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May 30, 2025 · — Emmi Mack
Calling all Chicago-style freaks! There’s lots to do this weekend, but if you’re up north for Windy City Hot Dog Fest, consider stopping by The Seventh Corner Gallery for their encased-meat-themed group show. After all, “Art is in the eye of the beefholder.”
Now, onto gangsters, “The Matrix,” Harold’s Chicken Shack — and your weekly news quiz 👇
What Chicago's Talking About
Illinois’ Plan for CTA Still Coming Into Focus
State lawmakers have finally unveiled reform bills to address the $700 million transit budget shortfall and create a new regional oversight board for CTA, Metra, and Pace. WTTW’s Nick Blumberg and South Side Weekly’s Jim Daley discuss that, and more, on today’s podcast. [City Cast Chicago 🎧]
This Chicago Gangster’s Sentence Was Commuted by Trump
Under founder Larry Hoover, the Gangster Disciples grew to become one of the nation's most notorious gangs. Hoover was sentenced to life over federal charges in 1997. On Wednesday, President Donald Trump commuted the 74-year-old's sentence, but Hoover remains in prison over an Illinois murder charge. [Sun-Times]
Harold's Chicken, Music Box Receive City Grants
The city is giving $20 million to businesses and nonprofits across Chicago. The new Chicago South Side Birth Center received the largest sum, $3.3 million, while The Music Box Theatre, Chicago Architecture Center, and Maplewood Brewing and Distillery got at least $1 million each. A Harold’s Chicken Shack in Washington Heights also received over $100,000 for improvements. [Block Club]
This Week’s Must-Read
Before “The Matrix,” Beverly natives — and fellow Whitey Young grads, go Dolphins — Lana and Lilly Wachowski made “Bound”: a steamy lesbian noir starring Jennifer Tilly and Gina Gershon. At tonight’s Sapphopalooza screening, Lilly will be in attendance. The trans filmmaker discusses the film's cult status and reflects on making "Bound" while she and her sister were both still in the closet. [WBEZ]
Sponsored Content
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Adventurous theatre lovers are gathering amongst the Berkshire mountains for the boldly reimagined Williamstown Theatre Festival, including a world premiere by Jeremy O. Harris, Tennessee Williams plays starring Pamela Anderson, Tony Danza, Whitney Peak, William Harper Jackson, and more. Discounted hotel rooms available through June 1. Choose a weekend, buy a pass.
Take This Week's News Quiz
Even with Monday off, this week was jam-packed with news from all around Chicago. Were you paying attention?
What To Do
Friday, May 30
- 🌭 Windy City Hot Dog Fest | 4-10 p.m. | Free | Portage Park
- 🎉 Do Division Street Fest | 5-10 p.m. | Suggested Donation | West Town
- 🏺 Wheel Throwing For Beginners (BYOB) | 5:30 p.m. | $40+ | Pilsen
- 🥃 Spirits & Spice Chicago Whiskey Experience | 5:45 p.m. | $13 | Streeterville
- 🍷 Wine Fest on the Beach | 6-9 p.m. | $42+ | North Avenue Beach
- 🎤 The Weeknd | 7 p.m. | $65+ | Soldier Field
- 🌟 Underscores B2B Umru | 10 p.m. | $25 | Wrigleyville
- 👑 The Queens: 4 Legends, 1 Stage | 8 p.m. | $97+ | United Center
- 🎱 Music Bingo | 8 p.m. | Free | Wrigleyville
- 🕺🏼 Feed Me | 9 p.m. | $37 | Wicker Park
- 🎵 La Bamba / Tiwa Bleu | 11 p.m. | $27 | Ukrainian Village
Saturday, May 31
- 💸 Jackson Park Highlands Community-Wide Garage Sale | 10 a.m. to 5 p.m. | Free | South Shore
- 🚴🏻♀️ Pilsen Canalport Cleanup with Bike Brigade and Afterparty | 10 a.m. to Noon | Free | Pilsen
- 💪 The Spring Volunteer Fair | 11 a.m. | Free | Bridgeport
- 🎉 Do Division Street Fest | Noon to 10 p.m. | Suggested Donation | West Town
- 🌭 Windy City Hot Dog Fest | Noon to 10 p.m. | Free | Portage Park
- 🎵 Get Down with Up Beat | 3-6 p.m. | $40 | Lincoln Park
- 🎨 Let’s Create: Open Studio | 11 a.m. to 2 p.m. | Free-$8 | Bronzeville
- 🌭 Chicago Style art show | 5-9 p.m. | Free | Portage Park
- ⛪️ Paul Elie on Postsecularism | 7-8 p.m. | $34 | Loop
- 🎵 The Weeknd | 7 p.m. | $65+ | Soldier Field
- 🎤 Karaoke Storytellers | 7:30 p.m. | $28 | Lincoln Park
- 🎶 Afro Fusion Saturday | 11 p.m. to 2 a.m. | $13+ | Uptown
Sunday, June 1
- 💃🏽 Afro Caribbean Day Party | Noon to 6 p.m. | $13 | Motor Row
- 🌳 Humboldt Park Arboreal Society (DJs) | Noon to Sundown | Free | Humboldt Park
- 🎉 Do Division Street Fest | Noon to 10 p.m. | Suggested Donation | West Town
- 🌭 Windy City Hot Dog Fest | Noon to 10 p.m. | Free | Portage Park
- 🪴 Bloom Collective Plant Club | 1-4 p.m. | $29 | Logan Square
- 🏠 Porchfest | 1-5 p.m. | $13 | Lakeview
- 💅 Divas Music Bingo | 2 p.m. | Free | West Loop
- 💪 Dads Of Love - Rooftop Sunday Tea Dance | 2-8 p.m. | $37+ | South Loop
- 🎭 “War of the Worlds” | 2:30 p.m. | $25 | Rogers Park
- 🧶 Digging Into Fiber | 5-7 p.m. | $8 | North Center
- 🌅 Sunset Soiree Yacht Party | 6-10 p.m. | $45 | DuSable Harbor
🎤 One more event rec: Karaoke Storytellers at Park West — hosted by City Cast Chicago’s own Jacoby Cochran! This Saturday at 7:30 p.m.
Free · Daily