My great–grandmother and grandfather moved to Calumet Heights in December 1967 and purchased a home in the Pill Hill neighborhood, named for the number of South Chicago hospital doctors who lived in the area. This is the home I learned to play spades in, have spent every Thanksgiving, and is the backdrop of many of the stories I perform around town.
My mother now calls the neighborhood home. Here are the spots I check out when I visit her.
Something to Eat
While S2 City Grill & Daiquiri Bar is the latest sit-down restaurant, I am always game for a quick trip to the Wingz It Iz on 91st and Stony Island for their famous garlic wings. It's been here since at least the ‘90s and is a neighborhood staple.
Something to See
When I first bought a drone, I knew I wanted a picture of “Stony Island Soul Part 2,” a mural by artists Rahmaan Statik, Max S, Cujo, Dred, and RK Crew. It’s located on 90th and Stony Island on the east side of the street. If you cross the road, there is also a great mural on the side of the Envision Lewandowski Family Center.
Something to Do
It technically sits on the border of Calumet Heights, but anytime I can mention The Rink, I will. This South Side skating rink has been important to my entire family since it opened in 1975 and relocated to its current location in 1985. (My mom also gave us a skating lesson at a different South Side rink last year.)

Boundaries of Calumet Heights. (Google Maps)







