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.

Driving back to Chicago from vacation always triggers me.

You fly down the highway, relaxed, windows cracked, thinking maybe this time will be different. And then you hit the outskirts of the city and – bam – tolls, brake lights, construction barrels, and that familiar sense of doom. The vibe is dead. The spiral begins.

I start seething at the thought that I still have to live here, in a city I actively dislike. Chicagoans (read: my wife and kids) seem to accept this place as “normal,” even though most other cities don’t function like this. So without further ado, here are Ten Things I Hate About You (Chicago Edition).

1. Traffic

According to INRIX’s 2025 Global Traffic Scorecard, Chicago is now the most congested city in the United States, officially surpassing New York. Let me repeat that for those who say, “All big cities are like this.”

No. They are not.

Sitting in traffic for hours every week is not normal. It’s not charming. It’s not “the price you pay.” It’s time stolen from your life. See, wife? The data backs me up.

2. Roads

It’s not just traffic – it’s the surface you’re stuck on. Potholes that could swallow a small sedan. Cracked streets. Stoplights every damn block, timed perfectly so you hit every single red. You can drive two miles in Chicago and feel like you just ran an endurance event.

3. Crime

The mayor can say crime is “down,” but no actual resident believes it. Last week, a co-worker’s son was murdered. I’m going to the service today.

Shootings are background noise here. People lose their minds over a school shooting – and rightly so – but Chicago loses that many people every month and it barely registers. It’s tragic, it’s numbing, and it’s unacceptable.

4. Taxes

Between the city and Cook County, we were already near the top. Thanks to recent changes, we’re sprinting toward number one.

So let’s recap:

• Worst traffic
• Worst taxes
• High crime
• Bad schools

And we stay here… why exactly? It’s not because we’re getting good roads, safe neighborhoods, or stellar education in return. The City Council just passed another budget raising—what else—more taxes.

5. Politicians

Just awful across the board.

The Chicago Teachers Union openly and unapologetically owns the current mayor. Every solution is more money. Every failure is met with demands for – wait for it -more money. CPS functions like a jobs program first and a school system second. Student outcomes are an afterthought.

The rest of the City Council isn’t much better. No reform, no accountability, just endless spending. It’s no mystery why the city is losing population. Smart people leave.

6. The Malört People

You know exactly who I mean.

Suburban kids who move here after college and suddenly think they’re urban pioneers. They can’t wait for their college buddies to visit so they can force them to take a shot of Malört and film the reaction.

Here’s a secret: no one who actually grew up in Chicago drinks Malört. Ever. In the entire history of Malört. It’s a performative personality trait, not a tradition.

7. The Weather Gaslighting

Nine months of cold, gray misery, but everyone insists it’s “not that bad” because we get three nice weeks in June. Summer is hot and humid, winter is brutal, spring is mud, and fall lasts about eleven minutes.  Why live with that?

8. Housing Prices That Make No Sense

Home prices in Chicago are wildly out of sync with what you actually get. You pay a premium usually reserved for safe streets, strong schools, and functional infrastructure… and receive none of the above.

Want to buy? Prepare to overpay for aging housing stock, high property taxes, and neighborhoods you’re constantly told are “up and coming.”

Prefer to rent? Same problem. Rents keep climbing while buildings stay old, parking is a nightmare, and you’re still dealing with crime, traffic, and underperforming schools.

Chicago somehow manages to be expensive without being excellent, which might be its most impressive trick.

9. The High Cost of Everything

It’s not just taxes and housing – it’s everything. Gas costs more. Groceries cost more. Parking costs more. (Dear God, don’t get me started on parking fees) Tolls, fees, “convenience charges,” and random surcharges pile up until you’re bleeding cash without noticing where it all went.

You pay more at every step, every day, just for the privilege of being here. And again, that would be one thing if the city delivered top-tier services in return – but it doesn’t. You’re paying premium prices for a very non-premium experience.

Chicago has somehow mastered the art of making ordinary life more expensive than it needs to be.

10. The Constant Sense of Friction

Nothing in Chicago is easy. Every routine task – commuting, parking, paying a bill, getting a permit, scheduling anything—comes with unnecessary resistance. There’s always a form, a fee, a delay, or some unofficial workaround everyone just accepts.

Life here feels permanently set to hard mode for no apparent reason. You burn an incredible amount of energy just navigating ordinary days. And you don’t fully realize how draining that is until you leave town and feel how much lighter everything suddenly becomes.  I spend a few weeks each year in Utah and it’s NOTHING like Chicago.  No traffic, wide open spaces, no crime where we stay, life is easy.

That contrast is brutal.

I know. There are good restaurants. There’s culture. There are moments when the lake is perfect, and the skyline looks incredible. I get why people love it.

I don’t.

And every time I crawl back into the city, sitting in traffic, paying a toll to enter my own misery, I’m reminded that accepting something as usual doesn’t make it normal.

It just makes you stuck.