$150 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 2/9. 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$493
Kingston
Kingston2 stops$7,107
Nassau
Nassau1 stop$493
Kingston
Kingston2 stops$7,107

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

Fri, Feb 27 - Fri, Mar 6
Multiple Airlines Logo
1:06 pm - 11:09 pm
EYW
-
SJU
9h 03m
1 stop
Multiple Airlines Logo
6:30 am - 12:26 pm
SJU
-
EYW
6h 56m
1 stop
$289Multiple Airlines
Fri, Feb 27 - Fri, Mar 6
Multiple Airlines Logo
1:06 pm - 11:09 pm
EYW
-
SJU
9h 03m
1 stop
Multiple Airlines Logo
10:12 pm - 8:06 am
SJU
-
EYW
34h 54m
2 stops
$314Multiple Airlines
Thu, Feb 12 - Sun, Feb 15
Multiple Airlines Logo
9:46 am - 2:53 am
EYW
-
SJU
16h 07m
1 stop
Multiple Airlines Logo
3:53 am - 12:26 pm
SJU
-
EYW
9h 33m
1 stop
$360Multiple Airlines
Sun, Mar 15 - Sun, Mar 22
American Airlines Logo
7:42 pm - 10:56 am
EYW
-
SJU
15h 14m
1 stop
American Airlines Logo
6:00 am - 7:12 pm
SJU
-
EYW
13h 12m
1 stop
$426American Airlines
Sun, Mar 15 - Sun, Mar 22
American Airlines Logo
7:42 pm - 10:56 am
EYW
-
SJU
15h 14m
1 stop
American Airlines Logo
6:00 am - 4:49 pm
SJU
-
EYW
10h 49m
1 stop
$466American Airlines
Thu, Mar 26 - Mon, Mar 30
Delta Logo
7:30 am - 4:45 pm
EYW
-
NAS
9h 15m
1 stop
Delta Logo
1:18 pm - 7:41 pm
NAS
-
EYW
6h 23m
1 stop
$510Delta
Thu, Feb 12 - Sun, Feb 15
Spirit Airlines Logo
2:25 pm - 10:17 am
EYW
-
SJU
18h 52m
2 stops
Spirit Airlines Logo
2:59 am - 1:30 pm
SJU
-
EYW
11h 31m
2 stops
$538Spirit Airlines
Thu, Feb 12 - Sun, Feb 15
Spirit Airlines Logo
2:25 pm - 11:09 pm
EYW
-
SJU
31h 44m
3 stops
Spirit Airlines Logo
2:59 am - 1:30 pm
SJU
-
EYW
11h 31m
2 stops
$577Spirit Airlines
Sat, May 9 - Wed, May 13
United Airlines Logo
4:47 pm - 1:47 pm
EYW
-
NAS
21h 00m
1 stop
United Airlines Logo
3:59 pm - 3:07 pm
NAS
-
EYW
23h 08m
1 stop
$812United Airlines
Sun, May 31 - Wed, Jun 3
United Airlines Logo
4:05 pm - 1:54 pm
EYW
-
KIN
46h 49m
2 stops
United Airlines Logo
2:59 pm - 3:15 pm
KIN
-
EYW
23h 16m
2 stops
$7,107United 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 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 American Airlines ($493) and Delta ($510).

Find deals

Good to know

Low seasonApril
Cheapest flight$150
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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 11206 reviews
6.9Entertainment
7.2Comfort
8.0Crew
6.4Food
7.5Boarding
Airline reviews

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

10.0 ExcellentCindy, Jan 2026
MIA - BHM
Read more American Airlines reviews

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Key West (EYW)