A weekend on the South Side is not enough time to see everything, but it is enough time to fall in love with it. Neighborhoods Hyde Park, Woodlawn, and South Shore brim with art and culture, with many things to do open and free to the public. History continues to be made on Chicago’s South Side, and its lasting influences and traditions are being revived and celebrated almost daily by the folks that live there. Come see for yourself.
Where to stay: The ultra-chic Sophy Hotel in Hyde Park, near the massive, always fun Museum of Science & Industry, offers specials and packages for visitors -- including the “SO - In Love” package, which recreates the Obamas’ first date in the neighborhood, the “SO - Cozy Package,” a discounted “Winter in Hyde Park” deal, and more. The hotel also houses Mesler Kitchen, which offers a full menu of breakfast, lunch, and dinner, as well as brunch. Then there’s the mini-mansion. Built in 1905 for Chicago opera singer George Hamlin, Hamlin House Bed & Breakfast on the University of Chicago campus is beautifully restored, with five guest rooms -- each with its own bathroom, a Victorian-style dining room, and gardens. Rooms vary in size and additional perks; the Green Room option occupies the entire third floor of the mansion, while the Orange Room includes a luxurious sauna tub, heated bathroom floors, and a California King bed. Visit the Smart Museum of Art during your stay, just steps away from the B&B’s front door.
Best restaurants: Virtue, led by chef/owner and South Side native Erick Williams, has been voted one of the best restaurants in Chicago time and time again, with Williams often cited as one of many Black chefs changing food in America. Built on a foundation of warm Southern hospitality and respect, Virtue serves unpretentious, upscale takes on soul food including catfish, red beans and rice, corn bread and honey butter, banana pudding, and more. Virtue also offers vegan and vegetarian options.
Daley’s Restaurant is Chicago’s oldest -- marking 128 years serving the Woodlawn neighborhood in 2020. The casual dining spot is a favorite of notable locals like President Barack Obama and has been used as a filming location in films such as Widows. Though the establishment moved to its new, more modern location at Woodlawn Station in 2019, its delicious staples -- chicken & waffles, homemade sweet potato pies, and rib-eye steak sandwiches to name a few -- have stayed the same.
Things to do: Stony Island Arts Bank, a former bank-turned-gallery and archive thanks to artist and educator Theaster Gates, in Chicago’s South Shore neighborhood often hosts curated events highlighting and supporting creatives looking to redefine or celebrate the history of Black art and life. It’s also close to Gates’ Currency Exchange Cafe.
For those looking to spend more time outdoors, Midway Plaisance -- designed by Olmsted & Vaux, the nationally renowned designers of New York’s Central Park -- knits the South Side together, taking you from Jackson Park on the east to Washington Park on the west, the University of Chicago campus to the north, and Woodlawn at its southern point. Lined with trees and gardens, the park also boasts soccer fields, an ice rink, and special events such as summer movies in the park and live performances.
A Blues town through and through, Johnny Twist Blues Museum in Woodlawn celebrates the Chicago Blues through the eyes of Johnny Twist himself. The musician will tell you everything you need to know as you peruse memorabilia, hundreds of photos, and more -- all for the bargain price of $5.
History nerds can also visit a number of notable homes and historical landmarks on the South Side including the Frederick C. Robie house designed by renowned architect Frank Lloyd Wright, as well as the homes of pioneering journalist and activist Ida B. Wells and playwright (best known for A Raisin in the Sun) and writer Lorraine Hansberry, Muhammad Ali, Louis “Satchmo” Armstrong, Al Capone, the Marx Brothers, and others.
More of a night owl? Promontory in Hyde Park is half restaurant, half live venue -- offering nearly nightly events from silent dance parties and salsa lessons to performers like Bbymutha, Jay Electronica, and Jidenna; curated parties, fashion shows, and more.
Bars and nightlife: Chant brings sounds and flavors from around the globe to Hyde Park. There’s live music, including Brazilian jazz and reggae, every Friday and Saturday, and over a dozen signature martinis make up part of the cocktail menu. For a place to drink and kick-back without the flash of the club, Peach’s at Currency Exchange Café hosts its weekly Cobber and Cocktails on Fridays. Yes -- homemade peach cobbler and craft cocktails served with a side of DJ sets and musical performances.