Chicago From A First-Timer’s Perspective

A little over a year ago, my best friend moved to Chicago. I was still getting over the whole ‘scared to fly’ thing, as well as the ‘too broke to buy plane tickets’ thing, so it took me awhile to visit. I was stoked when I finally made my way there last week—it’s the 3rd most populous city in America, so one can assume that there are some worthwhile sites to be seen. I wanted to love it. And I did! (Please take a moment to catch your breath while someone from New York admits to loving another city because, oh my god, the world revolves around us and we can’t appreciate any other city, ever. I’ll wait.) Here’s a tiny handful of what makes Chicago awesome (from my perspective):

No pigeons: While there may be pigeons of the Sporty Thievz variety, I didn’t see one bewinged rat during my entire stay. Chicago, whose D did you S? Point me in their direction. Share with me your secrets.

Sweet shopping: Chicago is full of both chains and boutiques, the inventory of which is suspiciously underpriced. In New York, I often find myself playing Tag. By that, I mean I see something I like, peep the price tag, then run away. In Chicago, I looked at a tag and was like, “I’ll take two, please wrap them so that I can present myself with a gift-like reward for being awesome at shopping.” One storeowner gave me a ring for free because “it’s the last one;” doesn’t get cheaper than that.

It’s small(er): Not small in the sense that you’ll run out of things to do, but small enough that you won’t lose friends and potential love interests because they live too goddamn far away. I can’t tell you how many friendships have been lost to the affordable housing in the Upper, Upper East Side. (Too many.)

Unassuming panhandlers: I’ve seen my fair share of panhandlers, but some of the Chicagoan panhandlers I encountered seemed to have graduated from the Oliver Twist School of Begging, constructing long and sorrowful narratives about their three-year-old son or their dead parents or both. They often look like they should be standing shirtless in front of an Abercrombie and Fitch rather than at the end of an off-ramp.

It’s clean: When my hostess and her boyfriend came to stay with me in Brooklyn, he (who had never been to New York, I think) was kind of shocked and appalled by all of the grime. I was confused by his reaction until I saw what he was comparing my block to—pristine sidewalks where the trash never peeks out of the bin, where there isn’t plastic-wrap from a bodega honey bun floating through the air, where the streets don’t resemble an ashtray – I GET IT. WE’RE DIRTY. Anyway, Chicago happens to have a few of those inexplicable tar stains on the sidewalk, which helped me feel at home.

Bloody Marys: Perhaps the proximity to Wisconsin helped stir this inspired recipe, but Bloody Marys in Chicago have Monterey Jack cheese in them. (For those of you who are curious, it’s cubed.) Also, I’m 98% certain you can drink from concealed containers on the street so long as you don’t act a fool. Chicago residents, confirm or deny.

Architecture: Aside from an impressive skyline, the residential architecture is equal parts aesthetic and functional (a result of the Great Chicago Fire). In New York, I’ve stumbled on beautiful blocks that are off the beaten path. They’re well maintained and expose you to tangible evidence of the city’s history. Almost every residential block in Chicago made me feel this way.

Jazz: The jazz scene in Chicago has roots and manages to bring several generations and races to the same clubs with the purpose of bonding over some seriously gifted talent. Coming from a city where your options are typically dive bar, sports bar, bro bar, club, overpriced music venue, or travelling an hour uptown to see something authentic; having an intimate, cheap music experience is nothing to knock.

There’s a lot more to enjoy about Chicago. The food is great, the public transportation is plentiful (and above ground), and I saw a yuppie woman unironically pushing her dog around in a stroller—an expensive one, at that. I got to see the Cubs win (apparently that doesn’t happen often). And of course, I got to see my best friend who, despite being a fellow East Coaster, is living a pretty sweet life there. I don’t see myself living there (I’m not pleasant enough), but I look forward to visiting again and again. Thanks for having me! (Is that how you act polite? Am I doing it right?) Thought Catalog Logo Mark

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