Axios Chicago Weekender

May 21, 2026
ποΈ It's the weeekeeeend! (in Oprah voice)
β±οΈ Situational awareness: Beaches open tomorrow! Also, check out CTA and OEMC for reroutes and road closures for big events this weekend.
Today's newsletter is 721 words β a 2.5-minute read.
1 big thing: The Colbert connection
When Stephen Colbert signs off permanently tonight, it'll also mark the end of an era for several "Late Show" staffers who got their start in Chicago.
The latest: "The Late Show With Stephen Colbert" is ending its run after CBS canceled the show, having produced nearly 1,800 episodes.
State of play: Colbert, who came up through The Second City, has hired many writers from Chicago over the years, including for his "Late Show" staff of more than 20 writers.
Between the lines: With Colbert off the air, Second City loses one of its biggest pipelines for placing up-and-coming talent in late-night.
What they're saying: "There's a kind of creative shorthand for comedy makers that have gone through the Second City ecosystem," the theater's Kelly Leonard tells Axios.
By the numbers: Writers with Chicago ties β some dating back to "The Colbert Report" days at Comedy Central β have included Paul Dinello, Tom Purcell, Ariel Dumas, Brian Stack, Jen Spyra, John Thibodeaux, Asher Perlman, Steve Waltien, Carley Mosely and many more.
The bottom line: Wherever Colbert lands next, don't be surprised if Chicago writers follow.
When to watch: "The Late Show with Stephen Colbert" airs its final episode tonight at 10:35pm.
2. Summer season launches
Memorial Day weekend marks the launch (or at least soft launch in chilly Chicago) of the summer season.
- Here are some ways to spend the long weekend.
πΊ Fleurs de Villes
- This exhibit is about more than flowers. It's fashion, creativity and mastery of the craft. Plus, cocktail and tea parties!
- Thursday-Monday at 900 North Michigan Shops, with a couple of installations at The Ritz-Carlton and the Four Seasons.
π Carrie's thought bubble: I was a judge for the show and was blown away by what these artists can do with fresh flowers and plants. There were dresses I would love to wear ... I'd just make sure my husband watered me throughout the night.
- Jurassic Park in the burbs! Visitors (young and old, let's be honest, dinosaurs aren't just for kids) can walk through a dinosaur ribcage tunnel, dig for fossils and get up close with a T. Rex.
- Opens Friday and runs through Oct. 25.
βπ½ Black Writers Weekend
- Meet other writers to share ideas and watch the film "Dear Black Writers."
- 2-7pm Saturday at Da Book Joint in South Shore.
π» Mayfestiversary
- Grab a cold beer from Bergyl or Dovetail, jam to live bands and sample the food trucks at the street fest.
- 11am-10pm Saturday and 11am-9pm Sunday between Begyle Brewing and Dovetail Brewery in the Ravenswood Corridor.
π΅ Rockin' in the Park
- Does anything say summer in Chicago more than a Styx cover band and fireworks? Exactly.
- 7-10pm Sunday at Parkway Bank Park's great lawn in Rosemont.
ποΈ Secret River Shows
- Take out a kayak or post up under the bridge for a live concert.
- Noon on Monday at Wild Mile at 905 W. Eastman St.
3. What to watch this weekend
Whether you want action, sci-fi or a comedy thriller, there's something new to watch.
Here are fresh titles streaming this week:
"Tom Clancy's Jack Ryan: Ghost War" β available now on Prime Video.
- John Krasinski, who co-wrote the script, returns as Jack Ryan for the espionage thriller that drops the CIA analyst into another globe-spanning crisis.
"The Boroughs" β available now on Netflix.
- Alfre Woodard, Alfred Molina, Geena Davis and Bill Pullman star in the sci-fi mystery series set in a New Mexico retirement community.
- What they're saying: The show is executive produced by Matt and Ross Duffer, the brothers behind "Stranger Things."
"Maximum Pleasure Guaranteed" β available now on Apple TV+.
- Tatiana Maslany stars in this dark comedy-thriller series about a newly divorced suburban mom pulled into blackmail, murder and the absurd politics of youth soccer.
"Wanda Sykes: Legacy" β available now on Netflix.
- In her third Netflix comedy special, Sykes doesn't shy away from politics and newsβ and "the cultural clash over washcloths," as Netflix puts it.
Thanks for reading!
π² Carrie has taken out her bike and is ready to ride!
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Edited by Carrie Shepherd.
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