Chicago, IL
- rachelew921
- Mar 31
- 14 min read
Updated: Jul 25
On the phone with a friend I am in a fit of tears in the dark of my apartment trying to dodge the motion sensing light outside in the courtyard that must actually be a 10,000-lumen spotlight controlled by a highly skilled and well-paid rat because wherever I am standing at any moment after the sun sets, it is shining on me. It can find me if I'm perched on top of the cabinets, wrapped in a blackout curtain, or in the microwave with the sweet potato I'm cooking for dinner. I've been wanting to move since 2019 but don't know to where and after five years of doing no research, forming no plan, and seeking no remote work arrangements, well I was just plumb discouraged that my non-efforts returned non-results. My friend gave me a figurative slap and a literal to-do list for leaving the city that's been home since July 2015. The weekend I moved into my first apartment I went to Bickerdike Square Park by recommendation of my brother and was pelted by firework debris from the illegal neighborhood 4th of July show. Vibrant... engaging... dangerous... now THIS is Chicago, I thought with figurative stars and literal ashes in my eyes.
My old boss-lady-turned-friend asked me what's on my Chicago bucket list. Get my eyebrows dyed black and cry in the sobering light of the Whole Foods bathroom again? No, I couldn't. That was simply once-in-a-lifetime. Besides riding the Lakefront Trail, begging one of the bakers at Aya to move out west with me to cook me my daily croissant; and petting a bunch of animals I can't text or call... there isn't anything on my bucket list. Chicago has always been what I made of it, and it was made of eating cookies off the bar floor of Coconutz; biking alongside the Blue Angels flying in the Air & Water show; celebrating birthdays at the Rainforest Cafe; and fervently woopin' and hootin' at my iO Theater classmates' objectively horrible comedy performances.
For 9 of my 10 years here I have lived across from a woman whose dog urine-soaked curtains I've frequently taken down and hung back up after being cleaned with an exorcism and half a bottle of bleach; the first half was poured down the cellar sewer pipe to keep the stink at bay. Whose two air conditioning units I've stuffed into her windows every summer and left a trail of condensed runoff down the stairs to the basement as she drunkenly followed me to lay them to rest for the season. To whom I paid an obscenely low amount of rent because the water doesn't always work and the hardwood floors were coated with uncured wall paint, complete with an embalmed spider. In return she told me when Mercury was in retrograde and gave me frozen dinners because that's what I look like I eat, I guess. (I do.) In 2016 she gave me her cat and for that I am eternally thankful. In 2022 she illegally unlocked my door looking for a refill of her vodka flask and for that I am eternally grateful for how close a Lowe's is (1.2 miles), and the chain lock I expeditiously installed.
For all but maybe five of the 39,560 hours I spent in my apartment, it was Rachel's Sanctuary where I felt like a circus elephant released back into my natural habitat: a wordless soundscape and jungle of animal-themed décor. I hugged the archway when I left.

The only time I have ever felt alone in Chicago is when I thought my landlord-gifted cat, Floo, was going to die of kidney failure. I don't like to say it out loud, as it is taboo and will lay a dastardly curse upon me that will scare off men with a personality score of 7 or lower, but I love my cat and not any amount of cheap wall art I mismeasure and hang on the third cavernous hole I've put in the drywall could make home feel like home like this stupid 6.5 pound cat. If JD Vance harnessed the heart of all the childless cat ladies instead of trying to bully them, he may have just been able to get the presidency instead of second-in-command like the The Ohio State University beta he is (Go Blue!).
For four days I was the personification of a puddle. For two nights I slept on the kitchen floor because, of the seven pillows on my bed, the tabby fur one kept tumbling off on her way to the bathroom as she lost feeling in her feet and went fully plantigrade. I watched her half hourly pilgrimage from the litter box to the water fountain for six restless evening hours and the second morning was shocked to find the ham-flavored Gerber baby food, recommended to me by the lovely childless cat ladies of FELINE CHRONIC KIDNEY DISEASE Facebook group (all capitals, because of course), that I'd jiggled out of the container was eaten by this chronic anorexic. At Jewel Osco (also 1.2 miles away) I fear they think I'm a baby food-eating creep because the quantity and frequency of my meat-flavored Gerber purchases outweighs what a baby would ever require. And, well, the way Floo scarfs it down... I'm tempted?
