Your Street-Level Food Guide to Chicago

Veteran food writer Dennis Lee’s walks us through the Second City’s best mom-and-pop kitchens, tavern pizza, and hidden neighborhood bars. “The Second City” was A.J. Liebling’s infamous 1952 hit job on Chicago in The New Yorker—a three-part essay so full of venom he eventually expanded it into a book. But living in the shadow of New York and Los Angeles doesn’t bother Chicago, which co-opted the slur as an unofficial nickname that gave rise to things like The Second City, the iconic comedy troupe that been stocking Saturday Night Live with future comedic legends ever since. Look past the cartoonish tropes—Al Capone, brutal winters, heavy beef, deep dish—and you’ll find something those other cities sorely lack: aggressive generosity. It shows up clearest in the food culture. Portions are unapologetic, service is disarmingly warm, and chefs focus on feeding you well rather than choreographing a performance. Chicago is a reality check in an era dominated by flashy, see-and-be-seen dining. “It’s a mix of sophisticated and down-to-earth food,” says veteran food writer Dennis Lee, who has covered the city for over sixteen years. “The balance of street-level food with high-end dining is hard to find in other places—I wouldn’t be surprised if an extra snack shows up on your table just because the kitchen is happy to see you.” A self-described “culinary troublemaker,” Lee authors two newsletters under the joyfully self-deprecating pseudonym Dickhole Dannis: Food is Stupid, where he documents absurd kitchen experiments, and The Party Cut, his dedicated Chicago food guide. As a Chicago native, he remains largely unimpressed by $300 white-tablecloth tasting menus in the West Loop. “I’m a much more street-level, mom-and-pop guy who’s into family cooking,” he says. What Dennis calls Chicago’s “come back tomorrow” down-home charm is what makes it a perfect place for his irreverent approach to food writing. Here is how to tackle the city on his terms. Continue reading Access this and all our other premium articles by joining our membership program. Plans start at $6.50 per month and include twice-weekly digital features, access to in-person events, and more.