Arts & Entertainment
From a 100-Foot Piece of Art to a New Billie Jean King Play, Here’s 6 Chicago Weekend Event Picks
“Paradise Lost” by Raqib Shaw.
Here’s a soulful and sometimes silly six-pack of the artistic and the fantastic — our shortlist of Chicago shows to kick-start your heart and make your brain buzz.
“Paradise Lost” – Art Institute of Chicago
We don’t often recommend a single piece of art, but when that work is more than 100 feet wide — and utterly stunning — we’ll make an exception. Contemporary artist Raqib Shaw spent years creating his allegorical painting. The story is rich, dense and ambitious, and visuals spring from sources in Eastern and Western art and mythology. You can lose yourself in “Paradise Lost.” Through Jan. 19, 2026
“That’s Weird, Grandma: Summer Vacation!” – The Neo-Futurist Theater
The mad scientists at PlayMakers Laboratory present original sketch comedy written by kids and performed by grownups. The skits are adaptations of stories written by young authors in creative writing residencies at Chicago elementary schools — and nobody has whacko imaginations quite like children. It’s family-friendly, funny and poignant too. Matinee performances begin July 26
“Chicago’s Soul: Words and Music of Gwendolyn Brooks and Curtis Mayfield”
Honor the artistry of Chicago poet Gwendolyn Brooks alongside the music of the great Curtis Mayfield. Cheryl Corley, singer Lucy Smith and a live band present this free presentation via the Chicago Park District. The 90-minute performance brims with themes of love, pride and inspiration. Three shows this summer, and the first is in Sherman Park on 1301 W. 52nd Street. Saturday July 26 at 5 p.m.
“Look! Look!” – Steppenwolf Theatre
This hit from the Chicago Puppet Theater Festival calls itself a celebration of “the gross and the beautiful, the sweet and the creepy.” If you like Weird Fun with a side of Weirder Fun, “Look! Look!” might be just the ticket for you this weekend. Note that it’s a short run – and yet another intriguing show presented by Steppenwolf’s summer LookOut series. July 24-26
“Billie Jean” at Chicago Shakespeare Theatre runs through Aug. 10, 2025. (Justin Barbin)
“Billie Jean” – Chicago Shakespeare Theatre
Still in previews — so critics haven’t seen it yet — but the advance word is good on this play about pioneering athlete Billie Jean King. An icon of tennis and the sporting world, King conquered Wimbledon and the court of public opinion through resilience in the face of discrimination. This hero’s journey promises to be as inspirational as the woman herself, and the show was co-developed by another inspirational icon, Lily Tomlin. Through Aug. 10
“Sunset 1919”– near 31st Street Beach
For the fifth year in a row, Lookingglass Theatre holds a ritual of movement, music and spoken word a quarter mile north of 31st Street Beach at the Eugene Williams Memorial Marker. Eugene Williams was the Black teenager killed for crossing into segregated waters on July 27, 1919, sparking the Chicago Race Riots. This solemn art ritual is a free and “spirit-guided” event. Sunday July 27 at 7 p.m.
Marc Vitali is the JCS Fund of the DuPage Foundation Arts Correspondent.
