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The final weekend of June hits every note—Pride, power, and performance. The 54th annual Chicago Pride Parade headlines Sunday with more than a million expected to line the streets, but the celebration stretches far beyond Northalsted. From a soul summit at Ravinia with Al Green and The O’Jays to rooftop DJs, comedy in River North, and tacos and tequila in Lincoln Park, the city is alive. Add in an extended run of The Color Purple at the Goodman and it’s clear: Chicago isn’t easing into summer—it’s throwing a block party at every turn. Here’s what not to miss.
All Weekend
The Color Purple at Goodman Theatre – Extended Run
Now through August 3 | Goodman Theatre
Directed by Lili-Anne Brown with a powerhouse cast including Brittney Mack as Celie, Aerie Williams as Shug Avery, and Shantel Renee Cribbs as Nettie, this Tony Award-winning musical adaptation of Alice Walker’s classic novel has added six performances by popular demand. Experience a stirring story of resilience and hope brought to life with vibrant choreography, music, and heart. Tickets available at GoodmanTheatre.org/Purple or 312.443.3800.
That’s What Friends Are For: Gladys, Dionne and Patti – Extended Run
Now through August 10 | Black Ensemble Theater
Black Ensemble Theater stages a musical celebration of sisterhood and soul, honoring the legendary voices of Patti LaBelle, Dionne Warwick, and Gladys Knight. Enjoy unforgettable hits and heartfelt storytelling at 4450 N. Clark Street.
Chicago Taco & Tequila Fest
June 27–28 | Friday 5–10 p.m., Saturday 11 a.m.–10 p.m. | Wrightwood Park, 2555 N. Ashland Ave.
Tacos, tequila, and tunes. Enjoy dishes from over 10 local restaurants, including Prime Tacos, Carnitas Roldan, and Tandoor Char House—plus live music and optional tequila tastings and margarita flights. Held in Lincoln Park’s Wrightwood Park.
Friday, June 27
The Roots at Ravinia
7 p.m. | Ravinia Pavilion
Hip-hop’s best live band takes over the storied stage with their signature blend of jazz, funk, and razor-sharp lyricism. Featuring special guest Nai Palm of Hiatus Kaiyote.
After 7 at City Winery (Night 1)
6 p.m. & 9:30 p.m. | City Winery Chicago
Kick off the weekend with smooth harmonies and throwback grooves from the R&B trio that defined a quiet storm era.
OhJay Lamont at The Comedy Bar
June 27 | 7:00–8:30 p.m. & 9:00–10:30 p.m. | The Comedy Bar
Born and raised on Chicago’s West Side, comedian OhJay Lamont brings viral skits and raw stand-up energy to the stage. Known for his self-produced roast videos and performances alongside comedy veterans, Lamont headlines a one-night show in River North.
Saturday, June 28
Main Street Fair
11 a.m.–9 p.m. | 700 Main St., Evanston
A brand-new summer celebration with deep Evanston roots, this all-day fest revives the spirit of the beloved Custer Street Fair. Expect over 100 artisan vendors curated by Evanston Made, along with live music, food, and a youth marketplace featuring teen makers and kid-friendly activities from Art Makers Outpost. Presented by Main Dempster Mile. Free to attend.
The Color Purple Book Club
4:30 p.m. | Goodman Theatre
Dive into Alice Walker’s Pulitzer Prize- and National Book Award-winning novel The Color Purple for a discussion that bridges the page and the stage, inspired by the Tony Award-winning stage musical adaptation. Ideal for book clubs, solo readers, and those experiencing the story for the first or hundredth time!
Al Green & The O’Jays
7 p.m. | Ravinia Pavilion
A masterclass in soul. Al Green returns with his velvet falsetto, while The O’Jays bid farewell with a final tour full of timeless harmonies and chart-topping hits.
Robert Glasper & Avery Sunshine – Grammy Night
Doors at 5:30 p.m., show at 7 p.m. | Country Club Hills Amphitheater
A night of genre-bending brilliance. Glasper’s jazz-rooted fusion meets Avery Sunshine’s radiant soul for an unforgettable performance under the stars.
Craft Brews at Lincoln Park Zoo
7–10 p.m. | Lincoln Park Zoo
Sip and stroll after hours with 100+ beer, cider, and cocktail tastings. Live music, lawn games, food trucks, and zero kids. 21+ only.
Taste of Chicago – Marquette Park Edition
All Day | Marquette Park
Food, flavor, and neighborhood pride as the city’s signature culinary fest lands on the South Side. Expect local vendors, music, and a vibrant community atmosphere.
Pride North (Day 1)
12–10 p.m. | Glenwood Ave.
DJs, drag, and dancing all day in Rogers Park. A no-cost, all-love celebration near the Morse Red Line stop.
Rhythm Fest with Third Coast Percussion
June 28 | 12–10 p.m. | Epiphany Center for the Arts, 201 S. Ashland Ave.
Celebrate 20 years of groundbreaking rhythm with GRAMMY®-winning ensemble Third Coast Percussion. Rhythm Fest transforms Epiphany into a percussive playground with over 30 hours of performances, family fun, and sound installations featuring artists such as Jlin, Clarice Assad, and a finale performance of “Murmurs in Time” by the late Zakir Hussain.
Navy Pier Pride
Begins at 10 a.m. | Navy Pier
A full day of queer joy and community partnership along the lakefront. Performances, family-friendly activities, and visibility for all identities.
After 7 at City Winery (Night 2)
6 p.m. & 9:30 p.m. | City Winery Chicago
If you missed Friday—or want more—After 7 returns with two more intimate R&B sets.
Sunday, June 29
Chicago Pride Parade
Steps off at 11 a.m. | Northalsted to Lincoln Park
One of the largest Pride parades in the world. Over 150 groups march, accompanied by music, floats, and movement. Free to attend. Theme: United in Pride.
Pride North (Day 2)
12–10 p.m. | Glenwood Ave.
The block party continues. Rogers Park stays loud, proud, and full of rhythm from afternoon into evening.
