WTTW's 2026 Be a Winner Sweepstakes launched on March 26, 2026 — enter today!

Watch WTTW's 2025 Be a Winner Sweepstakes Drawing!

Congratulations to this year’s winners! We'll be in touch with you soon, and will list the winners here when all prizes have been accepted.

WTTW's 2025 Be a Winner Sweepstakes Drawing was recorded live and held at 4:50 pm on Monday, November 24, 2025, in the WTTW Studios.

The entry period for the 2025 Be a Winner Sweepstakes is closed. See Official Rules. Sponsor: Window to the World Communications, Inc.