Chicago is home to a rich history, a growing economy, and cultural diversity, so it’s obvious to see why it’s the 3rd largest city in the U.S. The vibrancy and buzz of this city provides plenty of entertainment and a “something for everyone” feel.

We’ve researched and asked our team of locals for the inside scoop on what it’s really like living in Chicago. Read on to see 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!

LEARN MORE: Insider tips on finding your perfect Chicago apartment

Reasons to Live in Chicago

Chicago summers. While winter can seem to break city dwellers down, our summer is that much sweeter having made it through the cold, gray days. Once summer hits, every Chicagoan finds some real estate on an outdoor patio, roof-deck or on the lakefront to make the most out of these warm, balmy months.

Easy to commute within the city. Chicago Transport Authority has nearly perfected the art of public transportation. The train, aka the “L”, reaches every corner of the city. It’s reliable, mostly clean, and at $2.25 a ticket, totally affordable.

The food scene. Chicago is much more than deep dish pizzas and Italian beef. It’s home to Michelin-star awarded, historical, and line-inducing locales that are renowned, world-wide.

Midwestern mentality. Chicago is the perfect meet-in-the-middle between big-city curtness and sickly sweet Southern hospitality. Chicagoans are friendly, helpful, and good natured mid-westerners.

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.

Chicago Pros & Cons

Winter. It’s cold. Snow doesn’t melt but instead lines the roads and sidewalks, and turns brown, then gray, then black with dirt from the roads. People become less social, hibernating and ordering in. Work commutes get long and uncomfortable.

It’s cheaper than living on the coasts, but still expensive. This is to be expected of the third largest city in America. Average rent for a studio is $1,078. You may have 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 can often be temporarily closed. Noise from these projects seem to act as the soundtrack to a typical city day.

Wind from the lake. A crowd favorite in summers, Chicagoans can bemoan Lake Michigan as winter drags on and ‘lake-effect snow’ continues to flurry.

Tourists. 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.

Live Like a Local

There’s a never ending debate on Chicago style pizza. Our favorites are Pizano’s, Lou Malnati’s, and Pequod’s (veeeery local). Giordano’s is not Chicago-style pizza.

West Loop is the best foodie neighborhood. Home to both historic, award winning spots and new, innovative cuisine— West Loop is the place to be 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.

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 a great place 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 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

Malort. Was it strained through an old gym sock or aged in an old gas can?

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

In the past 2 years Chicago added 9,000 new units. This makes for a bustling, sometimes hectic housing market. Click here for the top luxury apartments in Chicago.

The city isn’t 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 are a swath of older buildings that date back to the 20s & 30s. 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 be gone by the end of the day.

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! Just 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.

Get in touch with your own personal apartment expert today! Click below to get started.

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About the Author
Abby Scott

Abigail is a freelance writer who loves exploring new places - especially in the southwest - and moved into her van full time last fall. When she's not working on writing gigs to support her #vanlife endeavors, she loves packrafting alpine lakes, floating lazy rivers, and trail running.