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Caribbean

$620+ Cheap flights from Stillwater (SWO) to Caribbean

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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWO — SJU
oct. 31 — nov. 71
vie. 10/31
vie. 11/7
1 adult, Economy
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Find flight deals from Stillwater to Caribbean

Cheapest flights from Stillwater to Caribbean
Explore the most affordable flight options available from Stillwater to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 1, 2025.

This American Airlines deal was found by Cheapflights users on 9/29. 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.
vie. 10/36:00 amSWO - SJU
2 stops11h 15mAmerican Airlines
lun. 10/65:00 pmSJU - SWO
2 stops22h 02mAmerican Airlines
Deal found 9/29$620

Best time to book a flight from Stillwater to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, September is the cheapest month in which you can book a flight from Stillwater to Caribbean (average of $254). Flying from Stillwater to Caribbean in June is currently the most expensive (average of $339). 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.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated octubre 1, 2025.
Read through reviews of airlines operating flights from Stillwater to Caribbean, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,030 reviews

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,030 reviews
American Airlines
7.2
Good
11,030 reviews

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

Food

6.4

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Stillwater to Caribbean. 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?

    If you book a flight to Caribbean 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.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Stillwater to Caribbean 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?

    Currently, September is the cheapest month in which you can book a flight from Stillwater to Caribbean (average of $254). Flying from Stillwater to Caribbean in June is currently the most expensive (average of $339). 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

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Top airline flying from Stillwater to Caribbean

Discover the top airline that operate flights from Stillwater to Caribbean. 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 octubre 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$444Average$796FlexibilityNo cancel feeOn-time71%

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