If you’ve never lived in the Midwest before, this friendliness can be straight up jarring; people are going to ask you about yourself and your day and actually mean it. Weird, right?
A move to Chicago is easier than, say, a move to Tulsa. There’s history! There’s amazing restaurants, museum, and architecture! If the city is too much for you, there are great ‘burbs! It really has it all (minus all the snow). Here’s what you need to know before you make your way to The Windy City.
Chicago is certainly in the pantheon of the country’s best food cities, and you need to take advantage of that. There are plenty of incredible new restaurants opening every quarter, but we recommend you hit up the classics first. That way you can more easily trick the locals into thinking you’re a local. Right? Right.
Deep dish pizza is a thing. Chicagoans don’t really eat it, but everyone has an opinion on it, so you need one too. There are 52 Lou Malnati’s locations, so you know where the tourists go. Our pick will forever and always be Pequod's Pizza, but you can read more about our thoughts on this casserole pizza in our Deep Dish Guide.
The other two things you’re going to need to eat are significantly more enjoyable. First is the Chicago Dog: A beef frank topped with onions, pickle relish, yellow mustard, a pickle spear, tomato wedges, pickled peppers, and some celery salt. If you put ketchup on it, you will reveal yourself as a fraud (it’s like that scene in Inglourious Basterds where he does the “3” wrong). We like The Wiener's Circle and Superdawg Drive-In, but...let’s be honest...any hot dog stand will suffice.
Chicagoans also love Italian beef sandwiches. It’s a lot like a French dip, but it’s topped with some giardiniera and served on an Italian roll. Go to Portillo’s and Al’s Beef.
If you’re really, really, really desperate to fit in, try a shot of Chicago’s signature drink: Malört. Blech.
Photo courtesy of Lou Malnati's
Chicago has five professional sports teams, which is kind of insane for one relatively small city. This is great news if you’re a sports fan in general, but if you’re not one, you better learn to love ‘em—or at least get good at faking it. A visit to Wrigley Field is a must, regardless of your interest levels. The only real issue is deciding if you’re going to be (or pretend to be) a Cubs or White Sox fan. Ask your friends or pick based on your color preference.
Like we mentioned at the start, Midwesterners are nice. Really nice. What you should do is check out some of our neighborhood guides and see which sounds the most like you (or the you you want to be), then plan accordingly, because that’s what everyone else is doing. Of course, the city is also full of people who have hobbies just like you, so keep your eyes peeled and do a little research. At the very least, start hanging around the neighborhood bar...just don’t become that guy who never leaves.
Unless you’re living deep in the ‘burbs, you probably aren’t going to want to deal with having a car in the city. Even if you have one, chances are that you’ll leave it in your garage—finding parking is a recurring nightmare we have. Get used to riding the “L” around town and walking, which will come in handy since you’ll be eating all those hot dogs. Of course, the city also is peppered with Ubers, so use them.
Chicago has a ton of amazing history. Once you’re all settled in, you should absolutely take the time to head to some museums, maybe go on some tours, and even scope out all the tourists at Navy Pier. Here’s our guide to the Chicago touristy activities actually worth doing.
We don’t like repeating ourselves, so just go check out our guide to Chicago’s best outdoor activities.