17 Things to Do in Chicago This Week · May 21–24, 2026

Music & Nightlife

Haitian Heritage Month Konpa Sware

An immersive evening of Haitian dance and music hosted by the Haitian American Museum of Chicago, with free food and a free drink for the first 50 guests.

Thursday, May 21, 2026 7:00 PM · Room43, Chicago

Jessimae Peluso at Chicago Improv

Stand-up comedian Jessimae Peluso performs four shows across Friday and Saturday at the Chicago Improv.

Friday, May 22, 2026 · Chicago Improv, Chicago

Heavy Crownz at Lincoln Hall

Chicago rapper Heavy Crownz celebrates his album Trench Baby Turned Farmer with a homegrown lineup at Lincoln Hall.

Friday, May 22, 2026 · Lincoln Hall, Chicago

Budweiser Concert Series at Gallagher Way

An ongoing outdoor concert series at Gallagher Way adjacent to Wrigley Field, running through June.

Sunday, May 24, 2026 6:45 PM · Gallagher Way, 3637 N Clark St, Chicago

Outdoors & Active

Vinyasa Flow With Rolled Oats (Live Music)

Stefanie Coslow leads a vinyasa flow class accompanied by live music from Chicago band Rolled Oats, blending restorative movement with a mini concert.

Thursday, May 21, 2026 6:00 PM · We The People Fitness Studio, Chicago

Free Events

Mobility & Meditation with Wellness Besties Chicago

A free session combining intentional mobility work and guided meditation, followed by a social hour hosted by Wellness Besties Chicago.

Thursday, May 21, 2026 6:00 PM · 1101 West Lake Street, Chicago

Rise Pilates Free Beach Series

Viral sensation Rise Pilates brings free beach Pilates classes back to Lake Michigan for a community-oriented summer series.

Saturday, May 23, 2026 · Lake Michigan, Chicago

Puerto Rican Arts Alliance: Studio Arts Program

A free open art studio for ages 12–25 offering painting, drawing, printmaking, and more in a safe and welcoming creative space.

Saturday, May 23, 2026 10:30 AM · El Rinconcito, Chicago

Festivals & Special Events

Skokie Festival of Cultures

A weekend festival celebrating music, art, food, and traditions from more than 30 cultures at Oakton Park in Skokie.

Saturday, May 23, 2026 · Oakton Park, Skokie

Forever Mine Music Festival

A one-day music festival taking over Union Park in Chicago.

Saturday, May 23, 2026 12:00 PM · Union Park, Chicago

Do Division Street Fest

Chicago's iconic 3-day street festival returns to West Town's Division Street with live performances and a family petting zoo.

Friday, May 29, 2026 · Division Street, West Town, Chicago

Arts & Culture

COVENANT at Goodman Theatre

A theatrical production currently running at the Goodman Theatre with evening performances through June 7.

Friday, May 22, 2026 7:30 PM · Goodman Theatre, 170 N Dearborn St, Chicago

Alice Tippit: Rose Obsolete at DePaul Art Museum

An exhibition of work by Alice Tippit on view at the DePaul University Art Museum through June 21.

Saturday, May 23, 2026 · DePaul University Art Museum, 935 W. Fullerton Avenue, Chicago

BAC 14th Annual Juried Art Competition

Bridgeport Art Center's 14th annual juried exhibition showcases selected works across its 4th floor gallery through July 3.

Saturday, May 23, 2026 · Bridgeport Art Center, 1200 W. 35th Street, Chicago

Kino, Kaffee und Kuchen

A Saturday morning German-language film screening with coffee and cake at the DANK Haus German American Cultural Center.

Saturday, May 23, 2026 10:30 AM · DANK Haus German American Cultural Center, 4740 N. Western Ave., Chicago

Date Night

Candlelight: 90s Unplugged

An intimate candlelit concert celebrating '90s unplugged hits performed live on strings at Wicker Park Lutheran Church.

Saturday, May 23, 2026 · Wicker Park Lutheran Church, Chicago

Food & Drink

Read & Run Chicago Turns 5: A Chicago Cookbook Potluck

Read & Run Chicago celebrates its fifth anniversary with a community potluck where attendees bring dishes inspired by Chicago cookbooks.

Wednesday, June 3, 2026 6:00 PM · Chicago