAINING AND STRENGTH INTO YOUR RUNNING PLANS, OR YOU WILL GET INJURED!!!!

CHICAGO #4: 2022

Ahhh, the implosion of the century. For all the good times I have had as a runner with Chicago, 2022 was where it all fell apart. Again, I let a couple years go by following the 2019 race, but coming off the isolation and lack of organized racing during and post-Covid, I was itching to try my hardest to PR again, and since I was familiar with the course, decided to attempt a 2:55 in Chicago in 2022.

However, my training looked absolutely nothing like my 2016 training, and as we will all learn in our running careers at some point, progress is not linear. I did not have the same dedication and desire to hammer out 100-plus mile weeks anymore, and the joy of tempo work had left me.

I felt like I was just going through the motions and praying for a miracle; a deadly combination. Also, at the risk of sounding like I’m making excuses, I also felt like I was coming down with something, so decided to get a full IV the day before, which my nurse best friend later told me was way too much for me at once.

Anyway, I showed up to race with the plan of staying with a friend of mine who was aiming for a 2:50, which even though five minutes doesn’t sound like a lot, in the world of racing, it’s make-or-break. We came out way too hot, holding a 6:00-6:10 pace per mile for the first ten miles, which caught up to me before the half.

I couldn’t get my breath to regulate, my nervous system was on overdrive, I felt congested and bloated from the excess IV the day before and the travel, and my body failed me by starting my period (sorry, TMI) a full week before it was supposed to. I quite literally felt like my body was shutting down. My feet started to swell rapidly and my shoes felt too tight—I could just tell my foot was covered in blood so at the mile 20 marker, I stopped. I walked. I came just shy of giving up and facing my first ever DNF, when an angel in the form of a client of mine walked up to me and said “you’re having a shitty race, too? Let’s have a shitty finish together.”

And with my friend Mark by my side, we slogged to the finish line, stopped at every half mile, smiling, taking selfies, and just generally making light of the entire situation. My estimated finish time went from 2:52 to a 3:26 finish and I was honestly just proud of making it to the line.

CHICAGO #5 & #6: 2024 AND 2025

My last Chicago experience was a redemption tour more than anything. I wanted a chance to make myself proud and enjoy the full race again, not have my last memories on my PR course being me dragging my bloody feet across the finish line almost forty minutes later than I planned.

As a Maurten ambassador, I was gifted the opportunity to run this race for Team Maurten, and it was an excellent day. My goal was to score another Boston Qualifying time (which I did, but then was unable to use because they bumped the age standards by five minutes, but that’s a topic for another blog!), and of course to have fun. This was the first Chicago I did solo as my wife was in another part of the country for a wedding, so it was all about the vibes from spectators I didn’t know, and honestly, it was amazing! The day was beautiful and the crowds were loud, and I felt like I was sailing across the finish line.

That Chicago finish line is probably my last one, as I was supposed to run the race this year as a legacy finisher, but ultimately decided to defer my race. My goals are slower and woodsier now, as my days of running world majors (with the exception of Boston) has come to a close. I wish everyone toeing the line at Chicago this year the absolute BEST vibes, and remember a few key things:

The GPS is WONKY the first few miles in the city. Don’t trust your watch; follow a pacer!

Don’t stress about running on the carpets over the bridges. They get crowded and it’s actually safer to just navigate the grates.

Take in all the sights! This is the best way to explore the city In so many different areas that are not always on the usual tourist list.

Deep dish pizza post 26.2 miles just hits different.

Xo

Coach Kelly

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10 Things I Wish I Knew Before My First Marathon