Stephanie's Unhelpful Guide to Chicago
I'm leaving, so here are pro tips about my home city
I feel like I have to be apologetic about writing a goodbye to Chi. The “Goodbye New York” essay is practically a subgenre of essay writing. But Goodbye Chicago? Basically, just one guy did that and he pissed everyone off.
Well, I’m leaving Chicago and I want to write about it. So sue me! (Please don’t.)
Tina Fey quipped in her book Bossy Pants that if you’re still in Chicago by 32 then you’re an alcoholic (cute joke). I was about 23 when I read that, so it made me laugh. But I had a lot of older friends who bitched about that line…between shots of Malort.
I heard their cries and I commiserated with them. “Chicago rules! Why not stay here?”
And then I watched many of those same people slowly, but surely, move away. Usually in their 30s.
I love Chicago. I really do. I always have. I’ve written before about how this is a beautiful city that is extremely hard to love. Corrupt politicians, segregation, and food and transportation deserts can make this place very difficult to live in. By its meteorological design, it doesn’t want you to comfortably be here for half of the year. But those subzero temperatures and snowy blizzards wash away by May (it will always snow one more time in April) and suddenly everything is lush. The entire city blooms, so we come together in our shorts to convene at street fests and lakeshore trails, marveling that we all made it out alive. It’s so beautiful that we forget how bad the winter was. We decide to try it one more time. This city is basically an abusive relationship and the summer is when he’s nice to us. The summer is what convinces us to stay.
Since I love Chicago so much, I think that I am uniquely qualified to give everyone a very special guide to Chicago that you can give to your distant cousin visiting for the first time.
Here is Stephanie’s Unhelpful Guide to Chicago:
Best train line for disassociating: Purple, because you accidentally got on the wrong train and now you’re stuck until you get to Evanston.
Best place to get dumped: Outside of the Cornelia Arts Building during a very beautiful lightning storm. Through your tears, you can appreciate the beauty and comment on that out loud to diffuse the fact that your heart is shattering. The two of you can share a laugh, but don’t let that fool you into thinking that you are not still getting dumped. You absolutely are!
The Best place to be solicited by Hare Krishna: Take an urban hike with your friends. Start in Old Town and then hike all the way up to Lincoln Square. When you hit Lincoln and Fullerton, you might run into some friendly Hare Krishna who want to sing to you and give you pamphlets. You can ignore them. It’ll be a nice day.
Best place to fall in love: The top of a parking garage on Western Avenue watching the sunset. Pro tip: watch sunsets and sunrises in parking garages. Just walk right up there and enjoy the view!
The most romantic place to watch the sunrise: Drive to the lake early one morning because you could not sleep. Get there just in time for the sun to rise only to realize that it is going to be a cloudy day. Like, a very cloudy day. You can’t see the sun at all! The sky barely changed! Laugh about it as you wait for a few more minutes. Stop at Chicago Bagel Authority on your way home.
Favorite Chance the Rapper sighting: I cannot believe that I never met Chance the Rapper. He literally circled my friend groups! He is a comedy fan! He repeatedly went to my friend’s improv show and even performed in it! My upstairs neighbor used to go to that show and invited Chance to come over once! My old roommate literally designed several music videos of his! He talked trash about open mic comedy and then did a set and was like ‘oh man this is hard’! How in the world did I NEVER meet him?!!? UGHHHHH nevermind, I’ll stay just to meet him.
The craziest place to get railed in a sundress: Conference rooms at Groupon
The absolute worst place to perform comedy: The Underground Lounge, especially if there is no one there and someone thinks that it’s still a good idea to do improv just for each other which ends up being way worse because no one wants to call blackout so you wind up doing the longest and most boring sets of your life. You want to leave, but someone starts confessing some deep dark secrets. Your improv show has suddenly become therapy. There is no laughter, but at least you won’t get paid and no one will buy you a drink!
A place that no one knows about: The waterfall at the North Park Nature Center. It’s off to the side of the entrance. Follow what you hear and you’ll find it. Also, the entire place used to be a tuberculosis sanitorium. So you’re either hearing running water or diseased ghosts.
Best breakfast food: This is the question that I feel I have spent every day in Chicago preparing to answer. I love breakfast, so here we go: Tre Kronor, Lou Mitchell’s downtown, Baker Miller, Sam and George’s, and the Daily Restaurant. One morning in 2008, I was eating my Stockholm omelet at Tre Kronor when a frazzled twenty-something woman ran in and announced to the entire restaurant: “John McCain just picked his running mate - and she’s a woman!” So, it’s that kind of place. Great food.
Most fun karaoke spot: Those rental rooms all up and down Lincoln Avenue towards Lincolnwood that inexplicably show videos of women pouring milk and honey on their boobies while you sing that one Eurythmics song.
CUBAN FOOD: La Unica and 1492. Esas son las respuestas solas. Adios!
