Yes, you are required to report the $550.00 in sweepstakes prize money.
To report the prize money in TurboTax Premier if you didn't receive a 1099:
1. Click Federal tab
2. Click Less Common Income
3. Click Start next to Miscellaneous Income
4. Click Start next to Other reportable income
5. Click Yes On the screen that asks if you have Any Other Taxable Income
6. Enter a description (ie. Prize Money) and amount (ie. $550)on the Other Taxable Income screen
It will show up on Form 1040 Line 21, other income, along with any gambling winnings.