Stories by CheapCaribbean

Deal of Fortune

April 2, 2018 0 Comments

Have you ever wanted to go on a trip but you just didn’t know where you wanted to go? Maybe you weren’t sure how to find the best deal or which resort was going to give you the most bang for your buck. Or, maybe, you’re like us, and you’re a thrill seeker! Then our Deal of Fortune is perfect for you! If you aren’t sure what it is or how to use CheapCaribbean’s Deal of Fortune deal we’re here to lay it all out for you.

Deal of Fortune is a mystery deal, that allows you to select the destination of your choice, with the resort being a surprise. This is one of the best deals you’ll find on our site, but the kicker is, you won’t find out which resort you’ll be staying at until you’re about to leave. Anytime within the 7 days before your departure date, you will find out which resort you are going to. That means, it could be the day before you’re supposed to head to the airport, or an entire week before you leave. It’s all part of the thrill, but fear not, you will definitely know which resort you will be staying at before the day of your flights.

When booking your beach vacation through our Deal of Fortune deal, you’ll first decide on your destination.

Next, you’ll pick which deal works for you and your destination.

  • You’ll want to pay close attention to the title: Some Deal of Fortune offers are for Adults-only properties and some are for family-friendly properties. If the deal is adults-only, it will be indicated in the title.
  • You’ll know the type of resort you could be staying at based on the sun rating of the deal which is found just under the title. This is the rating system we use to score our resorts. You are able to view all of the resorts in the destination you have chosen that have that the same sun rating, on our destinations pages.

Once you have booked your Deal of Fortune deal, you’ll receive a confirmation email with your flight information, confirmation numbers, and any excursion or transfer details you booked in the initial reservation.

Anytime during the 1 to 7 days prior to departure you’ll get an email confirming your trip, revealing your resort, and any other information! There is no set timeframe to receive your resort information, but don’t panic, you’ll definitely know where you’re going before you hit the airport!

You’re able to book any of the awesome Deal of Fortune deals directly on our website, but if you have any questions or need help, don’t hesitate to reach out to our Beachologists at 1-800-915-2322. You can also view more of our Know How To Beach series to get the best info on all of the awesome features of


Travel junkie with a passion for fabulous food and creative crafts!




Limited time and availability. To be eligible for this promotion you must 1) be an approved ER&R Club member by 11:59 p.m. CST on November 4, 2019 2) be within the first 25 ER&R Club members to sign up for the promotion 3) make a double or single occupancy booking for 5 or more nights. Bookings must be made and payment must be collected through a designated CheapCaribbean agent between November 11-20, 2019. Travel must be completed between January,1 and June 30, 2020. Blackout dates include but are not limited to April 3-19 and May 20-27, 2020.


Flight accommodations will be booked in economy class or lower on United Airlines. Flight requests will be taken into account but are not guaranteed. In areas that are serviced by more than one airport (for example New York, Chicago, San Francisco), clients are expected to use the airport that provides the lowest fare available.


CheapCaribbean’s travel protection and cancellation policies for the hotel portion of the booking will apply. Travel protection will only be valid on the hotel-portion of the booking. Cancellation or a rebooking of your hotel stay outside of the allowed travel period will result in forfeiture of the free flight(s). Any changes to flights will be subject to the airline’s policies.


Offer not valid on previous bookings. Offer may not be combined with other special offers, discounts or promotions (including promotional codes). This promotion is not available to employees, or family members of employees, of CheapCaribbean or affiliated companies of the Apple Leisure Group.