2026 Chicago Critics Film Festival Preview- 5 Must See Movies
At this point, there’s one film festival in Chicago that consistently lives up to the hype: the Chicago Critics Film Festival. This week-long celebration is packed with discoveries and beloved classics, offering audiences a curated taste of Hollywood right in the Windy City. What sets it apart is who’s behind it—professional film critics with a deep passion and understanding of what makes great cinema. Drawing from Sundance, SXSW, and top-tier genre festivals, the lineup rarely misses, ensuring there’s always something worth discussing.
Kicking off Friday, May 1st, and running through May 7th at the historic Music Box Theatre, this year’s edition boasts one of its strongest slates yet. Opening night features the Sundance hit The Invite, with director and star Olivia Wilde for a post-screening discussion of her tense relationship drama—and that’s only the beginning. Over the next seven nights, the festival offers an eclectic mix: classics like David Cronenberg’s The Fly, new work from Once director John Carney with Power Ballad, a standout shorts program, and the closing night film The Sun Never Sets, with director Joe Swanberg in attendance.
Here is my preview of the 5 Movies that I think you must see at the Chicago Critics Festival, but picking just five is never easy:
MOVIE: CAROLINA CAROLINE
STARRING: SAMARA WEAVING, KYLE GALLNER
DIRECTED BY: ADAM REHMEIER
SATURDAY, MAY 2ND @ 4:30PM
In the running for my most anticipated films of the festival is Carolina Caroline, largely because Samara Weaving and Kyle Gallner make a perfect duo. The stars of Ready or Not 2 and Smile have consistently exceeded expectations in genre films, and this time they play a romantic couple robbing banks. It’s a modern-day Bonnie and Clyde, and director Adam Rehmeier understands that pairing these two dynamic actors is more than enough. It recalls the underrated Queen & Slim, but with a heavier Southern twang, as the pair spend their days conning people, stealing from the rich, and falling in love along the way. Part character study, part heist saga, Carolina Caroline is simply too cool to miss.
MOVIE: MADDIE’S SECRET
STARRING: JOHN EARLY, VANESSA BAYER, KRISTEN JOHNSTON
DIRECTED BY: JOHN EARLY
SUNDAY, MAY 3RD @ 4:15PM
At a film festival, one of the greatest pleasures is discovering new faces and powerful voices. Cinema has the unique ability to let us live vicariously through the stories it tells. Maddie’s Secret is one I’m especially eager to discover- a comedy about a food influencer struggling with bulimia. Written and directed by John Early in their feature debut, it carries the kind of promise that always draws my attention. And if there’s ever a time to crave a film that balances humor with heart, Maddie’s Secret feels like it could deliver.
MOVIE: WHEN A WITNESS RECANTS
DIRECTED BY: DAWN PORTER
MONDAY, MAY 4TH @ 6:30PM
At nearly every Chicago Critics Film Festival, I try to catch at least one documentary- not because I’m always drawn to the genre, but because they consistently end up being among the best. In 2013, it was Sarah Polley’s Stories We Tell; in 2022, Stefan Forbes’ riveting Hold Your Fire; and in 2023, Lakota Nation vs. The United States. This year, I expect that trend to continue with Dawn Porter’s When a Witness Recants. The film follows three teenagers wrongfully accused and imprisoned for 36 years, with award-winning author Ta-Nehisi Coates investigating the case and examining the community it impacted. Porter’s film was a major hit at Sundance, and with the thoughtful audience that frequents the Music Box, this feels like a must-see for anyone who appreciates great documentary filmmaking.
MOVIE: CHILI FINGER
STARRING: JUDY GREER, SEAN ASTIN, BRYAN CRANSTON, JOHN GOODMAN
DIRECTED BY: EDD BENDA, STEPHEN HELSTAD
TUESDAY, MAY 5TH @ 7:00PM
When you read early reviews of a film, it never hurts to see it compared to the Coen brothers. That has been the consistent word surrounding Edd Benda & Stephen Helstad’s Chili Finger. Early reactions have called it Raising Arizona for the Midwest, which was all I needed to hear. On top of that, it stars the always-reliable Judy Greer, Bryan Cranston, and John Goodman- a stellar trio of character actors. The premise sounds absolutely wild: a woman discovers a severed finger in her fast-food chili and uses it as an opportunity to blackmail the chain for everything she can get. What follows is a battle of wits and greed that pushes just how far someone is willing to go to change their life. It’s playing on a Tuesday at the Music Box with Greer in attendance, and it doesn’t get much better than that.
MOVIE: THE SUN NEVER SETS
STARRING: DAKOTA FANNING, JAKE JOHNSON, DEBBY RYAN
DIRECTED BY: JOE SWANBERG
THURSDAY, MAY 7TH @ 7:30PM
Joe Swanberg is no stranger to the Chicago Critics Festival- his film Digging for Fire played there in 2015- and it certainly won’t be his last appearance. His return comes with The Sun Never Sets, a relationship drama starring Dakota Fanning. The pairing alone is worth attention, with Swanberg’s naturalistic writing seemingly tailor-made for Fanning’s seasoned, restrained performance style. Set against the Alaskan wilderness, the story follows a woman struggling in her current relationship, whose life is further complicated when her ex reenters the picture. Swanberg and co-star Cory Michael Smith are scheduled to attend closing night, offering a fitting end to what promises to be a standout festival.
