Hilton October Sweepstakes

Our resident Hilton expert, TPG contributor Nick, is a bit down that Hilton hasn't announced a fourth quarter promotion yet, but he's entering the chain's daily October sweepstakes. Here's what Hilton HHonors members can win this month.

Now that the fourth quarter has officially arrived, us loyal Hilton HHonors members are feeling a bit jilted about the lack of an announced promo. FlyerTalk is filled with some pretty solid leads on what exactly it will be, but in the meantime, Hilton has whetted our appetite (a bit) by starting a collection of daily changing sweepstakes for the month of October called “25 Days of Winning."

To take part, Hilton HHonors members need to enter their e-mail address at the bottom of the promo page, click “Enter now,” and fill-in their Hilton HHonors account information on the following page. You can also play the “Instant Win” game each day where 5 daily winners walk away with a $100 Hilton HHonors gift card. Be sure to bookmark the page, since you’ll need to enter each day to be eligible for that day’s prize. The site should give you the chance to get a daily reminder e-mail, which I would definitely say is worth it for a shot at some of the giveaways!

Here’s a list of the prizes for each day (not including the first three, as it’s too late to register for either one of those):

Thursday October 4^th: Diamond status for a year

Friday October 5^th: 1,000,000 Hilton HHonors bonus points

Saturday October 6^th: Bose Entertainment package

Sunday October 7^th: Ski & Spa package at the Waldorf Astoria in Park City (including airfare, four nights in the resort, three-day passes to the Canyons Ski Resort [accessed directly from the property], massages at the Golden Door Spa, $4,500 spending money, 100,000 Hilton HHonors bonus points, and a $1,000 Hilton HHonors gift card)

Monday October 8^th: $5,000 Hilton HHonors gift card

Tuesday October 9^th: 1-carat diamond earrings

Wednesday October 10^th: Trip to the GRAMMY’s (including airfare, three nights at the Beverly Hilton, tickets to the show, passes to the official after-party, $2,000 spending money, 100,000 Hilton HHonors bonus points, and a $1,000 Hilton HHonors gift card)

Thursday October 11^th: A Tag Heuer Aquaracer Quartz Watch

Friday October 12^th: Golf package for four to a professional golf tournament (including airfare, five nights accommodations, passes for four tournament days, three-hole course walk with a Golf Digest editor), a round of golf at a local course, $6,000 spending money, 100,000 Hilton HHonors bonus points, and a $1,000 Hilton HHonors gift card

Saturday October 13^th: An Xbox Kinect

Sunday October 14^th: A family four-pack of bikes

Monday October 15^th: Sports fanatic package (including airfare, two tickets to four different sporting events (Grand Prix, football, basketball, and horse racing), hotel accommodations at all four events, $10,000 spending money, 100,000 Hilton HHonors bonus points, and a $1,000 Hilton HHonors gift card)

Tuesday October 16^th: A 55” HDTV

Wednesday October 17^th: 1,000,000 Hilton HHonors bonus points to spend in the Hilton HHonors shopping mall

Thursday October 18^th: Double your Hilton HHonors account balance (minimum 100,000 bonus points, maximum 250,000 bonus points)

Friday October 19^th: $2,500 Hilton HHonors gift card

Saturday October 20^th: Four-piece luggage collection

Sunday October 21^st: Seven free nights at any Hilton HHonors property around the world

Monday October 22^nd: Grand Prix package (including airfare, four nights accommodations, VIP Paddock Club tickets to practice/qualifying/race days, signed merchandise, transportation to all events, $6,000 spending money, 100,000 Hilton HHonors bonus points, and a $1,000 Hilton HHonors gift card)

Tuesday October 23^rd: Canon PowerShot digital camera

Wednesday October 24^th: Jamaican getaway (including airfare, five nights at the all-inclusive Hilton Rose Hall Resort & Spa, unlimited water sports, Swedish massages for two, $2,000 spending money, 100,000 Hilton HHonors bonus points, and a $1,000 Hilton HHonors gift card)

Thursday October 25^th: All of these earlier prizes lead to a grand prize to be given away on the last day of the promotion period. Each time you register for a daily prize, you automatically get one entry into the grand prize. One lucky winner will be able to craft his/her own dream trip to one of the 3,900 Hilton family properties around the world. This final prize includes:

- Airfare for two to your “dream” destination
- $5,000 Hilton HHonors gift card
- 500,000 Hilton HHonors bonus points
- $15,000 cash

The winner for each of the first 24 prizes will be chosen randomly from all eligible entries on or around the day after they are listed, and the grand prize winner will be drawn on or around November 8^th. Additional details on each prize (including the approximate retail value of each used for tax purposes) are included in the sweepstakes’ official rules, located here.

Speaking of taxes, it’s important to remember the tax implications of these prizes, since anything you win may leave you on the hook for a potentially huge tax bill in April. Even the various point offerings can come back to bite you; the 1,000,000 Hilton HHonors bonus points are valued at $10,000! In other words, they are valuing a standard night in a Category 7 hotel at $500.

Everyone has their own valuations of these prizes, especially when it comes to the trips, so I won’t try to rank them from most to least appealing. Based on simple ARV, the most valuable is the sports fanatic option at a whopping $38,299. However, I’m sure many of you out there are like my wife and wouldn’t give a hoot about attending four different sporting events! Here are the ones that (in my opinion) offer great value without huge tax consequences:

1. Hilton HHonors Diamond Status (ARV: $500) – If you currently have Diamond Status (as I do), then obviously this isn’t worth anything, but this would be a terrific prize for those who don’t have top-tier status with Hilton HHonors. I have been treated very well as a Diamond, enjoying upgrades at incredible resorts (like the Conrad Bali), 50% bonus points, free internet, and other on-property benefits like spa discounts and Executive Lounge access, among others. A full list of Diamond benefits is available here.

2. Seven-night stay (ARV: $2,100) – It’s interesting that the 1,000,000-point prize (mentioned above) values each night in a Category 7 hotel at $500, whereas this prize values each night at $300. You would be better off using this prize at an off-the-beaten path property (like the Conrad Maldives), at a city property with sky-high rates, or at a Waldorf Astoria property.

Despite possible tax penalties, I still think it’s worth registering for most (if not all) of these prizes. My favorite thing about these types of sweepstakes is that they open up the door to experiences that normally aren’t possible. I doubt many of us would be able to get tickets to the Grammy’s, let alone passes to the after-party, for example. I will gladly foot a larger tax bill to experience some of these trips, and to me, those experiences are what makes travel so special. Isn’t that what points and miles are all about?

Also remember that each daily entry earns an additional entry into the grand prize sweepstakes. In addition, from now through the end of the promotion period (October 25^th), each night at a Hilton property earns yet another grand prize entry. While this certainly won’t entice me to stay with Hilton HHonors any more than I already have planned, every entry helps.

Good luck to all TPG readers! I know that some have hit it big before, so here’s hoping the trend continues!
[card card-name='Ink Bold® Business Charge Card' card-id='22125763' type='javascript' bullet-id='1']