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$288+ Cheap flights from Stillwater (SWO) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/1. Fares are subject to change and may not be available on all flights or dates of travel.
SWO — SJU
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Find flight deals from Stillwater to Caribbean

Best flights from Stillwater to Caribbean
Discover carefully curated flight deals from Stillwater to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 20, 2025.

This American Airlines deal was found by Cheapflights users on 11/18. 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.
Sun 4/262:28 pmSWO - SJU
1 stop12h 32mAmerican Airlines
Thu 4/306:59 amSJU - SWO
1 stop7h 50mAmerican Airlines
Deal found 11/18$595

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 November 20, 2025.

Round-trip from

$595
(American Airlines)

One-way from

$288
(American Airlines)
From Stillwater Searcy Fld to Caribbean
Search Deals
One-way flight from Stillwater Searcy Fld to Caribbean
Search Deals

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 November 20, 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

Sun 4/26

2:28 pm-4:00 am

1 stop12h 32m

San Juan Luis Munoz Marin Intl

Thu 4/30

6:59 am-1:49 pm

1 stop7h 50m

$595

StillwaterSan Juan

SWO - SJU

SWOSJU

Stillwater Searcy Fld

Mon 12/1

2:29 pm-10:10 am

2 stops17h 41m

$288

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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, July is the cheapest month in which you can book a flight from Stillwater to Caribbean (average of $157). Flying from Stillwater to Caribbean in June is currently the most expensive (average of $353). 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 November 20, 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
11,047 reviews

Food

6.4

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Overall

7.2

Crew

8.0

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.
American Airlines
7.2
Good
11,047 reviews
American Airlines
7.2
Good
11,047 reviews

Food

6.4

Comfort

7.2

Entertainment

6.9

Boarding

7.5

Overall

7.2

Crew

8.0

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.

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.

  • How long is the flight from Stillwater to Caribbean?

    American Airlines can get you from Stillwater to Caribbean in just under 12h 32m. Your travel time can differ by up to . There are 2250 mi between Stillwater and Caribbean.

  • 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, July is the cheapest month in which you can book a flight from Stillwater to Caribbean (average of $157). Flying from Stillwater to Caribbean in June is currently the most expensive (average of $353). 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$444Average$796FlexibilityNo cancel feeOn-time71%

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