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Find cheap flights from Key West to Caribbean Islands from $185

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 Islands departing on 7/26. 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
0 bags
Thu 6/6
Thu 6/13

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Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Nassau
Nassau1 stop$458
Kingston
Kingston1 stop$638

Good to know

Cheapest flight

$185
Flight from Key West to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands from Key West 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 Islands?

    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 to Caribbean Islands with an airline and back to Key West 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 Islands?

    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 to Caribbean Islands from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Key West to Caribbean Islands

 
Need help choosing which airline to fly with from Key West to Caribbean Islands? 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.
7.3
American AirlinesOverall score based on 14686 reviews
7.1Entertainment
6.6Food
8.0Crew
7.6Boarding
7.2Comfort
Airline reviews

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

2.0 MediocreRoberto, May 2024MIA - DFW
Read more about American Airlines reviews

They gave my seat away although it was a connecting flight with them and the flight was a bit delayed.

The Flight attendant had an attitude and didn't allow anyone any time to prepare for landing despite being absent throughout the entire trip

Ac was broken so we deplaned, waited 2 hours, taxiing for takeoff they said the plane would not fly so we went back to the gate and got a new plane which took another hour. In all a 4 hour delay for an 80 min flight.

Horrible people at the gate, they force me to check in my carry on, even thought no one behind me has to do it. I had to get out of the airport in NY to get my bag and go thru security again on my way to Honk Kong. The worst part is the employee threatened me with loosing the flights if don’t comply.

Delayed flight, few announcements with information, no comps, cluster f boarding because zones weren’t spread out and announced loud and repeatedly, staff did their job -nothing more nothing less, annoying kids were speaking and kicking the heck out of the back of my seat and parents weren’t willing to parent… so another typical day of air travel in the US.,

Flight was delayed until Next day as crew timed out

The flight was great until towards the end when the flight attendant read an excessively long commercial for purchasing an american airlines credit card. The worst part is that we are doing a lot of traveling this year so i was actually interested in getting the credit card, but I was so annoyed with the long commercial that I completely dismissed the flight attendant bringing around the information. Next time, keep the sales pitch to 10 seconds and then pass around the brochures!!

I was able to get on standby with relative ease

Terrible, oxygen masks were deployed mid-flight. We returned to airport. Took additional 12 hours to get home.

6 plus hour delay with no explanation. No wheelchairs to transport us on arrival. Very disappointed.

Book cheap flights from Key West to Caribbean Islands

Recent round-trip flight deals

6/3Mon
2 stopsAmerican Airlines
17h 56mEYW-SJU
6/11Tue
2 stopsAmerican Airlines
20h 07mSJU-EYW
$306
6/3Mon
2 stopsAmerican Airlines
16h 55mEYW-SJU
6/11Tue
1 stopAmerican Airlines
27h 00mSJU-EYW
$364
6/3Mon
1 stopAmerican Airlines
21h 09mEYW-SJU
6/11Tue
1 stopAmerican Airlines
25h 17mSJU-EYW
$422
7/8Mon
1 stopAmerican Airlines
5h 21mEYW-SJU
7/14Sun
1 stopAmerican Airlines
15h 20mSJU-EYW
$425
11/1Fri
1 stopDelta
21h 48mEYW-NAS
11/5Tue
1 stopDelta
5h 06mNAS-EYW
$458
11/1Fri
2 stopsSilver Airways
14h 40mEYW-NAS
11/5Tue
2 stopsSilver Airways
22h 50mNAS-EYW
$474
11/1Fri
1 stopSilver Airways
22h 50mEYW-NAS
11/5Tue
2 stopsSilver Airways
22h 50mNAS-EYW
$476
5/18Sat
1 stopDelta
13h 51mEYW-KIN
5/22Wed
1 stopDelta
9h 40mKIN-EYW
$638
6/3Mon
2 stopsUnited Airlines
12h 12mEYW-SJU
6/10Mon
2 stopsUnited Airlines
13h 30mSJU-EYW
$722
6/3Mon
1 stopUnited Airlines
8h 37mEYW-SJU
6/10Mon
2 stopsUnited Airlines
13h 30mSJU-EYW
$778

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Recent one-way flight deals

7/26Fri
1 stopAmerican Airlines
9h 50mEYW-SJU
$185
5/18Sat
2 stopsSilver Airways
48h 05mEYW-NAS
$254
7/26Fri
2 stopsAmerican Airlines
20h 16mEYW-SJU
$359

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Last minute flights from Key West to Caribbean Islands

Last minute flight, train and bus deals

5/9Thu
multi-stopJetBlue
7h 25mEYW-SJU
5/11Sat
multi-stopJetBlue
7h 45mSJU-EYW
$653
5/10Fri
multi-stopJetBlue
7h 25mEYW-SJU
5/11Sat
multi-stopJetBlue
7h 45mSJU-EYW
$681
5/9Thu
multi-stopAmerican Airlines
8h 33mEYW-SJU
5/11Sat
multi-stopAmerican Airlines
10h 55mSJU-EYW
$701
5/9Thu
multi-stopAmerican Airlines
5h 00mEYW-SJU
5/10Fri
multi-stopAmerican Airlines
11h 24mSJU-EYW
$704
5/10Fri
multi-stopUnited Airlines
10h 06mEYW-SJU
5/11Sat
multi-stopUnited Airlines
25h 16mSJU-EYW
$722
5/10Fri
multi-stopUnited Airlines
10h 06mEYW-SJU
5/11Sat
multi-stopUnited Airlines
25h 16mSJU-EYW
$751
5/9Thu
multi-stopUnited Airlines
24h 37mEYW-SJU
5/10Fri
multi-stopUnited Airlines
32h 50mSJU-EYW
$773
5/10Fri
multi-stopAmerican Airlines
8h 33mEYW-SJU
5/10Fri
multi-stopAmerican Airlines
11h 24mSJU-EYW
$787
5/9Thu
multi-stop
33h 50mEYW-SJU
5/11Sat
multi-stop
19h 44mSJU-EYW
$793
5/9Thu
multi-stop
33h 50mEYW-SJU
5/11Sat
multi-stop
25h 27mSJU-EYW
$914

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Key West - Caribbean Islands Flights

Departure:

Key West (EYW)United States

Return flight deals:

Caribbean Islands - Key West

Cabin classes:

$522
$749
$664
$47