Arts & Entertainment
Stand-Up Comedy and a Comic Books Fest: 4 Arts Picks for Your Weekend
Pretty Good Fest (Provided)
Every Thursday, WTTW News newsletter producer Josh Terry highlights his picks for the week’s must-see cultural events.
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For certain people, October hits like a breath of fresh air. The mild, crisp weather allows for all kinds of layered outfits. Cardigans, jackets, hoodies — you name it. You can take in the fall leaves and stroll around your neighborhood. It’s easy to be rejuvenated by fall. If you’re not a summer person for all its sunshine and heat, this is the season for you to experience all the art and culture the city has to offer. Here’s what’s on our calendar this weekend.
Comedy: Steven Castillo — Hideout
Steven Castillo is best known for his two stints as a writer on “Saturday Night Live.” Now, he’s the host of the “2 Amigos” podcast and he’s embarking on a stand-up comedy tour that hits Hideout on Saturday. Expect biting, pop-culture-infused humor from an Oklahoma-raised comic. Buy tickets here.
Art: Pretty Good Fest 2026 — Chicago Athletic Association
Head to the Chicago Athletic Association Saturday for Pretty Good Fest 2026, which brings more than 100 comics artists and small press publishers to celebrate and sell their work. The event runs from 11 a.m. to 6 p.m. and will feature special guests like the esteemed cartoonists Chris Ware, Tara Booth and Michael DeForge. The event is free and open to the public, and you can click here for more information.
Theater: “King Hedley II” — City Lit Theater
August Wilson, the Pulitzer-winning playwright, was the pen behind several well-known productions like “Fences,” “Ma Rainey’s Black Bottom” and “The Piano Lesson.” Ten of his best-known works, often referred to as “The Pittsburgh Cycle,” dealt with life in his home city. One of these plays, “King Hedley II,” is being staged at Edgewater’s City Lit Theater. It follows King Hedley, a man recently released from prison, as he “attempts to rebuild his life by selling stolen refrigerators so he can buy a video store.” For tickets, click here.
Performance: “Finlandia & Beethoven Eroica” — Chicago Symphony Center
Since 1919, the Civic Orchestra of Chicago has developed emerging musicians to become professionals with free or low-cost performances. Their next concert is Sunday, when they’ll run through a program of Ives’ “Variations on America,” Hernández’ “Parallax (or 33,000 Stolen Sunsets),” Sibelius’ “Finlandia” and Beethoven’s “Symphony No. 3 (Eroica).” Buy tickets here.
WTTW News arts coverage is supported by the JCS Arts, Health & Education Fund of the DuPage Foundation.
