Even though Chicago has all sorts of ancient and prohibitive street-food laws—food trucks, carts and, yes, even hot dog vendors are rarely seen—there are still some soulful dishes being served on the city’s sidewalks. You just have to know where to find them.
1. The Tamale LadyIf you’re in the Pilsen neighborhood, head straight for The Tamale Lady and don’t panic if you see she’s being hassled by a policeman. Whether she gets ticketed or not, she always stays on her corner, ready to reach into her stash and pull out warm tamales filled with pork and spicy red sauce. 18th St. at Ashland Ave.
2. The Gazpachos stand in Lincoln ParkStrolling the walking paths located in the northern part of Lincoln Park you’ll come across all kinds of vendors: Some sell chicharrones, some sell tacos, but none are as enticing as this “gazpacho” stand. Despite its name, the real specialty here is freshly cut pineapple, mango, melon, and more—all tossed with lemon and orange juice, cayenne pepper, and salt. On the lakefront path, near Wilson Ave.
3. 3J’s food truckEvery weekday morning, the good people of Three J’s restaurant in the South Shore load up a truck with some of their restaurant’s best dishes: Spicy (but not hot) jerk chicken, sweet barbecue chicken with mac-and-cheese, and thin, aggressively seasoned beef patties. Their truck roams around the Loop during lunch hours, but you never have to go looking for it if you don’t want to. Just call the driver, Jason, and he’ll be at whatever corner you want within minutes. But be warned: If you’re not there when he arrives, your food will probably get snagged by someone else. 773-661-1360
4. Pupusa stands in Montrose FieldIt doesn’t matter what time of day it is, or even what time of year really. These soccer fields are always seeing action. On the weekends, that includes some sideline cooking: $1 pupusa plates piled with coleslaw and crema. At Montrose Field in Lincoln Park, between Wilson Ave. and Montrose Ave.
5. Tacos D.F. at Maxwell Street MarketYou’re just as likely to come across a pile of old car radios as you are a great taco stand at this weekly outdoor market. Take my advice and spend all your money on the food. These tacos, stuffed with cecina (thin pieces of cured beef), are a sure bet. Those radios, on the other hand, probably haven’t worked for years. 548 W Roosevelt Rd.
6. Rico’s Huaraches at Maxwell Street MarketWhen a mere taco won’t cut it, the food at this market’s biggest food vendor certainly will. And while Rico’s specializes in ceviches as well as the eponymous huaraches, it’s the flats of masa that are the real draw. Eat them with both hands. If you don’t they’ll crack under the massive pile of chorizo and beans. 548 W Roosevelt Rd.
7. Piccolo Gelato cartJessie Oloroso—the former pastry chef at Stephanie Izard’s Scylla, and the current owner of Black Dog Gelato—is the mastermind behind the gelato served at the tiny Ukrainian Village storefront Piccolo. So her creations are always serious business and come in flavors like goat-cheese-cashew-caramel, roasted-red pepper, and sesame-oil-fig-chocolate. Yet somehow they taste even better when they’re served out of Piccolo’s gelato cart which, weather permitting, is wheeled out into Wicker Park during the summer. Wicker Park, Damen Ave. at Schiller St.
8. Thunderbird truckFrom where it’s usually parked during lunch hours (on Northwestern University’s law, business and medical school campus), the Thunderbird truck serves doctors, nurses, professors, students, construction workers—and anybody else who wants a quick cheeseburger, slice of pizza, or chicken-stuffed tamale. But its popularity doesn’t necessarily rest just with the food. Admit it, if you had access to a silver truck called the Thunderbird, wouldn’t you want to eat lunch there, too? Erie St. at Fairbanks Ct.