$264 Find Cheap Flights from Stillwater to Caribbean

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Stillwater to Caribbean departing on 1/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Book Cheap Stillwater to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Stillwater to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Stillwater to Caribbean

Sun, Jan 18 - Wed, Jan 21
American Airlines Logo
2:30 pm - 10:48 am
SWO
-
SJU
18h 18m2 stops
American Airlines Logo
6:00 am - 10:50 pm
SJU
-
SWO
18h 50m2 stops
$264American Airlines
Sun, Feb 15 - Thu, Feb 19
American Airlines Logo
2:26 pm - 10:07 am
SWO
-
SJU
17h 41m2 stops
American Airlines Logo
7:00 am - 10:56 pm
SJU
-
SWO
17h 56m2 stops
$301American Airlines
Sun, Jan 18 - Wed, Jan 21
American Airlines Logo
6:00 am - 10:26 pm
SWO
-
SJU
14h 26m1 stop
American Airlines Logo
3:54 pm - 10:50 pm
SJU
-
SWO
8h 56m1 stop
$387American Airlines
Sun, Feb 15 - Thu, Feb 19
American Airlines Logo
2:26 pm - 11:32 pm
SWO
-
SJU
7h 06m1 stop
American Airlines Logo
4:03 pm - 10:56 pm
SJU
-
SWO
8h 53m1 stop
$448American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
2:28 pm - 4:00 am
SWO
-
SJU
12h 32m1 stop
American Airlines Logo
3:20 pm - 10:05 pm
SJU
-
SWO
7h 45m1 stop
$530American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
2:28 pm - 11:00 am
SWO
-
SJU
19h 32m2 stops
American Airlines Logo
3:50 pm - 1:49 pm
SJU
-
SWO
22h 59m2 stops
$610American Airlines
Booking Insights

KAYAK's insights & trends for Stillwater to Caribbean flights

Get data-powered insights and trends into flights from Stillwater to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines fly non-stop between Stillwater and Caribbean?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Stillwater to Caribbean.

There is just one airline that flies from Stillwater to Caribbean direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is to San Juan Luis Munoz Marin Intl Airport (SJU) and costs $444.

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FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Stillwater to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Stillwater to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Stillwater to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Stillwater to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Stillwater to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Stillwater to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Stillwater to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Stillwater to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Stillwater to Caribbean

 
Need help choosing which airline to fly with from Stillwater to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 11047 reviews
8.0Crew
6.5Food
6.9Entertainment
7.5Boarding
7.2Comfort
Airline reviews

It was fine. No drinks nor snacks offered though. I thought that was unusual.

10.0 ExcellentJolene, Dec 2025
DFW - GNV
Read more American Airlines reviews

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

Liked that it was on time. Staff professional and friendly.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

My flight was delayed about three hours. I got home at 3:30 in the morning very bad experience.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Stillwater (SWO)