$101 Find Cheap Flights from Key West to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Caribbean departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Key West to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Nassau
Nassau1 stop$475
Kingston
Kingston1 stop$434
Nassau
Nassau1 stop$475
Kingston
Kingston1 stop$434

Book Cheap Key West to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Key West to Caribbean

Sun, Jan 25 - Thu, Jan 29
Multiple Airlines Logo
11:06 am - 12:34 am
EYW
-
SJU
12h 28m1 stop
Multiple Airlines Logo
4:22 pm - 9:09 am
SJU
-
EYW
17h 47m2 stops
$298Multiple Airlines
Sun, Jan 25 - Thu, Jan 29
Multiple Airlines Logo
11:06 am - 12:34 am
EYW
-
SJU
12h 28m1 stop
Multiple Airlines Logo
4:40 pm - 1:30 pm
SJU
-
EYW
21h 50m1 stop
$303Multiple Airlines
Sat, Jan 10 - Wed, Jan 14
Multiple Airlines Logo
10:49 am - 6:34 am
EYW
-
SJU
18h 45m2 stops
Multiple Airlines Logo
7:34 pm - 9:26 am
SJU
-
EYW
14h 52m1 stop
$306Multiple Airlines
Thu, Feb 5 - Thu, Feb 12
Spirit Airlines Logo
12:51 pm - 1:41 am
EYW
-
SJU
11h 50m2 stops
Spirit Airlines Logo
4:31 pm - 1:30 pm
SJU
-
EYW
21h 59m1 stop
$348Spirit Airlines
Sat, Feb 14 - Sun, Feb 22
American Airlines Logo
7:35 pm - 10:07 am
EYW
-
SJU
13h 32m1 stop
American Airlines Logo
7:00 am - 1:06 pm
SJU
-
EYW
7h 06m1 stop
$365American Airlines
Mon, Feb 9 - Mon, Feb 16
American Airlines Logo
6:06 am - 11:15 am
EYW
-
MHH
5h 09m1 stop
American Airlines Logo
2:01 pm - 7:20 pm
MHH
-
EYW
5h 19m1 stop
$455American Airlines
Sat, May 9 - Wed, May 13
United Airlines Logo
4:51 pm - 1:50 pm
EYW
-
NAS
20h 59m1 stop
United Airlines Logo
3:59 pm - 2:59 pm
NAS
-
EYW
23h 00m1 stop
$785United Airlines
Sun, Jan 18 - Fri, Jan 23
JetBlue Logo
1:00 pm - 3:12 am
EYW
-
KIN
14h 12m2 stops
JetBlue Logo
5:01 am - 12:05 pm
KIN
-
EYW
31h 04m2 stops
$992JetBlue
Fri, Jan 16 - Mon, Jan 19
JetBlue Logo
1:00 pm - 3:12 am
EYW
-
KIN
14h 12m2 stops
JetBlue Logo
11:00 am - 12:05 pm
KIN
-
EYW
25h 05m2 stops
$1,048JetBlue
Sun, May 31 - Thu, Jun 4
United Airlines Logo
4:05 pm - 1:54 pm
EYW
-
KIN
46h 49m2 stops
United Airlines Logo
2:59 pm - 10:11 pm
KIN
-
EYW
30h 12m2 stops
$1,915United Airlines
Booking Insights

KAYAK's insights & trends for Key West to Caribbean flights

Get data-powered insights and trends into flights from Key West to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between Key West and Caribbean?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Key West to Caribbean.

There is just one airline that flies from Key West to Caribbean direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is to San Juan Luis Munoz Marin Intl Airport (SJU) and costs $360.

Which airlines provide the cheapest flights from Key West to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Key West to Caribbean were found on Spirit Airlines ($348) and American Airlines ($365).

Find deals

Good to know

Cheapest flight$101
Flight from Key West to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Key West to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Key West to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Key West to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Key West to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Key West to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Key West to Caribbean

 
Need help choosing which airline to fly with from Key West to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11072 reviews
6.5Food
8.0Crew
6.9Entertainment
7.5Boarding
7.2Comfort
Airline reviews

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

10.0 ExcellentAnonymous, Dec 2025
MIA - MSP
Read more American Airlines reviews

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Key West (EYW)