$378 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 4/17. 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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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, Apr 17 - Tue, Apr 21
American Airlines Logo
3:02 pm - 4:32 am
SWO
-
SJU
12h 30m
1 stop
American Airlines Logo
5:45 am - 10:53 pm
SJU
-
SWO
18h 08m
2 stops
$378American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:02 pm - 9:11 am
SWO
-
SJU
17h 09m
2 stops
American Airlines Logo
6:56 pm - 2:32 pm
SJU
-
SWO
20h 36m
2 stops
$380American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:02 pm - 9:11 am
SWO
-
SJU
17h 09m
2 stops
American Airlines Logo
5:45 am - 10:53 pm
SJU
-
SWO
18h 08m
2 stops
$383American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:02 pm - 4:32 am
SWO
-
SJU
12h 30m
1 stop
American Airlines Logo
6:47 am - 10:53 pm
SJU
-
SWO
17h 06m
1 stop
$496American Airlines
Thu, Jun 11 - Thu, Jun 11
American Airlines Logo
6:05 am - 9:21 pm
SWO
-
SJU
14h 16m
2 stops
American Airlines Logo
12:39 am - 3:22 pm
SJU
-
SWO
15h 43m
1 stop
$691American Airlines
Thu, Jun 11 - Fri, Jun 12
American Airlines Logo
6:05 am - 11:16 pm
SWO
-
SJU
16h 11m
1 stop
American Airlines Logo
5:37 am - 3:22 pm
SJU
-
SWO
10h 45m
1 stop
$693American Airlines
Thu, Jun 11 - Fri, Jun 12
American Airlines Logo
3:52 pm - 9:33 am
SWO
-
SJU
16h 41m
2 stops
American Airlines Logo
7:09 pm - 3:22 pm
SJU
-
SWO
21h 13m
2 stops
$1,048American Airlines
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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 11174 reviews
6.9Entertainment
7.5Boarding
7.2Comfort
6.4Food
8.0Crew
Airline reviews

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

6.0 GoodMatthew, Jan 2026
CLT - CVG
Read more American Airlines reviews

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

Enough space,crew was helpful,food was good.The gates are way far especially for travelers with health issues

No enough space plus only allowing one laggage instead of two like other airlines.

There were no TV screens - even in Business class. 5 delays, and only given $12 meal voucher! Terrible!

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

It was a good trip. Flight Attendants were friendly and responsive.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Stillwater (SWO)