17 Things to Do in Chicago This Week · August 20–23, 2026

Festivals & Special Events

Food Aid Festival Day 1: Joe Pug

A two-day musical celebration addressing food insecurity on Chicago's West Side, with Joe Pug headlining day one.

Friday, August 21, 2026 · Chicago's West Side

Taste of Little Italy Festival

Little Italy shuts down Taylor Street for Chicago's biggest Italian street festival of the summer.

Saturday, August 22, 2026 · Taylor Street, Little Italy

Music & Nightlife

Haitian Heritage Month Konpa Sware

The Haitian American Museum of Chicago hosts an immersive evening of Haitian dance and music at Room43, with free food for all guests and a free drink for the first 50 arrivals.

Thursday, August 20, 2026 7:00 PM · Room43, Chicago

Sam Gellaitry at Concord Music Hall

Electronic producer Sam Gellaitry takes the stage at Concord Music Hall for a late-night set.

Thursday, August 20, 2026 Doors @ 10:00 PM · Concord Music Hall, Chicago

Lavell Crawford at Chicago Improv

Beloved stand-up comic Lavell Crawford performs five shows over the weekend at the Chicago Improv.

Friday, August 21, 2026 · Chicago Improv, Chicago

Arts & Culture

AirOtic Soirée

A dazzling aerial acrobatics and circus arts cabaret experience running through late August in Chicago.

Friday, August 21, 2026 · Chicago

Therapy Gecko Live at The Den Theatre

The viral internet comedian and podcast host Therapy Gecko brings his live show to The Den Theatre in Wicker Park.

Friday, August 21, 2026 7:15 PM · The Den Theatre, 1331 N. Milwaukee Ave, Chicago

IN/PRINT: Contemporary Printmaking Event in West Town

A new event bringing contemporary printmaking to Chicago's West Town neighborhood.

Saturday, August 22, 2026 · West Town, Chicago

Nando De La Gente: En Español at Chicago Improv

Spanish-language stand-up comedy show at the Chicago Improv.

Thursday, August 27, 2026 7:00 PM · Chicago Improv, Chicago

Free Events

House Music is Home at Navy Pier

A free RSVP event celebrating Chicago house music at Navy Pier.

Friday, August 21, 2026 · Navy Pier, Chicago

3rd Fridays Free Admission Museum Night at Heritage Museum of Asian Art

Free admission museum night at the Heritage Museum of Asian Art with tours, wine, and appetizers every third Friday of the month.

Friday, August 21, 2026 5:00 PM · Heritage Museum of Asian Art, 3500 S. Morgan St, Chicago

Grant Park Free Dance Series

Grant Park's free outdoor dance series returns with salsa, samba, and Chicago steppin' classes for all skill levels.

Saturday, August 22, 2026 · Grant Park, Chicago

Food & Drink

Stammtisch Open Haus at DANK Haus

Monthly German-American open house at the DANK Haus Cultural Center with food, drink, and community socializing.

Friday, August 21, 2026 7:30 PM · DANK Haus German American Cultural Center, 4740 N. Western Ave, Chicago

Date Night

Candlelight: A Very Laufey Day

A candlelit concert tribute to Laufey performed at the Congress Plaza Hotel.

Sunday, August 23, 2026 · The Congress Plaza Hotel & Convention Center, Chicago

Goapele at City Winery Chicago

Neo-soul icon Goapele performs two intimate shows at City Winery Chicago in the Fulton Market District.

Saturday, August 29, 2026 · City Winery Chicago, 1200 W. Randolph St

Sports

Saturday Night Superwrestlers at Concord Music Hall

A theatrical pro wrestling event at Concord Music Hall, where live entertainment meets athletic spectacle.

Saturday, August 29, 2026 Doors @ 6:00 PM · Concord Music Hall, Chicago

Family-Friendly

Illinois State Fair

The largest state fair in Illinois returns for two weekends with $5 opening-day entry, free kids' admission, and a scooter-riding Butter Cow.

Thursday, August 20, 2026 · Illinois State Fairgrounds, Springfield, IL