15 Things to Do in Chicago This Week · September 17–20, 2026

Music & Nightlife

Haitian Heritage Month Konpa Sware

An immersive evening of Haitian dance and music at Room43, hosted by the Haitian American Museum of Chicago, with free food and a free drink for the first 50 guests.

Thursday, September 17, 2026 7:00 PM · Room43, Chicago

Mark Paul: The Daddy Ball Tour

Stand-up comedian Mark Paul brings his Daddy Ball Tour to the Chicago Improv for one night only.

Thursday, September 17, 2026 7:00 PM · Chicago Improv

The Beths: Riot Fest Late Night Aftershow

New Zealand indie rock favorites The Beths headline a Riot Fest late-night aftershow at Concord Music Hall, joined by Lunar Vacation.

Friday, September 18, 2026 10:00 PM · Concord Music Hall, 2047 N. Milwaukee Ave, Chicago

Dolly Parton Tribute Night at Clever Coyote

A Dolly Parton tribute evening at Clever Coyote featuring themed cocktails, Riot Fest ticket giveaways, and donations benefiting Dolly's Imagination Library.

Saturday, September 19, 2026 · Clever Coyote, Chicago

MELISSA VILLASEÑOR

SNL veteran and comedian Melissa Villaseñor performs multiple shows across Friday and Saturday at The Den Theatre in Wicker Park.

Friday, September 25, 2026 7:00 PM · The Den Theatre, 1331 N Milwaukee Ave, Chicago

Free Events

3rd Fridays Free Admission Museum Night

Free admission to the Heritage Museum of Asian Art every third Friday, with a guided tour at 6 PM, wine, appetizers, and a special resident artist presentation.

Friday, September 18, 2026 5:00 PM · Heritage Museum of Asian Art, 3500 S Morgan St, Chicago

House Music is Home at Navy Pier

A free house music event at Navy Pier celebrating Chicago's homegrown genre — RSVP required for entry.

Saturday, September 19, 2026 · Navy Pier, Chicago

Festivals & Special Events

Long Grove Annual Apple Fest

The historic Chicagoland village of Long Grove hosts its beloved three-day apple festival with apple-themed treats, vendors, and fall fun — tickets just $7.

Friday, September 18, 2026 · Long Grove, IL

Little Brothers – Friends of the Elderly Fall Fiesta

A vibrant fundraiser evening at the National Museum of Mexican Art featuring tacos, music, dancing, and community in support of Chicago's elderly residents.

Friday, September 18, 2026 6:00 PM · National Museum of Mexican Arts, 1852 W 19th St, Chicago

Outdoors & Active

Volunteer: CARA's Ready to Run 20 Miler

Join Read & Run Chicago to volunteer at Aid Station #3 at Belmont Harbor and cheer on runners tackling CARA's 20-mile training race.

Sunday, September 20, 2026 5:55 AM · Belmont Harbor, Chicago

Date Night

Candlelight: Tribute to Adele

An intimate candlelit concert paying tribute to Adele's greatest hits at Stan Mansion — a gorgeous setting for a romantic evening.

Sunday, September 20, 2026 · Stan Mansion, Chicago

Arts & Culture

The Big Picture: Midwest Large Format Asylum – Large Format Photography

A large-format photography exhibition at the Chicago Cultural Center running through October 2 — sweeping images from Midwest photographers.

Friday, September 18, 2026 · Chicago Cultural Center, Chicago

Open House Chicago 2026

Chicago's beloved annual architecture open house event returns, offering free access to dozens of buildings across city neighborhoods.

Saturday, September 19, 2026 · Multiple neighborhoods, Chicago

Nosferatu – Live Score by Circuit Des Yeux feat. Alan Sparhawk

WBEZ presents F.W. Murnau's 1922 horror silent film Nosferatu with a live original score performed by Chicago's Circuit Des Yeux and special guest Alan Sparhawk of Low.

Saturday, September 19, 2026 · Chicago

Decadence Deux: Presented by Pigment International & September Gray Fine Art

A new group exhibition opening at Bridgeport Art Center's 4th Floor Gallery showcasing works from Pigment International and September Gray Fine Art.

Saturday, September 19, 2026 · Bridgeport Art Center, 1200 W. 35th Street, Chicago