The Summer Is Summering!

The sweltering, swampy heat is doing its best to ruin the glory of summer in Chicago.

Author

Conor Cawley
July 31, 2025

Since my last Conor Intelligence post, Chicago — along with a large percentage of the world — have been enduring high temperatures, humidity, and general crotch sweatiness this summer, and it’s enough to keep a guy inside for the next few months.

A Swampy Chicago Summer

Chicago was built on swamp in 1837. If you’ve ever told me you were hot while outdoors in the city over the last 4 years, you already know this, because I have told you. Probably multiple times.

It’s actually pretty obvious when you think about it. Despite being the third largest metropolitan area in the country, our summer nights sound like you’re in the depths of the rain forest thanks to a symphony of cicadas and other nightly bugs. Heavy swamp vibes.

4th of July in Chicago was a hot one in more ways than one. Source: Conor Cawley

Another fun fact, Chicago had to be built on top of a bunch of wood because of how swampy the area was, which is one of the reasons the Chicago Fire was so bad. Shout out to the kayak tour guide that seared these facts into my mind.

This summer in particular, though, has been a testament to Chicago’s swampy roots. If you’ve been outside for more than a few minutes during one of the several heat advisories issued over the last few months, your collection of moist under garments are likely all the proof you need of this fact.

At my ever-increasing age, this heat is becoming less of a fun obstacle to overcome and more of a full-on barrier to exiting the home. I’m not trying to induce heat stroke on an afternoon playground run, especially with a three-year-old whose cheeks turn bright red if you just say the words “heat index.”

As always, though, context is important. I’m currently putting the final touches of Conor Intelligence at my in-laws in Washington state, where temperatures are barely flirting with 80 degrees, it drops down to the low 60s at night, and the only inkling of humidity comes from leaving the shower on for too long.

And every time we leave the house, everyone except for my wife, my daughter, and I complain about how hot it is. If they only knew.

Dad tips of the month

  • Forts are friends - I’m no architect, but building forts has become the key to being the #1 played-with parent in our house. 🏰

  • Learn to hair - If you can’t put a pony tail in without pulling hair, you’re going to have a bad time. 👩 

  • Watch TV with them - Yes, their shows suck, but think about how annoying it is when someone you’re watching a show with just looks at their phone the whole time. 📺

Comic Spotlight

One of my oldest comedy friends and an absolute legend in Chicago, Deanna Ortiz is an outright delight to see on stage. Her quick wit and hilarious writing earned her the title of Best Comic in the city from the Chicago Reader not once, not twice, but three times, back-to-back-to-back, over the last few years.

She also has a background in porn (running the actors’ social media pages, not the other thing), and you can bet that makes a regular appearance in her set.

Deanna is headlining the legendary Zanies Comedy Club in Old Town TODAY (Thursday, July 31st) at 7pm and as of writing this, you can still buy tickets! So, ya know, do that!

Democratic Dictatorship: How to Be a Fantasy Football Commissioner

This week, for the 14th year in a row, I activated the two fantasy football leagues that I personally run and commission. One consists of college friends, most of whom lived in my freshman year dorm Camino (C4L). The other consists mostly of elementary, middle, and high school friends, who I have collectively known for more than 200 years.

Given the authoritarian aspects of being the lone commissioner of not one, but two fantasy football leagues, you can imagine the potential for drama. Uneven trades, sporadic rule changes, and frankly unfair point changes could conceivably tear friendships apart, and with a singular decider like me, I and I alone bare that responsibility.

Fortunately, over the last 14 years, I have been able to avoid these pitfalls with a strategy I lovingly refer to as a democratic dictatorship. Under this governing discipline, I regularly and consistently ask what my players want, encouraging votes, creating polls, and ensuring that everyone feels comfortable voicing their opinions about how the league should be run.

Then, I take all that feedback, evaluate it appropriately, and then ultimately do whatever I want. It takes the burden of cohesion off of the shaky infrastructure that can so consistently be democracy, and places it firmly where it belongs…

With me.

What I’m consuming this month

Sinners, HBO Max

It's hard to get to the theaters when you've got a three-year-old at home, which I now realize is very unfortunate, because this one would've been incredible on the big screen.

From the start, Sinners felt like a breath of fresh air, with unique storytelling, compelling writing, and deep characters that you are rooting for or against almost immediately.

Not a lot of movies have made me feel this level of enjoyment with my head pointed at a TV, especially over the last few years, so seriously check it out.

By the way, I am very much not a horror guy, just ask anyone that’s ever heard me talk about my PTSD from watching The Ring in theaters in seventh grade. I adamantly don’t like horror, but that didn’t stop this film from being extremely fun to watch.

Also, if you're letting some anti-woke nonsense prevent you from enjoying this movie, I genuinely feel bad for your whole life existence.

Now hot to trot on outta here

Remember when I said these sign offs were going to get weird?

As always, thank you for making it all the way to the end of Conor Intelligence. I mean, it’s not exactly a novel, or even a kind of long news article, but I still appreciate you making it all this way for little ol’ me.

Have an excellent summer, stay cool, and I hope to see you at the end of August for another edition of Conor Intelligence!