Look, there is a LOT to love about the Big Apple.
But when we asked our community exactly what Chicago does better than New York, the evidence started piling up.
Here are the things Chicago simply does better than NYC.
Do you agree?
1. Its Cleaner
If there is one hill Chicagoans will die on in this debate, it’s this one. The difference in cleanliness between the two cities isn’t just noticeable; it’s structural.
Chicago possesses a secret weapon that New York City sorely lacks: a comprehensive alley system.
Following the Great Chicago Fire of 1871, our city planners had the foresight to redraw the grid with designated service lanes behind buildings. This sounds like a mundane urban planning detail until you visit Manhattan in August.
In NYC, because there are almost no alleys, residential and commercial trash must be piled directly onto the sidewalks where people walk.
These mountains of black bags sit there, marinating in the summer heat, often leaking “garbage juice” across the pavement.
2. It’s more affordable
The price difference isn’t just a number; it completely changes your lifestyle.
In New York, finding an apartment with a dishwasher or a basement laundry room feels like winning the lottery.
In Chicago, that’s just the standard. A regular place in a cool neighborhood here often comes with central air, your own washer and dryer, a back porch, and a parking spot—amenities you have to be rich to get in Manhattan.
This value extends to everything, from hotels to happy hour. You simply don’t need to be a millionaire to live with dignity here.
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3. Easier to navigate
While New York has a subway train coming every few minutes, Chicago wins on pure logic.
Our city is built on a perfect grid system that makes it almost impossible to get truly lost—just remember the Lake is always East.
Unlike NYC, where having a car is a nightmare reserved for the super rich or the crazy, driving is actually a normal option here.
You can own a car, park it at the grocery store, and escape to the suburbs without a total mental breakdown.
Whether you take the ‘L’ or drive, getting around just feels less chaotic.
4. It’s more friendly
People love to debate “Midwest Nice” versus “East Coast Blunt,” but the difference here is real.
New Yorkers might help you fix a flat tire while calling you an idiot, but a Chicagoan will help push your car out of a snowbank without saying a word.
The city simply lacks that exhausting “rat race” energy. It’s calmer here. Bartenders want to chat, strangers say hello, and the vibe feels less like a battle for survival and more like a massive small town where neighbors actually look out for each other.
5. It Smells Better
This ties right back to the alley advantage. Because we don’t pile our trash bags on the sidewalk like New York does, our streets don’t reek of hot garbage juice cooking in the summer sun.
In Manhattan, walking down the block in August can be an assault on your nose.
Here, the trash is hidden away, and the air is cleared out by the fresh breeze off Lake Michigan.
It’s a simple difference, but it means you can walk around all day without holding your breath.
6. Food (of a certain kind)
New York might have the volume, but Chicago wins on the food regular people actually eat.
The consensus is that the “middle ground” in NYC—the stuff between cheap street eats and ultra-expensive fine dining—is often overpriced and disappointing. In Chicago, that sweet spot is where we shine.
You can have an incredible, memorable dinner here for a fraction of the price of a Manhattan equivalent.
From tavern-style pizza to top-tier neighborhood bistros, the food hits harder, costs less, and doesn’t require a reservation made three months in advance.
7. Architecture
New York is a concrete canyon; Chicago is an open-air museum.
Because our streets are wider and buildings are set back from the river, you can actually see the skyline here instead of just staring at a wall of steel.
As the birthplace of the skyscraper, we prioritize style over just packing things in.
The city feels open and designed, rather than suffocating. There is a reason the architecture river cruise is the one tourist activity locals actually recommend—it really is that stunning.
8. Interesting Neighborhoods
Chicago isn’t just the downtown Loop; it is a collection of distinct neighborhoods that feel like their own small towns.
While New York often feels like one massive, endless sprawl, spots here like Andersonville, Wicker Park, or Hyde Park have their own completely unique vibes.
You actually get tree-lined streets, front porches, and backyards—things that make the city feel livable rather than just dense.
It feels less like a concrete jungle and more like a real community where you can put down roots.
9. Outdoor Spaces
New York has Central Park, but we have the Lakefront—and unlike other cities, we didn’t ruin ours by putting a massive highway right in front of it.
Our 18-mile trail is a wide-open public treasure where you can bike, run, or swim without obstacles.
While New Yorkers might have better mountains a train ride away, Chicago wins on immediate access.
You can leave your office or hotel and be on a sandy beach in ten minutes. Plus, our waterfront holds the Shedd Aquarium, which beats the Coney Island equivalent any day of the week.9. Community
There is a saying that people move to New York to be someone, but they move to Chicago to live.
The vibe here is simply less frantic. You don’t feel that constant, exhausting pressure to be working on the “next big thing” every second of the day.
While New York can feel transient—like a stop on a career ladder—Chicago feels like a home.
We have our issues, but there is a deep pride here. People settle down, build real friend groups, and stick it out through the winters together, creating a bond you just don’t find in a city of transients.
10. Sports Culture
You simply cannot replicate Wrigleyville. New York has historic teams, but they don’t have a stadium dropped right in the middle of a residential neighborhood where you can watch the game from a rooftop across the street.
Whether you root for the Sox or the Cubs, sports here are a religion based on loyalty, not just winning.
Fans stick by their teams through decades of heartbreak, creating a die-hard atmosphere that makes a game day feel like a bucket-list event, even if you don’t care about baseball.
