$264 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 1/18. 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

Sun, Jan 18 - Thu, Jan 22
American Airlines Logo
2:30 pm - 10:48 amSWO-SJU
18h 18m2 stops
American Airlines Logo
7:12 pm - 2:00 pmSJU-SWO
20h 48m2 stops
$264American Airlines
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Wed, Jan 21 - Thu, Jan 22
American Airlines Logo
2:30 pm - 10:48 amSWO-SJU
18h 18m2 stops
American Airlines Logo
5:51 pm - 2:00 pmSJU-SWO
22h 09m2 stops
$296American Airlines
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Tue, Jan 20 - Thu, Jan 22
American Airlines Logo
6:00 am - 3:05 pmSWO-SJU
7h 05m1 stop
American Airlines Logo
3:59 pm - 10:50 pmSJU-SWO
8h 51m1 stop
$301American Airlines
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Sun, Jan 18 - Wed, Jan 21
American Airlines Logo
2:30 pm - 12:30 pmSWO-SJU
20h 00m2 stops
American Airlines Logo
11:38 am - 10:50 pmSJU-SWO
13h 12m2 stops
$326American Airlines
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Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
2:30 pm - 12:30 pmSWO-SJU
20h 00m2 stops
American Airlines Logo
3:59 pm - 10:50 pmSJU-SWO
8h 51m1 stop
$362American Airlines
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Sun, Jan 18 - Fri, Jan 23
American Airlines Logo
6:00 am - 10:26 pmSWO-SJU
14h 26m1 stop
American Airlines Logo
7:07 am - 2:00 pmSJU-SWO
8h 53m1 stop
$387American Airlines
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Thu, Jan 15 - Thu, Jan 22
American Airlines Logo
6:00 am - 10:26 pmSWO-SJU
14h 26m1 stop
American Airlines Logo
3:59 pm - 10:50 pmSJU-SWO
8h 51m1 stop
$407American Airlines
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Mon, Apr 27 - Wed, Apr 29
American Airlines Logo
6:01 am - 11:00 amSWO-SJU
27h 59m2 stops
American Airlines Logo
6:55 pm - 10:05 pmSJU-SWO
28h 10m2 stops
$448American Airlines
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Sun, Jan 18 - Sat, Jan 24
American Airlines Logo
6:00 am - 11:59 pmSWO-SJU
15h 59m2 stops
American Airlines Logo
6:00 am - 10:50 pmSJU-SWO
18h 50m2 stops
$473American Airlines
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Fri, Jan 16 - Tue, Jan 20
American Airlines Logo
6:00 am - 10:48 amSWO-SJU
26h 48m2 stops
American Airlines Logo
3:59 pm - 10:50 pmSJU-SWO
8h 51m1 stop
$493American Airlines
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Booking Insights

KAYAK's insights & trends for Stillwater to Caribbean flights

Get data-powered insights and trends into flights from Stillwater to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between Stillwater and Caribbean?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Stillwater to Caribbean.

There is just one airline that flies from Stillwater to Caribbean direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is to San Juan Luis Munoz Marin Intl Airport (SJU) and costs $444.

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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.
7.2
American AirlinesOverall score based on 11042 reviews
6.4Food
6.9Entertainment
7.2Comfort
8.0Crew
7.5Boarding
Airline reviews

We loved the steward on the plane. He made the night enjoyable

10.0 Excellentchloe, Nov 2025ORD - ATW
Read more American Airlines reviews

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Stillwater (SWO)