HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$362+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
SWO — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Stillwater to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Stillwater to Caribbean Islands

Best flights from Stillwater to Caribbean Islands
Discover carefully curated flight deals from Stillwater to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/10. 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.
Mon 2/26:00 amSWO - SJU
1 stop14h 26mAmerican Airlines
Mon 2/95:51 pmSJU - SWO
2 stops22h 09mAmerican Airlines
Deal found 12/10$362
This American Airlines deal was found by Cheapflights users on 12/9. 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.
Sat 4/182:28 pmSWO - SJU
1 stop12h 32mAmerican Airlines
Wed 4/226:59 amSJU - SWO
1 stop7h 50mAmerican Airlines
Deal found 12/9$485
This American Airlines deal was found by Cheapflights users on 12/10. 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 4/172:28 pmSWO - SJU
1 stop12h 32mAmerican Airlines
Tue 4/216:59 amSJU - SWO
1 stop16h 06mAmerican Airlines
Deal found 12/10$530

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 December 12, 2025.

Round-trip from

$362
(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 December 12, 2025.
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

Mon 2/2

6:00 am-10:26 pm

1 stop14h 26m

San Juan Luis Munoz Marin Intl

Mon 2/9

5:51 pm-2:00 pm

2 stops22h 09m

$362

StillwaterSan Juan

SWO - SJU

SWOSJU

Stillwater Searcy Fld

Sat 4/18

2:28 pm-4:00 am

1 stop12h 32m

San Juan Luis Munoz Marin Intl

Wed 4/22

6:59 am-1:49 pm

1 stop7h 50m

$485

StillwaterSan Juan

SWO - SJU

SWOSJU

Stillwater Searcy Fld

Fri 4/17

2:28 pm-4:00 am

1 stop12h 32m

San Juan Luis Munoz Marin Intl

Tue 4/21

6:59 am-10:05 pm

1 stop16h 06m

$530

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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 June is currently the most expensive (average of $346). 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 14h 26m. 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 June is currently the most expensive (average of $346). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Stillwater to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to John F Kennedy Intl flights
Dallas/Fort Worth to Las Vegas flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to Newark flights
Dallas/Fort Worth to Orlando flights
Dallas/Fort Worth to Los Angeles flights
Dallas/Fort Worth to Seattle flights
Dallas/Fort Worth to Denver flights
Dallas/Fort Worth to Cancún flights
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to Miami flights
Dallas/Fort Worth to San Francisco flights
Dallas/Fort Worth to Fort Lauderdale flights
Dallas/Fort Worth to Mexico City flights
Dallas/Fort Worth to Ontario flights
Dallas/Fort Worth to Dulles Intl flights
Dallas/Fort Worth to Baltimore flights
Dallas/Fort Worth to Midway flights
Dallas/Fort Worth to Sky Harbor Intl flights
Dallas/Fort Worth to Santa Ana flights
Dallas/Fort Worth to Atlanta flights
Dallas/Fort Worth to San Diego flights
Dallas/Fort Worth to Boston flights
Dallas/Fort Worth to Cozumel flights
Dallas/Fort Worth to Philadelphia flights
Dallas/Fort Worth to Salt Lake City flights
Dallas/Fort Worth to Detroit flights
Dallas/Fort Worth to Minneapolis flights
Dallas/Fort Worth to Honolulu flights
Dallas/Fort Worth to Hobby flights
Dallas/Fort Worth to George Bush Intcntl flights
Dallas/Fort Worth to Reagan-National flights
Dallas/Fort Worth to Tampa flights
Dallas/Fort Worth to New Orleans flights
Dallas/Fort Worth to Mexico City flights
Dallas/Fort Worth to West Palm Beach flights
Dallas/Fort Worth to Burbank flights
Dallas/Fort Worth to Nashville flights
Dallas/Fort Worth to San José del Cabo flights
Dallas/Fort Worth to Raleigh flights
Dallas/Fort Worth to Charlotte flights
Dallas/Fort Worth to Vancouver Intl flights
Dallas/Fort Worth to St. Louis flights
Dallas/Fort Worth to Jacksonville flights
Dallas/Fort Worth to San Jose flights
Oklahoma City to Denver flights
Oklahoma City to Las Vegas flights
Oklahoma City to LaGuardia flights
Dallas/Fort Worth to Portland flights
Dallas/Fort Worth to Kansas City flights

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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$444Average$796FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.