11 Things People Wish They Knew Before Moving to Chicago

Moving to the Windy City?

The brochures will tell you about the Bean, but they won’t prepare you for the city’s real quirks.

We scoured Reddit to find the most popular advice from locals and transplants on what they wish they knew before moving to Chicago.

Forget the official guides—this is the real deal.

1. You Need to Learn The Grid. No, Really.

This was, by far, the most passionate point.

Long-time Chicagoans are baffled by anyone—especially natives—who rely solely on GPS.

The city is built on a beautifully logical grid system, and learning it is considered a rite of passage.

As one Redditor explained,

“Learn the city grid by numbers. It’s not that hard and will make your life easier… 8 blocks to a mile.”

The system starts at the intersection of State Street (East/West) and Madison Street (North/South), which is the 0/0 point of the city.

From there, every 800 address numbers is roughly one mile.

Another user shared a handy trick learned from riding the train:

“800 N is Chicago Ave, 1200 N is Division, 1600 N is North Ave, etc.”

This isn’t just an “old school Chicagoan thing”; it’s the secret code to truly understanding your surroundings.

2. The Winter Hibernation is Real (and So is the Vitamin D Deficiency)

Everyone knows about Chicago winters.

But the cold is only half the story.

The real challenge is the psychological shift.

As one user warned, “they don’t talk about how much you will want to hibernate… and how bad the seasonal depression can get. The days get dark sooooo early.”

The advice? Be proactive.

Find indoor hobbies, stock up on Vitamin D and magnesium, and force yourself to be social, even if it’s just “hanging out at your hibernating friend’s house.”

A pro tip: Get your Illinois ID ASAP for free entry to the Garfield Park and Lincoln Park Conservatories—a lush, green escape when the world outside is gray.

3. Your Car Might Be More Trouble Than It’s Worth

If you’re bringing a car, prepare for a baptism by fire.

Redditors lamented the bureaucratic maze of “the city sticker or emissions test,” which blindsides many newcomers.

One user joked, “I’ve been saying, we need an orientation…”

Between aggressive drivers, street cleaning schedules, permit zones, and what one person called “bogus tickets and fees,” your car can feel like a part-time job.

In fact, many find they don’t even need it. “I overestimated how much I’d use or even want my car,” a transplant admitted. “Sold it 5 months into moving here.”

4. Chicago is a “Drinking Town”… With Options

“Chicago is a drinking kind of town,” one commenter stated bluntly.

“A lot of interaction with people, especially in the winter, will involve having a drink.”

While the city’s bar scene is legendary (start with a shot of Malört, if you dare), it’s not the only way to socialize.

The thread was full of people pointing out the boom in non-alcoholic options.

“TONS of places offer NA options and even cannabis infused drinks,” said one user.

Another added, “I have met a surprising number of people here that don’t drink.”

So while the culture is strong, you won’t feel out of place ordering a mocktail.

5. Your Entertainment Calendar Will Be Permanently Full

One of the biggest pleasant surprises for newcomers is the sheer volume of things to do.

“I may have gone to more comedy shows and concerts in the last year than I have in my entire life,”

one happy resident shared. Another, who had lived in NYC and LA, agreed: “Chicago just always has something going on that I want to attend.”

From summer street fests in every neighborhood to a thriving live music scene and endless parks like the 606 trail, you’ll never be bored.

6. The Weather Has Two Settings: “Sauna” and “Ice Planet”

You’re prepared for the cold.

But are you prepared for the heat?

“That it was gonna be hot as hell sometimes! I had no clue!!” exclaimed a user from California.

Chicago summers are no joke, with brutal humidity and days where the heat index soars past 100°F. Someone even dropped the terrifyingly accurate phrase: “Corn sweat.”

Basically, you need a wardrobe for two entirely different climates: one for surviving a blizzard and another for surviving a tropical swamp.

7. Making Friends is a DIY Project

While Chicagoans are proud and generally friendly, you can’t be passive about building a social circle.

“You can only be social by being proactive,” one commenter stressed in bold. “Waiting for others to reach out will leave you waiting a long time.”

The good news?

The city makes it easy. Join a rec sports league, take a class through the Park District, or find a volunteer group.

People are open, but you have to make the first move. As one user put it, “You can’t sit at the end of the bar waiting for people to come up and talk to you.”

8. The Wind is Not Just a Lake Thing

You think you understand the “Windy City.”

You picture a stiff breeze blowing off Lake Michigan.

You are wrong. “NO, it blows from all directions in all neighborhoods, brutally,” a user passionately explained. That bone-chilling gust will find you when you’re five miles inland, turning a 30-degree day into a test of survival.

The key, as locals know, is layering.

9. It’s the World’s Biggest Small Town

For a metropolis of nearly 3 million people, Chicago can feel surprisingly small.

“Everyday I run into someone I know on a first name basis,” a resident shared. “Coming from a teensy… suburb where everyone knew everyone, I thought this would be a land of anonymity. It is not.”

This is the charm and, occasionally, the curse of the city. You’re part of a community, whether you’re ready to socialize on your grocery run or not.

10. The City is a Patchwork Quilt of Segregation

Several users pointed out a stark reality that often gets overlooked in glossy brochures: Chicago is one of the most segregated cities in America.

“Drive in a radius around the city it’s very jarring,” one person noted.

Understanding this history and its present-day effects is crucial to understanding the city’s complex social fabric and the vastly different experiences people can have from one neighborhood to the next.

11. Civic Pride is Off the Charts

Finally, be prepared for an almost startling level of local pride.

Chicagoans love Chicago.

They will defend its pizza, its sports teams, and its flag with a passion that borders on patriotic.

One commenter summed it up perfectly with a tweet they saw: “Chicagoans are so patriotic for their country (chicago).”