Chicago Humanities Festival

The Chicago Humanities Festival is underway, featuring a wide range of discussions and performances. Notable speakers include Naomi Klein and Astra Taylor, who will engage in a conversation about ‘End Times Fascism’ on Friday. The festival features an array of talents, including Marlon James, Daniel Kraus, Leïla Slimani, David Byrne, and more. Expect talks, concerts, and performances focusing on cultural phenomena until November 14. Locations vary—visit chicagohumanities.org for tickets.

Chicago River Swim

The Chicago River Swim makes a comeback after last year’s successful event. Scheduled for September 20, swimmers will tackle courses of one or two miles, with proceeds supporting ALS research and swim safety programs for underserved communities. Spectators can watch from the Riverwalk. An earlier event, The Big Jump, will occur on September 18 and involves notable personalities including Olympians and civic leaders. Find more details at chicagoriverswim.org.

Navy Pier Chicago Live Festival

This weekend at Navy Pier, experience the Chicago Live Festival featuring performances from various beloved arts groups. Headlined by Common, the festival includes The Second City, Annoyance Theatre, Hubbard Street Dance Chicago, and many more. Enjoy the cultural showcase at no cost from September 19 to 20. More information is available at navypier.org.

Phoebe Bridgers Concert

Phoebe Bridgers will perform at the United Center, providing an unforgettable experience as described by Rolling Stone and Variety. Her no-phone policy ensures an immersive concert atmosphere. Events start at 7:30 p.m. on September 18-19. Tickets start at $84.75 and can be purchased at unitedcenter.com.

Role Model at The Salt Shed Fairgrounds

Role Model returns to Chicago after performing at Lollapalooza. Known for his hit song ‘Sally, When the Wine Runs Out,’ he promises engaging performances. Attend his concerts on September 19-20 at The Salt Shed Fairgrounds. Ticket information can be found at saltshedchicago.com.

Kany García Concert

Latin Grammy Award winner Kany García continues her tour following her album release ‘Puerta Abierta.’ Known for captivating performances, García will perform at The Auditorium Theatre on September 20. Tickets are available from $43.20 at auditoriumtheatre.org.

Reeling: The Chicago LGBTQ+ International Film Festival

Reeling offers an extensive film festival showcasing LGBTQ+ narratives, documentaries, and shorts. Start with ‘Before I Do’ on September 18 or watch ‘The Brittney Griner Story’ on September 20. The festival runs until September 27 across various locations. Tickets can be secured at reeling2026.eventive.org.

Destinos: Chicago International Latino Theater Festival

Destinos commences with a rich lineup in Latino theater. Access documentary-style plays, dance theater, and puppetry dramas. Workshops are available to support diverse voices. Runs through October 11 in various locations. Visit clata.org for tickets.

Christina P. Standup Comedy

Comedian Christina Pazsitzky is set to perform standup comedy inspired by her recent personal experiences and family life. Shows take place on September 18-19 at The Den Theatre. Tickets start at $31, view details at thedentheatre.com.

Retro on Roscoe

Celebrate nostalgia with Retro on Roscoe, featuring classic cars, live music, and vintage shopping. Cover bands perform for a throwback experience. The street fair runs from September 18 through September 20. A suggested donation of $15 supports the event. More details can be found at roscoevillage.org.