Bears’ Caleb Williams Spotted at Coachella with Kendall and Kylie Jenner

Caleb Williams attended Coachella alongside the Jenner sisters Kylie and Kendall Jenner, days before the start of the Bears voluntary workouts.

Bears’ Caleb Williams Spotted at Coachella with Kendall and Kylie Jenner

Bears quarterback Caleb Williams attended Coachella alongside Jenner sisters, Kylie and Kendall (Image via IMAGO/X screengrab)

In Short
  • Caleb Williams was spotted at Coachella with models Kylie and Kendall Jenner before joining the Chicago Bears' offseason workouts.
  • Williams had a challenging rookie season, with the Bears finishing 5-12 despite his impressive stats of over 3,500 yards and 20 touchdowns.
  • Super Bowl winner Charles Omenihu praised Williams as one of the scariest quarterbacks in the NFL following a strong second season.

Before joining his teammates at the Chicago Bears’ voluntary offseason workout session on April 20, Caleb Williams took a detour to enjoy music at Coachella in California. And the quarterback had celebrity company.

Fans who dropped by to watch Sabrina Carpenter rock the stage caught Williams sitting in close proximity to famous models Kylie and Kendall Jenner. Of course, both are half-sisters to the controversial reality star Kim Kardashian.

Anyways, Williams kept his drip simple. He went with a white t-shirt and bluish-black jeans. It’s unclear whether he arrived in Coachella with the sisters or met them afterwards. At the same time, the short X clip also failed to make it clear whether Williams actually spoke with the sisters.

For the excited fans of Caleb, they need to remember that he has very little chance of landing either of them. Kylie, as everyone knows, is dating renowned actor Timothee Chalamet. And Kendall may be officially single, but according to TMZ, she remains in touch with NBA star Devin Booker, with whom she broke up in 2025.

Williams is also single. That said, Sports Illustrated recently linked the 24-year-old to influencer and model Ashaley (Ash) Kaashh when she attended the Bears’ wildcard victory over the Green Bay Packers. That lead died after Kaash posted a video hugging the Packers running back Josh Jacobs in a pool.

According to reports, Williams used to date Alina Thyregod. The pair met in high school at Gonzaga College High School in Washington, D.C. After briefly breaking up, they reunited when Williams transferred to USC from Oklahoma. However, as of April 2026, they are no longer together.

Super Bowl winner believes Caleb Williams is one of the scariest quarterbacks in the NFL

The Bears drafted Williams first overall with the hope that he would be their messiah for the next decade. Chicago has not seen glory since the days when the Bulls dominated the NBA. So, the bar was set very high.

Bears' Caleb Williams Spotted at Coachella With Kendall and Kylie Jenner
Caleb Williams (Image via IMAGO)

Unfortunately, like most rookie quarterbacks, Williams’ first year wasn’t very good. The Bears went 5-12 and missed the playoffs for the fourth straight season. Despite that, the former Trojan threw for 3500+ yards, 20 touchdowns, and just 6 interceptions.

Chicago overhauled the coaching department by appointing former Detroit OC Ben Johnson as the new head coach. Johnson helped Williams become a clutch quarterback. He had the most game-winning drives (7) compared to any other QB in 2025.

The Bears won their first division title since 2018, beat the Packers in the wildcard round, and came very close to beating the Los Angeles Rams in the NFC Divisional playoff game. LA won by just three points. Williams finished the year with 3942 yards, 30 total touchdowns, and 7 interceptions.

Super Bowl-winning defensive end Charles Omenihu, who played against the Bears in preseason as part of the Kansas City Chiefs, claimed that Williams is one of the scariest quarterbacks in the league, alongside Patrick Mahomes, Josh Allen, Joe Burrow, Lamar Jackson, and Matthew Stafford.

I respect the hell out of his game. After this past year, I respect his game crazy.

Omenihu said on Speakeasy

The Bears’ offseason workouts start on April 20 at Halas Hall, followed by the rookie minicamp from May 1 to 4 and May 8 to 11. OTAs are scheduled to run from May 27 to 29 and June 2 to 4. The mandatory minicamp commences on June 9 and ends on June 11.

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