Ten Things I Hate About You (Chicago Edition)
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.