Sasha Velour
Photograph: Greg Endries

1 Russian Doll

Drag icon Sasha Velour showcases her range in The Big Reveal Live Show, featuring Gautier-meets-Guggenheim looks and musical numbers by two legendary Steves: Wonder and Sondheim. Aug. 1–3. steppenwolf.org/thebigreveal

A scene from ‘Gosford Park’
Photograph: Universal

2 Hollywood Iconoclast

The Siskel Film Center’s Robert Altman Centennial series includes Gosford Park, Short Cuts, and his savage 1992 satire The Player, whose influence extends to the recent Apple TV+ hit The Studio. Aug. 2–30. siskelfilmcenter.org/altman

3 A Lynching in Georgia

Sadly still relevant, the Tony-winning Jason Robert Brown musical Parade dramatizes the true story of Leo Frank, a Jewish man wrongfully accused of murder in 1913 Georgia. Aug. 5–17. broadwayinchicago.com

Actors in costume from ‘Uncanny Attic’
Photograph: Jesse Genito

4 Morbid Deaths ’R’ Us

Clowning, puppetry, dance, and more combine for the next edition of Newport Theater’s Edward Gorey–inspired Uncanny Attic, this time chronicling the irreverent ends of little Ernest, Fanny, George, and Hector. Aug. 7–16. theuncannyattic.com

5 Par-T.Rex

Toast to 25 years of T. rex fun when the Field Museum hosts Party Like It’s Sue-Thousand at Easy Does It in Logan Square. This 21-plus mingle (no cover) offers the chance to meet Field paleontologists. Aug. 15. fieldmuseum.org

Cynthia Erivo
Photograph: courtesy of Ravinia Festival

6 It’s Breezy Being Green

Gravity-defying Cynthia Erivo rockets into Ravinia, where the Tony-winning, Oscar-nominated superstar performs a wicked-cool concert, backed by the CSO. Aug. 15. ravinia.org

Dancers performing
Photograph: Todd Rosenberg Photography

7 Dancing With the All-Stars

The annual Dance for Life benefit features Chicago’s best companies — Joffrey, Giordano, Hubbard Street, and more. The dancers unite for the world-premiere finale, choreographed by Jonathan Alsberry. Aug. 16. cdhf.org/danceforlife

A poster for ‘Things With Friends’
Photograph: courtesy of American Blues Theater

8 Troubled Waters

What happens during a New York dinner party when the GW Bridge collapses into the Hudson? Playwright Kristoffer Diaz explores that premise in Things With Friends, an intriguing world premiere. Aug. 22–Oct. 4. americanbluestheater.com

9 Hail to the Chief

Impression king James Austin Johnson made a splash on SNL playing Trump and Biden. He brings his chameleon act to town for two shows. Aug. 23. thedentheatre.com

10 Spin City

Hot off a July 31 set at Lolla, Chicago’s own DJ Heather bookends August with another outdoor appearance, this time at Arc in Union Park. Aug. 30. arcmusicfestival.com