The First Timer’s Guide To Eating In Chicago

The pan-style at Pequod’s in Lincoln Park has the city’s best deep dish, mainly because of its caramelized crust. The crispy burnt cheese edge perfectly complements the spicy sauce and the thick, airy dough—it’s the crowning achievement that every pizza works towards its whole life.

La Chaparrita is inside of a Little Village grocery store, but don’t plan on doing any shopping. You’ll be too distracted by the smell of their tacos, which are made even better by tortillas dipped into a simmering broth. Eat as many as you can, then start planning your next meal here.

Steakhouses are a way of life in Chicago, and Bavette’s is our favorite. First, because the actual steak is the best in the city. Second, because the speakeasy atmosphere and 1920s jazz make it feel different from a traditional (i.e. corporate) Chicago steakhouse. Plus, you can come here, not order a steak (get the french dip), and still have a fantastic meal.

With hundreds of restaurants in the neighborhood, the best way to experience Chinatown is through a food crawl. And the first stop should be Chiu Quon, Chinatown’s oldest bakery. Flaky egg tarts, BBQ pork buns, dim sum—there’s no such thing as a wrong order. Just know that they’re cash-only (so the first stop should be an ATM).

Sometimes you find yourself needing, but not wanting, to eat a meal alone. Perhaps your discount flight lands at O’Hare 12 hours before your friend’s, or you simply require a break from your coworkers during a five-day offsite. Grab a seat at the bar at Sushi-san in River North. This Japanese spot comes with a fun crowd, club-level loud hip hop, and seriously good sushi.

Au Cheval has Chicago’s (maybe the world’s?) most famous burger, but The Loyalist is only a few blocks away, and just like Au Cheval, the space is dark and has big, comfy booths. Plus it’s home to the actual best burger in Chicago, with a patty made from chuck, short rib, and bacon.

Visit this ice cream stand near the Ferris wheel on Navy Pier for a scoop of the iconic rainbow ice cream. It’s made with a bunch of flavors, including one you’ve probably never heard of: palmer house (a mix of vanilla, walnuts, and cherries). Just make sure you get it in a dish. Navy Pier is hard enough to navigate without babysitting a melty, multi-layered ice cream cone through the crowd.

Ushering a group through breakfast and getting to a boat tour on time is like herding cats. Win Shepherd Of The Year with Beatrix in River North. Pancakes and shakshouka are like a Tom Hanks movie from the '90s: well-made and designed for mass appeal. There’s a to-go pastry counter too, in case someone wants to test the limits of their Dramamine.

The Green Mill is an iconic cash-only jazz club in Uptown known for its live music and underground tunnels. This place opened in 1907, and their most infamous regular, Al Capone, escaped police raids using the secret passageways. Nowadays, the tunnels are closed, but fedora sightings still trigger a double take.