In Transit: Chicago

Most photos by Zach Baker, artsy photos by Adam Jason Cohen

I had a bunch of flights get cancelled consecutively, leaving me with the realization that I was stuck in Chicago for about a day and a half.

I’ll start by penning a great big “fuck you” to Chicago O’Hare, its resident American Airlines staff, and every single person I had to watch cry while just trying to get into and out of Chicago, Illinois. But when life hands you a pile of shit: make shit salad. Or make a 24-hour travel guide.

cohen skyline

Chicago, Chiraq to some, Wikipedia’s “Chicagoland” to literally no one, is nestled quaintly in the southwestern curve of Lake Michigan. With over 2.7 million inhabitants, its the country’s third largest city. All kinds of noteworthy shit has gone down in Chicago since its founding. It’s had a citywide, heinous fire, leading to the building of the world’s first skyscraper, along with a bunch of other good and bad shit. It was host to Al Capone and one of the nation’s first underground crime syndicates. It’s been on the cover of a Wilco record. It’s the place where a talented young music producer once broke his jaw in a car accident, resulting in a long career of mediocre rap that for some reason has led him to believe that he’s the seconding coming of Andy Warhol. For over a hundred years, Chicago has been an epicenter of arts, culture, and industry.  It’s a hell of a town to be in. Anyway, if you get stuck here for a day, you should do what I say I did.



I don’t know where you’re from, but as a resident New Yorker, I’m not clamoring to get my hands on no damn goopy-ass Chicago deep-dish pizza. I’ve had deep-dish pizza in Chicago, and it’s good, but you can ask Jon Stewart—the shit ain’t pizza. Just wait ‘til you get stuck here. But while you’re there, I have to first ask, are you rich or broke?


I don’t know what rich means to you. I went to Greektown and ate some grilled octopus and had a beer and it cost like $40 or something. If you feel like being a show-off I’d say do that, and if you’re really rich and don’t think that creamed spinach is stupid, you should go to one of those steakhouses for which Chicago is apparently known. What am I doing?  Rich people don’t have layovers.


Good, me too. There are a variety of delights for you to sink your teeth into. Harold’s Chicken, for example, serves up bangin’ fried chicken that everyone told me to get with mild sauce so I did and I was down. Open ‘til 10PM, which is late by Chi standards. Go to one on 47th.

devon ave

Devon Ave is host to one of the country’s most happening Desi communities, so go there to get some great halal food for cheap as well. A Mongolian Uber driver named Bibimyap took me there at 3 in the morning on the way from the airport and he saved my life, and also has a beautiful child. There is a big ass Mongolian community neighboring Devon Ave but I don’t know how cheap their food is. Chicago plays host to the second largest Mexican-born population in the country—the first being Los Angeles. The Pilsen and Little Village neighborhoods are the places to go for some strong tacos and tortas. Just north is Humboldt Park, which is the only nationally recognized Puerto Rican neighborhood outside of Puerto Rico.

will backside seawall


It’s a city, use your head. There’s the Picasso statue that everyone skates. There’s the sea wall: photogenic, oververt, and an easy place to lose a board into one of, what Melville described as, ‘those fresh-water seas of ours.’ There’s a brand new skatepark in Grant Park with weird gravel pits and some opportunities to go vert, and there’s an old one in Burnham Park—both a stone’s throw from the lake.


Again, it’s the country’s third largest city, albeit a heavy-driving city, so worst comes to worst, get yourself downtown and go explore. Plus, driving city means pole jams galore!

You’re broke still, right? Okay, cool. Totally cool. When you’re done skating, or in between skating, go jump in the lake! It’s got a number of beaches scattered north to south along the city’s eastern border. This is easily one of the city’s greatest summer draws. Don’t go to Pitchfork—or Lollapalooza, obviously. You can probably get a cheap baseball ticket. Cubs fans will even sometimes throw tickets down to you from the bleachers onto Addison Street. You’re only there for a day though, you should probably just go skate.


Dude, I don’t know. There are wild multi-floor clubs downtown. I have a friend who sauntered into a topless boxing match on a visit to Chicago, and another who happened in on an intimate, barely-publicized Dinosaur Jr. set. I’d say just go with the flow, man.


But, wanna know what I would do if I was you? Okay. Get beers—like, a lot of them. Go to the beach, go for a swim, drink your beers.  When the beach patrol tells you to that the beach is closed, and they might, pack up and go to a footbridge to post up and stare at the skyline and finish said beers. Is it the fourth Tuesday of the month? Good. Go to The Smith’s night at Danny’s in Bucktown. Remember, we’re only in town for a night, so suspend any Moz prejudices you might have, you closed-minded prick.


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