19 Things to Do in Chicago This Week · May 14–17, 2026

Music & Nightlife

Tino Cochino: The Love Bomb Comedy Tour

Radio personality and comedian Tino Cochino brings his Love Bomb Comedy Tour to the Chicago Improv for one night only.

Thursday, May 14, 2026 7:00 PM · Chicago Improv

Drunk Shakespeare Chicago!

One cast member drinks five shots of whiskey before the show begins in this hilarious, irreverent twist on Shakespeare — running through September.

Friday, May 15, 2026 · The Lounge At The Lion, Chicago

Ragbagalia Fest at Sleeping Village

The first-ever Ragbagalia Fest sees punk-funk legends ESG pass the torch to the next generation of femme and queer artists at Sleeping Village.

Saturday, May 16, 2026 · Sleeping Village, Chicago

Ladies Love RNB Day Party at Joy District

A lively R&B day party at Joy District in River North featuring DJ Sean Mac — almost full so grab tickets fast.

Saturday, May 16, 2026 3:00 PM · Joy District, River North, Chicago

Mom's Night Out with The Mama's Den

A post-Mother's Day night out at City Winery Chicago featuring The Mama's Den — wine, live music, and a room full of women celebrating themselves.

Monday, May 18, 2026 · City Winery Chicago, 1200 W Randolph Street

Food & Drink

Neighborhood Nights at DANK Haus

Join neighbors for drinks and a spectacular social experience in the DANK Haus 6th Floor Skyline Lounge, a recurring second and fourth Thursday gathering.

Thursday, May 14, 2026 7:00 PM · DANK Haus German American Cultural Center, 4740 N. Western Ave., Chicago

Free Events

Evanston Arts & Craft Beverage Crawl

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

Thursday, May 14, 2026 · Evanston

The Moving Museum – Union Park

A free weekly outdoor gathering where participants practice 'flocking,' an improvisational movement exercise that turns the group into a living artwork — no dance experience needed.

Thursday, May 14, 2026 6:00 PM · Union Park, West Randolph Street, Chicago

3rd Fridays Free Admission Museum Night

Enjoy free admission at the Heritage Museum of Asian Art every third Friday, including a guided tour starting at 6 PM with wine and appetizers.

Friday, May 15, 2026 5:00 PM · Heritage Museum of Asian Art, 3500 S Morgan St, Chicago

Date Night

Napolita's Tenuta Rocca Wine Dinner

Napolita in Northbrook hosts a wine dinner featuring the bold reds of Piedmont's Tenuta Rocca, expertly paired with dishes for an intimate evening.

Thursday, May 14, 2026 · Napolita, Northbrook

Phil Angotti and Friends: A Hard Day's Beatles Tribute Brunch

A Beatles tribute brunch at City Winery Chicago with Phil Angotti and Friends — live music, Sunday brunch, and award-winning wines in an intimate West Loop setting.

Sunday, May 17, 2026 · City Winery Chicago, 1200 W Randolph Street

Champagne Dinner at LAUREL

An exclusive champagne dinner pop-up at LAUREL restaurant — a multi-course, bubbles-forward dining experience for a special evening.

Thursday, May 21, 2026 6:00 PM · LAUREL, Chicago

Arts & Culture

BAC's 14th Annual Juried Art Competition Opening

Bridgeport Art Center opens its 14th Annual Juried Art Competition alongside a 'Canvas, Color & Vision' show — two floors of fresh work from regional artists.

Friday, May 15, 2026 · Bridgeport Art Center, 1200 W. 35th Street, Chicago

Dabin Ahn: Nocturne at DOCUMENT

DOCUMENT gallery presents Dabin Ahn's 'Nocturne,' a moody, atmospheric exhibition running through June 6 in the West Town art corridor.

Friday, May 15, 2026 11:00 AM · DOCUMENT, 1709 W. Chicago Avenue, Chicago

Unheard Voices of Care: Filipino Nurses in America – Opening Reception

Opening reception for a new exhibit revealing the lives of Filipino nurses in America beyond stereotypes, with complimentary fare, beverages, surgeons, and artists.

Friday, May 15, 2026 6:00 PM · International Museum of Surgical Science, 1524 N Lake Shore Dr, Chicago

COVENANT at Goodman Theatre

Chicago's Goodman Theatre presents COVENANT, an acclaimed production running through May 31 — catch it before it closes.

Friday, May 15, 2026 7:30 PM · Goodman Theatre, 170 N Dearborn St, Chicago

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

Family-Friendly

Minecraft Experience: Villager Rescue

An immersive, walk-through Minecraft experience where visitors chop trees, gather resources, and enter the world of Minecraft in real life — open through September 7.

Friday, May 15, 2026 10:00 AM · EXP Rosemont, near Chicago

PAWS Chicago Spring Adopt-A-Thon

PAWS Chicago is hosting a spring adopt-a-thon this weekend — the perfect opportunity to meet adoptable pets and find your new furry companion.

Saturday, May 16, 2026 · PAWS Chicago