Transit Tees Expands Amazon Presence After Record Sales Years in Chicago

Chicago gift shop Transit Tees is riding high after two consecutive record-breaking years, with owner Tim Gillengerten reporting significant growth both in-store and online as the company expands its product lineup and digital footprint.

The Wicker Park and Andersonville retailer saw December retail sales climb 4% year-over-year, while online sales surged 33%, according to Gillengerten. The growth comes after what he called a record-breaking 2024, followed by improvements in 2025.

“It’s always great to have percentage gains from a best year,” Gillengerten said.

Much of the success stems from strategic investments in digital marketing, according to the owner. Transit Tees hired both full-time and part-time employees dedicated to social media, an investment Gillengerten said paid off. The company also dramatically expanded its Amazon presence, growing from eight products to about 30, with plans to add more.

Despite strong online performance, Gillengerten emphasized that the brick-and-mortar stores remain central to Transit Tees’ identity. He noted that visitors often comment on the shops’ authenticity compared to typical tourist stores.

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

Customer spending patterns reveal interesting trends, according to Gillengerten. Wicker Park shoppers average just over $50 per visit and purchase an average of four products, but those purchases often involve lower-priced items like stickers, magnets and small impulse buys.

“Stickers are actually our No. 1 volume driver,” Gillengerten said.

Chicago Transit Authority-stop magnets also sell in unusually high numbers, according to the owner. He attributes the success of small items to their accessibility during times of inflation and economic anxiety, allowing shoppers to “have fun, to spend a little money” without straining budgets.

Higher-priced custom items also perform well when they offer unique value. LED light boxes designed to look like the Old Style sign and other Chicago iconography sell for $130 to $220, according to Gillengerten.

“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.

The company has benefited from trend-driven products tied to TV shows like “The Bear,” sports teams and Chicago cultural moments, according to Gillengerten.

Managing the growing operation has become more complex, particularly with rising labor costs and the city’s paid-leave ordinance affecting the company’s 23 employees – the most in Transit Tees’ history, according to the owner.

Despite rising tariffs and material costs on supplies like poster paper, Gillengerten decided against passing increased costs to customers. Instead, the company pivoted to locally made items when overseas materials became too expensive, 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 annually and maintains about 2,200 stock-keeping units, according to the owner. This year, the company is developing two new board games and several puzzles, with board game development taking nine months to a year to complete.

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

The company celebrated the launch of a Portillo’s-themed Chicago-style hot dog puzzle with a packed event at the restaurant’s Downtown location last year, according to Gillengerten.

community-building events and partnerships will expand significantly in 2026, with Gillengerten citing opportunities to work with other Chicago companies.

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