$380 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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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

Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:08 pm - 4:32 am
SWO
-
SJU
12h 24m
1 stop
American Airlines Logo
7:00 pm - 2:38 pm
SJU
-
SWO
20h 38m
2 stops
$380American Airlines
Fri, Apr 17 - Tue, Apr 21
American Airlines Logo
3:08 pm - 4:32 am
SWO
-
SJU
12h 24m
1 stop
American Airlines Logo
6:45 am - 2:38 pm
SJU
-
SWO
8h 53m
1 stop
$490American Airlines
Mon, Mar 30 - Tue, Apr 7
American Airlines Logo
2:26 pm - 10:31 pm
SWO
-
SJU
7h 05m
1 stop
American Airlines Logo
3:34 pm - 10:53 pm
SJU
-
SWO
8h 19m
1 stop
$532American Airlines
Tue, Jun 23 - Fri, Jun 26
American Airlines Logo
3:39 pm - 9:39 am
SWO
-
SJU
17h 00m
2 stops
American Airlines Logo
12:40 am - 3:09 pm
SJU
-
SWO
15h 29m
1 stop
$573American Airlines
Tue, Jun 23 - Fri, Jun 26
American Airlines Logo
3:39 pm - 4:35 am
SWO
-
SJU
11h 56m
1 stop
American Airlines Logo
12:40 am - 3:09 pm
SJU
-
SWO
15h 29m
1 stop
$615American Airlines
Tue, Jun 23 - Fri, Jun 26
American Airlines Logo
6:05 am - 11:35 pm
SWO
-
SJU
16h 30m
1 stop
American Airlines Logo
12:40 am - 3:09 pm
SJU
-
SWO
15h 29m
1 stop
$656American Airlines
Tue, Jun 23 - Sat, Jun 27
American Airlines Logo
3:39 pm - 9:39 am
SWO
-
SJU
17h 00m
2 stops
American Airlines Logo
6:00 am - 10:48 pm
SJU
-
SWO
17h 48m
2 stops
$708American Airlines
Tue, Jun 23 - Sat, Jun 27
American Airlines Logo
3:39 pm - 11:03 am
SWO
-
SJU
18h 24m
2 stops
American Airlines Logo
6:00 am - 10:48 pm
SJU
-
SWO
17h 48m
2 stops
$750American 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.
7.1
American AirlinesOverall score based on 11375 reviews
6.4Food
8.0Crew
7.5Boarding
6.9Entertainment
7.2Comfort
Airline reviews

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

8.0 ExcellentCatherine, Mar 2026
STL - LGA
Read more American Airlines reviews

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

The worst Airline ever. They centered my second flight and leave me in NY. They don’t have any representatives at the airport and they don’t respond to calls. Basically I got stuck. I will never purchase through there again.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports