Old Town is a small neighborhood with a lot packed into it. It’s home to Second City, plus a bunch of sports bars that all seem the same. But there are a few great restaurants and bars to be found here, too. This is our guide to getting the best food out of Old Town.
There are only a few good drinks-and-a-light-bite options in the neighborhood, and Two Lights is one of them. It’s right across the street from Second City, and inside it looks kind of like an upscale seafood shack, with a long bar that works well for small groups or dining solo. The menu involves mainly seafood-focused small plates, and you should stick with dishes like the tuna poke tacos, shrimp, and oysters, all of which are good.
Topo Gigio Ristorante
The old standby Italian spot in the neighborhood. We love eating at Topo Gigio (a.k.a. getting lost in a big bowl of pasta and a few bottles of wine) any day of the week. This is the ideal place to escape the rest of the shenanigans happening on Wells St.
Of course we wouldn’t leave out Orso’s in the classic Italian category of Old Town. Orso’s is similar to Topo Gigio in style and ambience, but the service is a little more formal. It has a red sauce-heavy menu, but what really sets Orso’s apart is its enclosed back patio that feels like a garden. It’s a great spot for a laid-back summer dinner.
Twin Anchors Restaurant & Tavern
Twin Anchors is famous for serving excellent ribs, and for being a favorite Chicago hangout of Frank Sinatra back in the day. It’s been around since 1932, and the giant laminated menus here remind us of old-school supper clubs. The ribs are tender and juicy (they’re slow cooked rather than smoked, so they aren’t technically barbecue), and perfect for getting a little messy underneath the glow of the restaurant’s light-up beer signs.
Looking for food that’s affordable and fast, but still good? Old Jerusalem is a good bet for either a carry-out situation or a quick sit-down meal. Stick to the Mediterranean classics like hummus, shawarma, and a kebab or two, and remember to BYOB if you’re eating in.
On the spectrum of sushi restaurants, Kamehachi fits into the “pretty good, a little pricey but that’s just Chicago, casual enough to pick up, but nice enough to go out to on a Saturday night” category. The best strategy for tackling the big menu is to go heavy on the signature rolls (the Crouching Tuna Hidden Crab is a fun one), and get appetizers like gyoza and tempura for the table.
An Old Town diner staple for a casual breakfast, lunch, or dinner since 1973. Nookies has the familiar diner options not so concisely laid out on a menu with approximately 700 pages. You can eat everything from eggs and potatoes to a club sandwich to meatloaf or beef stroganoff. That said, we prefer Nookies for brunch - and we particularly like the crunchy French toast, battered and fried in cornflakes.
We salute the Happy Camper crew for creating a fun, casual atmosphere with solid pizzas and beers. The pizza here has toppings ranging from the usual suspects to buffalo chicken and pulled pork, plus a crust that’s soft and airy but also crunchy on the outside. The space is the major draw, though. It’s kind of like an adult playground, with tire swing barstools, a rehabbed Airstream camper, and an enormous neon outline of the Great Lakes on the wall. If you’re looking to gather some friends and kick it indoors, there’s no better place.
Kanela is trying to take over the breakfast and lunch game in Chicago, one diner at a time - there are now six locations across the city. The one in Old Town is good for breakfast, brunch, or lunch seven days a week from 8am-3pm. That makes Kanela a serious utility player, with everything from red velvet French toast to crab cake benedict and a croque madame. This place is slammed on the weekends, but if you come during the week you won’t have to wait long.
Burger Bar is the casual non-pizza counterpart to Sono Wood Fired, and it’s right next door. You can build your own burger here, choosing either prime, angus, or grass-fed beef - or order one of their specialty burgers, like the Wild Bill, which has bison and goat cheese. Think of it as a Chipotle for burgers, but with table service instead of a sneezeguard.