Welcome to the Midwest! Chicagoans are the perfect blend of Midwest hospitality with a slight East Coast edge. Immense civic pride, a love of sports, food, and corrupt politicians make up the fabric of the Second City. It’s is an easy place for transplants to navigate and make friends. Where other cities are harder to break into, Chi-town is a big city without the pretension of Los Angeles or the grittiness of New York. Before moving to Chicago, familiarize yourself with the things every local knows.
1. Eat and Drink Staples
Chicago is one of the best food cities in the country. Period. Moving to Chicago means getting acquainted to the classics and knowing where to get them.
Deep Dish Pizza
Locals rarely eat this cheesy ‘meal in a slice’ version of pizza. It’s a delicacy reserved for visiting friends and the occasional drunken craving. Pequod’s is some of the best in town, but the popular (and touristy) Lou Malnati’s is still pretty decent.
Classic Italian Beef Sandwiches
Originating in the 1930’s, this regional sandwich is composed of thin slices of seasoned roast beef, simmered and served with au jus on a long Italian roll, topped with spicy giardiniera. Italian beef is the answer to all that ails and appreciating this hometown staple is part of your initiation into becoming a Chicagoan. Mr. Beef, Portillo’s, and Al’s Beef are all great places to start experimenting with which Italian beef combination is best for you.
The Chicago Dog
An all-beef hot dog on a poppy seed bun topped with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato wedges, pickled sport peppers, and a dash of celery salt. No exceptions, and don’t even think about ordering ketchup on your dog; ordering it is the quickest way to out yourself as an outsider. Some of our favorite places serving Chicago dogs are Maxwell Street Depot, Portillos, and The Weiner Circle.
Make no mistake about it, Chicago is a drinking town. GQ recently named it the Greatest Drinking City in America! So yeah, get your drinking pants on and wash down any of these Chicago classics with your favorite brew.
(Local’s note: Not long after you start making local friends, someone will inevitably make you take a shot of Malört. It’s a rite of passage, don’t ask questions—just go with it.)
2. Find your people
Chicago is like a big city and a small town, which can either be a welcome surprise or give you claustrophobia. Chicago is a perfect blend of transplants and locals, and those who have lived here long enough to be considered local. The city is also widely known as a city of neighborhoods, so where you choose to live will start defining your identity and help shape your opinion of your new city. Like it or not, each neighborhood comes with its own stereotypes, income levels, nightlife options, etc. Don’t let your zip code unfairly define you! Do the research and figure out which one best suits your interests and budget. Millennials gravitate to Lakeview, River North, Wicker Park, Logan Square, and the West Loop. Check out our deeper dive of neighborhoods for young professionals and our Local’s Guide to Chicago’s 10 top neighborhoods.
3. Sports Authority
Not liking sports can be a deal breaker when moving to Chicago. Nothing can bring the city together like day drinking at Wrigley or complaining about the Bears at Lottie’s on NFL Sunday. With baseball, you have to pick a side: Cubs or White Sox. No one likes both, so don’t even try to be Switzerland—neutrality is not accepted. If baseball isn’t your thing, fear not! With five professional teams in all the major sports, pick your favorite sport, and root passionately for your new hometown squad.
Go ahead and ditch the car—your wallet and the environment will thank you. The CTA may be slow, unreliable, and a tad disgusting, but it’s essential. Between walking, cheap Ubers, The “L”, and your trusty bicycle, your reliance on a car is minimal. Familiarize yourself with the Pedway for traversing the city in the wintertime. The Chicago Pedway is a network of tunnels, ground-level concourses, and bridges connecting businesses in the Loop and beyond.
Pro tip: Put accessibility to public transportation at the top of your “non-negotiables” when searching for Chicago apartments.
5. Prepare for winter
Your first Chicago winter doesn’t have to be a miserable learning experience. Invest in quality winter gear, like boots, parkas, and so on, because the right gear makes all the difference in surviving your maiden winter voyage. Aside from clothing, always keep HotHands warmers close by for stuffing in your gloves and shoes.
Your body will also take some adjusting, so pick up a quality moisturizer for your cracking face and extremities, and stock up on your vitamins. If you’d rather do things the old fashioned way, book a warm weather getaway in the dead of winter and soak up all that delicious Vitamin D. Late January or early February is the perfect time to escape and find the sun, since spring still feels so far away and the novelty of snow has long passed.
6. So many activities
Summertime in Chicago is a magical time full of patio drinking, visits to the beach, and a plethora of summer festivals and events. You earned it after the brutal winter, and seeing the awakening of the city in spring is akin to seeing the cherry blossoms in Japan. Getting a grasp of all the events is crucial to experiencing peak summer in the city. From the Famous St. Paddy’s Day parade in the Loop to Lollapalooza in Millennium Park, each neighborhood packs its calendar with events large and small to help you discover what makes the city so great.
Despite what the national media wants you to believe, living in Chicago will not mean dodging bullets the second you step off an airplane. Downtown Chicago is safe and incredibly clean, especially when compared with the condition of other major metropolitan areas. The Southside of Chicago certainly has places you need to avoid (or, at the very least, you need to keep your wits about you), but other parts are lovely and full of culture, great food, beautiful people, and art.
8. Be a tourist in your own town
Moving to a cool new locale means you will be getting lots of out of town visitors. Learn the best ways to show off your Chicago without going crazy. That means avoiding the hordes of tourists at Navy Pier. The Chicago architecture river cruises are a great way to see the city, and are equally enjoyable to tourists and locals alike. The Willis Tower (née Sears) will likely top most tourists’ wish lists for the amazing views—instead, show off your savvy localness by taking them to the Signature Room on the 95th floor for bites and drinks, and forgo the standing in a long line and paying $25 for the Willis Tower observation deck.
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