Axios Chicago Weekender

October 23, 2025
ππΎ Hi! Moyo here with some weekend options for ya.
- There's no denying it, the fall breeze is here!
Today's newsletter is 766 words β a 3-minute read.
1 big thing: 'Twas the weekend before Halloween
Halloween is next Friday, but some of the best bashes happen this weekend and we didn't want you to miss out!
State of play: Don't worry, we've also got you covered for the actual holiday on Oct. 31, so you can plan ahead. After all, Halloween is more than just one day β it's an entire season.
Music Box of Horrors: Dead and Loving It!: From bone-chilling to silly, the beloved theater's annual fest is a must-see for movie lovers.
- Screenings through Oct. 31 at the Music Box Theatre in Lakeview.
- Tickets start at $11.
Trick-or-Treat on the Mag Mile: A Halloween sing-along concert and costume parade kicks off a day of trick-or-treating, cookie decorating and a petting zoo.
- Noon-3pm Saturday at 900 N. Michigan Ave.
- Tickets are $5 per child ages 4 and up, but free for parents and kids 3 and under. Proceeds benefit Make-A-Wish Illinois.
Halloween Boo Bash: The Halloween party/fundraiser includes karaoke, campfire stories, pumpkin carving and painting, trick-or-treating, costume contests, seasonal bites and brews, and it all benefits artists' wages at the American Blues Theater.
- 4-7pm Sunday at American Blues Theater in Peterson Park.
- Tickets start at $35.
Halloween in the Parks:
- DΓa de los Muertos, 5:30-8pm Friday at Marquette Park, free.
- Upside Down Halloween Parade, noon-2pm Saturday at Washington Park, free.
Montrose Monster Mash: Trick-or-treat at local businesses along Montrose.
- 4-7pm Oct. 31 on Montrose Avenue near the Brown Line stop.
- Free, but register.
"Scream" at Rooftop Cinema: Take in the cult classic under the stars.
- 10:50pm Oct. 30 and 7:30pm Oct. 31 at 311 N. Morgan St., 5th floor in Fulton Market.
- Tickets start at $23.
2. More things to do this weekend
Experience fall festivities, live music and theatrical performances happening across the city.
π Magic School Bus
- Travel down memory lane with the little ones to catch this '90s classic production on stage.
- 10am and noon Friday at George Van Dusen Theatre at North Shore Center for the Performing Arts in Skokie.
- Tickets start at $15.
π» Oktoberfest
- It's your last chance to experience this German celebration with beer, live music, food and outdoor games.
- Times vary, Thursday-Sunday at 171 N. Peoria St. in Fulton Market.
- Tickets start at $19.
- Watch this live performance spotlighting Black art and music.
- 6pm Friday at Harris Theater in Millennium Park.
- Tickets start at $20.
π€ Polyrhythmics
- Catch this Seattle musical group live for a night of funk and R&B, jazz and Afrobeats.
- 8pm Friday at Garcia's in West Loop.
- Tickets start at $20.
πͺ© Diva Royale Drag Queen show
- Experience celebrity impersonations of some of the greatest icons like Madonna, Dolly Parton, BeyoncΓ© and more.
- Don't party famished β dinner and brunch are served.
- Times vary Friday-Sunday at Y Bar in River North.
- Tickets start at $35.
π« Spooky Afternoon Tea
- Spend a spooky afternoon sipping tea and champagne at this fancy hotel with small bites and pastries.
- Saturday-Sunday at The Ritz-Carlton off Mag Mile.
- Tickets start at $105.
π―ββοΈ Slo 'Mo does the VMAs
- The long-running dance party celebrates iconic moments from VMA history before a walk-off for best costumes.
- 9pm Saturday at Sleeping Village in Avondale.
- Tickets start at $20.
π Fall Market
- Shop this curated indoor market and support local and small businesses.
- 11am-5pm Saturday-Sunday at Artifact Events in Ravenswood.
- Tickets start at $10.
3. "Mayor of Kingstown" and more premieres to stream
Here's what's new on HBO Max, Netflix, Paramount+, Hulu, Peacock, BET+, Prime Video, Tubi and PBS.
What we're watching: A new installment in the "It" franchise, a thriller from the director of "The Hurt Locker" and a new season of "Mayor of Kingstown."
"Mayor of Kingstown" season 4 available Sunday on Paramount+
Driving the news: "The Sopranos" star Edie Falco is introduced as a new adversary to Mike McLusky (played by Jeremy Renner).
Zoom in: Control over Kingstown is threatened as a power struggle ensues and McLusky is forced to confront the resulting gang war.
More titles:
"Nobody Wants This" season 2 available now on Netflix
- Leighton Meester reunites with her "Gossip Girl" co-star in a guest role as Abby, Joanne's (Kristen Bell) nemesis from middle school who is now an influencer.
"The Family Business" season 6 available now on BET+
- In the midst of family dissension, LC and Chippy Duncan are reeling from the discovery of a new son who was abducted at birth.
π’Moyo is dusting off her best fall fits.
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