13 Things to Do in Chicago This Week · May 7–10, 2026

Festivals & Special Events

Chicago Pickle Fest: Live Bands, Beer and Everything Pickle!

The largest pickle festival in Illinois takes over Wrigleyville's best bars with live bands, craft beer, and all things pickle-themed.

Saturday, May 9, 2026 11:00 AM · Wrigleyville's Best Bars, Chicago

James Beard Restaurant and Chef Awards

The prestigious James Beard Restaurant and Chef Awards ceremony comes to Chicago, honoring the country's top culinary talent.

Monday, May 11, 2026 · Chicago

Evanston Arts & Craft Beverage Crawl

Part gallery hop, part neighborhood crawl — the Evanston Arts & Craft Beverage Crawl brings art, local flavor, and energy to the streets of Evanston.

Thursday, May 14, 2026 · Evanston, IL

Music & Nightlife

JR De Guzman: Boyfriend Material

Comedian JR De Guzman brings his Boyfriend Material stand-up show to the Chicago Improv for five performances across the weekend.

Friday, May 8, 2026 · Chicago Improv

Arts & Culture

WINDFALL at Steppenwolf Theatre

Steppenwolf Theatre's production of WINDFALL runs through May 31 at the iconic North Side venue.

Thursday, May 7, 2026 7:30 PM · Steppenwolf Theatre, 1650 N Halsted St

MFA Thesis Exhibition: Too Much, Not Enough I at Logan Center

MFA thesis exhibition from University of Chicago graduates on view at the Reva and David Logan Center for the Arts.

Friday, May 8, 2026 · Logan Center Exhibitions, 915 E. 60th Street, Chicago

Paper Collages Workshop at Revolution Brewing

A hands-on paper collage art workshop held at Revolution Brewing's Brewery & Taproom in Chicago.

Friday, May 15, 2026 7:00 PM · Revolution Brewing - Brewery & Taproom, Chicago

Outdoors & Active

Rise Pilates Club: Sunrise Skyline Spring Series

Take a 45-minute Pilates class with a 5-minute meditation on the 99th floor of the Willis Tower, overlooking the Chicago skyline at sunrise.

Saturday, May 9, 2026 · Willis Tower, 99th Floor, Chicago

Vixen Bootcamp

A high-energy group bootcamp fitness class for all levels at the We The People Fitness Studio in Chicago.

Saturday, May 16, 2026 1:15 PM · 1229 N North Branch St, Chicago

Running Tour of From the West Side, With Love with Kenn Cook Jr.

Explore Chicago's historic Austin neighborhood through the lens of photographer Kenn Cook Jr. on this running or bike tour.

Saturday, May 16, 2026 2:00 PM · Austin neighborhood, Chicago

Free Events

Free Social Workouts - November Project Chicago

Free outdoor group workouts every Wednesday and Friday with November Project Chicago at various locations around the city.

Friday, May 8, 2026 6:06 AM · 600 E Grand Ave, Chicago, IL

Food & Drink

Get Lit: Art of the Cocktail

Author and illustrator Sarah Becan demonstrates cocktail recipes from her new book 'Let's Make Cocktails!' followed by a hands-on drawing session at the American Writers Museum.

Tuesday, May 12, 2026 5:30 PM · American Writers Museum, 180 N. Michigan Ave., Chicago

Napolita's Tenuta Rocca Wine Dinner

A Piedmont-inspired wine dinner at Napolita in Northbrook, featuring bold red wines expertly paired with seasonal dishes.

Thursday, May 14, 2026 · Napolita, Northbrook, IL