In Where It’s At, Phin Jennings walks you down the world’s less-trodden cultural paths, consulting with some of the most plugged-in locals to guide you through a world of beautiful, moving, delicious and enriching experiences. Eating, drinking, gallery-hopping, shopping, swimming, staring at the sky: nothing is off the table as he explores the outer reaches of our cultural world to find out where it’s really at.
Though I have never actually been there, I’ve always loved Chicago. As a teenager, I knew the Windy City as home of some of the coolest guys to ever exist: Obama, Davis, West. I have since removed all but one (guess which) of these names from my cool-guy directory, but as I grew older they were replaced by others: Theaster Gates, Wilco, Larry Heard, the Art Ensemble, the Imagists…
I am constantly surprised by my own ignorance. Or maybe it’s the world’s bottomless well of new facts, unknown until they’re discovered, that amazes me. No, I haven’t been to Chicago, but I basically have. That’s what I thought until I recently opened Google Maps and learned that the city, which I assumed to be a concrete jungle from east to west, is actually on the water, stretching upwards along a bank of Lake Michigan (Lake where?). As I look at the map now, half pin-pocked grid system and half blue expanse, I realise how little I really did know about the city. Next to nothing. I’m humbled.
I’m doing the work, though. I’ve been listening to and learning from some of the city’s most knowledgeable and big-hearted linchpins. Now, I really do know a thing or two; enough, at least, to offer you the below: an itinerary of art, food, drinks, educational and spiritual experiences that will see even the most ignorant pedestrian nestled among the folds of Chi Town’s rich cultural and culinary fabric — just in time for Expo Chicago, the city’s biggest art fair, which takes place this weekend.
Thursday, 24th April
It’s only fair that we begin our trip by getting acquainted with Chicago’s least-known (to this writer) feature. Now New York-based Artist Nereida Patricia, who lived in Chicago for a number of years, recommends taking a morning dip at Promontory Point, a man-made peninsula with rocks precision-designed for languishing. Splash, swim and marvel at the vast scale and sheer unknowability of the world around you.
Once dried up you’ll find yourself in Hyde Park, home to some of the city’s premium institutions. The nearby Renaissance Society is the city’s own kunsthalle and comes highly recommended by local gallerists Daisy Sanchez of Hans Goodrich and Milo Christie and Sam Dybeck of Weatherproof (we’ll visit both later). The connoisseur’s choice, though, is The University of Chicago’s Booth School of Business. Martin Wong, David Noonan and the late Chicago legend Pope.L are among the artists that line these corridors. Sanchez says look out for the Frances Stark video that plays on a laptop zip-tied to the wall.
There’s time for a quick peruse of the nearby Powell’s Books, where Christie and Dybeck say you’ll find insane deals on art books, and snack and drink at Cantina Rosa, a favourite of local artist Tony Lewis, before heading north for more art. In and around West Town and Logan Square, you’ll find a cluster of commercial galleries and project spaces including Bodenrader, Anthony, Patron, Regards, SECRIST | BEACH, M. LeBlanc and Corbett vs. Dempsey.
This will surely work up a thirst, and you’re surrounded by opportunities to quench it. Chicago collector Murat Ahmed’s preferred blues bar is Rosa’s Lounge. The California Clipper is the 1940s bar where you’ll find bex ya yolk, an artist and publisher currently in residence around the corner at the Chicago Artists Coalition. If you’re sick of the smoking ban, I’m told that you’ll be well catered for at Richard’s, where the surly bartenders are mostly inclined to turn a blind eye.
Whatever you do, drink up in time to head north again for Matt Ulery Mother Harp at Jazz venue Hungry Brain. This is part of a full live jazz itinerary compiled for me by the eponymous Jim Dempsey. Over the weekend, he also recommends Chis Foreman at Green Mill and the three-day Chicago Jazz String Summit. Thank you, Jim, recs like this are why Where It’s At exists.
