Official Contest Rules

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
12/7-12/8: New Orleans
12/9: Arts & Culture Pack
12/9-12/10: Athens & Santorini

Fall Pledge Drive 2024:
9/1-9/30: Choose Your Own Adventure
9/18-9/19: Madrid
9/20: Arts & Culture Pack & The Bear Food Tour
9/21-9/22: Napa
9/23: Radio Flyer E-Bike
9/24: iPads
9/25: Disney

Summer Pledge Drive 2024:
6/7: Prague
6/8-6/10: Italy
6/10: Alinea & Explore Chicago Arts & Culture Pack
6/11: iPads 
6/11-6/12: Paris
6/21-6/30: Cancun

Spring Pledge Drive 2024:
2/29-3/7: San Miguel
3/8: Topolobampo
3/9-3/10: Ireland
3/11: Staycation Package
3/12: The Bear Food Tour
3/12-3/13: iPads
3/13-3/14: Fiji

Winter Year-End 2023:
12/18-12/31: Costa Rica

Winter Pledge Drive 2023:
12/1-12/5: Barbados
12/8-12/10: Puerto Rico
12/9: Staycation Package
12/12: iPads
12/12-12/13: Hawaii

Fall Pledge Drive 2023:
9/6: Brazil
9/8: Alinea & The Bear Food Tour
9/9 & 9/10: French Alps
9/11: Electric Scooter
9/12: iPads
9/13: Amalfi Coast

Summer Pledge Drive 2023:
6/8: Iceland
6/9: Alinea & Topolobampo
6/10 & 6/11: Greece 
6/12: Springsteen & Hamilton
6/13: iPads
6/14: Tuscany

Spring Pledge Drive 2023:
3/8: Barcelona
3/9: Comedy of Errors Tickets
3/10: Lizzo & Madonna
3/11-3/12: Ireland
3/13: Alinea
3/14 - 3/15: iPads & Fiji

Winter Pledge Drive 2022: 
11/30: Visa Gift Cards
12/1: Maui
12/2-12/4: London
12/5: Alinea
12/6: iPads
12/7: Italy 

Fall Pledge Drive 2022: 
9/15: New Orleans
9/15: Radio Flyer E-Bike
9/16: Lizzo Tickets
9/16: Helicopter Tour
9/16-9/18: Scotland
9/20: iPads
9/20: Alinea
9/21: Machu Picchu  

Summer Pledge Drive 2022: 
6/9: Costa Rica
6/10: Lollapalooza & Pitchfork
6/11 & 6/12: Paris
6/13: Alinea
6/14: iPads
6/15: Alaska
6/15: Pitchfork & Lollapalooza

Spring Pledge Drive 2022: 
2/24-3/2: Beach Getaway
3/3: Cozy at Home
3/3: Lady Gaga
3/4: Alinea
3/4: Tock
3/5-3/6: Chicago Staycation
3/7: Florence
3/9: iPads
3/10: Portugal

Curious City Spring 2022 
3/3-3/31: Backstage Pass

Winter Pledge Drive 2021 
12/1: Visa
12/1: Elton John
12/2: Peloton
12/2: Chicago Staycation
12/3: Puerto Vallarta
12/4: Alinea
12/6: iPads
12/7: Iceland

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