City Cast Chicago logo
Advertisement image

How Transit Tees Turns Chicago’s Quirks Into Board Games

Posted on August 20
Kayleigh Padar

Kayleigh Padar

A person writing on a gridded paper that says "Chicago 1893" There's also a board game with an assortment of different houses for the board game on it. There is also A bowl of popcorn and a soda on the table

Transit Tees, located in Wicker Park and Andersonville, offers a plethora of Chicago-based board games, puzzles, and coloring books based on experiences we all share. (Courtesy Transit Tees)

Do you ever look around the city and think to yourself, “Someone should make a board game about this?” Well, for the past eight years, the independent artists behind the gift shop Transit Tees have been doing exactly that.

From board games about the city’s history to puzzles of iconic maps to card decks featuring local wildlife, Transit Tees’ teams of creators enjoy the challenge of capturing all the things that make Chicago unique through interactive activities.

“We always want to have an insider’s angle, like, ‘If you know you know,’ and if you live here, you get it,” said owner Tim Gillengerten. “There’s so much joy here. We love celebrating Chicago and expressing that experience in our products so people can connect with the city.”

From Real Life to Board Game and Back

In their most popular game, “El: The Chicago Transit Adventure,” players race to strategically visit five El stations and return to The Loop before anyone else.

“We had a family tell us that they draw their five destinations, play the game, and then make a day out of physically going to each of those stops and exploring those neighborhoods,” Gillengerten said. “I love that they found a way to use the game to expand their knowledge about the city.”

It typically takes the Transit Tees team about a year to design a game, but they usually repurpose some of the art to create lines of related gifts and apparel.

“It’s been really fun for us to draw and design the games, and to strategize about creating the gameplay,” Gillengerten said. “When we made The El, I laid out a map of the CTA in the office. We all grabbed stuff from our desks, like a box of Tic Tacs and a razor, just started strategizing about how we could turn the concept into a game.”

The team’s most recent release is “Chicago Handshake” — a drinking card game named after the classic dive bar combo of a shot of Malort and Old Style chaser. It’s filled with trivia questions and challenges based on common city experiences.

You can sign up to receive updates about their next board game project, “Dibs,” where players can build a parking empire by saving spots with junk from the garage.

Share article

Hey Chicago

Stay connected to City Cast Chicago and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.
Advertisement image

Keep It Local

See All
Keep It LocalNovember 5

Where to Order Thanksgiving Dinner in Chicago

Skip the cooking this year. These Chicago restaurants offer Thanksgiving catering, turkey dinner kits, and sit-down holiday meals for 2026.

A mural of a pie, ingredients, and cooking utensils on the side of First Slice Pie Cafe’s building.
Keep It LocalNovember 5

Chicago Pies That’ll Steal the Show at Thanksgiving

Skip the baking this Thanksgiving. Order classic and creative pies from five Chicago-area bakeries, with prices, deadlines, and pickup ti...

A cranberry fudge pie on a table surrounded by colorful fall leaves and pumpkins.
Keep It LocalOctober 29

Your Guide to Chicago’s Costume Shops

Need a last-minute Halloween costume? Chicago Costume Company, Beatnix, Fantasy Costumes, and Halloweenland have wigs, makeup, and rentals.

A man riding a bicycle that’s decorated like a hot dog poses for a photo at Millennium Park in Chicago.
Keep It LocalOctober 29

Strut Your Stuff at a Chicago Costume Contest

Show off your costume in Chicago, from $4,000 in prizes at the Haunted Halsted Parade to a dog and cat costume parade in Streeterville.

Three people wearing Halloween masks carry the Haunted Halsted Halloween Parade banner down the street to kick off the festivities.
Keep It LocalOctober 22

Your Guide to Chicago’s Spiritual Shops

Chicago’s spiritual shops are a great place to learn more about the occult, practice rituals, and meet others interested in magic.

A fireplace mantel displaying various gothic decorations, a golden skull, small ornate black frames, and three books about ghost stories and history.
Keep It LocalOctober 22

Explore Chicago’s Magical Markets and Folklore Tours This October

Check out events coming up in October where you can peruse local curators’ magical collections and hear stories of mystical happenings.

A Ouija board with other spiritual items scattered across it, including three candles, a deck of tarot cards, playing cards, a palm reading display, white gloves, and skull dice.
Keep It LocalOctober 15

Your Guide to Chicago’s Spookiest Spots

From a medieval torture museum to a horror-themed cafe, these spots serve up scares.

Pedestrians walk past and linger outside the Medieval Torture Museum on North State Street in Chicago, its facade featuring a large illustrated sign with a menacing red-hooded figure and skeletal imagery above the entrance.
Keep It LocalOctober 15

Open House Chicago Spotlight: Get Witchy at the Colvin House

Stop by the Colvin House in Edgewater during Open House Chicago.

The Colvin House in Chicago, a beige brick mansion with columns and an arched doorway surrounded by an iron fence.