Friday, 25th April
Today is another big art day. Probably prudent to begin with a smoothie from Chicago Health Foods, where Christie and Dybeck (who are quickly becoming our Chicago guardian angels) promise “the Erewhon smoothie experience, but you’re not in LA and don’t have generational wealth”. From here, it’s a walk along the lake to Expo. Honestly, it doesn’t feel great ushering you from our freshwater paradise into a global art fair but the time is upon us and we may as well enjoy it. My recommendation is the Exposure section, where you’ll find a selection of galleries less than ten years old. Remember that, despite appearances, attending art fairs is not a competitive sport and if you need to take a breather then you should do so. In fact I recommend it; march to Oasis Cafe, located inside a nearby jewelry shop, buy a falafel pita and munch it on your way back to the fair. Free will!
Chicago seems to be replete with good places to drink, so if this afternoon seems overly boozy then it’s only because we’re spoiled for choice here. Feel free to order a La Croix or, like, whatever. Gallerist Marc LeBlanc calls Rossi’s, a liquor store with a bar attached, “the only thing like it for a country mile.” I’m imagining this spot to be a bit like the Tabacs in Paris where you can also gamble and drink. I now notice that my mouth is watering. For dinner LeBlanc recommends avec, and gives strict instructions: “The pork shoulder is what you get. And any special, always the special that’s on offer.”
We’re spending Friday evening in LeBlanc’s world, which culminates at Rainbo Club, a dive bar where he has been curating shows since 2017. Tonight, he’s collaborating with Good Weather on an expansive group show. The opening runs until 2am but I won’t judge if, after a day like today, you opt to turn in early.
Saturday, 26th April
Artist Alicia Reyes McNamara was born and raised in Pilsen, a historically Mexican neighbourhood on the Lower West Side of Chicago. Through decades of gentrification, a few local spots have remained. Panaderia Nuevo Leon opens at 6am, El Milagro Tortillas at 8am, and there’s an argument to be made that — after two days spent swanning around art galleries — it’s your moral duty to patronise them. Patricia tells me that the latter makes the best tortillas in the US. The nearby National Museum of Mexican Art has an incredible collection which offers a partial genealogy of Reyes McNamara’s own symbol-laden figurative style of painting.
There are more galleries to visit nearby including Good Weather, Hans Goodrich (which Sanchez co-runs with Peter Anastos), Grunts Rare Books and Letters To Nora, which is opening a solo exhibition by Simon S. Belleau from 4–7pm. From here, it’s required that you take a bus up to Weatherproof to thank Christie and Dybeck in person for being the backbone of this itinerary. Their new exhibition, Work Wear Blues by Irish artist Liliane Puthod looks fantastic, too. Around the corner you’ll find Kim’s Home Cooking, which Ethan Kennemer, the founder of Bodenrader, tells me serves some of the best Korean food around.
Was that lunch or dinner? After a morning spent stuffing our faces with Mexican delicacies and an afternoon spent rolling, glassy-eyed, around the last of the weekend’s galleries, it’s hard to say at this point. If you want to keep the party going, Best Intentions is a favourite of the Logan Square crowd for a drink. No pressure, though. It’s been a big weekend.
Sunday, 27th April
It’s not a weekend in the Chi without a visit to the Leather Archives & Museum, at least that’s what Sanchez and Kennemer tell me. Dedicated to BDSM, kink and fetish culture, it comprises a library, theatre and collection of objects including a preserved glory hole salvaged from a shuttered gay bathhouse. Their world class merchandise is truly the perfect souvenir.
Too much art, too much drink, too many tortillas, too much kink. Exhausted and deeply fulfilled, this is where the journey ends. We’re near the northern edge of town now. For a surreal and beautiful experience to close things out, Kennemer suggests a drive up Sheridan Road towards Evanston. You’ll have the Calvary Catholic Cemetery on your left and the endless lake on your right. If it’s late enough the street lamps will be glowing, inexplicably, purple as you chug along into a new, unknown corner of the world. I wonder whether they have bars where you can smoke, or liquor stores where you can drink, in Evanston.
