How to Play the Chicago Handshake Drinking Card Game

If you want to bring true Chicago spirit to your next game night, look no further than the Chicago Handshake Drinking Card Game. Designed by Transit Tees in Chicago’s Wicker Park neighborhood, this game mixes trivia, dares, and iconic local traditions into a hilarious, fast-paced experience.

Watch It in Action

Want to see how it’s done? In our YouTube video tutorial, Transit Tees owner Tim Gillengerten walks you through the game step-by-step. Tim explains how to set up, draw cards, and score, while giving sneak peeks at some of the funniest challenges like naming all the toppings on a Chicago-style hot dog, impersonating a local sports announcer, or answering deep-cut city trivia.

The video even shows the signature finishing move—the legendary Chicago Handshake: a shot of Jeppson’s Malört plus an Old Style beer.

What’s in the Box

• 104 full-color cards featuring trivia, dares, and challenges inspired by Chicago’s food, culture, and history
• Easy-to-follow rules for quick setup and gameplay
• For 2–12 players, lasting about 30–60 minutes
• Designed and produced locally in our Wicker Park studio

How to Play

1. Shuffle the Deck – Place it face down in the center.
2. Take Turns Drawing – Each card contains a Chicago-themed trivia question, dare, or interactive challenge.
3. Complete or Forfeit – If you miss the challenge, you collect a token.
4. Game End – The player with the most tokens takes the Chicago Handshake, a Malört shot and an Old Style beer.
5. Non-Alcohol Option – Not a drinker? Substitute any beverage; coffee, soda, or even water, and keep the fun going.

Beyond the Game: The Chicago Handshake Collection

The card game is part of our full Chicago Handshake Collection, a lineup of barware, apparel, and accessories that capture the same dive-bar-meets-local-pride energy:

• Chicago Handshake LED Light Box – Retro tavern vibes for your home bar or man cave
• Chicago Handshake Mascot Tee – A wearable nod to this Chicago tradition
• Drink Local Dress Socks – Cozy and Chicago through-and-through
• Frosted Shot Glass, Pint Glass, Can Sleeve, Bar Mat, Sticker, and Enamel Pin – Perfect for gift shops, souvenirs, and stocking stuffers

Why This Game Belongs in Your Collection

The Chicago Handshake Drinking Card Game is more than just a night of laughs, it’s a taste of Chicago culture you can share. Whether you stick to Malört and Old Style or swap in your favorite drink, you’ll have a story to tell after every round.

Pick up your copy from the Chicago Handshake Collection today and bring home a piece of the city.