Fly To Caribbean From Many US Cities For ~$250 RT, Thxgiving & Winter

American Airlines has some good fares available from many US cities to the Caribbean. There’s availability for Thanksgiving and winter which is a great time to get away from the cold and into the great Caribbean weather. Prices vary a bit depending on your departure city and destination; the cheapest seem to be St. Kitts, St. Lucia, and Aruba. Seems to be more availability in February.

Travelers – Passenger details for your reservation – American Airlines.png


Some flights with have long layovers in Miami, so pay attention when booking if that’s not something you’re interested in. Here’s a list of destinations:

  • Antigua (ANU)
  • Aruba (AUA)
  • Curacao (CUR)
  • Nassau (NAS)
  • Punta Cana (PUJ)
  • Turks & Caicos (PLS)
  • St. Kitts (SKB)
  • St. Lucia (UVF)

And a list of US cities with the lowest prices available

  • Atlanta (ATL) – $251
  • Cincinnati (CVG) – $276
  • Cleveland (CLE) – $278
  • Denver (DEN) – $255
  • Detroit (DTW) – $265
  • Hartford (BDL) – $328
  • Houston (IAH) – $269
  • Jacksonville (JAX) – $260
  • Miami (MIA) – $259
  • Minneapolis (MSP) – $265
  • New York City (EWR) – $239
  • Orlando (MCO) – $249
  • Salt Lake City (SLC) – $269
  • San Francisco (SFO) – $255
  • Seattle (SEA) – $272
  • Washington DC (WAS) – $262

How To Book

You best bet is to search on Google Flights and then book directly at a airline’s website.

If you’re having trouble finding dates with quick connections, use ITA Matrix. Put in your cities (say, EWR and UVF), then click “Advanced routing codes” just beneath. In both routing code boxes, put in “/ maxconnect 360” in order to only search for flights with layovers of 360 minutes or less. Then click “see calendar of lowest fares” and put in a starting date plus a range of days, say, “4-7”.

Once the results come up, click dates and then the length of your stay that pops up after you click. Click the lowest fare on results page. On the full itinerary page, copy-paste the entire page (literally all the text on the page, not the URL) and paste it into BookWithMatrix. From there click to Book with Priceline. Hopefully the same price will still show up.

Make sure you use a credit card that will give you the most points, such as Amex Platinum tomorrow (5x on airfare), Citi Prestige (3x on airfare and hotels) or Chase Sapphire Reserve (3x on travel).

HT: Scott’s Cheap Flights

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