Chicago-loving Transit Tees takes its creativity into new markets

Editor’s Note: A new presidential administration aims to shake up the way businesses are regulated through its economic policies on everything from tariffs to taxes.

Against that backdrop, the Sun-Times reached out to 10 Chicago area entrepreneurs about their plans for the future.

Each Friday, we’ll introduce one of them. We’ll circle back at the end of 2025 to share how government policies — at the federal, state or city level — helped spur growth and innovation or led to cost-cutting measures that slowed hiring or raised consumer prices.

Business is booming for Tim Gillengerten, owner of longtime Chicago-themed gift shop Transit Tees in Wicker Park and Andersonville.

Gillengerten credits social media for bringing in more online and in-store traffic, which has helped his business exceed $1 million in retail sales in 2024, a major milestone for the quirky shops.

“I really wanted to mature as a company in 2024 and part of that is to have a serious social media outreach,” Gillengerten said. “We started working with a company and creating more social media content, and that has driven the online sales to double.”

Transit Tees

About: Gift shop specializing in Chicago-themed merchandise
Neighborhood: Wicker Park and Andersonville
Owner: Tim Gillengerten
Founded: 2001
Staff size: 23
Estimated annual revenue: More than $1 million

Biggest potential risk: Inflation
Biggest potential opportunity: Expanding to new cities

Transit Tees has marketed its unique merchandise — L train-themed trinkets, puzzles and card games, as well as socks and T-shirts featuring Chicago landmarks and flags — on TikTok, encouraging locals and tourists to stop in and check out the surrounding neighborhoods. That’s led to a sales boost in-store and online.

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“In-store sales went up 20-25%,” Gillengerten said. “People are still enjoying the in-person shopping experience. I think being in those neighborhoods has helped us a lot.”

Although fears about inflation are still swirling among consumers, Gillengerten said shoppers still need gifts, whether it’s a tourist picking out a poster of the city’s skyline to commemorate their trip or a neighbor buying a baby onesie with a Chicago-style hot dog design to give at a baby shower.

The board game “El: The Chicago Transit Adventure” and other Chicago-themed souvenirs on display at Transit Tees’ Wicker Park store.

The board game “El: The Chicago Transit Adventure” and other Chicago-themed souvenirs sold at Transit Tees’ Wicker Park store.

Pat Nabong/Sun-Times

“I know that inflation has crept up on our stores as well as the consumer. We’ve had to look at how to be strategic,” Gillengerten said. “We want high-volume products that everyone can afford, really approachable products. And then we’ve also added this premium level — items that are a little more expensive that we’ve never traditionally carried, but they’re unique and higher-end.”

Gillengerten has also adjusted his business around the recent changes to the city’s paid time off policy, he said.

“There was a change in the time off we have to offer, even for part-time employees. We’re up to 23 employees,” he said. “When there’s an increase in an expense, it can really multiply. And I still think of us as a small company, but we are growing and maturing and learning just how to manage that extra cost.”

Gillengerten said a multi-pronged sales approach — in-person, online, Amazon, Etsy and wholesale accounts — fueled the company’s success this past year.

“We are definitely hitting a stride with exposure and people getting to know us,” he said.

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While traditional retail trade shows dwindled during the pandemic, Gillengerten and his team pivoted to online platforms that allow him to showcase merchandise to would-be wholesalers. He’s doubled the company’s retail partners, which includes the Museum of Contemporary Art, from 40 to 80 stores for this year. Participating in local street festivals has also introduced Gillengerten’s wares to new groups of Chicagoans, he said.

Chicago-themed posters, apparel and other souvenirs on shelves at Transit Tees’ store in Wicker Park.

Chicago-themed posters, apparel and other souvenirs at Transit Tees’ store in Wicker Park.

Pat Nabong/Sun-Times

In addition to upping its wholesale accounts, staying creative has helped the business grow. Most of the items are created in Transit Tees’ design studio and produced on-site by local artists and craftsmen.

“We’re making things all the time. Even our store staff, while they’re between customers, they’re making pins, buttons and sketching ideas for new products,” he said. “We come out with about 250 to up to 400 new products every year.”

Transit Tees has also launched city-branded product lines in Boston, Seattle and San Diego, sold through its retail partners.

Looking ahead, Gillengerten is feeling optimistic and plans to repeat strategies that have been successful thus far.

“I’m excited. It should be a really good 2025. I hope our overall joy and love of the city continue to shine through in the products we carry and people connect with it,” he said.

“I love this city, and we show it with the creative things we make celebrating it. I love to see people in the store and experience new things in the neighborhoods. I would just encourage people to continue to explore Chicago and just take advantage of all the amazing culture that we have here.”

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Thanks to new social media efforts Tim Gillengerten’s gift shop — with locations in Wicker Park and Andersonville — surpassed $1 million in sales last year.
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