Welcome to the South Side of Chicago. See it for what it is: neighborhoods as pretty as any in the Windy City where, in spite of violence and decades of racism, the hustle and buzz of city life keeps rolling along. The South Side is brutally, beautifully American — righteously unpolished and radically authentic. Come here to see the leafy Hyde Park neighborhood — the tweedy home of the University of Chicago — and nothing less than the so-called “Black Metropolis” in all its grit and splendor. You cannot say that you know Chicago without having seen the South Side.
The University of Chicago proudly calls itself “the place where fun goes to die,” but at least its campus is gorgeous — a Collegiate Gothic vision of adornment-covered, ivy-covered gray stone with red tile roofs and gargoyles. Break the monotony with a tour of Frank Lloyd Wright’s Robie House. Finished in 1910, it’s an architectural watershed: one of the first buildings of the all-American Prairie School (1-312-994-4000). 53rd Street, the neighborhood’s main drag, is worth a stroll.
Unsurprisingly, Hyde Park’s attractions lean erudite. The Oriental Institute (1-773-702-9514) has a spectacular collection of ancient Middle Eastern and Persian artifacts. The Court Theater (1-773-753-4472) is one of the city’s notable playhouses; in spring it will put on the Chicago premiere of “The Hard Problem” by Sir Tom Stoppard, known for his heady postmodern absurdism. The Renaissance Society (1-773-702-8670), despite its name, is an intimate gallery with revolving contemporary American art exhibits. From February to April, it will show two of abstract sculptor Robert Grosvenor’s works that play with the line between industrial and handmade craft.
The neighborhood comes home in its dining and drinking. Valois is an old-school cafeteria and a favorite of former resident Barack Obama, with a great deal on steak and eggs (1-773-667-0647). For dinner, the chic Promontory has Midwestern seasonal farm-to-table cuisine with ample outdoor seating and great mixed drinks (1-312-801-2100). The best stand-alone bar is the divey Cove Lounge. Order big, cheap and tasty bottles of Croatian Karlovacko pilsner; a huge mural of No. 44 will smile over you in approval (1-773-684-1013).
The Black Metropolis
You can also begin to explore black Chicago near Hyde Park. Head first to the DuSable Museum of African American History, named for the Haitian Jean Baptiste Point du Sable, the first permanent resident of Chicago. My favorite exhibit is on Harold Washington, Chicago’s first black mayor and one of the most heartening politicians of the 20th century — he took on the evil Chicago machine and won, twice (1-773-947-0600).
The Bronzeville neighborhood was the historical hub of Chicago’s black intelligentsia. The WPA-founded South Side Community Art Center (1-773-373-1026) was the nation’s first African American art museum and today showcases local talent. Yassa (1-773-488-9630) is a spectacular Senegalese restaurant with jazz every other Saturday night. Thiebu djuen (fried fish with tomato sauce and vegetables) and djollof rice are the progenitors of Louisiana jambalaya and Low Country red rice, and the homemade baobab drink tastes like vanilla custard crossed with rainbow sherbet. Peach’s (1-773-966-5801), further south, is an airy brunch spot with intensely cheerful servers. Get the shrimp and grits or the French toast with peach–bourbon compote.
Johnny Twist, proprietor of the one-of-a-kind, not-on-the-map Chicago-Mississippi Blues Historical Museum (6455 S. Cottage Grove Av.), is a world-famous guitarist and living legend, says Johnny Twist. If you’re skeptical, he’ll show you decades-old photos and every newspaper article mentioning him. The museum brims with artifacts from the span of black music, and, for a donation, Mr. Twist will give a personal tour. It’s just down the street from Daley’s, Chicago’s grand old soul food restaurant. The menu changes by day, with smothered chicken or pork chops, greens, macaroni and cheese, fried catfish — and cobbler every day — making appearances (1-773-643-6670).
Visit the cultural institutions associated with the Rebuilt Project, a creative arts and neighborhood revitalization organization (1-312-857-5561). The Stony Island Arts Bank hosts periodic performances — spoken word, gospel, jazz and more — as well as changing art installations. The Black Cinema House hosts screenings and discussions of films by and about black people. To the west in Englewood, Kusanya Cafe, from the Swahili “to gather,” has top-notch house-roasted coffee and light fare. My barista talked me into the great baked oatmeal, served with sweet cream and berries (1-773-675-4758).
E. 75th Street has a number of good restaurants. Piquant and uniquely spiced sauce defines Chicago-style barbecue; pork ribs or hot link sausages are cooked for hours in an aquarium smoker, then soaked in it. Lem’s BBQ House has the best rib tips in town sauced as hot as you want them — but don’t ask for their recipe (1-773-994-2428). The Brown Sugar Bakery across the street serves classic Southern cakes. The thick, melt-in-your mouth frosting on a heavy slice of caramel cake has a shocking depth of flavor (1-773-224-6262). Vegetarians wary of soul food for its reliance on bacon and ham hocks, fear not: Original Soul Vegetarian has the staples made without animal products (1-773-224-0104).
On the far southern edge of the city, the new Pullman National Monument, beautifully preserved, recounts the complicated tale of how a would-be utopian industrial community eventually came to a violent 1894 strike (1-773-785-8901), while the A. Philip Randolph Pullman Porter Museum tells the story of the first black labor union (1-773-850-8580).
Lastly, know that Chicago is tethered to Lake Michigan by more than pretty views and yacht clubs at Calumet Fisheries at the mouth of the city’s port (1-773-933-9855). Their huge variety of house-smoked fish and exquisitely deep-fried catfish, lake perch and frog legs won a James Beard Award in 2010. Like many places on the South Side, it’s a no-nonsense diamond in the rough.
Hotels, transit and safety
For lodging in Hyde Park, choose between the upscale Hyatt Place (773-752-5300) or the lakefront La Quinta Inn & Suites with free parking (1-773-324-3000). The Welcome Inn Manor is housed in a red brick, richly decorated Queen Anne home, very close to the city’s “L” train (1-312-493-2953).
You can rely on public transit, though the “L” doesn’t run through the South Side with anywhere near the coverage that the North Side enjoys. A car is nice to have, and Uber is affordable.
Most restaurants are cash-only. Hyde Park is the safest neighborhood on the South Side, with security guards and campus police stationed throughout the area at all hours. Take note of your surroundings wherever you are. It is not advisable to walk alone after dark.