$549+ Deal of Fortune Packages

‘Deal of Fortune’ Packages to Caribbean & Mexico from $539 – Includes Airfare + Hotel Stay

  • These Deal of Fortune packages from include flights and three to five nights at resorts in the Caribbean and Mexico
  • Book now and find out your hotel assignment later!
  • Starting rate is for a 4-night Deal of Fortune package to the Punta Cana, departing from Ft. Lauderdale.
  • Click “Go to Deal” for more info and to book.

Want more options? See all available vacation packages now.

What’s the deal with CheapCaribbean’s Deal of Fortune packages?

deal of fortune packages

We love these “surprise” Deal of Fortune vacation packages because they’re great bargains, and they appeal to adventurous, open-minded travelers. So how does it work? Book your vacation package with CheapCaribbean to secure your spot at a resort, and then within a week of travel, they’ll notify you about which resort they’ve chosen. In case that sounds too risky, here’s something to give you some peace of mind: CheapCaribbean lists the available resorts they’ll choose from, so you can research them ahead of time to be sure they’ll meet your expectations.

Note that while some of the Deal of Fortune packages are all-inclusive, meaning they include all of your meals, snacks and beverages (even alcoholic!), some of the listed packages are airfare and room only. Deals that don’t include food and drinks are marked “Meals Not Included.” If you’re only interested in all-inclusive deals, check out their offerings in the Dominican Republic, Jamaica and the Riviera Maya, three major beach hot spots known for many affordable all-inclusive resort options.

Best time for a beach vacation

Interested in a Deal of Fortune package but not sure when to go? Prices soar in the high season, which falls between December and April for most destinations in the Caribbean and Mexico. You’ll have crowds to contend with, but the weather will be sunny and pleasantly warm. Bargain seekers will love the range of cheap vacation package options that come in the summer and fall months, when crowds have thinned and room rates have dropped dramatically. Temperatures are a bit balmier and there’s an increased chance of storms in these tropical regions, but the prices are unbeatable.

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The Deal Basics

Type: Vacation Packages

Book by: September 20, 2018 EXPIRED

Travel: Select dates through December 2018


The Fine Print

Starting rate from Los Angeles. Gateways displayed are samples; many more available in sale. Additional airline/hotel fees may apply. Starting rate last found on September 11, 2018 at 03:40 am PDT.


From Locations:

Alaska, Albuquerque, Atlanta, Austin, Baltimore, Baton Rouge, Boston, Buffalo, Burlington, Calgary, Charleston, Charlotte, Chattanooga, Chicago, Cincinnati, Cleveland, Columbus, Dallas, Denver, Detroit, Edmonton, Ft. Lauderdale, Ft. Myers, Halifax, Hartford, Hawaii, Houston, Indianapolis, Jacksonville, Kansas City MO, Kelowna, Las Vegas, Los Angeles, Memphis, Miami, Milwaukee, Minneapolis, Moncton, Montreal, Nashville, New Orleans, New York City, Newark, Norfolk, Omaha, Orange County, Orlando, Ottawa, Palm Springs, Philadelphia, Phoenix, Pittsburgh, Portland, Portland ME, Prince Edward Island, Providence, Quebec City, Reno, Richmond, Sacramento, Saint John, Salt Lake City, San Antonio, San Diego, San Francisco, San Jose, Santa Fe, Saskatoon, Seattle, Spokane, St. John's, St. Louis, Tampa, Thunder Bay, Toronto, Vancouver, Victoria, Washington DC, West Palm Beach, Winnipeg

To Locations:

Bahamas, Cancun, Cozumel, Curaçao, Dominican Republic, Jamaica, Los Cabos, Puerto Rico, Puerto Vallarta, Punta Cana, Riviera Maya, Turks & Caicos

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