Moving to Chicago: 10 Things to Know

We all know deep dish is life, ketchup is a sin & that we have a cloud that looks like a shiny bean. So, what do you actually need to know if you’re moving to Chicago? 

1) Festivals are a thing.  

Pride Fest, check. Ribfest, check. Every other fest known to man, check. Besides the obvious Lollapalooza, Chicago jam packs its summer with festivals and events, and we honestly pretty much love them all. It also helps that many offer free admission. Whatever you’re in the mood for, there’s always food to eat and music to listen to in the city. 

2) The Grid System  

You have no excuse not to know where you’re at in Chicago—our streets are based off of an almost perfect grid system. As long as you can remember the few major streets that run diagonally & Lake Shore Drive, you’re golden. 

Pro Tip: While on the topic of LSD (yes, many people do abbreviate it to that), it is only for cars. No trucks or bicycles please.

Photo by  Sawyer Bengtson

3) The Tamale Guy

Welcome to your new best friend. Obviously there’s more than just one guy, but ya know…he’s "the guy.” So depending on what neighborhood you’re in, there’s a guy who brings you fresh, delicious tamales at the bar. Yes, you read that correctly. Tipsy you can eat glorious tamales without ever leaving your barstool. Welcome to Chicago—you have truly made it.

4) We have the street art. 

Now, we’re no Miami or New York, but walking down the streets of the city, it’s hard not to find some inspiration from the pieces of work you see. From the exteriors of vintage buildings to the interiors of brand new construction, you’ll find art from some of the country’s hottest artists. 

5) The CTA is your friend.

If driving, your 2-mile commute might take 10 minutes or almost an hour. It’s really a toss up. Thankfully, we have an amazing public transportation system called the CTA, which is surprisingly (considering my career choice) one of my favorite methods of transportation. The CTA can get you almost anywhere in the city on a pretty dependable schedule and for not a lot of money. 

Pro Tip #1 (Yes, there is more than one. This is Chicago after all.)

So, we do have rules for using our escalators. Think of the rules of driving in relation to an escalator. The faster cars pass on the left while the slower cars stay on the right. Escalators are essentially the same—walk up on the left side, stand on the right. Please don’t be that person. 

Pro Tip #2
While one of our favorite L lines is the Red Line (24 hours baby), you know that if you’re traveling north during evening rush hour with a Cubs night game you are going to wait at least 2-3 trains before ever getting on. We Chicagoans have perfected the Sardine Shuffle or opting for the Brown Line or bus all together. 

Photo by  Sawyer Bengtson

6)  Breweries are a plenty.

What’s up, beer snob? Not so surprising—people love a good brew. Luckily, Chicago offers a great selection of local breweries. Some of the neighborhood gems even let you bring your pooch. 

7) The pizza really is that good.

Ok, ok…I’ll move on….

8) There’s a hobby for everyone. 

You can be almost anyone you want to be in Chicago. In one day, you could run and bike along the Lakefront Trail or the 606, enjoy some yoga or hit up some indoor rock climbing, and later go to an art gallery and cap it off with karaoke in a private room with your friends. Chicago’s got you, internet stranger. 

KM at  Dovetail

KM at Dovetail

9) Wind Tunnels are real.

Remember that grid system I mentioned? Well between that and Lake Michigan, we get this really awesome thing (spoiler alert: that was sarcasm) where things get pretty windy. So don’t be caught off guard if all of a sudden you’re swept up by the wind or feel like you're defeating some invisible force while walking across the street. We’ve all rocked the “I swear I brushed my hair this morning” look. 

10) Seasons aren’t real. 

The concepts of Spring & Fall are fairly unknown to most Chicagoans. Take today for example—as I'm writing this it’s mid-April, and it snowed today. IT SNOWED. Last week it was in the upper 60’s. Now just imagine that type of questionable weather every day, all year round. Basically, we've just learned to bring at least a light jacket everywhere with us at all times. 

Ready to find your Chicago home? Let's chat.