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Chicago's Vintage Photo Booths Are A Dying Breed. Meet The Women Trying To Keep Them Alive


Chicago's Vintage Photo Booths Are A Dying Breed. Meet The Women Trying To Keep Them Alive

WICKER PARK -- Anatol Josepho invented the first fully automated, coin-operated photo booth in 1925. It debuted in New York City's Times Square.

A century later, with the world in flux, younger generations are again seeking respite in vintage photo booths and other pursuits with a human touch, like vinyl records and board games.

A rare analog photo booth from the 1960s debuts this weekend at the grand opening of Vintage House Chicago, 1433 N. Milwaukee Ave. The 850-pound film photo booth was delivered Wednesday on a rented truck by Bre Conley-Saxon, a Connecticut-based photographer and owner of Auto Photo.

Conley-Saxon works in analog photography, installing, restoring and maintaining vintage booths in Chicago and across the nation. She has seen a surge in demand for her services.

"In the past, it was us trying to find locations," Conley-Saxon said. "Now, it is locations finding us."

Auto Photo has 20 operating booths in seven states. In Chicago, you'll find Auto Photo's analog booths at the Rainbo Club in Wicker Park, Skylark in Pilsen, Weegee's Lounge and Cole's Bar in Logan Square, Village Tap in Roscoe Village and Holiday Club in Uptown.

Conley-Saxon, 42, founded Auto Photo 10 years ago. She was a wedding photographer who attended the Brooks Institute of Photography, a now-defunct analog school in Santa Barbara, California.

In 2022, Conley-Saxon took over the Chicago "route" of analog booths owned by Jim Henderson, a Los Angeles-based former photo booth company executive she calls "The Godfather." He died earlier this year.

For years, Henderson's booths were cared for by an older Filipino man known as Eddie the Technician, described by a Rainbo Club bartender as "The True MacGyver." He had a big bag of tools and took hundreds of test photos.

"Eddie needed knee surgery, so he had to quit," Conley-Saxon said. "Jim didn't feel like training another technician, so he sold the route to me in 2022.

"Honestly, the booths were in the worst condition I had seen. These had been in bars for decades. It took me a year of going to Chicago to get them going. I'd spend a week every month living in Chicago, refurbishing them on location. No regrets."

"I like Bre's mission," said Maddie Rogers, owner of Vintage House Chicago and a photographer. "She only hires female techs. She's very easygoing. And from my understanding, there's nowhere in Chicago with an all-ages booth," as Vintage House's booth is.

Rogers learned about Conley-Saxon through Cole's Bar, 2338 N. Milwaukee Ave. The bar's analog booth was previously at Quimby's bookstore in Wicker Park.

Rogers founded Vintage House in 2021. Her pop-up markets have appeared all over the city, drawing up to 10,000 people at venues such as the Salt Shed, Artifact Events and Rockwell On The River.

In her search for a photo booth for Vintage House, Rogers talked to A&A Studios, the area's major digital photo booth purveyor in suburban Lyons, which has nearly 50 digital booths in Chicago bars. These are photo booths with a facelift. A&A Studios also has a really geeky link on analog photo booth manuals.

But Rogers was insistent on a classic booth. While a digital camera produces digital files, a film booth has a film camera inside, and film is developed in real time.

"Film obviously has limitations," Rogers said. "The digital company told me I could put my brand on it, and there's more customizing options. There is an option with film where they burn the brand in between the strips. I just wanted to keep it the way it was supposed to be. It is more experiential altogether."

One of Conley-Saxon's most memorable -- and challenging -- projects was refurbishing the photo booth at Smartbar, 3730 N. Clark St., in the basement of iconic music venue Metro.

"I went so often trying to save that booth. That booth smelled like death," she said. "The wiring had been redone a million times. I swapped parts for refurbished parts. One time, it smoked and they evacuated the building. Firefighters took an ax to the door of the booth. ... After that, I learned to leave a key for Metro."

After the photo booth smoked a second time, Smart Bar transitioned out of analog.

"I gutted it and made it digital, which breaks my heart," Conley-Saxon said. "I gave it my all. Even when it went digital, it continued to have problems. I swear it's a curse. Maybe we're OK now."

The most popular photo booth on her Chicago route is at Rainbo Club, 1150 N. Damen Ave., which is celebrating 40 years under its current owner, Dee Taira.

Taira and her partner, the late Gavin Morrison, bought the Nelson Algren haunt in October 1985. Taira had been a librarian at the Shedd Aquarium, and Morrison had been a bartender at the long-gone MaxTavern at George Street and Racine Avenue, which had a popular photo booth.

"Gavin ordered a booth when we moved into the Rainbo," Taira said. "Photos were a dollar when we started."

The other thing the Rainbo Club started was an annual 24-by-17-inch calendar of photo booth images.

"Everybody wants to get on the calendar," Taira said. "We put out our 2025 calendar in January and people were giving us photos for 2026."

The Rainbo's photo booth was cemented in pop culture thanks to musician Liz Phair when she lived in the neighborhood. Phair used a strip image from the Rainbo booth for the cover of her hit 1993 debut album, "Exile in Guyville."

When Conley-Saxon started her business, a vintage analog booth cost about $10,000, she said. Some were in exile from failed Kmarts, others were stowed away in old barns. They now fetch $40,000-$60,000, she said.

Her Chicago booth prices are $5 cash and $7 credit per session. A booth needs to make $1,000 to stay in its space, she said. Businesses do not rent the booths from Auto Photo.

"It brings a lot of foot traffic, and you're supporting a dying art," Conley-Saxon said. "From the beginning I've supported community over competition. Paper and chemistry is expensive. I do maintenance and make the money in sales. At least half of that goes back to the photo booths and my technicians. But with this popularity now, it may pay off someday."

Ah, the technicians: Auto Photo has two female Chicago techs. One of them, Emily Botelho, drove to Chicago from London, Ontario, to help with the Vintage House installation.

Conley-Saxon's mentors are two gentlemen she calls "the Russian guys." One lives in Los Angeles, the other in New Jersey.

"During the pandemic, they were refurbishing booths and I was buying from them," she said. "Jim [Henderson] had one in storage in California, and the Russian guys told me about him. I only heard rumors of 'The Godfather.' He was vice president of this photo booth company [Foto-Mat Entertainment] in the 1980s, so I knew he had the most parts and knowledge."

Conley-Saxon's business took a hit during the pandemic when bars and businesses closed. Later, after business restarted, Russia's war with Ukraine began, which impacted her supply of paper for the photo booths. Her analog booths used direct positive paper produced and cut in Russia.

Conley-Saxon now sources her paper from Ilford Photo in the U.K. It's brought by boat to the United States.

"Honestly, digital booths make more money in the long run because you're not spending as much time on them or on supplies," said Conley-Saxon, whose husband works in IT. "Chemical booths are like living, breathing creatures."

The analog photo booth will be honored in a 100th anniversary celebration Aug. 28-31 at the International Photobooth Convention in New York City, which Conley-Saxon is helping to organize. She also has her eyes set on creating an analog photo booth museum in New York City.

In Chicago, Pilsen dive bar Skylark is planning an analog photo booth celebration for May. That event is also on Conley-Saxon's calendar.

Conley-Saxon uses female pronouns when referring to her booths.

"I don't have children, so I guess the booths are my children," she said with a laugh. "I take care of them, and I hope they do well."

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