The Wieners Circle was more of a cathartic, broken hearts club on Tuesday evening when it hosted a Caleb Williams look-alike contest as a love-letter to the Chicago Bears quarterback, despite a gutting end to the season.

Men’s nails were manicured and painted in a plethora of colors.

Iced matcha lattes were a necessity.

And wired headphones added the final flourish.

If there ever was a fandom to dust off Sunday’s divisional playoff loss to the Los Angeles Rams and show up in 18-degree weather because the Clark Street hot dog stand said so, “it’s in Chicago,” said Regan Eggert, one of the staff members at the notoriously surly Wieners Circle.

“We were not going to cancel this. We love the Bears, we love Ben Johnson, we still love Caleb — s−−− happens,” Eggert said. “He got us this far and everyone is still super hyped. I mean, we beat the Packers twice. That was our Super Bowl. We can only go up from here.”

The Wieners Circle garnered national attention during the Bears’ regular season, when it offered free hot dogs on two occasions. Once, when the Bears quarterback threw four touchdown passes, and again because head coach Ben Johnson took his shirt off after a win.

It was only fitting that the hot dog stand had one final say.

Around 6 p.m., Eggert started passing out name tags to the few lookalikes waiting in the small space opposite the service counter. By 6:30 p.m., she’d given out 15 and the crowd had shifted to the back of the restaurant space.

Each tag Eggert was handing to a “Caleb” had a witty descriptor like “zesty Caleb,” “Boystown Caleb,” “Caleb from the hood,” “dreadhead Caleb,” “Caleb Bleu” (he looked more like actor Corbin Bleu from “High School Musical”), “white [expletive] Caleb” and more.

“[Expletive], I said no white people and no kids,” Eggert quipped.

But when Trenton Harrison walked in, Eggert joyously jotted down: “the real Caleb.” An hour later, she officially crowned him the winner.

Harrison was wearing a regular Bears puffer jacket and a navy blue beanie, with wired headphones tucked into his left pocket. The getup didn’t exactly scream Caleb Williams, but his wife, Kaylee, said she was confident he’d pull it off with his teeth, cheeks and the “little indent between his eyebrows and the forehead.”

Contestants gather for the Caleb Williams look alike contest at The Wiener’s Circle hot dog stand in Chicago on Jan. 20, 2026. (Terrence Antonio James/Chicago Tribune)
Trenton Harrison, of Bourbonnais, holds the trophy he won in the Caleb Williams look alike contest at The Wiener’s Circle in Chicago on Jan. 20, 2026. (Terrence Antonio James/Chicago Tribune)

“I knew he was going to win,” she said, laughing that their trek from Bourbonnais for the contest was worth it. “About a year ago, I had to do a double-take at the TV, because I was like, ‘Wait, hold on… you look like (Caleb).’ And then after that, everyone just started saying how much he looked like him.”

Harrison had fewer words, but admitted that people had stopped to tell him the same thing. As for where he sits post-brutal-playoff-loss, he had more to say.

“I know it’s hard to keep watching that one touchdown and then not be able to bring it home… It’s frustrating, but I’m hopeful for the future,” he said. “Caleb is one of the best in the league, hard not to be excited.”

What others lacked in facial resemblance, they made up for by curating some quintessential Williams looks, many using the quarterback’s Instagram as a point of reference.

Thomas McDonald, otherwise known as “Boystown Caleb,” copied Williams’ outfit from the Bears’ win over the Packers on Jan. 10, in an all-black blazer/T-shirt combo, with black pants, black shoes and a long black overcoat.

Bears fans watch the Caleb Williams look alike contest at The Wiener’s Circle hot dog stand in Chicago on Jan. 20, 2026. Contestants were evaluated on how much they resemble the Chicago Bears quarterback. (Terrence Antonio James/Chicago Tribune)

Another guy also came dressed in head-to-toe black, but had a “security guard” escorting him around the comically tiny space.

And Amit Chopra, a Hyde Park resident, contributed only a drink and his orange-and-blue nails, which his girlfriend had already painted for Sunday’s game.

“I’m coming at it with a bit of a genetic disadvantage, so I had to do the iced matcha,” said Chopra, who Eggert simply reduced to “Indian Caleb.”

Eggert said the contest was her idea of an ode to Williams and to the city. And the growing trend of lookalike contests that have swept in-person spaces over the last several months was encouraging, she said. Earlier this month, dozens turned out for a Ben Johnson lookalike contest in south suburban Bedford Park. Chicago also hosted a Jeremy Allen White contest in November, when lookalikes of the actor from “The Bear” descended on Humboldt Park to compete for $50 and a pack of Marlboro. The prize is not why people participate in these contests, Eggert said with a laugh.

On Tuesday, Harrison took home a small “Caleb Williams Wannabe” trophy, a $20 Wieners Circle gift card, a venti Starbucks iced matcha and some store merchandise.

The Wiener’s Circle hot dog stand on North Clark Street in Chicago held a Caleb Williams look-alike contest on Jan. 20, 2026. (Terrence Antonio James/Chicago Tribune)

But some onlookers hoped the crowd could have been more involved in picking the winner, as is generally the case with lookalike contests. Yazmine Valencia from Rogers Park said each “Caleb” should have individually walked on a “runway” through the crowd.

“I think in a good lookalike competition, the winner is always based on the loudest cheer from the audience,” Valencia said. “There were so many of us who came to watch, but we could barely see or hear anything.”

She said she may not have cheered for Harrison, the winner, and instead gone with “Caleb Bleu” or the tall guy with security for his creativity.

Meanwhile, Ken Robinson, dubbed as “Ice boy Caleb,” was dressed in a blue No. 18 jersey, jeans and a headband. He mostly came for the camaraderie.

“I’m still depressed,” Robinson said. “But I was like, you know what’s going to make me happy is showing up as Caleb today. We’re all here, we all witnessed (the loss) but we have so much to look forward to. We live and we die by them.”

https://www.chicagotribune.com/2026/01/21/wieners-circle-caleb-williams-lookalike/