Weekend Events in Chicago

Chicago Humanities Festival

The Chicago Humanities Festival, which began earlier this week, continues with events scheduled for Friday. Highlighted discussions include ‘End Times Fascism’ featuring Naomi Klein and Astra Taylor. The festival features diverse speakers such as Marlon James, Daniel Kraus, Leïla Slimani, David Byrne, and others. It runs until November 14, with a variety of talks, concerts, and performances in various locations. Tickets are available at chicagohumanities.org.

Chicago River Swim

Following its inaugural event last year, the Chicago River Swim returns on September 20, conditions permitting. This event supports ALS research and swim safety programs for underserved communities. Swimmers can participate in one or two-mile courses while spectators watch from the Riverwalk. An additional event, The Big Jump, takes place on September 18, featuring Olympians and civic leaders. For more details, visit chicagoriverswim.org.

A swimmer embraces the showers after competing in the Chicago River Swim on September 21, 2025, in downtown Chicago. (Audrey Richardson/for the Chicago Tribune)

Navy Pier Chicago Live Festival

The Navy Pier Chicago Live Festival takes place this weekend with performances from various arts groups, including The Second City, Annoyance Theatre, Hubbard Street Dance Chicago, and more. Common headlines the events. All performances are free and held at Navy Pier. More information can be found at navypier.org.

Phoebe Bridgers

Singer Phoebe Bridgers, known for her engaging performances and no-phone policy, will be performing at the United Center on September 18-19. Tickets start at $84.75 and are available at unitedcenter.com.

Role Model

Tucker Pillsbury, known as Role Model, is set to perform at The Salt Shed Fairgrounds on September 19-20. Known for his hit song ‘Sally, When the Wine Runs Out,’ his performances have garnered attention at previous Lollapalooza events. Tickets can be purchased at saltshedchicago.com.

Role Model performs at the Tito’s stage at Lollapalooza in Chicago’s Grant Park on July 31, 2025. (Dominic Di Palermo/Chicago Tribune)

Kany García

Latin Grammy Award winner Kany García will perform at The Auditorium Theatre on September 20, showcasing her recent album, ‘Puerta Abierta.’ Her performances are known to be ‘captivating and moving.’ Tickets begin at $43.20 and can be purchased at auditoriumtheatre.org.

Reeling: The Chicago LGBTQ+ International Film Festival

This weekend, the Reeling Film Festival features a selection of 25 narrative films, 11 documentaries, and over 50 shorts that explore the LGBTQ+ experience. Starting on September 18, highlights include ‘Before I Do’ and ‘The Brittney Griner Story.’ The festival runs through September 27. Tickets start at $16.79 and are available at reeling2026.eventive.org.

Destinos: 9th Chicago International Latino Theater Festival

The Destinos festival showcases over a dozen Latino theater productions throughout Chicago. Offerings include a documentary-style play, dance and movement theater, and coming-of-age puppetry. Workshops are also available. The festival runs through October 11. Tickets can be purchased at clata.org.

Christina P.

Comedian Christina Pazsitzky will perform at The Den Theatre on September 18-19. Known for her family-inspired comedy and Netflix specials, her recent personal experiences add depth to her current material. Tickets start at $31 and are available at thedentheatre.com.

Retro on Roscoe

Retro on Roscoe offers a nostalgic street fair experience with classic cars, live music, and vintage shopping. The event features cover bands performing hits from ABBA, Pearl Jam, and The Beatles. The fair runs from September 18-20 with a suggested donation of $15. Further details can be found at roscoevillage.org.

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