$244 Find Cheap Flights from Stillwater 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 Stillwater to Caribbean departing on 5/11. 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 - 9:11 am
SWO
-
SJU
17h 03m
2 stops
American Airlines Logo
7:00 pm - 2:38 pm
SJU
-
SWO
20h 38m
2 stops
$310American 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
7:00 pm - 2:38 pm
SJU
-
SWO
20h 38m
2 stops
$361American 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
6:45 am - 10:53 pm
SJU
-
SWO
17h 08m
1 stop
$370American 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
7:00 pm - 2:38 pm
SJU
-
SWO
20h 38m
2 stops
$381American Airlines
Fri, Apr 17 - Mon, Apr 20
American Airlines Logo
3:08 pm - 9:11 am
SWO
-
SJU
17h 03m
2 stops
American Airlines Logo
3:34 pm - 10:53 pm
SJU
-
SWO
8h 19m
1 stop
$404American 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
6:45 am - 2:38 pm
SJU
-
SWO
8h 53m
1 stop
$410American 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 - 10:53 pm
SJU
-
SWO
17h 08m
1 stop
$488American 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 - 10:53 pm
SJU
-
SWO
17h 08m
1 stop
$490American 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
$510American Airlines
Mon, Mar 30 - Tue, Apr 7
American Airlines Logo
2:26 pm - 10:31 pm
SWO
-
SJU
7h 05m
1 stop
American Airlines Logo
6:45 am - 2:38 pm
SJU
-
SWO
8h 53m
1 stop
$533American 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.
7.1
American AirlinesOverall score based on 11464 reviews
7.5Boarding
7.9Crew
6.9Entertainment
7.2Comfort
6.4Food
Airline reviews

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

4.0 OkaySteven, Mar 2026
JFK - HND
Read more American Airlines reviews

Aging planer and NO wifi on a 14 hour day flight. Unless you are retired or don't need to work or be in touch with the world... The lack of Wifif really ruined the flight. And the old plane - really showing it's age, wasn't great

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Our flight was delayed 3 times and this is why I am giving such low reviews. Everything else was okay but being in the airport at 4:30pm for my initial flight at 7pm to not leave until after 9:30pm is insane,

Flights were constantly delayed. CRW took 50 minutes to get bags

Flight has been delayed every time I've ever taken it. Seats uncomfortable. Children behind me yelling the entire flight. Some of this is out of their control but overall just consistently not a great experience.

Appreciate having multiple food options for allergies. Nice to have an extra seat between us for comfort.

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Where do I start!! I was delayed with my flight from Dallas to Tampa. On the way back from Tampa to Dallas the flight was delayed over 4 hours+. I was put on another flight that was also delayed but not as long. Traveling on American Airlines is becoming exhausing.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The gate got changed several times and the flight was delayed over an hour. Awful experience

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Stillwater (SWO)