Events to Explore in Chicago This Weekend

Chicago Humanities Festival

The Chicago Humanities Festival is underway with a captivating lineup. This Friday features Naomi Klein and Astra Taylor discussing ‘End Times Fascism.’ Expect to see renowned names like Marlon James, Daniel Kraus, Leïla Slimani, David Byrne, Barbara Kingsolver, Eric Idle, John Green, Jesmyn Ward, Ruben Molina, Emily St. John Mandel, and others. The festival runs till November 14, offering diverse talks, concerts, and performances exploring cultural topics.

Find tickets and details at chicagohumanities.org.

Chicago River Swim

Last year saw the first organized open-water swim in the Chicago River after 98 years. This year, it returns on September 20, benefiting ALS research and swim safety programs for underserved communities. Swimmers will navigate a one or two-mile course, with spectators watching from the Riverwalk. On September 18, join the Big Jump at 10 a.m., featuring Olympians and civic leaders.

For more information, visit chicagoriverswim.org.

Navy Pier Chicago Live Festival

This weekend, enjoy the Navy Pier Chicago Live Festival, where Common headlines a gathering of Chicago’s most cherished arts groups. Witness performances from The Second City, Annoyance Theatre, Hubbard Street Dance Chicago, and others, all for free. The festival spans from noon to evening on September 19-20.

See details at navypier.org.

Phoebe Bridgers Concert

Phoebe Bridgers’ recent Madison Square Garden appearance received high praise. Witness her live at United Center without phone distractions for a focused experience. Performances occur on September 18 and 19.

Tickets start at $84.75, available at unitedcenter.com.

Role Model at The Salt Shed Fairgrounds

Tucker Pillsbury, known as Role Model, returns to Chicago following his Lollapalooza appearances. He’ll end summer with performances on September 19 and 20 at The Salt Shed Fairgrounds. Expect his popular song, ‘Sally, When the Wine Runs Out.’

Tickets are available at saltshedchicago.com.

Kany García at The Auditorium Theatre

Latin Grammy Award winner Kany García visits Chicago as part of her extensive tour. Known for ‘captivating and moving’ shows, she performs on September 20 at The Auditorium Theatre.

Find tickets starting at $43.20 at auditoriumtheatre.org.

Reeling: The Chicago LGBTQ+ International Film Festival

This weekend, Reeling offers over 25 narrative films, documentaries, and shorts focusing on LGBTQ+ experiences. Begin with ‘Before I Do’ on September 18, or see ‘The Brittney Griner Story’ on September 20. The festival spans multiple venues through September 27.

Plan your visit at reeling2026.eventive.org.

Destinos: 9th Chicago International Latino Theater Festival

Destinos showcases a vibrant lineup in Latino theater. Experience documentaries, dance, puppetry, and more across the city. Workshops aim to elevate diverse voices. The festival runs through October 11.

Details available at clata.org.

Christina P. Standup

Comedian Christina Pazsitzky’s family life informs her humor, showcased in her Netflix specials. Catch her live performances at The Den Theatre on September 18 and 19.

Tickets start at $31 at thedentheatre.com.

Retro on Roscoe Street Fair

Experience nostalgic fun at Retro on Roscoe with classic cars, live music, and vintage shopping. The fair offers entertainment with bands covering hits from ABBA, Pearl Jam, The Beatles, and more.

Event occurs September 18-20 with a suggested donation of $15. Details at roscoevillage.org.