Round-trip flights to the Caribbean this winter for under $400

If you are sad about the end of summer, I hate to remind you that many parts of the country will be cold in just a few months.

Get ahead of seasonal depression by booking a winter flight to Turks and Caicos or the Cayman Islands, with round-trip flights from six U.S. cities ranging from $300 to $400 to both destinations, starting in November through the end of 2023 and into early 2024.

Deal basics


Airlines: Southwest Airlines, Delta Air Lines, United Airlines, American Airlines and JetBlue
Routes: From New York, Los Angeles, Baltimore, Houston, Atlanta and Chicago to Providenciales, Turks and Caicos, and Grand Cayman, Cayman Islands
How to book: Browse Google Flights and book directly with the airline — except for Southwest flights, which are not available on Google Flights
Travel dates: November 2023 through February 2024, excluding Christmas and New Year’s Eve, but some routes include Thanksgiving
Book by: Within the next three days

This deal was originally sent out by Going, formerly known as Scott’s Cheap Flights. Sign up for Going to get deals up to 90% off via its Premium membership, which users can try for free for 14 days and then $49 per year. You can also upgrade to the Elite tier for $199 per year and receive all the Premium deals plus premium economy, business-class and first-class alerts.

Sample flights

The following flights were priced as listed at the time of publication. We cannot guarantee the below round-trip flights will be available when you book:

  • Newark Liberty International Airport (EWR) to Providenciales International Airport (PLS), starting at $297
  • LaGuardia Airport (LGA) to PLS, starting at $301
  • John F. Kennedy International Airport (JFK) to PLS, starting at $304
  • Hartsfield-Jackson Atlanta International Airport (ATL) to Owen Roberts International Airport (GCM), starting at $340
  • William P. Hobby Airport (HOU) to GCM, starting at $370
  • Los Angeles International Airport (LAX) to GCM, starting at $374
  • Midway International Airport (MDW) to PLS, starting at $400

Note that sale flights on United, Delta, American and JetBlue are for basic economy fares. American’s basic economy fare includes one free carry-on, while United’s and Delta’s basic economy do not. American and Delta both charge $60 for your first checked bag, while United charges $70.

Southwest flights are not available on Google Flights, but you can search your desired routes and dates via Southwest’s Low Fare Calendar to book. All Southwest flights include one personal item, one carry-on and two checked bags.


If you come across a JetBlue sale fare, it’ll be for its Blue Basic, which only includes one personal item that can fit under the seat in front of you. Any full-size carry-on bag brought to the gate will incur a fee and need to be checked. The fee is $65 (for your first or second checked bag) or $180 (for your third).

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Maximize your purchase

If you book this deal, be sure to use a credit card that earns bonus points on airfare purchases, such as:

Bottom line


Chase away the winter blues with round-trip flights from major U.S. hubs to Providenciales and Grand Cayman for less than $400 for winter availability.

This deal is likely to last only a few days, so be sure to book soon to take advantage of it.

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