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A performer in the Broadway in Your Backyard series
Photograph: Porchlight Music Theatre

1 Belting It Out of the Park

Spread a blanket and hear some show tunes as Porchlight Music Theatre’s Broadway in Your Backyard series tours the city. Part of Nights Out in the Parks, Porchlight’s concerts visit a different park each Tuesday. Through Sept. 6. porchlightmusictheatre.org

A painting by David Hockney
Photograph: David Hockney

2 Spring Forward

The Art Institute exhibition David Hockney: The Arrival of Spring, Normandy, 2020 features dozens of landscapes created by the British pop artist, who spent the early months of the coronavirus pandemic in rural France. Notably, the octogenarian created these works on an iPad, using a custom-designed app. Aug. 20–Jan 9. artic.edu

A performance at Northalsted Market Days
Photograph: Steven Koch

3 Out to Market

Northalsted Market Days turns 40 this year, but don’t you dare call it middle-aged. One of Chicago’s biggest summer street fests and among the Midwest’s strongest LGBTQ tourist draws, Market Days features queer-favorite performers and top-tier people-watching. Aug. 6–7. northalsted.com

Taj Mahal
Photograph: Mint Talent Group

4 Mahal the Rage

The musical polymath Taj Mahal turned 80 this spring, but you wouldn’t know it from his busy touring schedule. He brings his eclectic blend of blues and world music to City Winery for two shows. Aug. 21. citywinery.com

5 Royal Reimagining

The theater company Babes With Blades, which focuses on plays that feature stage combat, mounts Shakespeare’s Richard III. The work, which famously depicts the English king as a deformed schemer, is performed here by a mix of disabled and nondisabled actors. Aug. 25–Oct. 15. babeswithblades.org

6 Classical Quencher

This city has no shortage of street festivals in the summer, but only one is devoted to classical music. Thirsty Ears Festival, now in its seventh year, stages classical performances from the baroque canon to brand-new works on Wilson Avenue in Ravenswood. Aug. 13–14. acmusic.org

7 This Is My Jam(s)

The vibe of Sacred Rose, a three-day music festival at Bridgeview’s SeatGeek Stadium, is basically Jam Band Camp. With acts like Phil Lesh, Umphrey’s McGee, and Animal Collective playing sets up to three hours long, fans of extended noodling will be in heaven. Aug. 26–28. sacredrosefest.com

Dave Attell
Photograph: Creative Artists Agency

8 Night Owl

Best known for his cult-favorite Comedy Central show Insomniac, comedian Dave Attell drops in for three not-too-late nights at Wicker Park’s Den Theatre. Aug. 18–20. thedentheatre.com

A dancer in the Chicago Black Dance Legacy Project
Photograph: Matt Karas

9 United Movement

As part of the Year of Chicago Dance, the eight partner companies of the Chicago Black Dance Legacy Project (including Deeply Rooted, Joel Hall Dancers, and Muntu Dance Theatre) present a free showcase at Pritzker Pavilion. Aug. 27. chicagoblackdancelegacy.org

10 Art to Heart

Browse handcrafted treasures made by more than 100 artists at the Glenwood Avenue Arts Fest, a Rogers Park favorite now entering its third decade. Aug. 19–21. glenwoodave.org