Ten Things I Like About You (Chicago Edition)
Ten Things I Actually Like About Chicago
After unloading on Chicago the other day, it feels only fair to admit something: there are things I genuinely like about this city. Quite a few, actually. My frustration comes from caring, not indifference. So in the spirit of balance—and maybe sanity—here are Ten Things I Like About Chicago.
1. The Lakefront
The lakefront really is special. Miles of running and biking paths. Beaches that actually feel like beaches. That moment when the skyline rises behind you on one side and open water stretches forever on the other.
You’ve got pickup soccer games, families grilling, twenty-somethings playing volleyball, people swimming, biking, running, walking dogs. It’s alive in the best way. On a good summer day, Chicago feels like a place you’d choose to be.
2. The Sports Teams
I’m a sports guy, and Chicago delivers there.
The Blackhawks, Bears, and Cubs are all top-tier for me. Even in bad years, they matter. Beyond that, we’ve got two basketball teams, two soccer teams (and yes, I do count women’s soccer), and enough sports culture that you’re never far from a game, a bar argument, or a shared heartbreak.
Sports bind people here in a real way.
3. Diversity (The Real Kind)
Not in the buzzword sense. Just… everybody’s here.
Different cultures, backgrounds, languages, traditions—all living on top of each other. It makes the city richer, louder, messier, and more interesting. Which leads directly to…
4. The Food
This is where Chicago punches way above its weight.
Yes, hot dogs. Yes, deep dish. (Also: tavern-style, which I eat far more often than deep dish.) But the real story is that you can get any cuisine you want—and it’s usually cooked by people who actually know what they’re doing because it’s their food.
Years ago, my younger son asked for Chipotle because he wanted Mexican food. I stopped the car and said, “Uh, we live in Chicago.” Then I took him to L’Patron. Lesson learned. Since then, he’s known what’s up.
5. The People
Not the politicians. Not the loudmouths. The regular people.
Midwest sensible. Friendly. Solid neighbors. People who shovel each other’s sidewalks, chat at the bar, help when something goes wrong. For all my issues with the city itself, I genuinely like the people who live here.
6. Public Transportation
I don’t use it as much as I probably should, but it’s there—and it works.
Trains, buses, bikeshares, scooters—you can actually live here without a car if you want. When I think about moving to Utah, this is one of the trade-offs that gives me pause. Out there, you’re driving. Always.
7. Neighborhoods
Chicago is truly a city of neighborhoods.
Some have higher crime, yes. And unlike New York, our neighborhoods tend to be more ethnic and class-segregated, which is a real flaw. But each neighborhood still has its own identity—its festivals, parks, murals, corner bars, and local spots that feel personal.
You don’t just live in Chicago. You live somewhere.
8. Health Care
This is a big one, especially as I get older.
Chicago has outstanding hospitals, many tied directly to medical schools. Top-tier doctors. Top-tier treatment. When something serious happens, you want to be in a city like this.
9. Four Seasons
This one’s mostly here because my wife insists.
I’ll be honest: winter can go pound sand, and August humidity is a crime against humanity. Somehow it feels colder here than in the Wasatch Mountains, which makes no sense. But fine—we get seasons. Snow, spring, summer, fall. Variety counts for something.
10. Colleges
We’re not Boston, but we hold our own.
Between Northwestern, the University of Chicago, UIC, DePaul, Loyola, IIT, and a bunch of others (no offense to the “lesser” ones), the city stays young. You feel it in places like Wrigleyville or Lincoln Park—energy, movement, people figuring things out.
That matters.
So yes, Chicago frustrates the hell out of me. But it also has moments—real ones—where I get why people love it. Maybe the truth is that Chicago, like most complicated things, is hard to live with and hard to leave.
Some days one side wins.
Some days the other does.