Axios Chicago Weekender

July 24, 2025
👋🏾 Hey, friends! It's the last week of July, so let's kick back and enjoy it.
Today's newsletter is 822 words — a 3.5 minute read.
1 big thing: Improv icons reunite at iO Fest
The iO Fest, the largest improv comedy festival in Chicago, returns to the Lincoln Park theater this weekend.
Why it matters: Improv is one of Chicago's greatest exports, next to deep dish pizza and 16-inch softball.
The latest: Starting tonight, over 100 acts, featuring several iO alumni return for shows, events, workshops and parties.
- Shows include 2 Square with Peter Grosz and John Lutz, 3Peat with Lisa Beasley, alternative comic Neil Hamburger, Chicago legend Susan Messing and a 10th anniversary live taping of the "Bear Down Podcast."

State of play: For the audience, it's a great way to see famous actors like Matt Walsh from "Veep" or Chris Kattan from "SNL" return to their improv roots.
What they're saying: "It's thrilling to see so many different types and styles of improv and for our giant community to come together to celebrate our artform," iO artistic director Katie Caussin tells Axios.
Zoom out: Chicago has been the epicenter of improvisation for decades, thanks to theaters like iO, The Second City and The Annoyance.
Flashback: Improv festivals have also been a big part of the city's comedy history. The Chicago Improv Festival was the biggest, bringing in huge shows starting in 1998 before folding in 2018.
- The iO Fest picks up where the CIF left off.
If you go: Tickets range from $20 to $35 per show.
- 4-day passes are also available for $55.
2. More things to do this weekend
It's going to be cooler this weekend so soak up those summer vibes with these fests and events.
🛍️ Andersonville Summer Sidewalk Sale
- Shop at more than 40 local businesses in the North Side neighborhood.
- 9am-9pm Friday-Sunday.
- Free.
- From "Love Jones" to "Scarface" to "Crazy Stupid Love," this outdoor movie house has something for every filmgoer.
- Friday-Sunday, times vary at Rooftop Cinema Club in Fulton Market.
- Tickets start at $25.
- Experience two stages of live music, plus good beer, food and vibes.
- 5-10pm Friday and Saturday, noon-10pm Sunday.
- Free, but a $10 suggested donation.
- Prep the kids for the school year ahead with complimentary supplies and physical exams.
- 10am-2pm Saturday at Proviso West High School in Hillside.
- Free.
🎶 Chicago's Soul: The Words and Music
- Wind down with an evening of soul music and poetry.
- 5pm Saturday at Sherman (John) Park in Back of the Yards.
- Free.
- Grab your blankets for this eye-catching event.
- 5:30pm Saturday in Humboldt Park.
- Tickets start at $34.99.
🏐 17th Annual Big Dig Tournament & Beach Party
- Beach volleyball, anyone? Play and drink under the sun at this day party.
- 8am-5pm Saturday at North Ave. Beach.
- Tickets start at $45.
- Make sure your pup's the best behaved on the patio with this training.
- noon-2pm Saturday at Chicago Burger Company patio at the Riverwalk.
- $35 per dog.
⚽ Premier League Summer Series
- Meet players, club legends and mascots, prizes and more!
- 11am-11 pm Monday and 11 am-5 pm Tuesday at Guinness Open Gate Brewery in West Loop.
- Free.
3. New movies and shows to stream this weekend
Here's what's new on Netflix, Hulu, Paramount+, Apple TV+ and Prime Video.
What we're watching: The highly anticipated sequel to "Happy Gilmore," a new adventure series about a young "Black genius" and a documentary chronicling the history of hip-hop.
"Happy Gilmore 2" available Friday on Netflix
What's inside: This sequel, almost 30 years in the making, follows the titular character's comeback to the golf course with Ben Stiller, Julie Bowen and Christopher McDonald reprising their roles.
What they're saying: "The chaos in golf, [how] the sport is changing, the different factions and different, wild ways you can play golf did inform the decision to make this movie now," director Kyle Newacheck tells Axios.
"Washington Black" available now on Hulu
State of play: Based on the novel of the same name, this series follows the 19th-century, globe-trotting adventure of an 11-year-old escaped slave and science prodigy.
What they're saying: Executive producer Selwyn Seyfu Hinds tells Axios that while the story begins on a plantation, "Washington Black" is not about slavery.
- "This is a story about a Black genius," Hinds says. "This is a story about a kid who literally flies."
"Shiny Happy People: A Teenage Holy War" available now on Prime Video
- This chapter in the "Shiny Happy People" series uncovers the stories behind evangelical youth organization Teen Mania — founded by Ron Luce in the 1990s. The docuseries examines the group's disturbing practices and how its shift toward militant rhetoric and political activism created a ripple effect that can still be seen today.
"Acapulco" Season 4 available now on Apple TV+
- The fourth and final season of this comedy follows present-day Máximo (played by Eugenio Derbez) as he works to restore Las Colinas before the grand reopening. In 1986, young Máximo (Enrique Arrizon) does whatever it takes to get Las Colinas back on top of the annual ranking of Acapulco's "Best Hotels."
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