Round-trip flights to Mexico and the Caribbean starting at $267 this fall and winter
Update: Some offers mentioned below are no longer available. View the current offers here.
Multiple airlines are offering discounted flights to destinations in the Caribbean and Mexico, including hot spots like Punta Cana in the Dominican Republic and Montego Bay in Jamaica.
There is plenty of availability this fall and winter, so you can escape the cold and lounge on the beach. There is also some scattered availability from March to August 2024.
Deal basics
Airlines: Alaska Airlines, American Airlines, Delta Air Lines, JetBlue, Silver Airways and United Airlines
Routes: Austin, Charlotte, Chicago, Denver, Los Angeles, San Francisco and Washington, D.C., to Belize, the Cayman Islands, the Dominican Republic, Jamaica and Mexico
How to book: Browse Google Flights, and book directly through the airline
Travel dates: October 2023 through February 2024, with some availability around the holidays and from March through August 2024
Book by: Soon before prices increase
Kudos to Going, formerly known as Scott's Cheap Flights, for scouting these deals. For $49 a year, the site's Premium membership offers discounts of up to 90% and comes with a 14-day free trial. The Elite membership also finds premium economy, business-class and first-class deals.
Sample flights
- Austin-Bergstrom International Airport (AUS) to Grand Cayman's Owen Roberts International Airport (GCM), starting at $267
- Charlotte Douglas International Airport (CLT) to Punta Cana International Airport (PUJ), starting at $296
- Chicago's O'Hare International Airport (ORD) to GCM, starting at $284
- Denver International Airport (DEN) to Belize City's Philip S.W. Goldson International Airport (BZE), starting at $294
- Los Angeles International Airport (LAX) to PUJ, starting at $378
- San Francisco International Airport (SFO) to Cozumel International Airport (CZM), starting at $365
- Washington, D.C.'s Ronald Reagan Washington National Airport (DCA) to PUJ, starting at $326
If you want to travel from Austin to the Cayman Islands this winter, there are plenty of discounted options.
American offers the cheapest option at $270, but the flight has two layovers. A similarly priced flight on Delta has a 14-hour layover, which also seems less than ideal, and the United option costs more without including a carry-on bag.
The 7:46 a.m. American flight leaves at a decent time and only has one short (though maybe too short?) layover, making it seem like the best option.
American offers two inexpensive return flights six days later — both of which only have one layover.
For just $285, you can fly round trip between Austin and the Cayman Islands. The fare includes one carry-on bag and a standard seat. If you want to check a bag or select a seat, you'll face some extra fees.
Still, these fares are lower than usual.
Maximize your purchase
If you have a credit card that corresponds to the airline you're flying, use it to purchase your travel.
For example, if you're booking with American, use the Citi® / AAdvantage® Platinum Select® World Elite Mastercard® (see rates and fees) to earn 2 American Airlines AAdvantage miles per dollar spent on eligible American Airlines purchases or the Citi® / AAdvantage® Executive World Elite Mastercard® (see rates and fees) to earn 4 AAdvantage miles per dollar spent on eligible American Airlines purchases.
If you're booking with Delta, use the Delta SkyMiles® Gold American Express Card to earn 2 Delta SkyMiles on Delta purchases or the Delta SkyMiles® Reserve American Express Card to earn 3 SkyMiles on Delta purchases.
Other credit cards that earn bonus points on airfare purchases are:
- Chase Sapphire Preferred® Card: 2 points per dollar spent on travel
- American Express® Gold Card: 3 points per dollar spent on airfare when booked directly through the airline or American Express Travel®
- The Platinum Card® from American Express: 5 points per dollar spent on airfare when booked directly through the airline or American Express Travel® (on up to $500,000 of these purchases per calendar year, then 1 point per dollar)
- Chase Sapphire Reserve®: 3 points per dollar spent on airfare
Bottom line
If you've always dreamed of a winter getaway to a warm-weather destination, check out these flight deals from several popular airlines to the Caribbean and Mexico. No matter what card you have or which airline you're loyal to, you're bound to find a flight that works for you since there are so many options.
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