Official Contest Rules

Winter Pledge Drive 2025:
12/2-12/9: In the Loop Live
12/2-12/9: Say More Live
12/3: Year of Coffee & Cozy Cabin Getaway
12/4: iPads & Weekend Getaway
12/5: Sommelier Experience & Carnivale Chef's Table Experience
12/6: Salt Shed Concert Pack
12/8: Year of Family Fun
12/9: Northern Greece Giveaway

Gala 2025:
10/9-10/18: New York City

Fall Pledge Drive 2025:
10/1-10/8: In the Loop Live
10/1-10/8: Say More Live
10/1: Chicago Film Festival
10/2: Lifelong Learners Giveaway
10/3: iPads
10/4 - 10/5: An Evening with Ira Glass 
10/6: Chicago Botanic Gardens
10/7: Private Chef Experience
10/8: Hoosier Mama Pies and Cookbooks & One of a Kind Holiday Show

9/11/25-9/18/25: Jeff Tweedy Tickets

Summer Pledge Drive 2025:
6/13: iPads 
6/18: Reset Live

Spring Pledge Drive 2025:
3/3-3/19: Vacation Getaways
3/13: Radio Flyer E-Bike & AIRE Spa Date for Two
3/14: iPads & Chicago Food Tour Pack 
3/17: Arts & Culture Pack
3/18: Helicopter Tour

Winter Year-End 2024:
12/16-12/31: Kauai

Winter Pledge Drive 2024:
12/4-12/5: San Juan
12/5: Smyth
12/6: iPads & Bookshop.org Shopping Spree
12/9: Arts & Culture Pack
12/9-12/10: Athens & Santorini
 

Want to see who won? Check out our list of lucky winners.