Gift shop Transit Tees looks to launch new products, sell more on Amazon

Editor’s Note: Last year, a new presidential administration stepped in with plans to disrupt the way companies do business through new policies, an effort to spur growth.

To help gauge the administration’s impact, the Chicago Sun-Times reached out to 10 Chicago area businesses in January 2025 and shared their plans and concerns for the future.

We’re now circling back, 12 months later, to see how they’ve fared.

Chicago retailer and design studio Transit Tees entered 2026 with momentum and renewed purpose.

“It was a record-breaking year in 2024, and we improved on it in 2025,” Transit Tees owner Tim Gillengerten said. “It’s always great to have percentage gains from a best year.”

The gains showed up in-store and online, Gillengerten said. In December, retail sales at its Wicker Park and Andersonville shops were up 4% year over year, with online sales up 33%.

Gillengerten said much of the growth was from hiring more staffing dedicated to social media and digital marketing. He added a full-time and part-time employee focused on social media — an investment Gillengerten said paid off.

The company also increased its presence on Amazon, expanding from eight products to about 30, with plans to sell more.

Despite the strength of its online sales, Gillengerten said the brick-and-mortar stores remain central to the company’s identity. Visitors often comment on the shop’s authenticity compared with the typical tourist shops, he said.

“The store is still a form of entertainment for a lot of people,” he said.

But he has noticed subtle changes in how customers spend.

“Wicker Park had an average sale of just over $50 per person … and they bought an average of four products per visit,” he said. But those purchases were often for lower-priced items like stickers, magnets or small impulse buys.

“Stickers are actually our number one volume driver,” he said.

Chicago Transit Authority-stop magnets also sell in unusually high numbers. The accessibility of small items, like magnets and stickers,help shoppers “have fun, to spend a little money,” without hurting their budget during a time of inflation and economic anxiety, Gillengerten said.

Some higher-priced items — like custom LED light boxes made to look like the Old Style sign, as well as other Chicago iconography — sell well because they’re unique. Prices are about $130 to $220 for LED signs.

“If you have a custom item that you really can’t get anywhere else, those things will always have a lot of value and interest,” he said.

Transit Tees has also seen a boost from trend-driven products tied to TV shows such as “The Bear,” sports teams and moments in local culture.

Gillengerten said managing the day-to-day operations has grown more complex, especially with rising labor costs and the city’s paid leave ordinance. The company employs 23 people — the most in its history.

As tariffs and material costs on supplies like poster paper rise, the company made a choice not to pass their increased costs on to customers.

“Our goal was to hold our pricing,” he said. “I just really wanted to hold the pricing and hope to sell more at this point, and we did.”

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Instead, Transit Tees got creative. For example, when materials imported from overseas became too pricey, the team pivoted to locally-made items — including a 56-page coloring book created with the Chicago Architecture Center.

“It was printed in Chicago and designed here at our Wicker Park studio,” Gillengerten said.

Transit Tees typically introduces about 200 new products each year and maintains about 2,200 stock-keeping units. This year, the company is developing two new board games and several puzzles. It expects to release the new board games in the summer and fall. Developing a board game can be intensive and time-consuming — often taking nine months to a year to complete.

Transit Tees owner Tim Gillengerten holds cards from the board game called El: The Chicago Transit Adventure.

Transit Tees owner Tim Gillengerten holds cards from the board game called El: The Chicago Transit Adventure.

Pat Nabong/Sun-Times

“Our games sell more than anything else in the store,” Gillengerten said.

Last year, it launched a Portillo’s-themed Chicago-style hot dog puzzle, celebrating with a packed event at the restaurant’s Downtown location.

“We filled the entire second story with participants,” Gillengerten said, adding that there were contests for the fastest puzzle-builder and best-decorated hot dog.

Those types of community-building events and partnerships will expand significantly in 2026, Gillengerten said.

“There’s so many great Chicago companies,” he said. “It helps them because we have this authentic Chicago flair to our work.”

And he emphasized that their work and designs are original.

A social media user recently claimed a Transit Tees design was made by AI, and Gillengerten used the comment to share how the team makes its products.

“Our art directors have been adamant about not using AI for any of our products,” Gillengerten said. “We draw everything by hand. A lot of people don’t realize that.”

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Looking ahead, he hopes for a strong small business ecosystem.


“A rising tide brings up all ships,” he said. “I want as many businesses for people to explore as possible. It helps us all.”

More in this series

The West Loop-based real estate firm started 2025 with concerns about tariffs and labor but have found that it was able to grow thanks to more work in states like Colorado.
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