Best Cash Prize Sweepstakes in Chesapeake, VA: 2026 Local Guide
Check deadlines, entry limits, and tax rules for cash drawings open to Chesapeake entrants this week.
Chesapeake entrants seeking cash prizes have two verified paths: a national sweepstakes entry and active Virginia Lottery drawings. A sweepstakes is a drawing where entry gives a chance to win and purchase cannot be required to participate or win. The national entry closes very soon, so timing controls your next step.
Lottery drawings require a paid ticket, while sweepstakes entries do not. Both paths can leave you owing tax on what you win.
Verification note: Program terms and availability can change. This page was checked against linked sources on October 27, 2026.
Sweepstakes or lottery — what is the difference?
The D.C. Office of the Attorney General states a legitimate sweepstakes must not require purchase or advance payment to participate or win consumer alert from the D.C. Office of the Attorney General.
That rule is the legality test for Chesapeake entrants. A request for payment to enter or claim breaks from that standard. Virginia Lottery drawings work differently because they require buying a ticket.
That purchase buys a chance to win, not a promised payout. Points for free play and drawing entries also offer another chance, not cash itself.
What can you still enter before the deadline?
HGTV states entrants in its Trick or Treat Yourself promotion can enter twice daily, once on HGTV.com and once on Food.com, through October 28, 2026 at 8:59 a.m. ET entry details on HGTV. The date limit sits beside the benefit.
Chesapeake entrants get one entry per site per day until that morning cutoff. Use the remaining window for the two permitted entries each day. No purchase is needed for this type of entry.
A missed cutoff ends the chance for this promotion.
Which Virginia Lottery options are active in Chesapeake?
On Oct. 27, 2026, Virginia Lottery listed Mega Millions at $443 million ($186 million cash) and Powerball at $716 million ($307 million cash), and Rewards lets account holders scan tickets for points toward free play and drawing entries Rewards FAQ from the Virginia Lottery. Eligible adults buy tickets for a chance at those amounts.
Points add more chances, not direct cash. Lottery play starts with a paid ticket at an eligible age. Rewards also needs an account before points accrue.
Treat each ticket as a paid chance, not a promised payout.
What about taxes and requests for payment?
The IRS states gambling winnings are fully taxable and must be reported, including cash plus the fair market value of noncash prizes such as cars and trips Topic No. 419 from the IRS. Set aside part of any win for tax.
A car or trip counts like cash for reporting. Do not pay to enter or claim. Pause when you hear these requests:
- pay a fee to enter or release a prize
- buy a lottery ticket to enter a sweepstakes
- treat free play as cash in hand