19 Things to Do in Chicago This Week · April 30–May 3, 2026

Festivals & Special Events

Mexico Fest at Navy Pier

A free three-day Mexican cultural festival at Navy Pier celebrating art, music, food, and heritage.

Saturday, May 2, 2026 · Navy Pier, Chicago

Spring's Alive on Central Street

A seasonal street celebration on Central Street in Evanston featuring strolling, shopping, and spring festivities.

Saturday, May 2, 2026 · Central Street, Evanston

Saturday Night at the Zoo - An Adults Only Evening at Lincoln Park Zoo

A going-fast adults-only evening event at Lincoln Park Zoo with a unique after-hours experience among the animals.

Saturday, May 2, 2026 6:30 PM · Lincoln Park Zoo, Chicago

Warm Love Cool Dreams Music & Arts Festival

A two-day music and arts festival at the Salt Shed making the case for the venue as Chicago's premier festival hub.

Saturday, May 23, 2026 · The Salt Shed, Chicago

Family-Friendly

Family Fun Fest at Ignite Arcade

A full day of games, costumes, crafts, and even reptiles for all ages at Ignite Arcade.

Saturday, May 2, 2026 · Ignite Arcade, North Shore

Music & Nightlife

Tomato Throw Show at The Comedy Bar

An interactive, audience-participation comedy show at The Comedy Bar where bad jokes may earn you a tomato.

Tuesday, May 5, 2026 · The Comedy Bar, Chicago

George Willborn at City Winery

Stand-up comedian George Willborn takes the stage at City Winery Chicago for an intimate dinner-and-show experience.

Wednesday, May 6, 2026 7:30 PM · City Winery Chicago, West Loop

JR De Guzman: Boyfriend Material at Chicago Improv

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

Friday, May 8, 2026 · Chicago Improv, Chicago

Date Night

Get Lit: Art of the Cocktail

Raise a glass and grab a sketchbook at this hybrid cocktail-and-illustration event at the American Writers Museum with author-illustrator Sarah Becan.

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

Chantal Kreviazuk at City Winery

Canadian singer-songwriter Chantal Kreviazuk performs live at City Winery for an intimate dinner-and-show evening.

Wednesday, May 13, 2026 7:30 PM · City Winery Chicago, West Loop

Outdoors & Active

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 guided running or bike tour.

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

Food & Drink

Chicago Pickle Fest: Live Bands, Beer and Everything Pickle

A festival dedicated to all things pickle featuring live bands, craft beer, and briny bites galore.

Saturday, May 2, 2026 · Chicago, IL

Street Vendors Association of Chicago Benefit at Monday Night Foodball

A comida del barrio benefit pop-up at Thattu featuring Chicago street vendors serving elotes, tacos, churros, and more.

Monday, May 4, 2026 · Thattu, Chicago

Arts & Culture

Oren Pinhassi: Into Your Arm's Length at The Arts Club of Chicago

A solo exhibition by sculptor Oren Pinhassi exploring tactile and spatial relationships at the landmark Arts Club of Chicago.

Saturday, May 2, 2026 · The Arts Club of Chicago, 201 East Ontario Street

WINDFALL at Steppenwolf Theatre

A new play running through May 31 at Steppenwolf Theatre, one of Chicago's most celebrated stages.

Saturday, May 2, 2026 7:30 PM · Steppenwolf Theatre, 1650 N Halsted St, Chicago

Beatles Concert in the Dark w Award Winning Violinist

An atmospheric, nearly sold-out concert experience performing Beatles music in complete darkness with an award-winning violinist.

Sunday, May 3, 2026 8:00 PM · Secret Location, Chicago

Free Events

Alice Tippit: Rose Obsolete at DePaul Art Museum

An ongoing exhibition of works by Alice Tippit at the DePaul University Art Museum, running through June 21.

Saturday, May 2, 2026 · DePaul Art Museum, 935 W. Fullerton Avenue, Chicago

Puerto Rican Arts Alliance: Studio Arts Program

El Rinconcito is a free open art space for creative expression including painting, drawing, and printmaking for people ages 12-25.

Saturday, May 2, 2026 10:30 AM · Puerto Rican Arts Alliance, Chicago

Alain Biltereyst + Larissa Borteh Opening Reception at Devening Projects

Opening reception for two simultaneous exhibitions — Alain Biltereyst's 'Great Moments' and Larissa Borteh's 'In the Wind' — at Devening Projects.

Sunday, May 3, 2026 3:00 PM · Devening Projects, 3039 W. Carroll Avenue, Chicago