Chicago is one of those cities that rewards curiosity. Whether you’re squeezing in a few extra hours before sessions start or making a full weekend of it, there’s no shortage of ways to experience the city like a local. We asked Chicagoans in our community to share their go-to spots across four categories — Coffee, Food, Nightlife, and Attractions — and the result is the guide below. Consider it your cheat sheet for eating, drinking, and exploring one of the best cities in the country.
Coffee
Cafe Deko is by far the prettiest coffee shop in Chicago. Come here for smoothies, sandwiches, pastries, and one of the most extensive coffee and tea selections in the city. – Meena
The cafe LUCKYCAT in Lakeview serves some of the best coffee and breakfast the duo has tried in the neighborhood. Jake ordered a vanilla latte with smoked sea salt, while Lucia went with a black sesame latte. If you’re nearby, it’s a must-try. – Jake and Lucia
Nothing beats the winter blues like the smell of freshly brewed coffee, especially when I’m not the one making it. Some cool spots to check out are Back of the Yards Coffee (1621 W. 47th St.) and The Stockyard Coffeehouse (558 W. 37th St.) or head to Casa Cactus (4595 N. Elston Ave.) and Hexe Coffee (2000 W. Diversey Parkway) on the North Side. – Francia
It’s a bit of a walk from the Hilton, but Dark Matter coffee is rich, flavorful, robust, and eccentric. Their Meddle location is just west of the loop and features all their signature roasts. – Peter
Food
Art of Pizza isn’t just one of the best deep dish pizzas in Chicago, it’s a deep dish pizza that’s available by the slice within blocks of the conference hotel. Art of Pizza is better than Gino’s East and Lou Malnati’s, but for the best deep dish in Chicago, head to Pequod’s. – Meena
This might be the hardest pick, but I’ve had the best meal of my life at Bavette’s Bar and Boeuf. Stunning, dimly-lit atmosphere, superb drinks, and absolutely mouthwatering steaks. It’s tough to get a reservation, but it’s absolutely life-changing. The bone-in Rib Eye is my recommendation, but you honestly can’t go wrong with anything on the menu. – Peter
Dig into the large combo deal with a cup of chicken noodle soup and a heaping turkey and veggie sandwich from Bockwinkel’s, 222 N. Columbus Dr. – Colin
Drop by Little Village’s Osito’s Tap, a speakeasy-style bar at 2553 S. Ridgeway Ave. for their Sunday happy hour. Specials included $4 mezcal pours and $10 cocktails, but the kitchen’s tlayuda was the afternoon’s stunner: a thin, pizza-size crunchy blue tortilla topped with beans, Oaxaca cheese, pickled vegetables and savory chapulines (roasted and spiced grasshoppers). It was the best expression of the dish he’d had outside of Mexico. – Stephen
Take advantage of False Spring by going to Shawn Michelle’s Homemade Ice Cream in Bronzeville, which sells the best ice cream in the city. – Joe
I’m obsessed with Brulee’s fried catfish and grits and plans on making a return trip to the South Loop for it soon. She also recommends Buttercup in the South Loop, where she enjoyed the roasted pork collar, anchovy toast and boozy milkshake. – Jamie
Dig into the history of some of Chicago’s most iconic foods and then try them for yourself, from the Rainbow Cone (with a new location on Michigan Avenue) to the Palmer House Hilton brownie to the Jibarito, a steak sandwich with plantains subbed in for bread. – Christine
If you want authentic Chicago pizza, skip the deep dish. Tavern style hits the taste buds in a way that the pile of cheese and sauce could never. If you’re flying through Midway Airport, stop by Vito & Nick’s in the Ashburn neighborhood for a blast from the past of their cracker-thin crust (but make sure to bring cash). But if you are tempted, check out this guide from Block Club Chicago and local pizza legend John Carruthers to devise this ultimate guide to all Chicago pizza — yes, even deep dish. – Christine
Attractions
If the weather cooperates, the absolute best use of time in Chicago is the Chicago Architecture River Cruise. There’s nothing like seeing the city from the river, and you’ll learn all about the history of Chicago’s great landmark buildings. – Peter
I want to spend an entire day this winter at the Art Institute of Chicago in an attempt to look at every painting, sculpture and other work on display in one go. The museum is typically open 11 a.m.-5 p.m., which gives me six hours to accomplish this likely impossible task. Caffeine, snacks and multiple breaks will be required. – Quinn
A second vote for the Art Institute of Chicago – Take yourself on an hour-long tour to see some of the most famous paintings in the world, including Grant Wood’s “American Gothic,” Edward Hopper’s “Nighthawks,” and Pablo Picasso’s “The Old Guitarist.” – Meena
Explore the range of cultural and art museums scattered across the city — not just the big ones Downtown — especially if it’s in a neighborhood you haven’t been to before. Peruse the galleries at the National Museum of Mexican Art in Pilsen, learn the history at the Swedish American Museum in Andersonville, marvel at the architecture at the National Museum of Puerto Rican Arts & Culture in Humboldt Park or travel through time at the DuSable Black History Museum and Education Center in Washington Park. – Christine
Tour the city’s neighborhoods with a deep sense of history — and fun — in a bus with Dilla of Chicago Mahogany, the viral TikTok historian of Chicago. If you’re here the Saturday before ONA kicks off, Dilla is hosting a special Women’s History Month tour. Or ride along to Bronzeville and learn about the history of the Black press in one of the city’s most storied neighborhoods in a special just-for-ONA-attendees event on Tuesday, March 31 at 4pm. This tour has limited capacity. A sign up form will open one week prior to the conference. – Christine
Nightlife
Buddy Guy’s – This is one of the best blues clubs in the world, and it’s located just steps from the conference hotel. It’s owned by blues legend Buddy Guy, who still performs at the club regularly. – Meena
Visit the city’s blues clubs! I’ve seen Buddy Guy at his eponymous South Loop club, 700 S. Wabash Ave., but I also want to take in shows at Rosa’s Lounge, 3420 W. Armitage Ave., and Kingston Mines, 2548 N. Halsted St. – Stephen
Go for a cocktail at Cindy’s rooftop. It’s only a 15 minutes walk from the Hilton. It has a wonderful view. You will see The Bean (the most popular piece of public art whose real name is Cloud Gate), Grant Park and the lake. If it’s too cold to go out then there is a cosy bar with a fire a couple of floors down in the same building which is called Chicago Athletics Association. If you want to do some sight seeing on your way from the Hilton to Cindy’s Rooftop, take a detour midway to the Art Institute to see Edward Hopper’s famous Nighthawks painting. – Clare
It’s hard to choose, but I’ve had so many memorable (and not so memorable) nights at Brando’s Speakeasy. Nestled in the heart of the loop, this karaoke bar is home to the most encouraging audience you’ll ever find. Even if you don’t sing, it’s hard not to get swept up in the party. – Peter
Thank you to our Chicago-based contributors Colin Boyle, Jake Cox, Francia Garcia Hernandez, Jamie Nesbitt Golden, Peter Kosmal, Stephen Montemayor, Quinn Myers, Christine Schmidt, Lucia Preziosi, Clare Spencer, Meena Thiruvengadam, and Joe Ward. Many of these contributors came to us from our friends at Block Club.
Photo by Sawyer Bengston via unsplash.
