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High-Value Sweepstakes ($3,000+ Prizes)

WTTW’s 2026 Be a Winner Sweepstakes

Other Last day to enter: Mon, Oct 26 LoadingSave post

TravelCash & gift cardsHigh valuePrize value: $36,000

https://www.wttw.com/sweepstakes-2026/entry-form?s=t-swp-wb-apr26-website&cid=%20#entry-form
Sweepstakes open only to those individuals who are at least eighteen (18) years of age (or the age of majority in their jurisdiction of residence) on the date of Sweepstakes entry and are legal residents of and physically residing in Illinois, Indiana, Michigan, or Wisconsin as of the date of their entry. Sweepstakes void outside of Illinois, Indiana, Michigan, and Wisconsin and where prohibited by law.

PRIZES:

(1) Spring Early Bird Prize: Two (2) prizes for the InquisiTours “Walla Walla Deluxe Wine Touring Package” for two (2) people. Does not include transportation to Walla Walla, Washington. Package excludes the following tour dates: 4/1/27-4/4/27, 4/30/27-5/3/27, 5/28/27-5/31/27, and 9/3/27-9/6/27. (ARV: $3,899 each).

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

(3) Bonus Prize: One (1) $10,000 gift card and one (1) in-home design consultation to Walter E. Smithe Furniture & Design. (ARV: $10,100).

The winners of any of the three prizes noted above are also eligible to win any general prize noted below.

(4) General Prize Pool: All entries submitted in the 2026 Be a Winner Sweepstakes will be entered into the General Prize Pool. Prizes in this pool are detailed below:

Grand Prize: One (1) 2027 Subaru Crosstrek Hybrid from McGrath Evanston Subaru. Read more

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Ford “Drive Them Home” Sweepstakes

One Entry Last day to enter: Mon, Oct 12 LoadingSave post

VehiclesHigh valuePrize value: $4,600

https://www.forddrivethemhome.com/login
PRIZES:

Entry Period 1:

1 Grand Prize winner will receive their choice of a 2026 Ford F-150 Lariat Truck with available PowerBoost Hybrid V6 (MSRP $71,355), a 2026 Ford Expedition Platinum SUV (MSRP $77,045), or a 2026 Ford Bronco Badlands SUV (MSRP $53,770)
2 First Prize winners will each receive a trip for 2 to Philadelphia, PA, including round-trip coach airfare, 3 nights hotel accommodations, 2 tickets to the 2026 MLB All-Star Game at Citizens Bank Park (July 12-14, 2026), and a $750 gift card (ARV $3,600)

Entry Period 2:

1 Grand Prize winner will receive their choice of a 2026 Ford F-150 Lariat Truck with available PowerBoost Hybrid V6 (MSRP $71,355), a 2026 Ford Expedition Platinum SUV (MSRP $77,045), or a 2026 Ford Bronco Badlands SUV (MSRP $53,770)
2 First Prize winners will each receive a trip for 2 to Game 1 of the 2026 MLB World Series, including round-trip coach airfare, 2 nights hotel accommodations, and a $500 gift card (ARV $4,600)

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2026 ford bronco wild fund sweepstakes

One Entry Last day to enter: Mon, Nov 30 LoadingSave post

VehiclesHigh valuePrize value: $60,000

https://fordeventreg.com/BWFGeneralRegistration
Prize (1): The prize includes: (i) one (1) 2026 Ford Bronco® Big Bend® SUV (with a Manufacturer’s Suggested Retail Price (“MSRP”) inclusive of dealer fees, registration/title/license fees, and sales tax of up to $50,000 (the “Bronco”); and (ii) $10,000, in a check made payable to the confirmed winner (collectively, the “Prize”). The Approximate Retail Value (“ARV”) of the Prize is up to $60,000. Note that if the Bronco is more than $50,000, including dealer fees, registration/title/license fees and sales tax, the winner is responsible for those costs. If the Bronco is less than $50,000 including dealer fees,
registration/title/license fees and sales tax, the difference between the actual price and the MSRP will not be paid to the winner, but the IRS form set forth below will reflect the actual Prize value of $60,000.

