Get us in your inbox

shutterstock, chicago, chicago skyline, downtown, downtown chicago, chicago river, bridge, loop, the loop, cityscape, skyline view
Photograph: Shutterstock

11 dumb questions people from Chicago get asked all the time

If you live in Chicago long enough, you'll hear these questions from people who don't understand how great our city is

Written by
Time Out Chicago editors

When you live in Chicago, you're bound to get hit with some fairly annoying questions whenever you leave the city. For some reason, living in a major city seems to give everyone the license to grill you with variations on the same set of of questions, each seeking your opinion on a different (and typically inaccurate) stereotype. From your tolerance of cold weather to your run-ins with a certain notable Chicagoan, you might as well start formulating your answers to these commonly asked questions.

"Do you eat deep dish like all the time?!"
Nope, it's more of a meal for special occasions, like every time we host an out-of-town visitor (which must be giving them the impression that it's our go-to option). In reality, while the best pizza in Chicago certainly includes the extremely cheese-y, eat-one-slice-and-you're-full deep dish variety, most of us enjoy thin-crust, Detroit-style, Roman pies or Neapolitan 'za on a more regular basis.

"How do you survive without a car?"
We've got trains, buses, bikes, taxis and rideshare services that get us around the city, so life without a car is entirely possible. Plus, nearly everyone has at least one friend who owns a set of wheels and is inevitably saddled with helping us move or ferrying us to and from IKEA.

"You must spend most weekends downtown, huh?"
Believe it or not, staring at the Bean and walking up and down the Magnificent Mile loses its luster pretty quickly. While most Chicagoans appreciate all of the great museums, parks, shopping and attractions in and around the Loop, it's only a small slice of a city that's filled with exciting new things to see and do.

"How do you handle the winters?"
Buy a warm coat, invest in a decent pair of boots and go about our lives. We may complain about it, but many of us like experiencing the seasons (even the one that's accompanied by polar vortexes and piles of snow).

"All I ever hear about is how violent Chicago is—do you feel safe?"
This one's complicated. There's no denying that gun violence is a problem in Chicago, but homicides in the city are on the decline and Chicago still doesn't rack up nearly as many violent crimes per 100,000 people as cities like Detroit and Baltimore. Like any major city, tragic violence can be an unfortunate part of life (often rooted in the city's historic segregation and an inequitable distribution of its economic resources), but most residents feel safe in their communities—and there are lots of people working to make them even safer—so keep your bulletproof vest "jokes" to yourself.

"Do you actually like Malört?"
It's an acquired taste, but some people genuinely enjoy Malört's singular blend of flavors, with notes of citrus, charcoal and rubbing alcohol. What we really love is watching the faces people make after taking their first shot.

"How's the weather? Must be windy, right?"
Sure, we get some gusts by the lake, but the nickname "the Windy City" doesn't actually refer to drafty conditions. Feel free to look it up its origins for yourself, we're all tired of explaining this.

"What's the best neighborhood?"
Everyone is going to have a different answer to this question, and not one of them is correct. Chicago is a city of neighborhoods, and every one of those communities is special in its own way. Visit every one of them and you can form your own answer to this question.

"Do you shun people who like ketchup?"
You may get a few strange looks if you ask for a bottle of ketchup at an old-school hot dog joint, but the average Chicagoan doesn't give a shit about your condiment preferences. Add the sugary tomato sauce to whatever you like and if you get any guff from somebody, pointedly ask them what they dip their fries in.

"Have you met Chance the Rapper?"
Every few years there seems to be exactly one famous Chicagoan that everyone outside of the city (including your aunt and family friends you only see once a year) latches on to, whether it's Harry Caray, Roger Ebert, Oprah Winfrey, Michael Jordan or Kanye West. As of late, it's Chance the Rapper—a guy who still live in the city and frequents local events, restaurants, bars and clubs. Many of us get the opportunity to watch him perform and some of us get lucky and spot him in a public setting, but Chance is an ultra-famous guy, so, no, we haven't actually met him.

"When are you going to move to New York or Los Angeles?"
While many people use Chicago as an affordable springboard to careers on either coast, there are lots of Chicagoans who are perfectly content to remain in the midwest's largest metropolis. There's no shame in sticking around a city filled with amazing people, delicious food and plenty of experiences you won't find anywhere else—plus, it's a hell of a lot cheaper than New York or L.A.

    You may also like
    You may also like

    The best things in life are free.

    Get our free newsletter – it’s great.

    Loading animation
    Déjà vu! We already have this email. Try another?

    🙌 Awesome, you're subscribed!

    Thanks for subscribing! Look out for your first newsletter in your inbox soon!