Celebrate Chicago-Style Hot Dogs with Portillo’s & Transit Tees

Looking for fun things to do in Chicago this October? Two hometown favorites, Portillo’s and Transit Tees, are teaming up to bring puzzle lovers and food fans something new. The Portillo’s Chicago Style Hot Dog Puzzle is a limited-edition 500-piece jigsaw that celebrates one of Chicago’s most beloved foods and local icons.

The collaboration launches on Thursday, October 23, 2025, with an in-person release party at Portillo’s Ontario Street restaurant (100 W. Ontario Street, Chicago, IL). The event runs from 6:00 p.m. to 9:00 p.m. and includes puzzle-building contests, prizes for the fastest builders, and a “Best Dressed Dog” competition for guests who show off their photo-worthy Chicago-style hot dogs.

Tickets start at $35 and include:

• Two Portillo’s Chicago-Style Hot Dogs (vegan option available), fries, and a drink
  
  
• Entry to all contests and puzzle competitions
  
  
• Early access to purchase the new Portillo’s Chicago Style Hot Dog Puzzle
  
  

Reserve your spot at https://www.transittees.com/event-calendar/.

A Local Collaboration Worth Celebrating

The Portillo’s Chicago Style Hot Dog Puzzle was designed and produced right here in Chicago by Transit Tees, a local Chicago gift shop known for turning everyday city culture into collectible design. The vivid artwork features all the ingredients that make a true Chicago-style dog: mustard, relish, onions, tomatoes, sport peppers, a pickle spear, and celery salt on a poppy seed bun.

The puzzle makes its debut at the Portillo’s launch party on October 23 and will be available at Transit Tees Wicker Park and Andersonville stores starting October 24, as well as online at TransitTees.com.

Shop Exclusive Chicago Products at the Event

During the launch party, Transit Tees will host a pop-up shop featuring the new Chicago Style Hot Dog Puzzle along with popular Chicago-made products such as the Chicago Style Eats Puzzle, Chicago Style Hot Dog Trucker Hat, stickers, and other locally designed merchandise. As a Chicago gift shop, Transit Tees is known for offering unique items that capture the humor, creativity, and spirit of the city.

Join Transit Tees and Portillo’s for one of the most unique Chicago events of October 2025. Enjoy puzzles, prizes, and authentic Chicago-style food all in one night. Follow Transit Tees on Instagram and TikTok for event updates and behind-the-scenes sneak peeks