Sweet Treats: Cafe Selmarie for later in the evening treats, Bake on North Avenue for the best cookies, Alliance for special cakes, Bang Bang for pie (and breakfast), and Spinning J for everything in between. Stephanie’s pro tip for getting an extra cookie or slice of pie at a bakery: act VERY excited about how good everything looks and very indecisive about having to choose just one. The person working there will be so endeared that they will give you an extra! This might be my pretty privilege talking, but try it!
Strongest martini that will cause you to cry on a Saturday night about your fears regarding motherhood even though you are not pregnant nor are you currently trying to be: The Charleston
The best place to make the worst decisions of your life: The Owl.
Best burgers, but everyone who works there is definitely on coke and it’s only 5pm: Au Cheval
Bar to go to late at night with coworkers after your company holiday party when you are all already fucked up and not ready to sleep: Web Pub. The bartender will even offer to make you a “special holiday cocktail” and then simply toss a peppermint candy into a glass of whiskey. Happy holidays.
Best beach: get a friend who lives in the northern suburbs and has access to the private beach up there. It’s the same lake, but ~NiCerRr~.
Bar that serves coffee and donuts in the morning so you can work, but the oldest dude you’ve ever seen wants to drink at 9AM and scold the polite barkeep for being too “woke”: The Map Room
Best place to see a movie that will make you go ‘huh…I don’t get it’: Facets!
Best view of the city: Everyone will tell you it’s the women’s bathroom in the Hancock Tower and, yes, that view is fire. But also? I like looking at downtown from a clearing on 16th Street in Pilsen.
Best place to see comedy: My living room, amiright? JK (see? I’m filled with jokes! Tip your waitstaff, folks, they use that money for things like rent and insulin). The answers are Paper Machete and the free improv set at Second City.
Best place to try molly for the first time and then get really freaked out cause nothing is really happening and you really want to dance but people are just standing around and talking and it’s harshing your vibe so you start panicking because it turns out that you are actually the first person in history to have an anxiety attack on molly: Anywhere in Logan Square.
Ideal spot for a cartwheel contest: Oz Park
Most haunted statue: Eternal Silence in Graceland Cemetery. They say if you try to take a picture of it, something bad will happen to you or the photo. I took a picture of it in 2013 and my life has been shit ever since. Good photo tho.
Grave of a person who never existed: Inez Clarke in Graceland Cemetery
The only public statue of a woman in Chicago: Dorothy in Oz Park and, yes, she is fictional. Women aren’t real :)
Best ‘za: Okay, the answer is actually Luisa’s in Crestwood, but for something more centrally located try Roots or Pequods or Johnny’s on Western Avenue for a classic greasy ‘za. Oh, and Boiler Room has good slices. OR go for a true Chicagoland classic and find yourself an Aurelio’s. Chicago pizza IS the best and it’s because of the cheese, you dummies. Midwestern cheese is cheesier!!! Stop this whole ‘Chicago pizza is lasagna madness’. That’s libelous! We have several types of pizza. That’s how superior Chicago pizza is. Woof, I’m getting heated. Gonna order a tavern-style ‘za about it and go for the middle square first.
Best place to get your incense, crystals, bird bones, or whatever other full moon shit you need: Sideshow Gallery
Coolest dance party: Soul Summit, baby. I used to go alone and I always had a great time. I once left at midnight and the donut shop next door to the venue was closing, so they gave me two free red velvet donuts. Let this be a lesson to you! Go dancing by yourself and you will be rewarded with treats! Getting free treats might actually be my superpower!!!
Best brunch that used to be run by a cult: Lucy’s Cafe. It’s vegetarian! It used to be Victory’s Banner and it was run by a meditation cult. Everyone wore saris, even and especially the whites, and when it was your birthday they would put a candle in a muffin and sing an original birthday song whose lyrics included: “we love your soul/raaaaaaaaiiiiinbow dreams”
#1 best to live: A bohemian studio apartment in Lakeview because I got an amazing deal after the landlord wanted me to write a play for his theater group. He never followed up on that, but I got to rent the biggest and coolest studio apartment I’ve ever seen for only $700 a month. He sold the building and the next landlord (rightfully) raised the rent to over $1,000 so I had to bounce.
The thing I’ll miss the most: All of it. It’s time to say goodbye, but I will miss it all from the Midwestern cheese to the sneaky shots of Malort to any and all sentences that begin with “you’s guys”. I’ll miss allayous.
And that’s it! That’s my handy how-to guide to loving and living in Chicago. I am about to embark on a new adventure in Savannah, Georgia (ohmygod, the south?! How will I survive?! I talk WAY too fast!), where I can aspire to someday write a similar list about my adopted home.
Until then, I love you, Chicago. Never change…except for all of the bad things about you that you should definitely change.
(Kidding! I learned comedy from YOU!)
This list is both affirmation and triggering. Especially for the Underground Lounge flashbacks