When it comes to Chicago’s rap scene, the name Taylor Bennett might not ring a bell. In a city that’s bursting at the seams with talented young MCs (from Mick Jenkins to Lil Bibby), Bennett’s still a relatively unknown quantity to outsiders; however, that doesn’t mean he hasn’t already staked his claim as a worthy Chi-Town representative.
Scroll through the Chatham native’s Soundcloud and you’ll see an assortment of short EPs, loosies, and his first feature-length—and underrated—project, 2014’s Mainstream Music. Type his name into YouTube and you’ll come across tracks he’s cut with the who’s-who of Windy City up-and-comers, from King Louie to Lil Herb (a.k.a. G Herbo). And if you Google him, you’re bound to stumble upon a few publications—from Rolling Stone to Complex—that wrote up his latest single, “Broad Shoulders.” That song features perhaps Chicago’s brightest star, Chance The Rapper, who also happens to be Taylor’s older brother.
This is all to say that Taylor is Chicago through and through, and a person whose brain we wanted to pick about the best late-night grub. From a jerk chicken joint co-signed by Vic Mensa, to deep-dish recs, here’s a vetted list of OG spots to hit up the next time you find yourself in the 312 after sundown.
The Loop calls for hot dogs and cake batter milkshakes.
Bennett says: “If you’re downtown in The Loop, you’ve got Portillo’s (100 W. Ontario St.) right there. You can never go wrong with their hot dogs and burgers. And they have cake shakes, which are basically like milkshakes that have cake batter in them. It’s essentially like drinking a chocolate cake. They’re amazing.” (Photo: Yelp/Norm J.)
Pay homage to the titan of deep-dish pizza.
Bennett says: “I mean, if you’re in the city, you have to have deep-dish, even if you’re going out later. Giordano’s (130 E Randolph) is one you have to try (I actually just put in an order right now), and make sure to try their pan pizza as well as their deep-dish. They have both and they’re amazing. But if you really want deep-dish, then it has to be Lou Malnati’s (439 N Wells St). It’s Chance’s favorite deep-dish spot in Chicago. Their pies are really, really intricate. And their service is incredible.”
But keep this low-key ‘za spot on your radar, too.
Bennett says: “I think the best pizza in Chicago is Connie’s Pizza (2373 S. Archer), which is at 21st and Archer. Without a doubt. That’s my family’s spot. We’ve been going there forever, me and Chance. It’s our favorite pizza. But the specific thing we’d get has changed. We used to get this thing called pie pizza, which basically means they put the bread on the top and the sauce, cheese, and the meat in the middle. It’s amazing. Now I’ll usually get the pan pizza. From the service to the ingredients, it’s probably my favorite spot in Chicago, but I know everyone in my family feels the same way.” (Photo: Facebook/Connie’s Pizza)
Don’t sleep on Chicago’s Mexican cuisine.
Bennett says: “There’s also Big Star (1531 N. Damen) in Wicker Park. I know they don’t use sour cream, but instead use a type of yogurt, which is amazing. When I go, I really just keep it simple. I love their chicken tacos. It’s all about the seasoning and the marinade that they use on it. I can just get the chicken tacos with some cheese and be straight. Their lemonade is amazing, too.” (Photo: Yelp/Ryan M.)
Peep the G.O.A.T. Jerk chicken (co-signed by Vic Mensa)
Bennett says: “I want to make sure you put that a go-to place is jerk chicken. The spot I love is actually just called Jerk (811 W. Chicago Ave.) and it’s Jamaican food. It’s amazing. It’s right on Chicago and Halsted. I know that’s me and Vic Mensa’s favorite spot. We always go there.” (Photo: Yelp/Brett G.)
When all else fails, get the double cheeseburger.
Bennett says: “At a certain time, most of the restaurants close because it’s Chicago. But there are a few spots open like Maxwell Street Grill (7901 S South Chicago Avenue), which is very well-known, and White Palace Grill (1159 S. Canal St.), that stay open 24/7. But if I had to choose one place, I’d go with Maxwell Street Grill. My go-to order there is a double cheeseburger with everything on it.” (Photo: Yelp/Andres D.)