Rejuvenated by subcutaneous fluids plus pureed meat and cornstarch, she stopped walking off the bed and resumed very deliberately stomping on my hair and meowing in my face after my alarm sounds. I'm never sure what the rush to rise is. I do eventually wake, just to follow her around the apartment while she looks back and meows, like I'm on a showing to rent the place and she's working on commission with three kittens to feed. "Here's the sizeable den where I poop when I don't feel well. Here's the bathroom which I really only enter between 7AM and 9AM. This is a windowsill that I sit in if it's sunny which it is, often. The listing didn't lie! Sometimes bugs crawl around in this corner but if you just call me I can give 'em a whack and eat them."
Chicago can be whatever you want it to be. I don't think there's anything you could list off that Chicogland doesn't offer. Try! Chicago is everything and will give it all to you if you ask. Tell me what Chicago doesn't have accessible within 90 minutes.
Sports spectating? Everywhere, within 200 steps. The most scrumptious piece of buttered lobster you've ever tasted? Joe's Seafood downtown (I've been told; I myself would never). A puppet show that will give you nightmares? 2 PM Sunday at the Studebaker. A shadow puppet show that I won't shut the fuck up about? 730 PM Wednesday, also at the Studebaker. Just 60 minutes on public transport you can be sitting on a curb eating hot dogs from Janson's watching kids dab in the Chinese New Year parade in an Irish neighborhood. Drive an hour and a half to Alpine Valley Resort and get mowed over by an adult who has managed to reach 40 MPH on a 1% incline. 30 minutes to Palos Park and you can be cruising hills on a mountain bike. Movies, art, farmers markets, triathlons, dogs, ballet, chemical peels, craft fairs, NASCAR, French toast, architectural landmarks, Magic: the Gathering tournaments, botanical gardens, boats, rock climbing, a shoe repair shop that looks like a speakeasy, carpentry, swing dancing, skydiving (indoor and outdoor), car upholstery, jigsaw puzzle swaps, architecture, EDM, whirlyball, geese, drugs, BBQ festivals, museums, state parks, night clubs, Prada. EVERYTHING!
To what potency the things Chicago offers is what I cannot, in good faith, assert to, and that is the unfortunate caveat that has me blubbering in the darkness, wanting to leave a place that objectively offers
e v e r y t h i n g.
Everything! Chicago is tinged with a film of Midwest, meaning the potency of that
e v e r y t h i n g
is diluted by compounded years of prioritizing survival in the Interior Plains over being the most potent, first place contender, in everything it offers. As a master of none, Chicago lacks the depth that gives cities strong character and sense of self. If I were a therapist I may remark to Chicago that it seems she's lost her identity in a black hole of people pleasing. But thankfully I am not a therapist; I am a childless cat lady.
I'm proud of the juice I squeezed out of this city citrus. I let it ferment too long because it's given me everything I've asked for, and as the saying I just made up goes, if the lime's still in the margarita...

Having unsuccessfully found friends within two weeks of my new job, I looked for alternatives in long form improv classes at iO Theater. I thought I found a ton but didn't realize until I was 25 that unless we were seated shoulder to shoulder uproariously laughing at a group of fellow adults on stage pretending to be an octopi family eating spaghetti dinner, we didn't have all that much in common. Eventually I felt like a literal clown in my own shows and stopped improv altogether when my second house team imploded. From four years of improv I have taken so much:
an imperviousness to shame and embarrassment
the ability to carry a conversation by pretending everyone with whom I engage is a scene partner and we have to make a meaningful show so that we're not ousted from the theater
a couple of the most supportive and encouraging friendships I've ever known
the tiniest capacity to enjoy company
other things but I feel this is getting too personal... zip zap zop!
Improv evolved into stand up and stand up into... whatever this public diary is.
Chicago is friendly and making friends isn't difficult. Sometimes I have to defend myself with a bat against people trying to forge new friendships but they just say "Amazing swing, do you want to join our social softball league on Tuesdays?" or "Your technique isn't refined but I can see you have raw talent... come to the Chicago Swordplay Guild and let's work on it!"
My friends range in age from 16 to 82 and my favorite ones remind me of my parents: comedically inappropriate or irrationally kind. They cover super gay to super straight and come from so many states and countries -- some of which I've never set hoof -- and they all take advantage of everything Chicago offers: my brother holes up in his music studio with his electronic slide whistle making beep boop soundtracks and then draws naked people who must be doing rejection therapy because why else would you do that? My friend in the suburbs is raising the most loving little boys. One wrote a book. One launched her own thriving photography business. One sits down in Wrigley field at the season opener and lives out of the stadium until the end of the Cubs season. A lot are on stage, or at yoga, at least once a week. Another ran a Serbian community council where they decide from where to source all of the city's feta cheese. Another smoked meat on his balcony. Yet another vies for national standings in Orangetheory workouts. The smallest man tried to convince me to be an anarchist after we picked up some cucumbers at the public seed library and played a rousing game of ping pong in his apartment that most certainly was not zoned for residential living. All of them have a phone note with their favorite restaurants.
I did eventually convince my co-workers to be my friends, some of my best, and thankfully had no sinking realization that we had nothing in common unless we were shoulder to shoulder analyzing multifamily mortgages. I consider them a found family. And by found family I mean most of them have moved away and I will find them and invite myself there.
Without watching seventeen improv shows a week, performing in two, and overanalyzing that one group scene where everyone was a bubble floating around a jacuzzi but I didn't hear that so I thought we were astronauts in space and said "we'll be landing on Mars any second now," sending the show on an unrecoverable tail spin of confusion... I had newfound hours to fill with horses. Tons of horses are an hour outside of Chicago. Tons! With people begging you to ride them, and ride them fast. Gallop them! We found this one running feral in my backyard. Get on her! Ride them all together, side by side, 5-wide. We don't have enough halters for all of them so just lasso the naked ones around the neck with some baling twine and hold on to that. Don't forget your helmet!
Saddle Up, Sister: A Screenplay
INT. COURT ROOM - DAY
CARINA, an endearing buckskin mare, is seated at the defendant's table. She blinks infrequently and her eyes, as usual, are looking in two different directions like she sees many ghosts. RACHEL, a white woman lacking muscle tone, is seated on the witness stand. CARINA'S LAWYER approaches the stand.
CARINA'S LAWYER
Rachel, you have alleged that
when on the back of my client
Carina, she conspired with both
a deer and a second horse to rip
you from the saddle and pull all
four of your limbs in different
directions, with the intention of
making claims to your life
insurance after such
dismemberment?
A diagram flashes up on the court room TV.

RACHEL
Yes, that's correct.
CARINA'S LAWYER scans the court room, knowingly, then pivots to face the judge.
CARINA'S LAWYER
Your honor do I have permission
to approach the jury box with
a piece of evidence?
JUDGE
Permission granted.
CARINA'S LAWYER
Ladies and gentlemen... mares, geldings, and stallions of the jury,
here I have a digitally signed
document titled "Release of
Liability" relinquishing my client of any responsibility for anything that may happen while in her presence, as the plaintiff has knowingly, willingly, and voluntarily acknowledged culpability for serious bodily injury, trauma, pain, suffering, permanent disability, paralysis, and death. In fact the plaintiff's signature unnecessarily includes a footnote that says "yee haw" followed by two exclamation points.
The jury gasps, whinnies. RACHEL winks and kicks her boot heels together.
I was adopted by the coolest polo family who still thinks that because I'm from Wisconsin I grew up in a town of 128 people; bathed in the crick; milked our cows daily; towed the dairy spoils around to the neighbors in a handmade wagon built by great peepaw; and bought our produce from a stand down yonder. They are everything my biological family is not: spontaneous, reckless, inclusive, and charismatically magnetic in a way that only spanish-speaking people seem to be. They are some things my biological family is: generous, genuine, funny. I am forever grateful to them and the family -- horse, human, and dog -- to which they added me. From 2020 to 2022 I spent every day on the farm, much of it doing donuts in a UTV and being made fun of by teenage boys. It was almost like being in Wisconsin, the real Wisconsin, again. Their little Carina taught me so much about intention, patience, and reactivity. Also about how to dodge a charging horse, and catch a bolting one (you can't). You can only be laughed at by the 230-pound stable manager Dino who can fix everything, build anything, save anyone, and thrive in all climates. I trust him more than anyone and wish that he would come out west with me and the Aya pastry chef.
Eventually, post-COVID congestion landed me in rehab for uncontrolled road rage when the hour commute turned into two. I spent so much time in stop-and-go traffic exercising my ankles in my manual transmission VW Bug only to get out and fight for my life in a sport that was requiring too much skill than I made time to hone. In rage rehab they advocated for going off driving cold turkey, which put me back in a surplus of horseless hours to fill. I filled them with mechanical horses -- bikes. Hours and hours and hours of bikes. Building bikes, repairing bikes, cleaning bikes, researching bikes, riding bikes, breaking bikes. The Lakefront Trail, Chicagoland Forest Preserves, North American dirt roads, and Midwestern rail trails have taken me thousands of miles. In those heaps of cruise time I may think about work or friends or family or what kind of beans I will have for dinner, but usually I am listening to Sean Kingston and thinking about how lucky Earth is to know his music, fraud conviction be damned.