NRA Truck Sweepstakes

Other Last day to enter: Sat, Jan 30, 2027 LoadingSave post

Cash & gift cardsVehiclesHigh valuePrize value: $70,000

https://trucksweepstakes.nra.org/Enter
Void in Minnesota, Montana and Washington
PRIZE:
One Grand Prize winner will receive three prizes:

Winner’s choice of a truck or vehicle (or $70,000 cash). ARV: $70,000
Winner’s choice of an adventure prize (or $15,000 cash). ARV: $15,000
$25000 Cash prize
Total Grand Prize VRV: $110,000

Fast Entry Prizes (10):

Each winner will win $1,000 prize or $1,000 cash each.

Ecco Domani Italian Getaway Sweepstakes

One Entry Last day to enter: Thu, Dec 31 LoadingSave post

TravelHigh valuePrize value: $10,000

https://www.eccodomani.com/italy-sweepstakes.html
The prize will consist of a trip for winner and one guest (both aged 21 or over) to one of the following destinations in Italy, which shall be mutually agreed by winner and Sponsor: Florence, Milan, Rome, or Venice. The trip will include roundtrip airfare for winner and one guest from a Sponsor-specified major airport nearest winner’s residence to a Sponsor-specified major airport nearest the mutually agreed upon destination in Italy, ground transportation to and from the airport, and five (5) night standard accommodations (single room, double occupancy, room and tax only) to be selected by Sponsor. The ARV of the prize is $10,000.

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Peroni Nastro Azzurro 0.0% Las Vegas Race Weekend Sweepstakes

Daily Last day to enter: Sun, Dec 6 LoadingSave post

TravelHigh valueLots of winnersPrize value: $5,308

https://mc.beveragepromo.com/262189
ONE (1) GRAND PRIZE: A trip for the winner and one (1) guest to the Las Vegas Race Weekend from November 19, 2026 – November 22, 2026. Trip package includes round trip, coach-class air transportation for two (2) from a major airport near winner’s home (determined by Sponsor in its sole discretion) to Las Vegas, NV; three (3) nights’ accommodations at a hotel determined by Sponsor in its sole discretion (single room, double occupancy); a $250 transportation voucher; $250 spending money awarded in the form of check made out to the winner, and two (2) 3-day Las Vegas Race Weekend grandstand tickets for the winner and guest. Terms and conditions of tickets and vouchers apply. Winner must travel on the dates determined by Sponsor in its sole discretion or prize will be forfeited. Trip must be booked at least forty-five (45) days prior to departure. Travel and accommodations are subject to availability and blackout dates. ARV: $5,308.

TEN (10) FIRST PRIZES: Each winner will receive a Peroni 0.0% Racing LED sign. ARV: $152.

TWENTY (20) SECOND PRIZES: Each winner will receive a Peroni 0.0% mechanic shirt (size determined by Sponsor in its sole discretion). ARV: $40.

THIRTY (30) THIRD PRIZES: Each winner will receive a Peroni 0.0% cross-body bag. ARV: $12.

B. Total ARV: The total ARV of all available prizes in the Sweepstakes is $7,988.

Hilton Grand Vacations Jackpot Sweepstakes

Other Last day to enter: Sun, Jan 31, 2027 LoadingSave post

TravelHigh valuePrize value: $18,600

https://hgvsweepstakesamoe.com/

One (1) Grand Prize is available. The Grand Prize consists of a deluxe vacation package to winner’s choice of Hawaii, Las Vegas, or Orlando for seven (7) nights for up to two (2) people (winner and one (1) guest) (“Trip”). Trip includes round-trip economy class air transportation for the winner and one (1) guest from a major airport (selected at the sole discretion of Sponsor) near winner’s residence, Hilton deluxe accommodations in the destination city (one (1) room, double occupancy), $1,000 spending money for the winner only, one-week car rental and destination-based gift (i.e. events/tours/tickets/cruises/etc.; determined by Sponsor – ARV up to $1,000), and 2,000,000 Hilton Honors Points. The approximate retail value (“ARV”) of the Grand Prize is $18,600. Grand Prize winner will have the option to accept $10,000 as an alternative to the Trip.

Twelve (12) Monthly Prize are available (one (1) per Monthly Entry Period). Each Monthly Prize consists of three (3) nights Hilton Hotel accommodations (one (1) room, double occupancy) at any participating Hilton location in the continental United States (excludes Hawaii and New York), 250,000 Hilton Honors points; and $500 spending money for the winner only (“Vacation Package”). The ARV of each Monthly Prize is $1,825. Monthly winners will have the option to accept $1,000 as an alternative to Vacation Package.