Radio Sweepstakes
Radio Sweepstakes - Listen to Win
In addition to radio sweepstakes, there are also radio giveaways that provide listeners with a chance to win prizes simply by participating in fun games or answering trivia questions. The idea of "Listen to Win" contests has become increasingly popular, where you just have to stay tuned to win big. Whether you’re commuting to work or relaxing at home, listening to your favorite station could reward you in unexpected ways. Make sure to check out the latest radio giveaways, stay alert during "Listen to Win" events, and maximize your chances by staying tuned to all announcements. These promotions make the radio experience even more thrilling!Radio Giveaways & Listen to Win Sweepstakes
Found 21 total
Enter to win the iHeartRadio Ultimate iHeartCountry Christmas Vacation Sweepstakes. One winner and a guest get a Las Vegas trip with airfare, 3 nights at Caesars Palace, Thomas Rhett at Caesars and Luke Bryan and Jason Aldean at Allegiant Stadium, meet-and-greets and a $200 gift card (ARV $3,993). Open to US and DC residents 21+. Ends 11/15/2026 at 11:59 PM EST. To enter, complete the form on the promotion page once per day; earn 20 bonus entries daily for listening on iHeartRadio.
Win $3,993 in value – iHeartRadio Ultimate iHeartCountry Christmas Vacation Sweepstakes - Enter Now
Enter to win the YYG Charlottetown Airport From Island to Island Contest.
One winner gets a trip for two to Punta Cana with Air Transat flights from Charlottetown, 7 nights at the all-inclusive Majestic Colonial, a $300 excursion certificate and a $1000 spending allowance.
Open to Prince Edward Island residents 18 and older. Ends October 30, 2026 at 11:59 PM EDT.
To enter, fill out the online form on the YYG Island to Island page (one entry per person); daily text-in entries are also offered through the partner radio station. The winner is drawn after the contest ends.
Win $2,000 in value – YYG Charlottetown Airport From Island to Island Contest - Enter Now
Enter to win the Arm & Hammer Flyaway Sweepstakes.
One winner gets a trip for two to Z100's Jingle Ball at Madison Square Garden: round-trip coach airfare for the winner and a guest departing December 11 and returning December 12, 2026, one night in a standard hotel room on December 11, two Jingle Ball tickets for December 11 and a unique artist experience (ARV $5,966).
Open to legal residents of the 50 US states and DC, 18 or older (or the age of majority in their state). Ends November 15, 2026 at 11:59 PM EST.
To enter, complete the entry form at iheartradio.com/AHFlyaway, limit one entry per day. The winner is drawn on or about November 16, 2026.
Win $5,966 in value – Arm & Hammer Flyaway Sweepstakes - Enter Now
Enter to win the Virgin Radios Vacay A Day Contest - 25 Winners.
25 winners each get an 8-day/7-night all-inclusive trip for two to Sandals Jamaica, Ocho Rios, Jamaica, with round-trip economy airfare, meals, drinks and transfers (ARV $7,738 CAD each).
Open to residents of Alberta, British Columbia, Manitoba, Nova Scotia, Ontario and Quebec who are the age of majority. Ends November 27, 2026 at 8:30 PM EST.
To enter, listen to your local Virgin Radio station for the weekday keyword and submit it on the station's contest page between 7:00 AM and 8:30 PM local time that day; up to 3 bonus entries are available on the entry page.
Win $193,450 in value – Virgin Radios Vacay A Day Contest - 25 Winners - Enter Now
Enter to win the Rise and Rhythm Cruise for Two with iHeartRadio Sweepstakes.
One winner and a guest get a 4-night Rise and Rhythm Cruise aboard the Norwegian Jewel from Miami, January 14-18, 2027, with round-trip airfare, a KEM toast and signed swag.
Open to legal residents of the 50 US and DC who are 21 or older. Ends November 1, 2026 at 11:59 PM EST.
To enter, sign in and enter once every 24 hours on the contest page at iheart.com or in the iHeartRadio app; click Listen on iHeartRadio for 20 bonus entries a day. The winner is drawn on or about November 2, 2026.
