Chicago, the 3rd largest city in the U.S., is shaped by its rich history, a growing economy, and cultural diversity. This vibrant and buzzy city provides plenty of entertainment for fans of virtually any activity you can think of, with broadway, comedy, art, sports, and food standing out as some its strengths. If the thought of living in the big city appeals to you, Chicago delivers on all fronts.
To guide your exploration of Chicago as you decide whether or not to move here, we asked our team of locals for the inside scoop on what living in Chicago is really like. Read on to learn everything you need to know before moving to the Windy City.
Moving to Chicago and don’t know where to start? Reach out to AptAmigo to find the perfect apartment and neighborhood for you. The best part? It’s completely free!
Reasons to Live in Chicago: The Pros
Chicago summers. While winter is no laughing matter in this upper Midwestern city, our summer feels that much sweeter after the cold, gray days. Once summer hits, every Chicagoan finds some real estate on an outdoor patio, roof-deck, or the lakefront in order to make the most out of these warm, balmy months.
Easy to commute within the city. The Chicago Transit Authority (CTA) has nearly perfected the art of public transportation. The train, a.k.a. the El, reaches every corner of the city, extending outward from The (literal) Loop in downtown. It’s reliable, mostly clean, and at $2.50 a ticket, totally affordable.
The food scene. Touted by the late Anthony Bourdain as the only city in America able to compete with New York, Chicago stands for much more than deep dish pizzas and Italian beef. A trip to the original Al’s Beef will give you a genuine taste of this city, but really grasping its flavor requires additional meals at some of the Michelin-starred, historical, and line-inducing eateries found around every corner, many of which are renowned world-wide.
Midwestern mentality. Chicago represents the perfect meet-in-the-middle between big-city curtness and sickly sweet Southern hospitality. Chicagoans come across as friendly, helpful, genuine, and good natured.
Urban greenery. The city’s official motto is “Urbs in Horto,” meaning “City in a Garden.” All around Chicago, throughout spring and summer, rooftop gardens, sprawling lawns, and hidden flowerbeds spring up and color the city, making it feel less like a concrete jungle and more like, well, a city in a garden.
Related: Best Restaurants in Lincoln Park
Learn More: Insider Tips for Finding Your Perfect Chicago Apartment
The Cons of Living in Chicago
Winter. It’s cold. Although pretty at first, the snow doesn’t melt, but instead lines the roads and sidewalks, turning brown, then gray, then black with dirt from the roads. People become less social, hibernating and ordering in. Work commutes feel longer and more uncomfortable.
It’s cheaper than living on the coasts, but still expensive. A higher cost of living is to be expected in the third largest city in America. The average rent for a studio is around $1,400. You may need to rely on having roommates for longer than you’d like just to be able to pay the rent and have money left over to try all of Chicago’s delicious restaurants.
Construction. As the city grows, so too does the need for housing and commercial space. Roads and sidewalks often temporarily close. Noise from these projects act as the soundtrack to a typical Chicago day, a pretty standard facet of big-city life anywhere though.
Wind from the lake. A crowd favorite in summers, Chicagoans can bemoan Lake Michigan as winter drags on and a freezing chill blows off of it and through the icy streets.
Tourists. There’s no getting around this one. International travelers flock to Chicago in the summertime to tour the city, grab a Chicago dog, and stroll down Michigan Avenue. Locals (like you) know how to avoid tourists like a pro, wandering the area, for instance, during winter after visitors flee for warmer climes.
Live Like a Local
There’s a never-ending debate on Chicago-style pizza. For actual deep dish pies, our favorites include Pizano’s, Lou Malnati’s, and Pequod’s (veeeery local). Giordano’s is not Chicago-style pizza. But, Chicago-style tavern pizza, which many locals view as the true Chicago variety tastes equally good (or maybe even a little better).
West Loop is the trendiest foodie neighborhood. Home to both historic, award-winning spots and new, innovative cuisines — West Loop is the place to go no matter what you’re craving.
No one goes to Michigan Ave. Except tourists. Steer clear if you don’t want to get whacked in the nose with a selfie stick.
Chicago summers are packed with street festivals, with music, food, and everything in between. Locals love Mole De Mayo, Taste of Randolph, and Do Division Street Fest among dozens of others.
Where the best dive bars are. The Empty Bottle, Rossi’s, Cole’s Bar, The Hideout, and The Green Mill are true-to-form dive bars and great places to hear tales of old time Chicago over cheap beers.
Windy City Must-Haves
A big, long, puffy winter jacket. You won’t be able to brave Chicago winters without it.
A bike or a Divvy subscription. Chicago’s summers beg for weekend bike rides around the city. It’s the nicest way to get around when the weather is good.
A good attitude. Don’t complain about the winter. We know, as do all Chicago natives, that it’s cold, bitter, miserable, etc. Embrace it with your big ole jacket, and it will be easier to get through.
Comfy walking shoes. Wide streets, (mostly) calm drivers, and plenty of parks encourage strolls from neighborhood to neighborhood. Plus, you’ll get a better feel for the city and learn the lay of the land quicker if you walk.
A strong liver. Chicago bars are open late — many until 4 a.m. — and Chicagoans fully embrace it. There’s always a party, festival, concert, or happy hour going on.
Malort. Originally sold door to door by its creator, Carl Jeppson. No one can pinpoint what inspired Malort’s cult following, but one thing is for sure, you can’t leave Chicago without taking a shot of this distinctive liquor.
Things You Don’t Need When Living in Chicago
Malort. Was it strained through an old gym sock or aged in an old gas can? Taste it once to qualify as a local and move on.
A car. Parking is pricey and hard to find. Once you’ve secured a parking spot, chances are you won’t want to move your car all winter long. Chicago also sold their parking rights for billions less than they were worth. As a result, they only make money from ticketing and towing, and boy are they good at it!
The Chicago Housing Landscape
New construction in Chicago goes up all the time, with luxury apartments leading the charge. This creates a bustling, sometimes hectic housing market marked by great concessions and high competition for units at the same time. (You can explore some of the top luxury apartments in Chicago on our site.)
The city doesn’t sit on a fault line, so the sky’s the limit! There aren’t restrictive laws on building height or skyline, so high-rises are common and new construction can block your view at any point.
In contrast to these flashy skyscrapers, a swath of older buildings that date back to the 20s & 30s dot the landscape. Their beautiful architecture epitomizes Chicago’s historic neighborhoods and provides a textured relief from the otherwise glass and steel landscape.
Renters are extremely competitive, especially during the spring and summer months: When touring, bring your checkbook and sign immediately, or your dream apartment could disappear by the end of the day. Pro tip: avoid peak season and move during the winter because buildings offer the best rent deals while demand remains lower.
Explore Some of Chicago’s Top Neighborhoods: Best Neighborhoods in Chicago for Young Professionals
Find Your Dream Chicago Apartment
If you’re looking to call Chicago home, call AptAmigo, and we’ll help find the perfect place to start your next chapter. Let us know your preferences, favorite neighborhood, and any other relevant information, and one of our apartment experts will compile a list of buildings you’ll love. Pick your favorites from the list, and our team will schedule tours (or gather virtual tours) of the apartments you’re interested in, so you don’t have to. As your apartment dream team, we’ll be here for any questions or concerns you might have along the way.
* The original version of this article was first published on March 12, 2019.
Abigail is a freelance writer who loves exploring new places, especially in the Southwest, and lived in her van during the Covid-19 pandemic. When she's not working on writing gigs to support her #vanlife endeavors, she loves packrafting alpine lakes, floating lazy rivers, and trail running.
