You know the “don’t wear anything new on race day” and all the basics… you can get that anywhere else. So let’s focus on Chicago alone now.
Note to keep in mind: the marathon I did the most is NYC, so I might be biased and comparing, okay?
Pre-Race
This course is flat. Sit down. Think. Talk to your coach. Find a strategy and STICK to it. Whatever it takes.
If you want my opinion on how to race this course. This is very very simple, but won’t for everyone. On a course like this, you should execute a classic negative split. If you don’t know what that is, look it up and aim for the sky. I met some friends so I started a few corrals back -this can really help you to slow down the first few miles as it will be crowded. And don’t go around people, ok? NEVER NEVER, it’s wasted energy, distance, and they are there for a reason: to hold you accountable.
Study the course. The course seems simple because it’s all straightaways and out and backs (and it’s flat) but it is NOT simple. I was lost the whole race and that can really mess up your strategy. It is hard for people like me that don’t know the city, but still, take some time to look at the course, and memorize some landmarks, neighborhoods, water stops, and direction (for wind, etc). I really wished I had done that and it was my biggest mistake and regret. There are many bridges and big out-and-back turns that can really anchor your race strategy. Also, make a note of where are you going to see groups, have friends waiting, etc. All I remembered was to be ready for Chinatown, mile 21, and it was something but not enough. There is some here.
Also, this course is super flat. Hope you trained on long runs for flat. If you did this right, your last 5K will be amazing. BUT, right as you’re about to finish, there is a tiny little hill when you make the turn off Michigan Avenue onto Roosevelt Road that will look and feel like HELL. I am still upset about it. I knew it was there, but forgot, and thee b!tch beat me. It was the only time I walked during the race and I might be salty about it forever.
Check the temperatures for previous races, and prepare/pack for everything, it’s been really hot and also really cold. But mostly hot. So prep especially for that if you see it coming a few days ahead. Have at least two electrolytes drink the day before, have some that morning and bring saltabs for the race. You’ll be sweating. And chafing.
Learn to run tangents if you haven’t. Necessary.
I took the train to the city, you have to buy some card but I think your cell phone’s apple pay works just as well. It was so easy. And I also took the train to the expo back and forth twice, only once we took the wrong train. Learn the metro system and use it up (to avoid stupid not needed walking!)
Do not go to pick up your bib at the last minute, or on Saturday if you can avoid it Last year the lines were insane. I went Friday at 10 am and it took me about an hour, but I went back on Saturday with a friend at 12 to keep her company: she was in line for 2.5 hours – by the time we left lines were about 6 blocks long, crossing streets, and it was warm to be standing out there for so many hours the day before the marathon. If you’re coming directly from the airport, pick up some food and water bottles to make sure you hydrate through it. Don’t wait until you get there, last year was a real mess and the drinks vending machines were empty.
Race Day
The GPS!!!! The race starts in the city, big tall buildings everywhere and your GPS WILL be wonky. I like to go by manual lapping. Basically, turn off your auto lapping for every mile and lap when you see a mile marker. I remember last year my gps distance by the first mile was 2.5 miles, insane! You’ll also need last lap time and current lap distance, as well as elapsed time obviously.
The start is SUPER chill, do not stress about it, but get there with time to enjoy it, there is a bunch of walking. And check a bag, it is so easy to leave and retrieve.
Check the wind and wind direction that morning. You are doing long stretches in the same direction and once you know where you’ll have a wind coming at you, go towards a building or tuck behind a group, etc. Try not to be dumb to want to beat the wind.
I’d say this was the most shocking, THE CARPETS!! yeah, there’s carpets!!!!!! The race organization covers the gritty road/grates on the bridges with carpets. I don’t think the carpets are there to make the footing smooth but more so to warn you to pick up your feet and be careful. Okay? Those carpets are the alarms. I also remember a bunch of potholes, so keep an eye down.
Use your brain for pacing. Seriously. If you start too fast (remember that you’re going in the same direction for the first 10 miles) you’re gonna hate yourself. Also, think of mind games to kill the monotony of running straight: look for tangents, look for mile markers to lap your watch, etc. One thing I like to do in very flat races to switch my form and not get the same muscles to get stiff or to set on a motion is do pick – ups -maybe every time you see a mile marker you sprint to it (that’s what I do!).
There is not a lot of shade in the second half so if you’re not into squinting or getting sun in your face bring sunglasses, visors, SPF, whatever it takes.
You better have a reservation for lunch post-race. There’s some amazing places to eat in Chicago, plan it, and get a ressie ahead of time. I went to La Mar, as it was close to our hotel.
Sports stores on Michigan Ave might have some of the race gear and souvenirs, worth a little walk. The Nike store had more stuff than the expo.
If you want a few extra pictures and stuff, there’s some in my insta highlights, as I am now officially too lazy to write race recaps…
What else? Questions? What did I miss?
runningandthecity 
Love this perspective from someone who is less familiar with Chicago’s geography. And your descriptions of the “hill” on Roosevelt, the lack of shade on the Southside, and the carpets are spot on and bring back memories.
For the wind, you generally tend to get more of a headwind going north, especially as you get closer to the Lake. I always found the Westside, Miles 14 to 20 to be the hardest part of the race for me. There’s less energy from spectators, some of the stretches are a bit humdrum, and you may get feelings of hunger as you hit Pilsen and the aroma of tortilla chips and Mexican bakeries fill the air.
And, yes, the weather can be a mixed bag. One year there was such heavy rain that the winner feel after crossing the finish line, a few years later it was so hot and humid that they stopped the race and had a water shortage.
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