This Week in Wicker Park & Bucktown: Salt Shed to Big Star

Your week-ahead guide to Wicker Park & Bucktown — 4 picks worth planning around

By Raj Singh · Published June 21, 2026.

Rain hangs over the start of the week before clearing, but the indoor bookings carry it: Ty Dolla $ign at the Salt Shed today, a free taco fest at Big Star to close it out. Plan around the 606 staying slick early in the week.

SUNDAY 6/21

Ty Dolla $ign @ The Salt Shed

The Black Yacht Weekend finale brings Ty Dolla $ign to the Salt Shed in West Town for a standing-room, high-energy 3 PM set. $50–$132, 21+, rain or shine.

Keep it easy beforehand at the Goose Island taproom up Clybourn — a 312 and a pretzel before you head in.

SUNDAY 6/21

Thee Marloes / Hollyy @ Empty Bottle

Soul straight out of Surabaya, Indonesia — weighty drums, crooning guitar, a gorgeous voice — at the Empty Bottle in Ukrainian Village. Doors 8, show 9, $27, 21+.

Grab the falafel plate at Bite Cafe next door before the openers.

THURSDAY 6/25

Sketch Playlist @ The iO Theater

A weekly all-new sketch show at iO on Kingsbury, on the Bucktown edge — fresh material every week from the next wave of Chicago comedy. 9:30 PM.

Cap the night with a late slice at Piece Brewery back in Wicker Park.

SATURDAY 6/27

Pepsi Eats Fest @ Big Star

Big Star in Wicker Park gets taken over for a free fest, 4–8 PM, with free food, a Dylan Efron taco collab, and sets from Lauren Watkins and DJ JayFunk. Blue Line to Damen.

The free food is the draw, but Big Star’s own tacos al pastor are worth the line regardless.

Plan around the rest — see more Wicker Park & Bucktown events.