Guilty Pleasures Every Chicagoan Secretly Loves

portillo's cake shack
Kailley Lindman/Thrillist

There are certain guilty pleasures that everyone living in Chicago seems to draw enjoyment from -- and no, we’re not referring to your penchant for watching disgusting blackhead extraction videos on YouTube every night before bed. Whether rude, gluttonous, or downright ridiculous, these are more universal guilty pleasures that every Chicagoan deep down secretly loves.

Smugly reminding our friends in other cities how cheap our rent is

“You’re paying $1,200 a month to sleep in a closet in San Francisco? Wow, that must really suck. That’s how much I’m paying for my one bedroom. Did I mention that I also have a den and a patio? My apartment is like, one block from the Red Line.”

Complaining about tourists...

Yet still going out of your way to prove how nice locals are. One minute, you’re cursing the existence of every tourist on the Red Line, and the next minute, you’re thoroughly answering their ridiculous question about how to get from the Addison stop to Wrigley Field in your most polite, friendliest voice while internally rolling your eyes.

Ordering far too much food on GrubHub

You’ve definitely ordered two drinks so the delivery guy didn’t totally judge you -- one for you, and one for your invisible friend who’s really, really hungry. Anyway, whatever. It’s the restaurant’s fault for having a $25 delivery minimum.

Using brunch as an excuse to eat a day’s worth of calories for breakfast

Somehow, brunch makes it completely excusable to eat things you’d never eat during the week. We’re well-aware of the fact that “red velvet French toast” are actually slices of red velvet cake that have been battered and fried, and the Bloody Mary we’re drinking is a meal in itself, but whatever. If our favorite brunch spots call it breakfast food, then gosh darn it, it’s breakfast food!

Becoming an absolute hermit from November to March

The best thing about winter? It’s a free pass to be lazy. After four months of day drinking that leads into all-night drinking, countless street festivals and music festivals and weekends spent weaseling your way onto other people’s boats, your sofa and Netflix start looking mighty appealing.  

Pretending to be a fan of Chicago-based TV shows

But really watching for the novelty factor. “That front door that was on Chicago 911 Operators last night? That was totally my best friend’s cousin’s ex-boyfriend’s old apartment!”

Secretly loving the tourist spots that you swear are so cheesy

Nobody needs to know how much you love visiting the Sears Tower Skydeck and the Ferris wheel at Navy Pier.

Eavesdropping on other people’s conversations

Admit it: you’re totally guilty of listening to other people’s conversations on the CTA or at your local coffee shop and texting the most ridiculous anecdotes to your best friend. It’s the little things -- like being a snarky, nosy jerk -- that make living among millions of people tolerable.  

Suburban shopping malls

Ahh, the suburbs: land of free parking, buildings that house every single store you’d ever want to patronize, and no tourists, with Ikea right down the street. Ooooh, do I smell Cinnabon?

Instagramming your arrival in Chicago

If you’ve ever gotten the window seat on a flight back into Chicago, you likely have this exact same shot posted to your Instagram account -- probably with the caption, “Sweet home, Chicago.”

Portillo’s chocolate cake shake

Whatever. In Texas, I hear they eat deep fried butter.

Talking smack

While we’re true professionals at talking crap to each other based on our baseball team of choice, our real area of expertise is dissing other cities while touting our superiority. Anyway, it’s not like it isn’t well-deserved. Chicago smells like glorious chocolate, and yours just smells. YOU KNOW WHO YOU ARE.    

catching a cab chicago
<a href=";pl=edit-00">Tupungato</a> / <a href=";pl=edit-00"></a>

Driving or taking a cab when we could easily take public transit (or walk)

Remember: no matter how lazy you feel after your six block cab ride, it could be worse. At least you’re not one of those suburbanites that circle the parking lot 500 times to find a spot by the front door so they don’t have to walk an extra 30ft.  

Drinking holidays

People love to go on about how ridiculous holidays like St. Patrick’s Day or events like TBOX are, and yet so many Chicagoans participate that Clark St inevitably gets shut down every ‘holiday’.

Living in the past

It doesn’t matter that it’s been 31 years since the Bears won the Superbowl, 24 years since Ditka was “da coach,” 11 years since the White Sox won the World Series, and 18 years since Michael Jordan played for the Bulls -- all that matters is that it once happened, damn it.

Judging everyone you meet based on what neighborhood they live in

“Wrigleyville? Oh. So... you’re originally from Michigan and just moved here after graduating from Ohio State University, I take it?”

Sign up here for our daily Chicago email and be the first to get all the food/drink/fun in town.

Lisa Chatroop is editor of DailyUrbanista and has probably beat you at a sidewalk race at least once. Say hi on Twitter: @Chicagoista.