$170 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 4/20. 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$523
Kingston
Kingston1 stop$694
Nassau
Nassau1 stop$523
Kingston
Kingston1 stop$694

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

Tue, Apr 28 - Sat, May 2
Multiple Airlines Logo
1:01 pm - 7:22 pm
EYW
-
SJU
30h 21m
2 stops
Multiple Airlines Logo
4:11 pm - 10:21 am
SJU
-
EYW
18h 10m
1 stop
$338Multiple Airlines
Sun, May 17 - Sun, May 31
Multiple Airlines Logo
1:57 pm - 10:18 am
EYW
-
SJU
20h 21m
1 stop
Multiple Airlines Logo
8:04 pm - 3:46 pm
SJU
-
EYW
19h 42m
2 stops
$366Multiple Airlines
Sun, May 17 - Wed, May 27
Multiple Airlines Logo
1:57 pm - 10:18 am
EYW
-
SJU
20h 21m
1 stop
Multiple Airlines Logo
8:32 am - 1:24 pm
SJU
-
EYW
28h 52m
2 stops
$371Multiple Airlines
Tue, Apr 28 - Sat, May 2
Multiple Airlines Logo
1:01 pm - 9:05 am
EYW
-
SJU
20h 04m
1 stop
Multiple Airlines Logo
4:11 pm - 10:21 am
SJU
-
EYW
18h 10m
1 stop
$411Multiple Airlines
Tue, Jun 2 - Tue, Jun 23
Multiple Airlines Logo
1:14 pm - 4:01 am
EYW
-
SJU
14h 47m
2 stops
Multiple Airlines Logo
5:15 pm - 11:06 am
SJU
-
EYW
17h 51m
1 stop
$413Multiple Airlines
Mon, Jun 15 - Fri, Jun 19
Delta Logo
11:58 am - 10:27 pm
EYW
-
SJU
10h 29m
1 stop
Delta Logo
6:00 am - 5:29 pm
SJU
-
EYW
11h 29m
1 stop
$436Delta
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
1:50 pm - 11:59 pm
EYW
-
SJU
10h 09m
1 stop
American Airlines Logo
6:00 am - 1:05 pm
SJU
-
EYW
7h 05m
1 stop
$441American Airlines
Sat, Aug 1 - Thu, Aug 6
American Airlines Logo
7:55 pm - 9:26 am
EYW
-
NAS
13h 31m
1 stop
American Airlines Logo
7:45 am - 6:39 pm
NAS
-
EYW
10h 54m
1 stop
$536American Airlines
Thu, Aug 13 - Thu, Sep 3
Delta Logo
2:35 pm - 8:04 pm
EYW
-
KIN
6h 29m
1 stop
Delta Logo
9:00 am - 7:45 pm
KIN
-
EYW
9h 45m
1 stop
$694Delta
Thu, May 14 - Thu, May 21
United Airlines Logo
4:05 pm - 1:54 pm
EYW
-
KIN
46h 49m
2 stops
United Airlines Logo
2:59 pm - 3:07 pm
KIN
-
EYW
23h 08m
2 stops
$2,322United 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 Delta ($436) and American Airlines ($441).

Good to know

Cheapest flight$148
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.
7.1
American AirlinesOverall score based on 11581 reviews
6.9Entertainment
6.4Food
7.5Boarding
7.9Crew
7.2Comfort
Airline reviews

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

2.0 MediocreSuzanne, Apr 2026
TPA - MIA
Read more American Airlines reviews

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

I have never been assaulted they way I was today in Charlotte - shame on American

The staff are very, very professional. It's what flying should feel like.

The flight attendant in business class was excellent! Professional, friendly and attentive.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

I would have liked a pillow. The vegetarian wrap and oaten cake was good.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports