Our picks for events in and around Chicago this weekend.
Teddy Swims
Rolling Stone declared Teddy Swims “an old-school, old-soul charmer.” See him perform live at the United Center — and then tune in Sunday for MTV’s Video Music Awards. The genre-bending singer-songwriter will perform a tribute alongside Raye and Sombr, honoring the 10th anniversary of George Michael’s death. 7 p.m. Sept. 25 at United Center, 1901 W. Madison St.; tickets $49.40 at unitedcenter.com
Sara Bareilles
With an album inspired by the deaths of close friends, Sara Bareilles brings her “Good Grief” tour to the Chicago Theatre. According to The Globe and Mail, free packs of tissues branded with Bareilles’s name were handed out earlier this month at a Toronto show. Be prepared. 8 p.m. Sept. 27-28 at the Chicago Theatre, 175 N. State St.; tickets at msg.com
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Bassem Youssef
The comedian dubbed “the Egyptian Jon Stewart” returns to Chicago with his distinct brand of political satire. His “Belly of the Beast” tour reflects on what it means to live in a tech-mediated world brimming with contradictions. 7 p.m. Sept. 26 at the Chicago Theatre, 175 N. State St.; tickets from $36.36 at msg.com
Melissa Villaseñor
You’ve got four chances to catch Melissa Villaseñor, the former “Saturday Night Live” cast member and voice actor. In her 2025 special, “Welp … What Now?” she explores life after “SNL.” She’s known for her impressions, including one of the late, great Dolly Parton. 7 p.m. and 9:15 p.m. Sept. 25 and 6 p.m. and 8:30 p.m. Sept. 26 at Den Theatre, 1331 N. Milwaukee Ave.; tickets from $28 (two-item minimum) at thedentheatre.com
WWE: Worlds Collide
CM Punk, Rey Mysterio and Penta will compete at this weekend’s WWE: Worlds Collide, a crossover event featuring matches with wrestlers from Raw, SmackDown and NXT as well as Lucha Libre AAA, the Mexican promotion WWE acquired last year. Some controversy has been brewing about when and whether the event will be streamed. Good thing you’re local, so you can see it in person. 7:30 p.m. Sept. 26 at Allstate Arena, 6920 N. Mannheim Road, Rosemont; tickets from $57.10 at rosemont.com
St. Alphonsus Oktoberfest
’Tis the season to raise a stein — this weekend at St. Alphonsus Oktoberfest. Expect oompah bands, polka dancing, bratwurst and, of course, plenty of beer, local and international. On Sept. 27, bring your kids to the Kinderfest. 5 p.m.-10 p.m. Sept. 25, noon-10 p.m. Sept. 26 and noon-7 p.m. Sept. 27 around 1429 W. Wellington Ave.; suggested donation $10 on Sept. 25-26, $5 Sept. 27; details at chicagoevents.com
Armitage County Fair
A county fair in the middle of the city? Absolutely. Or at least a spin on one. You can even enter contests to win blue ribbons. Categories include: best dog dressed as a farm animal, best ball game-style beer call, best look-alike contest, best street parking dibs item, and best Chicago tattoo. Plus, expect all the usual Chicago festival accoutrements, including stages featuring La Luz and Sun Ra Arkestra. Noon-10 p.m. Sept. 26 and noon-9 p.m. Sept. 27 on Armitage Avenue between California Avenue and Humboldt Boulevard; $10 suggested donation; details at armitagecountyfair.com
Clark Street Live
The Cubs are away this weekend, but head to Wrigleyville anyway as it kicks off a new street festival. It’ll feature two stages of live music —one for country acts, another for rock and cover bands — as well as food and arts vendors. Remember, festival season is growing short. 11 a.m.-10 p.m. Sept. 26 and 11 a.m.-9 p.m. Sept. 27 on Clark Street between Addison Street and Newport Avenue; suggested donation; details at clarkstreetlive.com
“Top Gun: Maverick” in Concert
The Chicago Philharmonic will accompany a screening of “Top Gun: Maverick,” the 2022 sequel starring Tom Cruise, Miles Teller, the late Val Kilmer and Jennifer Connelly. The soundtrack features work by original “Top Gun” soundtrack composer Harold Faltermeyer as well as Hans Zimmer, Lorne Balfe and Lady Gaga — who sang the movie’s main ballad, “Hold My Hand.” 7:30 p.m. Sept. 26 at The Auditorium, 50 E. Ida B. Wells Drive; tickets from $54.35 at auditoriumtheatre.org
“KPop Demon Hunters” on the Plaza
Fans assemble: The Obama Presidential Center will host an outdoor screening of the beloved animated Netflix film on its John Lewis Plaza. Bring a cozy blanket to watch Rumi, Mira and Zoey face off against the Saja Boys — and discover that good and bad aren’t always so clear-cut. It’s gonna be, gonna be golden. 6 p.m.-8:30 p.m. Sept. 25 on John Lewis Plaza, Obama Presidential Center, 6001 S. Stony Island Ave.; details on the free event at obama.org
Have something to do around Chicago? Email events to [email protected].
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