From the remarkable food to the year-round community events to the bucket boys banging up beats on white buckets at each exit of the Dan Ryan Expressway, HBO Max’s South Side centers on overlooked parts of the city with a depth that showcases its influence and greatness.
South Side — created by Chicago natives and brothers Bashir and Sultan Salahuddin with friend Diallo Riddle — gives viewers an honest, funny, and fresh look into neighborhoods that deserve more positive attention.
Previously on Comedy Central, South Side’s second season premiered on November 11 on HBO Max, bringing more quirky and absurd money-making schemes from Rent-T-Own employees Simon and Kareme (Rent-T-Own is a parody of Chicago staples Rent-A-Center and Aaron’s). Season 2 also brings back familiar faces such as real-life married couple officers Turner (Chandra Russell) and Goodnight (Bashir Salahuddin), and goofy but well-meaning public defender-turned-alderman Allen Gayle (played by Riddle). Gayle’s 51st Ward is fictional, as Chicago only has 50 wards.
Season 1 aired before mask mandates and lockdowns, and Season 2 premieres at a time when America needs laughs and adventure. South Side takes advantage of a few of Chicago’s restaurants and bars throughout both seasons, and also name-checks prominent spots that are essential to the culture of the South Side.
Here is a list of restaurants, eateries, and bars throughout Chicago that have been highlighted on the show.
Warning: Spoiler alert
815 W. Van Buren Street
In Season 1, Episode 2, Uncle Spike enlists Simon and Kareme to sell his male-enhancement pills to elderly men. After successfully completing the task, the duo meets up with Uncle Spike at Giordano’s. Known for their stuffed pies — a hefty, flaky, cheesy, and saucy version of deep dish — Giordano’s has been around since 1974, and at one point counted Englewood native and former Chicago Bulls star Derrick Rose as an investor.
737 E. 87th Street
In Season 1, Episode 3, newly appointed landlord Officer Turner wanted to make a peace offering to tenant “The Dorothy Loreen Brown, the maverick of the Chicago civil rights movement,” with a tub of Garrett Popcorn. Stop by any location in the city to order the signature Garrett Mix, a delicious blend of their famed cheesy and caramel varieties. And folks should stay far away from Ms. Brown if they value those precious sweet-and-salty kernels.
Harold’s Chicken Shack
917 W. 87th Street
Harold’s is one of Chicago’s biggest culinary staples. In Season 1, Episode 9, Kareme experienced a mild sauce dilemma while ordering lunch there. He was denied extra sweet-and-tangy sauce by a rude associate. Contrary to Kareme’s mishap, everyone can order extra mild sauce and is encouraged to do so.
6257 S. Cottage Grove Avenue
The start of Season 2 takes viewers on a wild ride (literally) as we follow Simon and Kareme around the city on a mission to salvage Simon’s ill-fated but precious Omaha steaks. They rush the steaks over to Daley’s, a diner that happens to be Chicago’s oldest restaurant, hoping a chef will prepare them. Unfortunately, Daley’s isn’t a “BYOS: Bring Your Own Steak” restaurant, but customers can still enjoy the friendly faces, the welcoming atmosphere, and great food like salmon croquettes, fried catfish, and grits just the same.
Guaranteed Rate Field (Sox Park)
333 W. 35th Street
On Episode 4, Turner visits her celebrity friend Brenda Cole on the set of her TV show. The two girlfriends play hooky from the set for what ends up being a Ferris Bueller-esque ditch day of rollicking fun. Their first activity is a baseball game at Guaranteed Rate Field, home of the White Sox, and the ladies visit the concessions on the outfield concourse.
Union League Club of Chicago
65 W. Jackson Boulevard
Episode 4 continues with Turner and Brenda moving on to their next event, with Keisha anxiously joining in on the fun. They find themselves trying to get into the Union League Club of Chicago, a members-only social club for professionals, artists, and wine enthusiasts that is known for hosting exquisite culinary experiences. The ULCC serves top-tier steak and the freshest seafood dishes. Members can relax and have a poolside dining experience with exceptional cocktails and small bites.
5311 S. Lake Park Avenue W
At the start of Episode 9, officers Turner and Goodnight are attempting to arrest a man they suspect has stolen some windshield wipers whose alibi is partying at the Promontory, the Hyde Park music venue and bar known for its “Third Thursdays.” Turner was visibly upset about missing the event, but patrons can subscribe to their mailing list to stay up-to-date on shows, events, and parties. “Third Thursdays” doesn’t exist at the Promontory — the reference seems to be a South Side version of the Museum of Contemporary Art’s First Fridays.
2207 N. Clybourn Avenue
Though Pequod’s is on the North Side in Lincoln Park, Episode 9 features a scene among Chicago’s illuminati, a group that includes the bow tie-wearing CEO of Pequod’s Pizza, the spot with the deep dish with caramelized edges. While the scene doesn’t take place at Pequod’s, it’s a sign of respect for one of Chicago’s premier deep-dish pizzas.
1306 E. 47th Street
Chance the Rapper plays a disgruntled currency exchange worker named Herb who has aggressive confrontations with Simon throughout Episode 10. A sad Herb expresses that Italian Fiesta, a Chicago-style thin-crust pizza joint, is his favorite restaurant on the South Side. Italian Fiesta is actually a favorite for most locals on Chicago’s South Side, happy or sad — just ask the Obamas. Their super-thin-crust pie is flavor-packed with loads of cheese, fresh ingredients, and their signature homemade marinara sauce.
Reggie’s On The Beach
6259 S. Lake Shore Drive
In Season 2, the Rent-T-Own employees make a pact to face their fears, such as practicing extreme parkour (RIP Kardell Sr.), getting sprayed by a skunk, and learning how to swim. Simon and Kareme, along with Simon’s son Magnus, head over to 63rd Street Beach to overcome Simon’s and Magnus’ fear of swimming. 63rd Street Beach is home to Reggie’s On The Beach, a waterfront bar serving up beer, shots, and some of the best jumbo wings around town. Although temporarily closed for the season, Reggie’s has an indoor restaurant on State Street in the South Loop where patrons can enjoy a bar menu and live music.