$167 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 3/6. 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$458
Kingston
Kingston2 stops$2,081
Nassau
Nassau1 stop$458
Kingston
Kingston2 stops$2,081

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

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 - 10:58 am
SJU
-
EYW
4h 58m1 stop
$365American Airlines
Wed, Jan 21 - Sun, Jan 25
Multiple Airlines Logo
10:49 am - 7:26 pm
EYW
-
SJU
31h 37m2 stops
Multiple Airlines Logo
8:05 pm - 12:26 pm
SJU
-
EYW
17h 21m1 stop
$391Multiple Airlines
Wed, Jan 21 - Sun, Jan 25
American Airlines Logo
6:06 am - 5:01 pm
EYW
-
SJU
9h 55m1 stop
American Airlines Logo
6:00 am - 4:49 pm
SJU
-
EYW
11h 49m1 stop
$405American Airlines
Tue, Jan 13 - Tue, Jan 27
American Airlines Logo
6:06 am - 12:27 pm
EYW
-
SJU
5h 21m1 stop
American Airlines Logo
1:58 pm - 9:47 pm
SJU
-
EYW
8h 49m1 stop
$425American Airlines
Mon, Dec 29 - Sat, Jan 3
Multiple Airlines Logo
1:10 pm - 6:34 am
EYW
-
SJU
16h 24m2 stops
Multiple Airlines Logo
9:58 pm - 8:15 am
SJU
-
EYW
11h 17m1 stop
$453Multiple Airlines
Sun, Feb 1 - Sun, Feb 8
Multiple Airlines Logo
12:51 pm - 7:15 pm
EYW
-
NAS
6h 24m1 stop
Multiple Airlines Logo
7:15 am - 11:56 am
NAS
-
EYW
4h 41m1 stop
$458Multiple Airlines
Thu, Jan 1 - Mon, Jan 5
Spirit Airlines Logo
12:20 pm - 10:05 pm
EYW
-
SJU
8h 45m1 stop
Spirit Airlines Logo
4:55 pm - 11:20 am
SJU
-
EYW
19h 25m3 stops
$563Spirit Airlines
Thu, Jan 1 - Mon, Jan 5
Spirit Airlines Logo
12:20 pm - 2:12 am
EYW
-
SJU
12h 52m2 stops
Spirit Airlines Logo
4:55 pm - 11:20 am
SJU
-
EYW
19h 25m3 stops
$598Spirit Airlines
Mon, Jan 26 - Fri, Jan 30
United Airlines Logo
4:15 pm - 4:15 pm
EYW
-
EIS
47h 00m2 stops
United Airlines Logo
3:00 pm - 3:17 pm
EIS
-
EYW
49h 17m2 stops
$1,729United Airlines
Mon, Jan 26 - Fri, Jan 30
United Airlines Logo
4:15 pm - 4:15 pm
EYW
-
EIS
47h 00m2 stops
United Airlines Logo
8:15 am - 11:26 am
EIS
-
EYW
28h 11m2 stops
$1,865United 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 American Airlines ($365) and United Airlines ($1,729).

Good to know

Cheapest flight$167
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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $404 on average. Morning departures are around 10% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $448.

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 11055 reviews
8.0Crew
6.5Food
7.5Boarding
7.2Comfort
6.9Entertainment
Airline reviews

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. :)

8.0 ExcellentAustin, Dec 2025
ECP - CLT
Read more American Airlines reviews

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

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports