$595 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 10/10. 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

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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

Fri, Oct 10 - Tue, Oct 14
American Airlines Logo
6:00 am - 9:14 pmSWO-SJU
14h 14m2 stops
American Airlines Logo
7:00 am - 10:43 pmSJU-SWO
16h 43m2 stops
$595American Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
American Airlines Logo
6:00 am - 2:20 pmSWO-SJU
7h 20m1 stop
American Airlines Logo
7:00 am - 10:43 pmSJU-SWO
16h 43m2 stops
$635American Airlines
Find Deal
Fri, Oct 10 - Tue, Oct 14
American Airlines Logo
6:00 am - 2:20 pmSWO-SJU
7h 20m1 stop
American Airlines Logo
3:34 pm - 10:43 pmSJU-SWO
8h 09m1 stop
$680American Airlines
Find Deal
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.

How long does a flight from Stillwater to Caribbean take?

The duration of a flight to Caribbean depends on your arrival airport. The shortest route to Caribbean from Stillwater is to San Juan, which takes 11h 15m.

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 10000 reviews
6.9Entertainment
8.0Crew
7.2Comfort
7.5Boarding
6.5Food
Airline reviews

Boarding: Boarding was a bit of a mess. Our tickets indicated "BC" for Business Class, but we and many others were confused as that was not indicated anywhere in the airport, so we didn't know when we're supposed to board. The airplane: The airplane was nice. However, we sat near the back of the business class cabin and the flight attendants and passengers from other cabins would constantly move the curtain (which was very loud), preventing me from fallling asleep on my 8 hour flight. The flight crew: Amazing, generally. However, they nearly forgot to serve breakfast to me. The flight food: I was able to select my meal for dinner, which was really good. Breakfast was a bit of a mess, however. The crew forgot to serve me breakfast until the last minute. Very little was available by the time they remembered. The entertainment: Paltry, underwhelming, and dated. Not one new movie was available. Bottom line: For the money, you might want to consider other options for your international business class flights.

6.0 GoodRicky, Aug 2025CLT - MAD
Read more American Airlines reviews

Boarding: Boarding was a bit of a mess. Our tickets indicated "BC" for Business Class, but we and many others were confused as that was not indicated anywhere in the airport, so we didn't know when we're supposed to board. The airplane: The airplane was nice. However, we sat near the back of the business class cabin and the flight attendants and passengers from other cabins would constantly move the curtain (which was very loud), preventing me from fallling asleep on my 8 hour flight. The flight crew: Amazing, generally. However, they nearly forgot to serve breakfast to me. The flight food: I was able to select my meal for dinner, which was really good. Breakfast was a bit of a mess, however. The crew forgot to serve me breakfast until the last minute. Very little was available by the time they remembered. The entertainment: Paltry, underwhelming, and dated. Not one new movie was available. Bottom line: For the money, you might want to consider other options for your international business class flights.

We fly American Airlines quite a bit. And we always fly business class when traveling internationally. We were a bit disappointed with the comfort of this particular plane as well as the entertainment options.

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

Did not get the seat I selected and paid for.

We arrived 4 hours early and still almost missed the flight because they weren’t able to access one of the boarding tickets. They then sent hour bags late and we were all of our without clothing and eventually had to take an expensive cab back and forth to the airport as they wouldn’t deliver the bag which arrived late at night that day and we would have to wait until noon the began day (messing up a second day of plans). Also, all the food has dairy or pork. No vegan or even vegetarian option in the flight—even for purchase.

The flight was canceled 3 hours after original take off time

My flight was delayed for several hours. Sitting at gate 16 for several hours, I got a text from Kayak the gate changed to 9 before it was announced. Very bad communication at each gate from American Airlines employees. I received 10 notifications of delay from Kayak. My vacation started off horrible! I will write to American Airlines corporate office also.

The AA staff person who checked our bags was curt and almost rude. The FA also seemed unhappy doing her job. Overall it was like riding the school bus back in grade school.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Ring in first class for an overnight flight, there was no blankets nor pillows for first class customers.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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