$270 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 - 11:02 pm
SWO
-
SJU
6h 54m
1 stop
American Airlines Logo
5:45 am - 10:53 pm
SJU
-
SWO
18h 08m
2 stops
$270American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:08 pm - 9:11 am
SWO
-
SJU
17h 03m
2 stops
American Airlines Logo
5:45 am - 10:53 pm
SJU
-
SWO
18h 08m
2 stops
$380American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:08 pm - 10:53 am
SWO
-
SJU
18h 45m
2 stops
American Airlines Logo
10:03 am - 10:53 pm
SJU
-
SWO
13h 50m
2 stops
$388American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:08 pm - 4:32 am
SWO
-
SJU
12h 24m
1 stop
American Airlines Logo
6:45 am - 10:53 pm
SJU
-
SWO
17h 08m
1 stop
$490American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:08 pm - 4:32 am
SWO
-
SJU
12h 24m
1 stop
American Airlines Logo
6:45 am - 2:38 pm
SJU
-
SWO
8h 53m
1 stop
$506American Airlines
Thu, Feb 26 - Mon, Mar 2
American Airlines Logo
2:25 pm - 10:00 am
SWO
-
SJU
17h 35m
2 stops
American Airlines Logo
7:01 pm - 1:36 pm
SJU
-
SWO
20h 35m
2 stops
$516American Airlines
Tue, Jun 23 - Fri, Jun 26
American Airlines Logo
3:39 pm - 4:35 am
SWO
-
SJU
11h 56m
1 stop
American Airlines Logo
12:40 am - 3:09 pm
SJU
-
SWO
15h 29m
1 stop
$573American Airlines
Thu, Mar 5 - Sat, Mar 7
American Airlines Logo
2:25 pm - 11:56 am
SWO
-
SJU
19h 31m
2 stops
American Airlines Logo
1:30 am - 12:56 pm
SJU
-
SWO
13h 26m
1 stop
$574American Airlines
Thu, Mar 5 - Sat, Mar 7
American Airlines Logo
2:25 pm - 11:56 am
SWO
-
SJU
19h 31m
2 stops
American Airlines Logo
1:30 am - 12:56 pm
SJU
-
SWO
13h 26m
1 stop
$575American Airlines
Thu, Mar 5 - Sat, Mar 7
American Airlines Logo
6:00 am - 3:11 pm
SWO
-
SJU
7h 11m
1 stop
American Airlines Logo
1:30 am - 12:56 pm
SJU
-
SWO
13h 26m
1 stop
$586American Airlines
Useful Info

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.
7.2
American AirlinesOverall score based on 11275 reviews
8.0Crew
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
Airline reviews

The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.

8.0 ExcellentGail, Feb 2026
ATL - DCA
Read more American Airlines reviews

The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.

One day, I do so hope for a gluten free snack! Seems like with the rest of the world FINALLY figuring out what gluten free is, American Airlines would too. Fingers crossed!!

The flight was significantly delayed for 6.5 hours because of snow. There was no communication once the plane returned to the gate regarding when the flight would resume. Other flights were departing while our flight was being unloaded for reasons unknown. Our flight also seemed out of the queue regarding further deicing, refueling, and waiting to Taxi to the runway.

Flight was on time and the meal and service were good.

The accessible bathroom should be visible to people in Economy class.

Flight was delayed for 2 hours, then last minute the change to on time. The satélite location is far and a nightmare to get to.

This was a horrible experience. I’ve experienced several delays at this point and still not home. I was supposed to be home by 8:30 last night and here I sit at 7 am on a plane STILL unable to go home because of American Airlines.

Lexus in first class was absolutely amazing! Beat flight attendant i’ve ever seen.

Generally good. Flight left on time and the seats are comfortable. Plenty of space in front if you in you choose a comfort plus seat, completely worth spending the extra money given the amount of hours the flight lasts. The food tastes good but I would say it’s a the amount is too little. The crew was friendly and efficient. There was a some turbulence at different points into the flight. American Airlines has good deals to NZ if you book with plenty of time before you plan on going.

the plane was so hot!! the air-conditioning was barely blowing. The flight was delayed, and we had to sit on the hot plane before take off for an extended amount of time, waiting on international passengers. Would not have been so bad if it was not so hot. They said it would get better after take off, but it did not.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Stillwater (SWO)