Enter Now: Contest Winnings Could Set You Up for Life
Most of us are in need of a little extra cash, right? Who among us would turn down the chance to win thousands of dollars with no catch? Well, if you invest the time and apply to any of these cash sweepstakes, you may be in for a financially sweet surprise. Sure, your chances aren’t sky high, but what’s the worst that can happen — you try again next year? At least you’ll know how it’s done.
The Time to Enter Cash Contests Is Now
Don’t delay in entering contests to win cash — the more you enter, the greater your chances of walking away with a check.
1. CableTV.com’s Chief of Cheer
Our friends over at CableTV.com partnered with DIRECTV to search for a Chief of Cheer to complete 12 days of holiday-themed challenges. Spoiler alert: The challenges involve watching holiday-themed movies and TV shows. At the end of the 12 days, the Chief of Cheer gets $2,500 for themselves and $2,500 to give to the charity of their choice. What better way to get in the holiday spirit? Apply here by Dec. 6, 2026, at 11:59 pm MT.
Make Quick Cash Outside of Contests to Win Money
We all dream of winning a sweepstakes contest, but the odds are pretty slim. If you’re looking for ways to make cash outside of contests to win money, we’ve got some ideas for you. From completing short surveys to trying out apps, these are our favorite ways to make quick cash.
| Offer | What You Can Earn | What You Have to Do | Take Action |
|---|---|---|---|
| InboxDollars | $225/month | Complete short surveys | |
| Branded Surveys | $600+/month | Share your honest opinion | |
| Kashkick | $1,000/month | Try out apps |
2. Publishers Clearing House
Even if you’re not big into sweepstakes, chances are you’ve heard of Publishers Clearing House. Although the company has declared bankruptcy, there are some active sweepstakes. Among them: They’re giving away a Cadillac Escalade ESV 4WD Sport — or you can take $75,000 in cash. You can enter as many times as you like before the Dec. 17, 2026, deadline.
3. HGTV and Food Network
HGTV and the Food Network have multiple sweepstakes for you to enter. Among them is the Home for the Holidays Giveaway, with a $5,000 cash prize. You can enter twice daily — once on HGTV.com and once on FoodNetwork.com — through Jan. 6, 2027, at 8:59 am ET. The Food Network also has a Season of Sweetness Sweepstakes, where you enter to win $10,000 and VIP tickets to the Museum of Ice Cream. The deadline for that one is Dec. 21, 2026.
4. The Spruce
The home decorating and gardening site is giving away $10,000 to help you spruce up your own abode (or however you prefer to use the cash prize). You can submit an entry once a day at thespruce.com. The deadline is Feb. 28, 2027.
5. Various Sweepstakes from People.com
People keeps a running list of sweepstakes run by it and its family and partner sites. Right now, you can enter to win $25,000 for a new wardrobe, a trip to New York and much more.
Writer Elizabeth Djinis is a contributor to The Penny Hoarder, often writing about selling goods online through social platforms. Her work has appeared in Teen Vogue, Smithsonian Magazine and the Tampa Bay Times. Senior Managing Editor Tiffany Wendeln Connors updated this post for November 2026.
