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Our picks for events in and around Chicago this weekend.

Chicago Air and Water Show

Get your earplugs and look up. The Chicago Air and Water Show roars over the city this weekend. Among those set to soar through the sky: the U.S. Air Force Thunderbirds, the U.S. Army Golden Knights Parachute Team, and civilian pilots Susan Dacy and Kevin Coleman. 10:30 a.m.-3 p.m. Aug. 15-16 (rehearsal on Aug. 14) centered on North Avenue Beach, 1600 N. DuSable Lake Shore Drive; details on the free event at chicago.gov

Brahms X Radiohead

Ravinia is hosting a unicorn of a performance this weekend: something refreshingly new and reasonably priced. Steve Hackman has created a “hybrid orchestration” fusing Brahms’s First Symphony with Radiohead’s “OK Computer.” The Chicago Symphony Orchestra and three guest vocalists will perform an arrangement that shifts from one piece of music “to the other so seamlessly that many times the audience is left wondering which is which, and how the combination was even possible.” 7:30 p.m. (gates at 5 p.m.) Aug. 14 at Ravinia Festival, 201 Ravinia Park Road, Highland Park; tickets from $30 at ravinia.org

Mon Laferte

Latin Grammy Award-winner Mon Laferte performs at Allstate Arena following the release of “Femme Fatale Vol. 2.” Pitchfork called the latest album by the Chilean-Mexican singer-songwriter “ambitious and unhinged, playful and poignant.” Think showgirl pop. 8 p.m. Aug. 15 at Allstate Arena, 6920 N. Mannheim Road, Rosemont; tickets from $56.45 at rosemont.com

Mon Laferte performs on the main stage of the Coachella Valley Music and Arts Festival at the Empire Polo Club in Indio, California, in 2019. (Drew A. Kelley/SCNG)
Mon Laferte performs on the main stage of the Coachella Valley Music and Arts Festival at the Empire Polo Club in Indio, California, in 2019. (Drew A. Kelley/SCNG)

James Austin Johnson

You know him for his Trump impersonations on “Saturday Night Live.” The Nashville native brings his “Ideal Man” stand-up tour to Den Theatre. Don’t wait long to get tickets; two shows are already sold out. 7:15 p.m. Aug. 14 and 7:15 p.m. and 9:30 p.m. Aug. 15 at the Den Theatre, 1331 N. Milwaukee Ave.; tickets from $28 (two-item minimum) at thedentheatre.com

Tori Amos

Yes, she’s been around since the mid-’90s, but she’s hardly been silent all these years. On her latest album, “In Times of Dragons,” Tori Amos turns her spooky piano chords towards the political turmoil of our times. Watch her perform it live. 8 p.m. Aug. 14 at the Auditorium Theatre, 50 E. Ida B. Wells Drive; tickets from $47.80 at auditoriumtheatre.org

Singer Tori Amos performs at the Erkel Theatre in Budapest, Hungary, on May 3, 2026. (Marton Kovacs/MTI via AP)
Singer Tori Amos performs at the Erkel Theatre in Budapest, Hungary, on May 3, 2026. (Marton Kovacs/MTI via AP)

Moe. and Umphrey’s McGee

If jam bands are your thing, get to Ravinia this weekend to bob along with Chicago’s Umphrey’s McGee and moe. Both bands share a genre-bending approach, improvising to create performances that — in theory, at least — are singular. 6:30 p.m. (gates at 5 p.m.) Aug. 15 at Ravinia Festival, 201 Ravinia Park Road, Highland Park; tickets from $60 at ravinia.org

 

“K-Love Live”

Grammy Award-winning gospel singer CeCe Winans headlines “K-LOVE Live,” a showcase featuring music from the Christian broadcast and streaming network. Winans released her latest album, “The Hymns,” earlier this summer. Contemporary Christian musicians Jeremy Camp and Andrew Ripp fill out the bill. 7 p.m. Aug 16 at the Chicago Theatre, 175 N. State St.; tickets from $85.45 at msg.com

Concert-goers hold up flowers during an Umphrey's McGee concert on Northerly Island in Chicago on August 17, 2013. (Chris Sweda / baiduhai)
Chris Sweda / baiduhai
Concert-goers hold up flowers during an Umphrey's McGee concert on Northerly Island in Chicago on August 17, 2013. (Chris Sweda / baiduhai)

Elston Skate Club

Grab your skates and glide to the grooves of live DJs as the Salt Shed transforms into the Elston Skate Club. Get in on lessons, roller-derby races, contests and more. Limited skate rentals will be available. 3-10 p.m. Aug. 16 at Salt Shed, 1357 N. Elston Ave.; tickets from $21.38 at saltshedchicago.com

World’s Largest Karaoke

Love to sing? The Salt Shed and Empty Bottle are once again seeking 5,000 people to help set a record for the World’s Largest Karaoke. And even if the details around the record are a little fuzzy, that’s not really the point. Get out for some free fun. 4-10 p.m. Aug. 15 at Salt Shed, 1357 N. Elston Ave.; details on the free event at saltshedchicago.com

Fan Expo

Kurt Russell, William Shatner, Danny Glover, Christopher Lloyd, Elijah Wood, Mr. T … the lengthy list of stars appearing at this weekend’s Fan Expo checks a lot of nostalgic boxes. While most are stars of a certain vintage, you can also meet Cara Buono, aka “Stranger Things” mother-of-the-year Karen Wheeler. Directors Sam Raimi and John Carpenter will also appear, along with a bunch of stars from “Lord of the Rings,” “The Goonies,” “Young Sheldon,” and more. Through Aug. 16 at Donald E. Stephens Convention Center, 5555 N. River Road, Rosemont; tickets from $51 at fanexpohq.com

Have something to do around Chicago? Email events to [email protected].