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Caribbean Islands

$378+ Cheap flights from Stillwater (SWO) to Caribbean Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWO — SJU
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap flight deals from Stillwater to Caribbean Islands

Cheapest flights from Stillwater to Caribbean Islands
Explore the most affordable flight options available from Stillwater to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.

This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/173:08 pm
SWO
-
SJU
1 stop12h 24m
American Airlines
Tue 4/217:00 pm
SJU
-
SWO
2 stops20h 38m
American Airlines
Deal found 2/3$378

Find flight deals from Stillwater to Caribbean Islands

Keep the following information in mind while searching for Stillwater to Caribbean Islands flight deals. Data was last updated February 4, 2026.

Round-trip from

$378
(American Airlines)
From Stillwater Searcy Fld to Caribbean Islands
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stillwater to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Stillwater to Caribbean Islands that are best for you.

Fly from

Stillwater

Fly to

Caribbean Islands

Route

Depart

Return

Price

StillwaterSan Juan

SWO - SJU

SWOSJU

Stillwater Searcy Fld

Fri 4/17

3:08 pm-10:53 am

2 stops18h 45m

San Juan Luis Munoz Marin Intl

Tue 4/21

7:00 pm-2:38 pm

2 stops20h 38m

$378

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Best time to book a flight from Stillwater to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Stillwater with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Stillwater to Caribbean Islands

What is the cheapest month to book a flight from Stillwater to Caribbean Islands?

Currently, July is the cheapest month in which you can book a flight from Stillwater to Caribbean Islands (average of $156). Flying from Stillwater to Caribbean Islands in January is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Stillwater to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Stillwater to Caribbean Islands?

    If you book a flight to Caribbean Islands from Stillwater, you will be flying from Searcy Fld, which is the city’s only airport. Stillwater Searcy Fld (SWO) is located 3.5 mi from the center of Stillwater.

  • How long is the flight from Stillwater to Caribbean Islands?

    Departing from Stillwater to Caribbean Islands will take you 18h 45m. The distance from Stillwater to Caribbean Islands is about 2250 mi.

  • Can I find deals for flights from Stillwater to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Stillwater to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stillwater to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stillwater to Caribbean Islands.

  • Can I find deals for business class flights from Stillwater to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Stillwater to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Stillwater to Caribbean Islands?

    Currently, July is the cheapest month in which you can book a flight from Stillwater to Caribbean Islands (average of $156). Flying from Stillwater to Caribbean Islands in January is currently the most expensive (average of $336). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Stillwater to Caribbean Islands

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Top airline flying from Stillwater to Caribbean Islands

Discover the top airline that operate flights from Stillwater to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$444Average$796FlexibilityNo cancel feeOn-time71%

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