Clear Skies, Hometown Indie and Park Haunts

Your daily guide to what's popping in Chicago

By Raj Singh · Published October 22, 2026.

THURSDAY, OCTOBER 22

Whitney @ Metro

Whitney is about as Chicago as a touring band gets: Julien Ehrlich and Max Kakacek started the project here in 2015, broke out with 2016's Light Upon the Lake, and followed it with the restless Forever Turned Around. Tonight they bring their soulful, tender-melancholy sound back home to Metro behind their new record, Small Talk.

Doors are at 6:30pm with the show at 7:30pm, it's all ages, and tickets run $35 in advance or $40 the day of. Metro sits on Clark Street up by Wrigley Field.

Adult Book Discussion: Culpability @ Harold Washington Library

The main library's adult book club takes on Culpability, Bruce Holsinger's techno-thriller about a family road trip that turns tragic when their self-driving van causes a fatal crash — and the guilt, buried secrets, and questions about AI's role that follow. It's a timely one to argue about out loud.

The discussion runs noon to 1pm on the 7th floor of the Harold Washington Library Center in the Loop, and it's geared to adults 18 and up — a low-commitment way to spend a lunch hour downtown.

Natan Badalov: Community Service @ Red Room Comedy Club

Comedian Natan Badalov (Netflix, Adult Swim, the New York Comedy Festival) brings his new hour, Community Service, to Red Room Comedy Club. It's stand-up built from growing up Bukharian in New York City — navigating Jewish identity, family expectations, and finding your place in the American Jewish community, told through sharp personal storytelling.

The show is 7:30 to 9pm, tickets are $29.21, and the club is up on Western Ave. Check transit if you're coming from downtown.

4x4x4 Happy Hours @ Charlie's Chicago

Here's some weekday math in your favor: at Charlie's Chicago in Lakeview East, four days a week, starting at 4pm, every drink is $4 — U-Call-It cocktails, pint beers, bottles and cans, no cover.

Today's window runs 4 to 8pm. The deal is presented by the Lakeview East Chamber of Commerce.

FRIDAY, OCTOBER 23

Amateurs @ Indian Boundary Park

The Park District's Night Out in the Parks series brings Amateurs to Indian Boundary Park on Friday — an experimental theater piece about the unpolished world of adult recreational ballet. Inspired by the experiences of four queer women with minimal ballet experience, it moves between dance, storytelling, and connection, and ends with an invitation to the barre.

It's Friday, October 23, 5:30 to 6:30pm, all ages, and free, at Indian Boundary Park.

Campfire Horrors @ Big Marsh Park

Another free Night Out in the Parks pick for Friday, this one down on the Southeast Side: an outdoor, closed-captioned screening of the 2005 stop-motion film Corpse Bride at Big Marsh Park. A gentle-spooky, all-ages way to kick off Halloween weekend.

The movie runs 7:00 to 8:17pm on Friday, October 23, and it's free. It's an outdoor screening, and Friday's forecast is overcast with a high near 64 and an evening dropping toward the mid-40s — bring a blanket and a warm layer.

ON THE HORIZON

Ravenswood Costume Crawl @ Teddy's Ice Cream

Looking ahead to Halloween week: the Ravenswood Costume Crawl turns Montrose and Ravenswood Avenues into a costumed stroll stocked with local dessert, snack, and drink samples, starting from Teddy's Ice Cream in Lincoln Square. Afterward, the party moves to Koval Distillery for a costume contest, tarot readings, and more.

It's Wednesday, October 28, with the crawl running 5:30 to 8:30pm and tickets at $34. It's a ticketed, one-evening event in the thick of Halloween week, so lock in your costume and grab tickets ahead.