Quote Originally Posted by Dan Druff View Post
Hey everyone, I have good news for you if you want Diamond for CHEAP, without having to gamble.

You can apply for the Amex Hilton HHonors Surpass Card, which has a $95 annual fee. That gives you instant Hilton Gold status, which can then be converted via status matches to Caesars Diamond.

Here's how:

1) Get a free Hilton HHonors account. If you're already a member, you can skip this step.

2) Apply for the card. If you already have Hilton Gold, good news! You can skip this step, and you'll get Caesars Diamond for free! (Just follow the below steps.)

3) Get a Wyndham Rewards account. If you already have a Wyndham account, you can skip this step.

4) Once you've been approved for the card and get upgraded to HHonors Gold, do a free (and instant) status match to Wyndham Diamond.

5) Once you are Wyndham Diamond (verify it says Diamond when you log into your Wyndham account), go do a status match to Caesars Rewards Diamond. First login to your Caesars Rewards account on caesars.com. Then come back here and click this link to do the match. Then wait 7 days for it to take effect.

You will have Caesars Diamond until January 31 of the following calendar year.

Do NOT worry about Wyndham's scary message that you'll lose Diamond within 90 days. This will NOT downgrade your Caesars Rewards status. Once matched, you will have Caesars Diamond until January 31 of the following year, no matter what.

None of this is illegal or against program terms.
It worked! So easy a technological cave man could do it!
Here are a few comments on the steps:
1) Pretty simple
2) Also simple
3) OK
4)When Wyndham asks for a photo of your "card", they mean a screenshot of your Hilton Honors program card, NOT the credit card you will get in the mail.
Once I figured this out (D'OH!) I realized I don't know how to do a screen shot. A little Google session taught me to hit the "Windows" Button and the "prt sc" at the same time and it saves a screen shot which you can then paste into the space on the Wyndham site. (OK, I can see most of you yawning, but if there's one person out there that was helped, it was worth it, so shut up!)

The status match to Wyndham wasn't instant, it took 48 hours.

5)The seven day wait is business days, so real time it could be 9 or 10. I requested my match on a Tuesday and got upgraded the following Wednesday (Today)
They didn't send me any notification but when I logged in to my ceasers rewards account this morning my status was diamond.

Also, I booked a room at the Rio several weeks ago and the agent I spoke to said it would be no problem to call back when I got Diamond to call back and get the resort fees removed.

Thanks again Todd! I first heard you talk about this on the podcast, which I love.