2. Sears Shop Your Way $50,000 Pick Your Dream Car Sweepstakes
Entry frequency: 1 time per day per person
Eligibility: Open to the U.S.
End date: February 28, 2017
If you’re tired of driving your 2003 Toyota Camry with a battery you probably need to replace this week, you should enter this sweepstakes run by Sears. You could win a $50,000 that includes a vehicle of your choice (insurance not included, sadly) and up to $13,000 in cash to cover taxes. This sweepstakes ranks highly simply because it also includes the cash to cover taxes, which is quite rare to see. I always get nervous when I see people giving away cars because I think of the fact that taxes are so high as well as insurance for brand new cars. And now, let’s see the number one on our list of easiest contests and sweepstakes to win.