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Book flights to the Caribbean from cities across the US starting at $179

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Escape to the sun and sand this year … at a bargain. Round-trip flights to various places in the Caribbean and surrounding countries are as low as $179.

Even better, multiple airlines are offering these cheap fares from many major cities across the U.S. Fly to Jamaica, Honduras, Colombia, Mexico or the U.S. Virgin Islands from cities like Chicago, Atlanta and Boston.

Looking out on the water in the U.S. Virgin Islands. EYEWOLF/MOMENT/GETTY IMAGES

While there’s ample availability, with travel dates ranging from May 2023 to March 2024, a deal this flexible won’t last for long, so be sure to get your flights booked in the next couple of days.

Deal basics

Airlines: Aeromexico, Alaska Airlines, American Airlines, Avianca, Caribbean Airlines, Delta Air Lines, JetBlue Airways and United Airlines.
Routes: Atlanta, Austin, Baltimore, Boston, Chicago, Charlotte, Chicago, Dallas, Houston, Los Angeles, Miami, Newark, New York City, San Francisco, Seattle and Washington, D.C.
How to book: Use Google Flights to determine your dates, then book directly with the carrier of your choice.
Travel dates: May 2023 to March 2024.
Book by: The next one to two days.

Kudos to Going for finding these deals. At $49 a year, Going’s Premium membership gives discounts of up to 90% and includes a 14-day free trial. The Elite membership also scouts premium, business-class and first-class deals.

Sample flights

These deals give you multiple choices. With so many airlines and wide availability, you can head down to the Caribbean with your preferred carrier and book these trips for any season within the next 10 months.

Here are the flights that caught our eye:

  • United: George Bush Intercontinental Airport (IAH) to La Aurora International Airport (GUA), starting at $179.
  • Aeromexico: Denver International Airport (DEN) to Cancun International Airport (CUN), starting at $232 (includes a layover in Mexico City).
  • American: O’Hare International Airport (ORD) to CUN, starting at $252.
  • Avianca: Miami International Airport (MIA) to Tocumen International Airport (PTY), starting at $263 (includes a layover in Bogota, Colombia).
  • American: LaGuardia Airport (LGA) to Sangster International Airport (MBJ), starting at $273 (includes a layover in Charlotte).
  • American: Dulles International Airport (IAD) to Los Cabos International Airport (SJD), starting at $346.
  • American: San Francisco International Airport (SFO) to Lynden Pindling International Airport (NAS), starting at $381 (includes a layover in Miami).

We recommend using Google Flights to determine your availability and then directly booking your flights on the airline’s website. Direct airline bookings are more dependable if your flight faces a cancellation, delay or booking change.

If you’re traveling from Chicago and looking to visit the beaches and resorts of Cancun, Mexico, from June 24 to July 4, American offers two flights departing from ORD priced at $252.


As for returning flights, American has similar options — it’s just a matter of preference for what time you’d want to leave.


Keep in mind that these bargain fares are only for basic economy, the most restrictive seat class. American’s basic economy passengers can bring one carry-on bag and must pay an additional fee to choose a seat. They also can’t make ticket changes or receive refunds.


Seats cost anywhere from $25 to $51 each. At the time of publication, standard seats were almost sold out, so make sure you get these tickets as soon as possible.


Maximize your purchase

For your flights, be sure to use a credit card that earns bonus points on airfare purchases, such as The Platinum Card® from American Express (5 points per dollar spent on airfare booked directly with the airline or through American Express Travel, on up to $500,000 on these purchases per calendar year), the Citi Prestige® Card (5 points per dollar spent on airfare), the Citi Premier® Card (3 points per dollar spent on airfare), the Chase Sapphire Reserve (3 points per dollar spent on airfare), the American Express® Gold Card (3 points per dollar spent on airfare when booked directly with the airline or through Amex Travel) or the Chase Sapphire Preferred Card (2 points per dollar spent on travel). See this post for more on maximizing airfare purchases.

The information for the Citi Prestige Card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Bottom line

Overall, this deal is hard to beat. From the wide set of travel dates to the availability at most of the largest airports in the U.S., these deals to the Caribbean, Mexico and South America are worth booking.

Flights are almost certain to sell out with these cheap fares, so snag them while you can.