Chicago Pride Fest Headliners this year include Estelle, Big Freedia, and the Veronicas; there's also the usual colorful street fair, comprising food and drink vendors, art items, and "unique merchandise tailored to the gay community." The Pride Parade is next weekend. 6/20, 11 AM-10 PM, and Sun 6/21, 11 AM-9 PM, Halsted and Waveland, chicagopride.gopride.com.
Chicago Women's Funny Festival Hundreds of women comics perform on four stages over four days (it's also the fourth anniversary of this fest). 6/18-6/21: Thu 8-10 PM, Fri 8-11 PM, Sat 5-11 PM, Sun 2-8 PM, Stage 773, 1225 W. Belmont, chicagowomensfunnyfestival.com, $15 per set, $100 festival pass.
Chigaygo! The lineup at this queer comedy showcase features Marla Depew, Ali Clayton, Cody Melcher, Peter S. Kim, Gwen La Roka, and Rachel McCartney; Scott Duff hosts. Sun 6/21, 8 PM, Laugh Factory, 3175 N. Broadway, laughfactory.com, $27.
Daughter of Pridezilla LGBTQ sketch-comedy troupe GayCo Productions presents a special showcase of Pride Month improv and storytelling. 6/19-6/27: Fri-Sat 10 PM, Playground Theater, 3209 N. Halsted, gaycodaughterofpridezilla.eventbrite.com, $13.
Drag Queens! Drag queen Muffy Fishbasket hosts a Pride Month show. Fri 6/19, 8 PM, Uptown Underground, 4707 N. Broadway, uptownunderground.net, $20, $15 in advance.
Gay Today: A Pride Cabaret Performers from Pride Films and Plays sing songs about "modern romance and self-discovery." Mon 6/22, 7 PM, Mary's Attic Theatre, 5400 N. Clark, pridefilmsandplays.com, $15.
Night of a 1,000 Divines Berlin stalwart Trannika Rex, playing John Waters for the night, hosts a "Debased and Divine Runway Show" paying tribute to the famous drag queen and Waters muse; Lucy Stoole, Shea Coulee, and Valentine Addams also perform. Costumes encouraged, naturally. Sat 6/20, 10:30 PM, Berlin, 954 W. Belmont, berlinchicago.com.
Out in the Harbor A Pride pool party at Six Flags' Hurricane Harbor, featuring music by DJ Jalil Z and Scarlet's resident disc jockeys. Hosted by Andrew Christian and Trannika Rex. Mon 6/22, 5-10 PM, Six Flags Great America, 1 Great America Pkwy., Gurnee, chicago.gopride.com, $33.
Queerest House in Chicago? Every Wednesday in June, Hull-House hosts discussions about the role of the settlement house and its founder, Jane Addams, in Chicago LGBTQ history. 6/3-6/24: 3-4 PM, Jane Addams Hull-House Museum, 800 S. Halsted, hullhousemuseum.org, $5 suggested donation.
Slave 4 Britney: Extended Pride Edition DJ Riley York's monthly Spears-centric dance party gets a special Pride upgrade. Sun 6/21, 6 PM, Roscoe's, 3356 N. Halsted, 773-281-3355, roscoes.com.
Slo 'Mo Presents: Paradise The popular dance party celebrates Pride with live covers—backed by a ten-piece band!—of D'Angelo, Sade, and others. DJs follow. Fri 6/19, 9 PM, the Promontory, 5311 S. Lake Park Ave. West, promontorychicago.com, $25, $20 in advance.
Warming Up Pride Films and Plays presents the first installment in its LezPlay Salon Series; screening tonight are Chicago-based webseries including the first season of #Hashtag. Comic Shannon Noll hosts. Fri 6/19, 8 PM, Apollo Theater, studio, 2540 N. Lincoln, pridefilmsandplays.com, $10.
When You Believe The Windy City Gay Chorus and Windy City Treble Quire take a musical spin through the history of the LGBTQ movement. Sat 6/20, 5 and 8 PM, Ebenezer Lutheran Church, 1650 W. Foster, windycitysings.org, $18-$30.
You're Being Ridiculous: Pride Show A special edition of Jeremy Owens's storytelling showcase, highlighting LGBTQIA stories. BYOB. Sat 6/20, 7 PM, Women & Children First, 5233 N. Clark, womenandchildrenfirst.com, $10 suggested donation.