$443 Find Cheap Flights from Stillwater to Caribbean

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Stillwater to Caribbean departing on 4/17. 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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Flight Deals

Book Cheap Stillwater 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 Stillwater 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 Stillwater to Caribbean

Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:08 pm - 4:32 am
SWO
-
SJU
12h 24m
1 stop
American Airlines Logo
7:00 pm - 2:38 pm
SJU
-
SWO
20h 38m
2 stops
$443American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
6:00 am - 11:02 pm
SWO
-
SJU
16h 02m
1 stop
American Airlines Logo
3:34 pm - 10:53 pm
SJU
-
SWO
8h 19m
1 stop
$523American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:08 pm - 11:02 pm
SWO
-
SJU
6h 54m
1 stop
American Airlines Logo
6:45 am - 2:38 pm
SJU
-
SWO
8h 53m
1 stop
$556American Airlines
Tue, Jun 23 - Sat, Jun 27
American Airlines Logo
3:35 pm - 11:03 am
SWO
-
SJU
18h 28m
2 stops
American Airlines Logo
7:15 pm - 3:05 pm
SJU
-
SWO
20h 50m
2 stops
$616American Airlines
Tue, Jun 23 - Fri, Jun 26
American Airlines Logo
3:35 pm - 11:39 pm
SWO
-
SJU
7h 04m
1 stop
American Airlines Logo
12:44 am - 3:05 pm
SJU
-
SWO
15h 21m
1 stop
$656American Airlines
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FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Stillwater 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 Stillwater to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Stillwater 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 Stillwater 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 Stillwater 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 Stillwater 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 Stillwater 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 Stillwater to Caribbean

 
Need help choosing which airline to fly with from Stillwater 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 11552 reviews
7.5Boarding
7.9Crew
6.9Entertainment
7.2Comfort
6.4Food
Airline reviews

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

2.0 MediocreSerena, Apr 2026
DCA - TPA
Read more American Airlines reviews

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

I cancelled my ticket less than 24 hours deadline but I didn’t get refunded.

Early morning flight and no food in First Class except a "salmon" box. No thank you. Was informed before take off by Captain that the plane was not serviced before we boarded in Phoenix. How does that happen? Need more frequent additions/turn over on the Entertainment. Thanks

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

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

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Better snacks but flight and crew were amazing on this flight

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

It was the most un-special flight experience in my life.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports