In the summer of 2014, Tom Simmermaker took the Amtrak to Chicago from his hometown of Little Rock, Arkansas. He and his friend Paul traveled to the city for 10 days of intensive study with the famous improv comedy troupe, Second City, crashing in hostels and on relatives’ couches throughout their stay. They left on a magical June-time morning on Chicago’s north side on the eleventh day, which came too soon.


Tom returned a year later but stayed for six weeks this time. He devoted his days again to the study of improv, but the nights were for stumbling into new pockets of fun. Without a car or a clue, he got to know the city, spending (potentially illegal) nights on the beach with friends, having run-ins with street dogs, and discovering the tantalizating late-night tacos of Bucktown. He became obsessed with Chicago and “really moped” when he left this time around.

I know Tom from our time at Rhodes College, a small school down South with a sleepy, serene campus that he always brought to life with his humor and joie de vivre. I remember several occasions when I was having one of those days, where nothing was going right, and I just wanted it to be over — that is, until I saw Tom’s lanky frame barreling between academic buildings on his rollerblades. He was fast, but he was never in a hurry. In a world that’s so busy, he always had time, for you and for life. That sincerity, contrasted with the rollerblades, is what made him so damn funny.

I think it also made him determined to return to Chicago, for good this time. In 2016, he graduated and convinced one of his best friends to move with him up to the Windy City. They packed up a U-Haul van with two mattresses, a grandparents’ couch, and nothing else — no jobs, no plans, just a lot of blind hope.

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Two years later, Tom is still as obsessed with Chicago as ever. He’s based in the Chicago’s north side neighborhood of Wicker Park, the city’s “Little Paris.” When I called him up and asked to take me on a little theoretical tour, he was thrilled to share his favorite corners of the city with me. We hadn’t spoken in awhile, but his enthusiasm was like I’d shown up on his doorstep to start a long-planned rendezvous.  

Any day in this corner of Chitown should start off with a memorable breakfast, the only kind the locals know how to produce. At Toast on Damen Ave, you can have an “orgy” — a plate of pancakes or french toast of all different flavors available on the day — in a chic room full of wood-furnished cabinets and… toasters. For a slightly more traditional (but perhaps more colorful) experience, opt for the Hollywood Grill, a 24/7-365 diner that serves beer and wine.

Whether you’re energized or sedated by your breakfast, Tom has recommendations for the rest of your day. The 606 is a nearly three-mile concrete path built on the site of an old train line — perfect for biking, running, walking, blading, or just stopping to relax and enjoy the finer things, such as the murals that adorn both sides of the path. Spend a quirky afternoon in Quimby’s Bookstore exploring the magical world of zines, or getting lost in the four stories of Myopic Bookstore among their 70,000 books. Whatever you choose, follow it up with a pick-me-up coffee at the Wormhole, a retro spot with lunchboxes and a DeLorean hanging from the ceiling.

If you think the day has been eccentric so far, prepare for an even stranger night by making sure you’re fueled up — preferably on tacos. Las Asadas on Western Ave. is Tom’s favorite taqueria, though he notes that theirs are heavy on the cilantro and onions. If those aren’t your toppings of choice, head down the street to neighboring joints Lazo’s or Arturo’s. Still, Las Asadas wins on account of convenience, their mouth-watering salsa verde, and the best steak tacos Tom’s ever had. For vegetarian taco lovers, walk north on Western until you reach Quesadilla La Reina del Sur, a casual spot with a vegan juice bar and no corkage fee for you to BYOB.

The nightlife around Wicker Park is hip and unique enough that it needs to be seen but does not possess even a hint of pretension. Dives and dance halls provide something for everyone, and those who don’t enjoy a typical night out can be reassured that the evenings here are anything but typical. Danny’s is one spot that supports this idea through and through, a cash-only bar in a space so homey that Tom says at times it feels “like an apartment party.” It’s lit only by candles and scattered lamps, an ambience that’s supplemented by a DJ who only spins vinyl LPs. The Charleston has a similarly chill vibe — perhaps necessitated by its position sandwiched between residential properties — and feels like a lounge “from the good ole days.” Finally, Estelle’s serves up grilled cheeses and vintage movies until the small hours of the morning in art-deco digs.

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If you’ve ever had the peculiar hankering for a manicure while busting a move on the dance floor, the Beauty Bar was made for you. It’s not exactly in the Wicker Park area, but it’s a short taxi or Uber ride away into West Town. The energy of its dance floor is unmatched, and the incredibly creative theme nights (such as “My Chemical Romance Sad Hour” and “Drake vs. Weezy”) will make you feel like you’re in a music video. You’ll get a similar feeling at Slippery Slope, a red-lit bar where the DJs are suspended in cages above the groundlings. Here, you can at least get a break from the sensory overload by retreating to the intimate cocktail lounge upstairs, the Heavy Feather — though you’ll find yourself landed in Baz Luhrmann’s version of “The Great Gatsby.”


End your night with a visit to Emporium, an arcade bar with air hockey, Space Jam pinball, and a rare head-to-head version of Pacman. Just in case you’re not filled up on tacos yet, there’s a residential taco truck inside the building — yes, a vehicle that never moves. Finally, if you’ve gotten this far without trying a classic Chicago dog, join the rest of the 3 a.m. crowd at Redhot Ranch back on Western Ave. It’s open even later, until 4 a.m., and puts a secret sauce on all its dogs and burgers that keeps the customers coming until then. It’s just a small stand, so the only seating available is outside — at that hour, you’re sure to make some new friends.

Though Chicago is widely known as the Windy City, Tom says that to him, “wild city” would be more appropriate. He stresses the importance of getting out and stumbling around the town, having had his favorite experiences rollerblading and taking public transport. Get off the blue line L at Western, and give yourself over to a side of the city that will take you as you are and give you anything but typical in return. Just try not to mope when it’s time to leave.

Header image by @rafa.diaz_

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Joseph Ozment
Originally from Tennessee, Joseph Ozment is a writer and musician whose relationship with travel was shaped by growing up between the Southern U.S., Wales, and Hong Kong. So far, he's written for a newspaper in Russia, released a handful of home recordings, and started a novel (with plans for more, someday). When he's not busy running country roads or cheering on Liverpool FC, he's most likely making the next cup of coffee, or plans for the next trip.