What I Learned About Chicago
My big trip for 2025 was to head up to the Windy City and spend some time with John and his wife Janice. The more you travel, the more you realize the importance of good travel partners. John is retired and Janice is a digital nomad. They travel a lot and it always seemed like they had great adventures. John is also a super fun person to be around and my oldest friend. So at the end of 2024, I started talking to them about doing a trip together. After batting around a few ideas, the planets aligned, and a trip to Chicago per the time of year and schedule worked out best.
The trip was phenomenal. Chicago is such an amazing city with delicious food, great neighborhoods, and surprisingly warm people (especially for such a big city).
As with any city, there are certain things that you learn when roaming its streets, eating in its restaurants, and drinking in its bars. Chicago has several fun nuances that I’ll discuss below.
Women are confident: This is probably the first place that I’ve been in some time, maybe ever, where there’s a high volume of women (attractive women) hanging out on their own. Spoiler alert, I went out pretty much every night in Chicago. It has a million bars, it's easy to do so. Most nights, I’d encounter a woman or a group of women just hanging out and having drinks. While you may be saying “duh, women can hang out on their own”, really think about it. Aside from the occasional bachelorette party or some girls nights out, how often do you see women hanging at bars? And really, women by themselves at night. I do realize that safety is a consideration.
Since I was solo for some of my trip, I talked to a number of women hanging out on their own and there was a confidence that they exuded that was interesting, alluring, add whatever adjective you choose. None of these women were waiting for someone. None of them were looking for dates or to be picked up. They were just out, having a good time, decompressing on a Tuesday. I may not be the right person to convey this message, but I feel it takes a woman or anyone a lot of confidence to go out on their own. I admire it and found it very attractive.
Chicago is crazy walkable: Aside from Mexico City, Chicago may be the most walkable city that I’ve ever visited. You can easily loop from neighborhood to neighborhood, pretty seamlessly. Especially on the northside. Especially via scooter. Pretty much everyday that we were there, we took a long walk through a bunch of tree and historic building-lined streets. It never felt like a heavy lift and we were always close to an interesting restaurant or bar. I’m sure this is a much more challenging walk in the winter, but that’s why you go during the spring or summer. Right?
Deep Dish Pizza is the truth: This may seem cliche, but the second best thing I put in my mouth while in Chicago was the deep dish pizza from Giordano’s (yeah, I know, but it was the closest to my Airbnb). The sauce was sweet and delicious, the crust was perfectly flaky, and the cheese had a mouthfeel that just worked with all the other parts. Most guides tell you to avoid the deep dish pizza because it’s super touristy but some of the best things are. This pizza was one of the best things I had in a trip full of delicious treats. No regrets.
Hanging on the Beach: When you are on Lake Michigan in the late spring, early summer, you might as well be on St. Pete Beach or Cocoa Beach. The area comes alive with sunbathers, beach volleyball players, picnic-ers, and people in love. There’s nothing like the energy of a place when weather is close to perfect for the first time in a long time. I was lucky to catch Chicago at this time of year. I know the weather is mostly brutal. But for now, it’s in the low 70’s and sunny and life feels simple and festive.
Iconic Architecture: The first thing we did when met up in Chicago, besides eat a hot dog and drink a beer, is take an architecture tour on the Chicago River. I’m in awe of the buildings. The architecture here is next level and represents some of the best found anywhere in the world. From the “Honeycomb” building to the Wrigley Building and so many quirky spots in between, there’s so much to geek out on, if you’re into it. Coming from Florida, it’s nice to see a place that’s so intentional about the look and feel of its buildings. It’s a combination of history and aesthetic appeal. It’s true eye candy.