$700 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 12/24. 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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Cheap Flights from Stillwater to Caribbean

 
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

Wed, Dec 24 - Wed, Jan 7
American Airlines Logo
6:00 am - 12:25 amSWO-SJU
16h 25m2 stops
American Airlines Logo
6:50 pm - 1:43 pmSJU-SWO
20h 53m2 stops
$700American Airlines
Find Deal
Wed, Dec 24 - Wed, Jan 7
American Airlines Logo
6:00 am - 2:48 pmSWO-SJU
6h 48m1 stop
American Airlines Logo
6:50 pm - 1:43 pmSJU-SWO
20h 53m2 stops
$775American Airlines
Find Deal
Tue, Dec 23 - Wed, Jan 7
American Airlines Logo
2:29 pm - 12:25 amSWO-SJU
31h 56m2 stops
American Airlines Logo
6:50 pm - 1:43 pmSJU-SWO
20h 53m2 stops
$827American Airlines
Find Deal
Mon, Dec 22 - Wed, Jan 7
American Airlines Logo
2:29 pm - 11:55 amSWO-SJU
19h 26m2 stops
American Airlines Logo
6:50 pm - 10:05 pmSJU-SWO
29h 15m2 stops
$875American Airlines
Find Deal
Wed, Dec 24 - Tue, Jan 6
American Airlines Logo
6:00 am - 12:25 amSWO-SJU
16h 25m2 stops
American Airlines Logo
6:50 pm - 1:43 pmSJU-SWO
20h 53m2 stops
$895American Airlines
Find Deal
Tue, Dec 23 - Wed, Jan 7
American Airlines Logo
2:29 pm - 5:05 amSWO-SJU
12h 36m1 stop
American Airlines Logo
6:50 pm - 1:43 pmSJU-SWO
20h 53m2 stops
$921American Airlines
Find Deal
Mon, Dec 22 - Wed, Jan 7
American Airlines Logo
2:29 pm - 5:05 amSWO-SJU
12h 36m1 stop
American Airlines Logo
6:50 pm - 1:43 pmSJU-SWO
20h 53m2 stops
$924American Airlines
Find Deal
Sun, Dec 21 - Wed, Jan 7
American Airlines Logo
2:29 pm - 1:35 pmSWO-SJU
21h 06m2 stops
American Airlines Logo
6:50 pm - 10:05 pmSJU-SWO
29h 15m2 stops
$930American Airlines
Find Deal
Wed, Dec 24 - Thu, Jan 1
American Airlines Logo
2:29 pm - 11:55 amSWO-SJU
19h 26m2 stops
American Airlines Logo
6:50 pm - 1:51 pmSJU-SWO
21h 01m2 stops
$950American Airlines
Find Deal
Thu, Dec 18 - Wed, Jan 7
American Airlines Logo
6:00 am - 1:35 pmSWO-SJU
29h 35m2 stops
American Airlines Logo
6:50 pm - 1:43 pmSJU-SWO
20h 53m2 stops
$954American Airlines
Find Deal
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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 13h 33m.


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
7.2Comfort
8.0Crew
7.5Boarding
6.5Food
Airline reviews

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

4.0 OkayX_and.the.city, Jul 2025SDF - DFW
Read more American Airlines reviews

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

Initial flight was cancelled at the time of arrival to the airport, flight alternative requires switching from direct to flight with a layover, and the plane felt like it would split apart, it was so rattle-y.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

Flight was delayed again and again ultimately almost three hours getting us to our location at close to midnight by the time we got in and out of airport to destination. I had taken time off work to enjoy an evening at destination and that was now wasted

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

The flight delay in Dallas created a domino effect that impacted all of the connecting flights. It also increased the number of connections. I missed my flight from Casablanca to Marrakech because of the tight turnaround when landing in Casablanca. . CMN airport was understaffed. Only one person could help while other employees were just watching him. It was an extremely frustrating situation. People were crying and slamming their palms on the counter when speaking to the customer service provider, Allabough (man’s name?). Allabough couldn’t change my flight in the system. simultaneously, I was on the call with America. Airlines customer service rep named Solomon that said he couldn’t change it either. So, I took a ONYA voyages train to from Casablanca to Marrakech to get there on Friday June 26. This was unpredictable trip.

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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