12-06-2025
- Entertainment
- Chicago Tribune
What to do in Chicago this weekend: Puerto Rican Parade, Counting Crows and Old Town Art Fair
The parade is Saturday but the 44th Annual Fiestas Patronales Puertorriqueñas is already underway in Humboldt Park. Featuring a packed music lineup, a carnival, a fashion show, a Father's Day picnic, dominoes, cultural performances, artisan vendors and more, you could plan your whole weekend here. The parade will step off at noon on June 14, on Division Street from Campbell Avenue to Humboldt Drive.
The holiday falls on Thursday this year but you can start your Juneteenth celebrations early this weekend in Bronzeville and Beverly/Morgan Park. Both neighborhoods will feature family-friendly festivals centered on Black culture. More events are planned throughout the city on June 19 and beyond, including the Juneteenth Music Fest, featuring Ashanti, Lil Kim, Mýa and more.
Now in its 90th season, the Grant Park Music Festival continues its opening week with chorus director Christopher Bell leading 'The Planets' by Gustav Holst — perfect music to enjoy under a summer sky. The Grant Park Orchestra and Chorus will perform Lili Boulanger's 'Psalm 24' and Jake Runestad's 'Earth Symphony.' This free concert series is a Chicago delight.
On her first tour since 2018, the Mexican singer-songwriter will perform introspective songs from her latest album, 'Cancionera.' Recorded in one take and inspired by her 40th birthday, 'Cancionera' was produced by Adȧn Jodorowsky; he also collaborated with Lafourcade on her Grammy-winning 2022 album, 'De Todas las Flores.'
The Canadian singer-songwriter plays The Salt Shed on the heels of her spring release, 'Paid in Memories.' Counting Crows roll into Ravinia with more than 30 years of tunes to play. Their tour marks the release of 'Butter Miracle, the Complete Sweets!' Special guest The Gaslight Anthem lends a Jersey Shore edge.
He's back, this time with the Chicago Philharmonic backing him — and in an era when AI is no longer a mere plot device. Feel the buzz of '80s synth in your gut as you watch a 30-something Arnold Schwarzenegger star as the iconic cyborg assassin in James Cameron's sci-fi classic.
Old Town will be awash in art this weekend as both the Old Town Art Fair and Wells Street Art Festival set up shop. Celebrating 75 years and featuring fine art, the Old Town Art Fair will host more than 200 artists, a garden walk, live music and children's entertainment (magic show, face painting). A few blocks away, the 50-year-old Wells Street Art Festival will feature more than 100 artists, live music and children's entertainment (art-making activities, petting zoo). Each has its own tone — Old Town plays more garden party to Wells Street's block party — so take a day to explore them both.
Sure, Midsommarfest fetes Andersonville's Swedish roots, but it also serves as a joyous kick-off to Pride season in Chicago. Drop in for the maypole dance Saturday morning, stroll Clark Street to browse artisan and vintage vendors, listen to live music, check out the drag lineup and visit the kids activity area. Or, just go to enjoy one of the city's most welcoming neighborhoods.
Get your game on this weekend at the Chicago Public Library. Gamer's Universe, organized by Chicago Teen Gamer's Guild in partnership with high school-aged interns at CPL, celebrates all aspects of gaming culture. Explore original video games created by guild members, cosplay or show off your skills at gaming stations throughout Harold Washington Library Center.
