WTTW Sweepstakes – Win Subaru Car, Trips, Home Makeover and More!

What if one entry could unlock a world of completely different dreams? From adventure travel to home upgrades and once-in-a-lifetime experiences, this giveaway is all about variety—and big wins.

The WTTW’s 2026 Be a Winner Sweepstakes brings together dozens of incredible prizes, headlined by the Grand Prize: a 2027 Subaru Crosstrek Hybrid—a modern, eco-friendly SUV built for both city drives and outdoor escapes. But that’s just the beginning of what you could win.

Imagine heading out on an African safari adventure, enjoying a relaxing Walla Walla wine escape, or hosting your own countryside private party. Prefer something closer to home? You could score an expertly designed home makeover, a cabinet upgrade, or even a smart grill & chill setup to elevate your everyday living.

This isn’t a one-size-fits-all giveaway—it’s a collection of lifestyle prizes, travel experiences, and home transformations, all in one place. Whether you're dreaming of a new car, a luxury getaway, or a home refresh, there’s something here waiting for you.

So many prizes. So many possibilities. Enter now for your chance to win something truly unforgettable.

Limit: Maximum of 20 tickets + 2 bonus tickets per household, regardless of entry method. The  minimum age limit to enter the giveaway is 18. It is open only for the legal residents of Illinois, Indiana, Michigan, or Wisconsin. 

How to Enter in WTTW’s 2026 Sweepstakes:

Online Entry:

Visit wttw.com/sweepstakes and complete the online entry form with your name, address (no P.O. boxes), city, state, and ZIP code. Select the number of entry tickets (up to 20) and optionally request two bonus tickets by including the bonus word “WINDOW.” Submit the form by October 26, 2026.

Mail Entry:

Complete the official entry form and include your entry tickets with your name, address (no P.O. boxes), city, state, and ZIP code printed on each ticket. Mail it to: Be a Winner Sweepstakes, WTTW, 5400 N. Saint Louis Avenue, Chicago, IL 60625-4698.

Request a physical Official Entry Form by:

(i) Mail: Legibly print your Name, Address, City, State, ZIP Code, and the words “Be a Winner Sweepstakes” on a 3.5″ x 5″ card and mail it to: Be a Winner Sweepstakes Entry Form Request, WTTW, 5400 N. Saint Louis Avenue, Chicago, IL 60625-4698, or

(ii) Online: Go to wttw.com/sweepstakes and fill out the Official Entry Form request, or

(iii) Phone: Call (773) 509-1111 and select option 2.

WTTW’s 2026 Be a Winner Sweepstakes Winner Selection:

Winners, including one winner and ten runners-up for each Early Bird and Bonus Prize, will be selected through random drawing on or around June 15, 2026 (Spring Early Bird) and November 23, 2026 (Fall Early Bird, Bonus Prize, and General Prize Pool).

Bonus Prize entries must include the word “WINDOW” and are only eligible for the Bonus drawing.

WTTW Sweepstakes Prizes:

Early Bird & Bonus Prizes:

(2) Spring Early Bird Prizes: Walla Walla Deluxe Wine Touring Package for 2. (ARV: $3,899 each)

(1) Fall Early Bird Prize: Weber Summit Smart Gas Grill. (ARV: $5,299)

(1) Bonus Prize: $10,000 Gift Card + In-home design consultation. (ARV: $10,100)

General Prize Pool:

(1) Grand Prize: 2027 Subaru Crosstrek Hybrid. (ARV: $36,000)

(1) Road Scholar Prize: Kenya & Tanzania Safari Trip for 2. (ARV: $21,800)

(1) Rug Prize: Hand-woven rug. (ARV: $6,500)

(1) Private Event Prize: Event for up to 50 guests. (ARV: $5,000)

(1) Fitness Membership Prize: 1-year membership + training sessions. (ARV: $2,718)

(2) Restaurant Party Prizes: Private party for up to 10 guests. (ARV: $2,500 each)

(1) Cabinet Gift Certificate Prize: $2,500 gift certificate. (ARV: $2,500)

(1) Hotel Stay Prize: 1-night stay for 2. (ARV: $900)

(4) Candle Class Prizes: Private candle-making class. (ARV: $700 each)

(1) Running Gear Prize: Gift certificate + training voucher. (ARV: $650)

(1) Skydeck Dinner Prize: Dinner for 4. (ARV: $600)

(1) Popcorn Prize: Gift tin + $500 eGift card. (ARV: $562)

(1) Grooming Package Prize: Full grooming experience. (ARV: $525)

(1) Apparel Prize: Custom clothing package. (ARV: $500)

(1) Restaurant Gift Cards Prize: Five $100 gift cards. (ARV: $500)

(4) Theater Ticket Prizes: Four tickets. (ARV: $400 each)

(1) Hotel Stay Prize: 1-night stay. (ARV: $350)

(1) Sports Tickets Prize: Four tickets + parking. (ARV: $320)

(4) Membership + Cookbook Prizes: Digital membership + cookbooks. (ARV: $314.94 each)

(1) Zoo Package Prize: Membership + passes. (ARV: $300)

(2) Arboretum Membership Prizes: 1-year membership. (ARV: $275 each)

(10) Map & Guide Prizes: Atlas + wall map. (ARV: $266.99 each)

(2) Seafood Gift Card Prizes: $250 gift certificate. (ARV: $250 each)

(2) Distillery Tour Prizes: Private tour + merchandise. (ARV: $250 each)

(3) Spa Gift Card Prizes: $250 gift certificate. (ARV: $250 each)

(1) Furniture Gift Card Prize: $250 gift certificate. (ARV: $250)

(5) Theatre Membership Prizes: Membership + $100 gift card. (ARV: $200 each)

(3) Pizza Tour Prizes: Two tickets. (ARV: $167 each)

(4) Art Studio Pass Prizes: 10-pass booklet. (ARV: $150 each)

(1) Flower Class Prize: Two tickets. (ARV: $130)

(1) Festival Ticket Prize: Four tickets. (ARV: $120)

(6) Wine Tasting Prizes: Tasting for up to 6 guests. (ARV: $100 each)