Big Gay Ice Cream The iconic New York ice cream manufacturer transports its treats in the Gold Coast at Nico Osteria for Pride weekend, raising money for Howard Brown Health with a dessert menu featuring boozy collaborative creations such as Out and Proud Pops, freeze pops served submerged in a shot of tequila. Sat 6/23, 9 AM-11 PM, Sun 6/24, 9 AM-10:30 PM, Nico Osteria, 1015 N. Rush, 312-994-7100, nicoosteria.com.
Cards Against Humanity Live Inspired by the ribald party game Cards Against Humanity, the improvisers in this group solicit sordid suggestions from the audience. This particular evening incorporates LGBTQ-themed segments. Sat 6/16, 10 PM, Pride Arts Center, 4147 N. Broadway, 1-800-737-0984, pridefilmsandplays.com, $10.
Chicago Pride Fest This street festival kicks off the city's Pride celebration. Features include live music, local vendors, a dance party, and a pup parade. Sat 6/16-Sun 6/17, 11 AM-10 PM, Halsted and Waveland.
Chicago Pride Parade It has arrived! The route for this year's parade begins at Montrose and Broadway, ending at Diversey and Sheridan. Expect drag performers and elaborate balloon sculptures among the floats and revelers. Sun 6/24, noon, various locations.
Drag Brunch Regular Reader contributors the Triibe present Yams, a drag-themed meal with performances by Delikate Doll and Bambi Banks. Unlimited mimosas! Sat 6/30, noon-4 PM, Throop Studio, 1500 N. Throop, throopstudio.com.
Let's Make It Perfectly Queer: A Salute to Pride The Annoyance's Mick Napier directs a cast composed of all-LGBTQ comedians performing new and classic Second City sketches concerning queer topics. Corey Caldwell, George David Elrod, Lanny Fox, Maya Haughton, Claudia Martinez, and Riley Mondragon take the stage. Through 6/24: Fri and Sun, 7 PM, Second City, 1616 N. Wells, 312-337-3992, secondcity.com, $20, $15 students.
Raks Geek: Smoke + Wonders Composed of self-professed sideshow geeks, the Raks Geek dance troupe performs pieces inspired by "gods, demons, midi-chlorians, and superheroes with bellydance and fire." A portion of the proceeds will be donated to the National Runaway Safeline to help LGBTQ+ youths. Sat 6/16, 10 PM, Uptown Underground, 4707 N. Broadway, 773-867-1946, uptownunderground.net, $25-$39.
Steamworks: The Musical This comedic play, returning to the Annoyance for a limited run, is set in a Chicago bathhouse populated by gentlemen ready to welcome the new kid in town. Through 7/6: Fri 8 PM, Annoyance Theatre, 851 W. Belmont, 773-697-9693, theannoyance.com, $20, $15 students.
Striking Out (A Gay Baseball Musical) In order to play baseball for the Chicago Otters, Jimmy Roberts must hide his horrifying secret: He's straight. Will his shame tear the team apart? Sat 6/16, 8 PM, Annoyance Theatre, 851 W. Belmont, 773-697-9693, theannoyance.com, $20, $15 students.
The T Join in the festivities at this launch party for The T, a new webseries prominently featuring LGBTQ characters. Mon 6/18, 7 PM, Chicago Cultural Center, 78 E. Washington, 312-744-6630, chicagoculturalcenter.org.
30 Queer Plays in 60 Straight Minutes The Neo-Futurists perform a queer-themed version of their tentpole show the Infinite Wrench to raise money for Brave Space Alliance, the first black-led, trans-led LGBTQ center on the south side. Thu 6/21, 7:30 PM, Neo-Futurarium, 5153 N. Ashland, 773-275-5255, neofuturists.org, $25.
You're Being Ridiculous Some of Chicago's finest storytellers take center stage to raise money for the Women's Voices Fund. The pride-themed lineup includes Carly Ballerini, Ada Cheng, Erin Diamond, Nestor Gomez, Jeremy Owens, and C. Russell Price. Sat 6/16, 7 PM, Women & Children First, 5233 N. Clark, 773-769-9299, womenandchildrenfirst.com, $10 cash. v