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Mystery Getaway - ORD

✈ Latin America Mystery Getaway: 3-Night Latin America or Caribbean with Flights & Hotel

Highlights

Flights & Hotel Included: Roundtrip economy flights and a minimum 3-star hotel stay to a surprise destination in Latin America or the Caribbean.

Share the Experience: Price is per person, based on 2 travelers sharing a room. Solo travel is available for an additional $199 supplement.

Mystery Destination: Your destination is drawn from a curated pool of 18 popular Latin America & Caribbean destinations.

Perfect Gift Surprise: Give loved ones the thrill of a mystery vacation — just as fun to gift as it is to experience.

Not Included: Checked baggage, airport transfers, breakfast, optional tours, city tax or travel insurance.

What You Get

Skip the planning — just pick your dates and departure airport, and let the mystery unfold. Roundtrip flights, a pre-booked hotel, and airport taxes are all taken care of. Your destination somewhere in Latin America or the Caribbean will be revealed within 72 hours of booking.

Roundtrip Flights

Roundtrip Flights
Economy Class

Hotel Stay

Hotel Accommodation
(min. 3-star Hotel)

Mystery Destination

Mystery Destination
Latin America or Caribbean

Per Person

For 1 Person
(Based on 2 Sharing)

Every hotel is guaranteed 3-star or above, independently rated 7/10+ on Booking.com or 3.5/5+ on Tripadvisor. Each private ensuite room is based on double occupancy. One personal item (purse, tote, computer bag, briefcase, or kids’ backpack) is included with your flight.

How To Book

1

Get Your Voucher

Each person must buy a voucher. Minimum 2 travelers required. Solo travel available for an additional $199 fee, payable when finalizing the booking with the tour operator.

2

Make Your Booking

Book via the Online Redemption Form using your Groupon voucher code or share the code by calling toll-free 1-929-207-0129 (Mon–Sun, 9am–9pm ET) along with the dates you are available to fly and preferred departure airport.

3

Your Trip Is Revealed

You will be contacted within 72 hours to reveal your mystery vacation destination. Once confirmed, tour operator will proceed with airline and hotel bookings.

4

Receive Your Documents & Enjoy!

Travel documents are issued within 48 hours after the booking is confirmed — then it’s time to pack and get ready for your trip!

Destinations Included

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Your destination is randomly drawn from our pool based on your preferred travel dates and departure airport. All trips in this deal are 3 nights. Each booking is part of a limited draw pool to ensure fair allocation across all customers.

  • 🇲🇽 Cancun, Mexico
  • 🇲🇽 Los Cabos, Mexico
  • 🇲🇽 Puerto Vallarta, Mexico
  • 🇲🇽 Mexico City, Mexico
  • 🇦🇼 Aruba
  • 🇨🇼 Curaçao
  • 🇧🇸 Nassau, Bahamas
  • 🇩🇴 Punta Cana, Dominican Republic
  • 🇩🇴 Santo Domingo, Dominican Republic
  • 🇵🇷 San Juan, Puerto Rico
  • 🇯🇲 Montego Bay, Jamaica
  • 🇧🇧 Bridgetown, Barbados
  • 🇨🇴 Cartagena, Colombia
  • 🇨🇴 Bogotá, Colombia
  • 🇵🇪 Lima, Peru
  • 🇦🇷 Buenos Aires, Argentina
  • 🇨🇷 San José, Costa Rica
  • 🇵🇦 Panama City, Panama

Destination pool is subject to change. If a drawn destination is unavailable due to travel restrictions, the Tour Operator will offer a suitable alternative.

Find Your Departure Gate

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Your price reflects your local flight market — no hidden fees, no surcharges. Every traveler has an equal shot, regardless of where they fly from. Select and purchase the deal option that corresponds to the gate your departure airport is listed under.

GATE A: $399 PER PERSON

  • Atlanta Hartsfield-Jackson (ATL)
  • Chicago O'Hare (ORD)
  • Dallas/Fort Worth (DFW)
  • Denver (DEN)
  • Houston Intercontinental (IAH)

GATE B: $449 PER PERSON

  • Baltimore/Washington (BWI)
  • Orlando International (MCO)
  • Fort Lauderdale (FLL)
  • Philadelphia International (PHL)
  • Miami International (MIA)

GATE C: $499 PER PERSON

  • New York JFK (JFK)
  • Newark Liberty (EWR)
  • Boston (BOS)
  • Los Angeles (LAX)
  • Phoenix (PHX)

Know Before You Go

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  • Included: Roundtrip economy flights, 3-night 3-star+ hotel, one personal item (purse, tote, computer bag, briefcase, or kids’ backpack), and airport taxes.
  • Not Included: Checked baggage, in-flight meals, airport transfers, breakfast, city tax, and personal expenses.
  • Solo Traveler Supplement: $199 per person — payable when finalizing the booking with the Tour Operator.
  • Checked Baggage: Not included in the Groupon price; must be arranged and paid for directly with the airline.
  • City Tax: Not included; rate varies by destination — ask the Tour Operator at booking.
  • Valid passport is required for all international travel. Check travel.state.gov for destination-specific validity requirements and current entry/exit information before your trip.
  • Your passport must be valid for at least six months after your travel date and contain at least two blank visa pages.
  • A credit card is required at hotel check-in. Resort or city fees may apply depending on destination.
  • Travelers must be 18 or older to check in to hotels.
  • Bookings are non-refundable and non-transferable to another destination once confirmed.
  • Weekender Breaks has insolvency protection in place to refund payments and ensure repatriation where transport is included.

FAQs

What kind of destinations are included in the mystery vacation?

This mystery deal includes destinations randomly selected from our pool of 18 destinations in LATAM and the Caribbean. The pool includes Cancun, Punta Cana, Bogotá, Buenos Aires and more. For the full list, please refer to the Destinations Included section above.

Are my preferred travel dates submitted via form or by phone guaranteed?

Your preferred dates are used to enter the lottery draw for your trip, so they are not guaranteed as your final departure date. Once your destination is revealed, the tour operator will work with you to confirm a suitable departure date, finding alternatives if your selected dates are unavailable.

Can I choose my destination or receive a refund if I don’t like my assigned destination?

The excitement of a Mystery Getaway lies in the surprise — destinations are assigned at random and cannot be chosen. Once you submit the online booking form, your entry is placed in the draw. Refunds are not available if you’re unhappy with the assigned trip; however, the tour operator’s sales team can help explore alternative options based on your departure date and preferred airport. To secure the best availability, redeem your voucher promptly once your destination is confirmed.

How are the destinations drawn?

Destinations are drawn at random from our destination pool, based on your selected travel dates and departure airport. All trips in this deal are for 3 nights. Each booking is part of a limited draw pool to ensure fair allocation across all customers.

What type of hotel/resort is included?

We always book accommodation rated by independent reviewers, scoring at least 7/10 on Booking.com or 3.5/5 on Tripadvisor. Your accommodation will also be clean, comfortable and safe, and you’ll stay in a minimum of 3-star accommodation with a private room and ensuite bathroom.

What is the full cancellation policy?

Your voucher is fully refundable to your original payment method or as Groupon Bucks until your booking is confirmed with the merchant or within 3 days of purchase, whichever comes first. After 3 days and until the deal expires (“Book by” date available in “Need To Know Info” section), refunds for unredeemed vouchers are issued as Groupon Bucks. Once the deal has expired, vouchers are no longer eligible for a refund; however, amount paid never expires. For full details on the merchant’s cancellation policy, visit this site.

Fine Print

  • Must book by 11/30/2026
  • Travel must be completed by 12/20/2026
  • Limit 2 per person
  • May buy 2 additional as gifts
  • Destination assigned by random draw—package price does not affect tier
  • Valid only for option purchased
  • Reservation required, subject to availability
  • Must be 18+ to check in
  • Credit card required at booking and check-in
  • Must use promotional value in 1 visit
  • Solo passenger surcharge is $199
  • Please note that city tax is not included and may be applicable; its rate depends on the destination—please enquire upon booking
  • No departures available from July 1-6, Sep 4-8, Nov 21-30
  • No modification or cancellation allowed after booking confirmation
  • Bookings are non-refundable and non-transferable to another destination once confirmed
  • This offer is only refundable if you do not fill out the redemption form
  • Once the booking form is submitted, the voucher will be considered redeemed and will no longer be refundable
  • A valid travel document is mandatory
  • Valid for a stay in a standard double room for 1 person, based on 2 people traveling together and sharing a room
  • Additional fee applies for solo travel
  • Weekender Breaks aka Mystery Vacations will be fully responsible for the proper performance of the package as a whole
  • Additionally, as required by law, Weekender Breaks aka Mystery Vacations has protection in place to refund your payments and, where transport is included in the package, to ensure your repatriation in the event that it becomes insolvent
  • Weekender Breaks aka Mystery Vacations has taken out insolvency protection with the Civil Aviation Authority and ABTA
  • Travelers may contact this entity or, where applicable, the competent authority at [https://www.abta.com/help-and-complaints/legal-facts-about-making-a-claim](https://www.abta.com/help-and-complaints/legal-facts-about-making-a-claim) if services are denied because of Weekender Breaks insolvency
  • You can select a date up to 90 days in advance and at least 14 days ahead of departure. Airfare Fine Print: Departure Airports: Atlanta Hartsfield-Jackson (ATL), Chicago O'Hare (ORD), Dallas/Fort Worth (DFW), Denver (DEN), Houston Intercontinental (IAH), Baltimore/Washington (BWI), Orlando International (MCO), Fort Lauderdale (FLL), Philadelphia International (PHL), Miami International (MIA), New York (JFK), Newark Liberty (EWR), Boston (BOS) Airfare includes a free personal item
  • Airport taxes are included
  • Not included: checked baggage and airport transfers

About Mystery Getaway

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