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$575+ 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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
SWO — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Stillwater to Caribbean

Keep the following information in mind while searching for Stillwater to Caribbean flight deals. Data was last updated July 31, 2025.

Round-trip from

$575
(American Airlines)
From Stillwater Searcy Fld to Caribbean
Search Deals

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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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.
Thu 8/142:34 pmSWO - SJU
2 stops8h 25mAmerican Airlines
Mon 8/185:15 pmSJU - SWO
2 stops21h 48mAmerican Airlines
Deal found 7/30$575

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stillwater to Caribbean 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 July 31, 2025.
Use the filters below to find and compare flights from Stillwater to Caribbean that are best for you.

Fly from

Stillwater

Fly to

Caribbean

Route

Depart

Return

Price

StillwaterSan Juan

SWO - SJU

SWOSJU

Stillwater Searcy Fld

Thu 8/14

2:34 pm-11:59 pm

2 stops8h 25m

San Juan Luis Munoz Marin Intl

Mon 8/18

5:15 pm-2:03 pm

2 stops21h 48m

$575

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 31, 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
10,000 reviews

Comfort

7.2

Crew

8.0

Food

6.5

Overall

7.2

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Comfort

7.2

Crew

8.0

Food

6.5

Overall

7.2

Boarding

7.5

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Leonardo,May 2025

JFK - BGI

Good airline and so far i give them 8 out of 10.

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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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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$444Average$796FlexibilityNo cancel feeOn-time71%

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