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Woman's World--$300 Cash Prize Sweepstakes
Enter for a chance to win a $300. You can enter this one daily on multiple websites - see the rules for links to the others.
Restrictions:  13 or older
End Date: November 14, 2017posted on October 16, 2017
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Urban Decay Cosmetics--Halloween Contest (Facebook)
Enter for a chance to win one of four prizes of a $500 assortment of Urban Decay beauty products. There will be one prize awarded in the US and one in Canada.
Restrictions:  18 or older--also open to the UK and Hong Kong
End Date: November 2, 2017posted on October 15, 2017
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iHeartRadio--AT&T Fiesta Latina Giveaway
Enter for a chance to win a trip for two to Miami with tickets to the iHeartRadio Fiesta Latina on November 4 and an Enrique Santos experience (whatever that is). It's worth $4,999 and includes airfare with a two night hotel stay.
Restrictions:  18 or older
End Date: October 22, 2017posted on October 15, 2017
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Bob Evans--Cruise To Comfort Sweepstakes & IWG
Enter for a chance to win a cruise vacation for two, worth $5,800. There are also prizes of a Bob Evans dinner for a year awarded as a gift card or one of 15 Comfort prize packs of a t-shirt, two mugs and a plush toys. There are 500 instant win prizes of $10, $15 or $25 Bob Evans gift cards.
Restrictions:  18 or older
End Date: November 23, 2017posted on October 15, 2017
Thanks to: cabn44 for telling me about this one
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Farberware--Holiday Helpers Sweepstakes
Enter for a chance to win one of five prizes of a Farberware cookware sets, worth between $60 and $130.
Restrictions:  18 or older
End Date: January 1, 2018posted on October 15, 2017
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iHeartRadio--Ultimate London Experience Sweepstakes
Enter for a chance to win a trip for two to London, England with VIP tickets to the Country 2 Country Festival on March 9-10. It's worth $5,000 and includes airfare with at three night hotel stay.
Restrictions:  18 or older
End Date: October 22, 2017posted on October 14, 2017
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Spirit Halloween--Stranger Things Sweepstakes
Enter for a chance to win a trip for two to the premier of Stranger Things 2. It's awarded as a $2,000 American Express gift card plus two VIP tickets to the show.
Restrictions:  no AK, HI or QC
End Date: October 17, 2017posted on October 14, 2017
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Kim Komando--Epson Printer Giveaway
Enter for a chance to win an Epson wireless printer.
Restrictions:  18 or older
End Date: November 30, 2017posted on October 14, 2017
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iHeartRadio--Macy's Jingle Ball Fly Away Sweepstakes
Enter for a chance to win a trip for four people to New York City with tickets to the Jingle Ball Concert on December 8th. It includes airfare and a two night hotel stay - worth $4,500.
Restrictions:  18 or older
End Date: November 5, 2017posted on October 14, 2017
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CMT--Boots On The Boulevard Sweepstakes
Enter for a chance to win a trip for two to Las Vegas with tickets to a concert. It's worth $2,100 and includes airfare with a two night hotel stay.
Restrictions:  21 or older--no HI or AK
End Date: November 8, 2017posted on October 13, 2017
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