If you ask Chicago for help, its people provide it. Maybe professionally - my two behavioral psychologists who pointed out the discrepancy in what I said I am doing versus what the circumstantial evidence suggested. My endocrinologist who bursts into the room demanding why I haven't yet left for Montana before treating me like an American adult who has a right to remain silent when questioned by the health police. My dermatologist who told me to... wash my face.
If you're not self reflective enough to figure out what help you need, the people of Chicago will just tell you. Sometimes it will be things that you need to hear, but don't want to. Like the man on the train who told me I looked like "that chubby blonde comedian." (Jim Gaffigan? I hope.) Or like my first boss who told me "you know everyone at work is hanging out without you?" Other times it will be things you need AND want to hear. Like the bus driver who told me "not to look at or talk to anyone and just get on the next bus as soon as possible" when he kicked me off at the last west-side stop of the 65 Grand bus because he was going out of service. I was dressed in an iridescent rain jacket my grandma bought me from Boston Store and rain boots with whales on them; it was my second week in the city and I naively assumed that though I had boarded the bus going the wrong direction like some dumb country bumpkin from Wisconsin, I could just ride it to the end and it would turn around and I would be back on course (ahoy!) navigating to the Walmart Express in the Loop to pick up my very tasteful, very mature lady in the big city grey glazed ceramic plates I ordered online. Alone in the rain, five miles deep into the west side of Chicago, I was mistaken.
If you're looking not for help, but for love you can find it in many ways in Chicago. You can sign up for singles skeeball. If you're like me you won't find love, only your high school French classmate who is more interested in your brother and curious if he still smokes weed, then end up scaring everyone off with your batting cage performance. You could look for it online. If you're like me you'll give free rein of your profile to your brother's girlfriend and end up unable to maintain the extreme, and frighteningly effective precedent she set. You could hope for a meet cute with a service worker. If you're like me you'll go into diabetic ketoacidosis, throw up in the urgent care lobby, give your phone pass code to the ambulance EMT and imply that should you pass out, your nutritional food log may be helpful to figuring out why you're yaffing in public (was it the blueberries... were they poisoned by Jewel??), then beg him to drive you in the wee-oo wee-oo mobile to the hospital. He literally had my phone pass code and what is a more obvious way of asking that someone put their number in your phone?
I didn't find much of that type of love, but I did find the type that filled up the theater for my debut stand up performance. The type that cooked me dinner and accompanied me to expensive shows. That gave me the honor of officiating their wedding, escorted me to the Filipino grocery store to get sioapao, visited me in the hospital, scream-sang with me in my Bug, and suffered through my maturation from a completely inflexible person to a moderately inflexible person. For as much as I shit on the people of Chicago for lacking the desire to participate in anything sober, ideally type II fun, and are therefore uNfAtHoMaBlE to me, I know I'll regret taking their good nature, nay MOST potent good-naturedness of any city in the USA, for granted. Chicago: The Second City, first in good nature.
So... I didn't really review Chicago because your Chicago is not my Chicago and that's why Chicago is cool. If I was a different person I may have written about getting dressed to the nines and shopping at Nordstrom. Had I lived in the Loop maybe I would have had more to say about the train and Daniel Burnham. Wherever I land, I don't want to tell them I'm from here, not because I don't love it, but because I don't want the interpretation of the city, and therefore of me, to be reduced to the stereotype of worshipping a chrome bean and gallivanting around Michigan avenue eating cheese and caramel popcorn (although I've done all these things).
I'm almost ten years in and Chicago is still giving. If I were to stay here, my next era would be desecrating the tennis courts of the city and surrounding suburbs with my stale high school skills; my old co-worker-turned-friend and I have been playing regularly and I'm sad to leave him. I would keep up with my weekly personal trainer (read as: man that I pay to be my friend); he makes organized exercise something I look forward to and I am sad to leave him too. I've paid an exceptional number of people to assist me with things involving my crotch including saddle sores, laser hair removal, and egg freezing. But my apartment building was sold and my new landlord is no longer a lady that survives on red wine, but an investor who gave notice to vacate by February. It's the excuse I need to get out of Chicago before it so completely fulfills the next thing that I ask of it and I find myself still here, planning my 40th birthday celebration at the Lincoln Park Farm-in-the-Zoo, catered by Aya, and all the guests leave together on rented tandem bikes in matching custom t-shirts I got printed on Damen Ave, riding the Trail as the sun sets over the lake, and my 30s.







































































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