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?) TC mark

More From Thought Catalog

  • http://twitter.com/emilybelden emily belden

    Less pigeons, more bros.

  • http://twitter.com/emilybelden emily belden

    Less pigeons, more bros.

  • http://www.facebook.com/msteffen1 Mark Steffen

    Refreshing.
    And yes, from a former Chicagoan, it may not be “legal” to drink from concealed containers, but no one is going to do anything about it. 

    More bros, for sure, but you can avoid them in the same way you avoid Murray Hill.

  • http://www.facebook.com/msteffen1 Mark Steffen

    Refreshing.
    And yes, from a former Chicagoan, it may not be “legal” to drink from concealed containers, but no one is going to do anything about it. 

    More bros, for sure, but you can avoid them in the same way you avoid Murray Hill.

  • http://twitter.com/thatchigirl Kennyetta

    Chicago totally has pigeons did you go downtown at all? Everything else about this is absolutely true.

  • Alcoletrane

    Go back in winter sometime. **shudder**

    • http://www.nosexcity.com NoSexCity

      WORST IDEA EVER.

  • Wubbles

    Thought Catalog, aka I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN I LIVE IN BROOKLYN but it’s not rly that big of a deal lol hipsters r dum. also i live in broklyn.

  • DechonMustard

    a-to-the-men on the panhandlers. LORDY!

  • Smafa

    Sadly, after living in Chicago for three years a pigeon did poop on my head last weekend.  So they do exist, but I still love Chicago.

    • http://www.facebook.com/ohfaith Faith Wright

      at least it didn’t happen to you on valentine’s day

  • 3NTZL

    Love it! but as for the clean…you obviously didn’t visit the lake while you were here

  • http://twitter.com/Flarfer Dave P

    Yes, Chicago is good. Winter-fuck-me-in-the-ass? Not so good. So now I live in L.A.  

    Also, you forgot to mention the bars. It’s hard to beat Chicago for drinking and bar culture more generally.

  • Patrick

    thought catalog articles = self-congratulatory poop

  • elonsdale

    Did you visit Wicker Park at all? It’s Williamsburg’s twin brother.

    • http://twitter.com/mung_beans 371747

      did you see the movie Wicker Park?  man that was awful

  • Linnybob

    What chicago did you visit. I think texas has a chicago. The minute I stepped outside on arrival in cheecahgo, a penetrating waft of stench assaulted my pores and never left my tongue. It smelled of trash and seemed to punch you in the throat around every corner. You mentioned the fire. That fire was carried along the river due to them dunping oil, trash, and pig carcasses in it. They basically put their dump in the river smack dab on the boardwalk. That fire may have leved the wooden city and theIr boardwalk but it solidified the dump stench into the air particles and soil.
    Oh Chicago what is that smell?

    • http://staugustinian.wordpress.com/ STaugustine

      Dude, just thankgawd you (probably) aren’t old enough to have detected The Chicago Stockyards by nose. You have NEVER encountered a stench so vast and vivid… a universe of pigshit and carcasses. Also: nice article, but I always thought of Chicago as one of the most segregated and mean-spirited cities of the North

      • Damenhandle

        Mean-spirited? Chicago is not mean-spirited at all. They are some of the nicest big-city folk you’ll ever meet.

  • http://twitter.com/tannnyaya Tanya Salyers

    Minus the winter, Chicago is in my top five of places to live in the US. Also thanks for clearing up the cheese in a bloody mary thing, I saw that on another article and was quite curious!

  • http://www.facebook.com/profile.php?id=1363230138 Michael Koh

    I was wondering when you’d write this

  • http://www.twitter.com/mexifrida Frida

    Depends which part of Chicago you happen to be stuck in..
    Otherwise everything seems so far away. But I do love downtown.

  • Anonymous

    Chicago, born and raised. Glad we treated you well. :)

  • Gfklc32ytfd

    Where in Chicago were you? I think it definitely makes a difference (there are pigeons all over my neighborhood, hiding under the metra tracks, and we have some crazy homeless people).

    But overall, I’m glad you liked it! Thanks for visiting our beautiful city (and I love New York, too, just in a very different way).

  • Annie

    so glad you loved Chi city. born and raised here! but where did you see these hot homeless men??

  • http://theopenend.com/bookstore/ herocious

    Chicago is the best city in North America, even Canadians think so.

  • Samantha

    Glad you liked it! Yes, you can drink freely on the street as long as you aren’t acting like an idiot. :)

  • Marcus Halberstram

    The only bad smell in Chicago that you all may be referring to comes from that chocolate factory. It is indeed (and surprisingly, considering its making chocolate) pungent. One of my least favorite smells in the world. Next to the smell of Columbus, Ohio.

  • Anonymous

    Being from Milwaukee (an hour to the north), we see people in Chicago as rude, abraisive and the streets as sardine cans full of people.  Remind me never to go to New York if Chicagoans are nice by comparison.

    • http://www.facebook.com/ohfaith Faith Wright

      chicago is probably the friendliest city I’ve ever lived in. sardine cans? maybe on the red line after a cubs game, or during rush hour.

  • Janedoe1120

    Those mysterious tar patches???? It’s chewing gum.

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