Win $10,000 in value – Rise and Rhythm Cruise for Two with iHeartRadio Sweepstakes - Enter Now
Enter to win the Radio Flyer Halloween Haul Giveaway.
One winner gets a $500 Radio Flyer gift card.
To enter, post a picture of your Radio Flyer wagon costume creation on Instagram, tag @radioflyerinc and include #RadioFlyerHalloween in the post. One winner is picked at random.
Terms and conditions apply. Ends November 1, 2026 at 11:59 PM EST.
Win $500 in value – Radio Flyer Halloween Haul Giveaway - Enter Now
Enter to win the iHeartRadio Jingle Ball x JCPenney Sweepstakes - 27 Winners.
27 prizes across 4 entry periods (drawings about 10/26, 11/16, 11/30 and 12/21). Prizes include a trip for two to Z100 Jingle Ball at Madison Square Garden on 12/11 with airfare, 2 hotel nights, tickets and a Bella Kay artist experience ($3500), JCPenney gift cards from $250 to $1000, and signed artist items. Total ARV $13050.
To enter, submit the online form once per day at iheartradio.com/JCPJingleBall. JCPenney or Aeropostale Rewards members get 10 one-time bonus entries (free to join). Non-winning entries carry over to later drawings.
No purchase necessary. Open to legal US and DC residents 18+. Ends December 20, 2026 at 11:59 PM EST.
Win $13,050 in value – iHeartRadio Jingle Ball x JCPenney Sweepstakes - 27 Winners - Enter Now
Enter to win the iHeartRadio V101.1 Legends of Laughter Sweepstakes - 5 Winners.
At least five winners each receive two tickets to Legends of Laughter 2027 on February 20, 2027 at Hard Rock Live Sacramento (ARV $120 per prize).
To enter, complete the entry form on the V101.1 Sacramento promotions page; limit one entry per person/email/household per day. Bonus: click to visit iHeart.com once for 10 bonus entries.
No purchase necessary. Open to legal California residents 21+. The sweepstakes runs October 7, 2026 to February 15, 2027 at 11:59 PM PT; winners are drawn on or about February 16, 2027.
Win $600 in value – iHeartRadio V101.1 Legends of Laughter Sweepstakes - 5 Winners - Enter Now
Enter to win the HitchFire Ultimate Tailgating Giveaway.
One winner receives the whole kit from 8 brands: a HitchFire Forge 15 hitch grill ($599), Polaris P2000i inverter generator ($699.99), MoonShade vehicle awning ($500), Turtlebox Gen 3 speaker ($430), Midland radio bundle with a $100 gift card ($379.98), Rugged Road 65 cooler ($374.99), 2 Cliq ClassiQ chairs ($299.90) and Hollow alpaca socks and beanie ($199). Total about $3,482.
To enter, submit your name and email on the HitchFire giveaway page. Get bonus entries by following each partner brand on Instagram and sharing with or tagging friends.
No purchase necessary. Open to US residents 18+. Entries close October 28, 2026 at 11:59 PM PT; the winner is drawn and notified by email November 2.
Win $3,482 in value – HitchFire Ultimate Tailgating Giveaway - Enter Now
Enter to win the Pure Country's Big $50K Payday Contest - 29 Winners.
One grand prize winner receives a $50,000 CAD cheque, and 28 secondary prize winners each receive a $500 CAD cheque (daily $500 prizes; $64,000 total).
To enter, listen to Bell Media's Pure Country stations weekdays every hour between 6 AM and 6 PM for the Big $50K keywords and enter them on the contest page on iHeartRadio.ca; bonus entries are available for sharing your unique link.
The contest runs October 13, 2026 at 6:00 AM through November 20, 2026 at 6:59 PM local time. Winners are drawn at random and must answer a mathematical skill-testing question. Open to legal residents of Saskatchewan, Manitoba, Ontario, Quebec and New Brunswick who are at least the age of majority. No purchase necessary.
Win $64,000 in value – Pure Country's Big $50K Payday Contest - 29 Winners - Enter Now
