1. Your Neighborhood Defines You
Despite the numerous changes and facelifts the city has seen over the years, the backbone of Chicago is still its neighborhoods.
Residents are fiercely loyal to their area and everyone will be able to guess your demographics from your income level down to the beer you drink based on where you live.
2. Be Nice
Manhattan is always so quick to remind Chicago that the two cities don’t compare. So let’s clarify the biggest difference: you won’t find that self-important attitude here in Chicago.
They’re proud to be the third largest city in the country but no one feels the need to brag. People are nice here so check any attitude at O’Hare.
3. Pay The Extra For The Good Umbrella
On a rainy and windy day, you won’t walk a block without finding a mangled umbrella haphazardly discarded in a trash can. Invest in an umbrella with wind vents, they’re worth every penny in this city.
4. But That “Windy City” Name Has Nothing To Do With The Wind
It’s a common misconception but it’s actually in reference to the political climate in the city. And yes, everyone in Chicago knows it’s a circus.
5. And No One Calls It Chi-Town
Unless they’re trying to be ironic, of course. But even then it’s not all that popular.
6. Chicago Has Beaches
Just because you’re in a major city in the Midwest doesn’t mean you’ll never see a beach. Lake Michigan might not be an ocean, but it looks remarkably like one and you don’t have to worry about jellyfish or getting salt in your eyes.
No matter where you are in Chicago, you can be at the beach in 15 minutes.
7. Navy Pier Is For Tourists
You’ll go once and realize that’s more than enough. The Chicago Shakespeare Theater located there is the notable exception, so good it’s worth the crowds.
8. The Look Of Chicago Never Gets Old
The art and architecture of Chicago alone will make you truly proud to live here. And yes, it’s a giant mirrored bean. Because why not?
9. Respect Sidewalk And Escalator Etiquette
Keep sidewalks flowing in a standard traffic pattern by staying to the right and avoiding abrupt stops. On escalators, stand on the right and move on the left. It’s courteous.
10. Don’t Believe All That Ketchup Hype
You will see signs and hear rumors that putting ketchup on a world-famous Chicago dog is a crime so heinous, you’ll be excommunicated.
But the truth is, you’re free to use ketchup on whatever food you’d like, including hot dogs. Is it weird? Well, yeah. Will people stare? Probably.
You can search condos for sale, open houses for this weekend, new listings and price reduced homes in Chicago and beyond.
11. But Cheese Goes With Everything
Did I say the backbone to Chicago is the neighborhoods? I was wrong. It’s cheese. Glorious, glorious cheese. It can be put on everything and no meal is complete without it.
12. There Is No Such Thing As Spring Or Fall
If you believe the calendar, you’d think that winter starts in late December and ends in March. Keep dreaming!
Winter begins in mid-October and lasts through April in Chicago, so give up any plans for skimpy outdoor Halloween costumes and don’t be surprised if your Easter egg hunt gets snowed out.
13. You’ll Gain 10 Pounds Every Winter
Don’t let it make you feel bad, everyone does. The food is delicious and the temperatures are cold. You’ll shed it when the ground thaws out and you’re back outside again like everyone else.
14. Chicago’s King Sits On A Cooler Filled With Tamales
Lesser known than their hot dogs and deep dish, Chicago does tamales better than anywhere else this side of Mexico.
And if you see a man appear out of nowhere with nothing but a cooler filled with tamales, bow down. That’s The Tamale Guy and things are about to get delicious.
15. Chicago Pizza Isn’t Just Deep Dish
To many people’s surprise, there are plenty of thin crust options around including traditional and square-cut tavern style.
You can keep the comparisons to New York pizza to yourself, though. No one here is competing, they’re too busy stuffing their faces with awesome pizza.
16. But OMG, The Deep Dish!
There’s a reason why Chicago is known for their deep dish. Not only did it start here, but there’s nowhere else that will ever blow your mind this hard.
Grab the utensils, though, because deep dish is a legitimate meal.
17. You Don’t Need A Car
By El, bus, or train, the CTA will take you around every corner of the city that you need to be. Granted, it’s outdated, you’ll meet some interesting characters on your journeys, and you’ll probably be late, but you will get there.
18. If You Have A Car, Get Used To Tickets
Finding parking will become the bane of your existence in Chicago and parking tickets will be routine. But, your parallel parking game will reach gold medal status.
19. No, You’re Not The Only One Who Gets Nervous Looking At This
Speaking of parking, you’ll undoubtedly have many Final Destination style thoughts whenever you see the Chicago Parking Deck, no matter how long you live here. You’re not the only one.
20. Respect The Buskers
Chicago has some really great street performers. When you have a minute to spare, stop and watch, give them a clap, and then give them a little spare cash–especially if it’s Puppet Mike with his Puppet Bike.
21. Cubs Or Sox, Make Your Choice
The Chicago Cubs or The White Sox. You don’t have to be a native to cheer for the home team, but you have to pick one and stick to it.
You can’t have both. If you can’t decide, use the map to make your choice.
22. There’s No Point In Mentioning Anyone’s Accent
You have a better shot finding someone in Chicago who cheers for the Yankees than finding someone who admits that they have even the slightest hint of an accent.
23. Pass On The Chains
If you want to be a true Chicagoan, then give your cash to the little guys, not the big chains. Pass on Starbucks and try one of the many awesome coffee shops here like HERO, Bad Wolf, Wormhole and more.
24. Watch Out For The Bikes
Chicago has worked really hard in building a system for cyclists to get around the roads and the two-wheeled community is growing. But, it definitely makes the roadways crowded. Keep a look out, especially while parking and opening your car doors.
25. Your Cabbie Doesn’t Want Your Card
Don’t believe the cab driver who is yelling at you that he only takes cash, even when you’re staring at a credit card machine. He’ll probably even tell you that it’s broken. It’s all a big sham.
But if you know you’re going to be taking a cab and don’t feel like dealing with the hassle, carry cash.
26. The Truth About The South Side
Don’t take your Chicago geographical advice from the news or a few TV shows that will have you believing that Chicago’s South Side is nothing short of the gateway to hell. It’s just not true.
There are plenty of places you can go in the South Side that are good, just as there are some West Side areas that aren’t.
27. Michael Jordon Wins Life
Perhaps the greatest athlete of all time, Michael Jordan is legend. And Chicago is proud to claim him as their own.
28. John Belushi > Jim Belushi
Just know that John Belushi love runs strong. Jim Belushi hate runs even stronger.
29. You’ll Get An Education In Polish
Chicago has a large Polish population and the bars here are a popular destination. You’ll learn that “zimne piwo” is Polish for “cold beer” fast.
But if you’re not a heavy weight and someone offers you a shot of Malort, walk away.
30. How To Say The Street Names
If you want to blend in, don’t pronounce Paulina like the female name. It’s “Paul-eye-nuh.” Likewise, Devon is “Dev-on” and Throop is pronounced like “Chroop.” No one said it makes sense, that’s just the way it is.
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