$125 Find Cheap Flights from Gulfport to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Gulfport to Caribbean Islands departing on 8/21. 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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Cheap Flights from Gulfport to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stops$712
Montego Bay
Montego Bay2 stops$646
Bridgetown
Bridgetown1 stop$702
Punta Cana
Punta Cana2 stops$712
Montego Bay
Montego Bay2 stops$646
Bridgetown
Bridgetown1 stop$702
Booking Insights

KAYAK's insights & trends for Gulfport to Caribbean Islands flights

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

Can I save money by flying with a layover from Gulfport to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $344, prices are generally cheapest when you fly direct.

Good to know

Low season

September

Cheapest flight

$125
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 30% lower on average.
Flight from Gulfport to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Gulfport to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Gulfport to Caribbean Islands 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 Gulfport to Caribbean Islands?

    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 Gulfport to Caribbean Islands 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 Gulfport to Caribbean Islands?

    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 Gulfport to Caribbean Islands 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 Gulfport to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Gulfport to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Gulfport to Caribbean Islands? 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 11915 reviews
6.4Food
7.9Crew
6.8Entertainment
7.5Boarding
7.2Comfort
Airline reviews

The flight had a 6 hours delay. This should not happen to anyone. Airlines should provide an alternative with no additional costs.

2.0 MediocreMiguel, Aug 2026
Read more American Airlines reviews

The flight had a 6 hours delay. This should not happen to anyone. Airlines should provide an alternative with no additional costs.

Flying on this airline is nothing short of a full blown circus clown show. On a recent return from my mother’s funeral, my only available choice from IND to PWM was American, which I hesitantly booked as I rarely fly them for many of the following reasons and never will again. I was booked IND-PHL-PWM totaling about six hours. The flight was cancelled due to NE weather. They rebooked me on a two stop flight IND-DFW (Yes DALLAS)-PHL-PWM, still all on the same day. After arriving in DFW, they continually delayed the DFW-PHL flight due to maintenance issues on the arriving flight. Finally it was delayed to the point that my PHL-PWM connection was no longer possible. They then rebooked me thru LGA with the short flight the NEXT DAY to PWM and offered to put me up for the night in NYC (or so I assumed). The flight DFW-LGA was then delayed so much that I asked to be put in an earlier flight with a lessor delay. Throughout this day chats with their AI assistant were useless as were subsequent chats supposedly with a real person(?). Only one customer service agent in DFW was actually helpful and appeared to care. Upon arrival at LGA post midnight, they issued me car and hotel vouchers in Trenton NEW JERSEY at a very old Howard Johnsons ONE HALF HOUR from LGA. The hotel was an $85, 1.5 rated hotel in a very sketchy area of NJ that I would have never voluntarily booked. As I prepared to catch the car back to LGA the next morning I received a text that my flight was cancelled. TWICE IN TWO DAYS. I went to LGA hoping to have AA book me on an earlier Delta flight. The full service line was at least 200 people deep, so I tried to reach a real person agent by phone. After 1/2 hours on hold I gave up and waited for my later LGA-PWM flight. It actually started boarding on-time, but only shortly after announced a maintenance hold. We were told it was nothing serious, just an adjustment to the Captains seat. Only one update was given while we waited 1.5+ hours for a “SEAT ADJUSTMENT”. Can’t forget to mention that on all of these planes the WiFi only worked on two. During that time at least three others flights in my area announced that they were overbooked and were taking volunteers before bumping people. Another flight to ORD announced a gate change and less than five minutes after announced that they were really not changing and announced for everyone to return to that gate. Can’t forget to mention that on all of these planes the WiFi only worked on two.🤡🤡

Paid for wifi but it didn't work once. Seats were incredibly cramped and passengers sitting in front was reclined the entire time and staff did nothing

Delays and cancellations. Mechanics weren’t on site. Replacement plane took hours to arrive although it should have arrived within 90 minutes. Flight back was cancelled. Ended up driving over 12 hours and wasting 3 days between everything.

Flight was delayed multiple times and rerouted to different concourses in the airport because of all of American's delays. App/boarding pass would not update with changed gate information.

Absolutely infuriating. I was flying standby to get home earlier after flying 4 times with American in 6 days. I was #2 on the list with seats near the front and middle, in addition to the 4 first class upgrade seats that came back into the pool. I am a Platinum member, have their card, and they put me in the 2nd to last row in the middle. No loyalty whatsoever and they lost a fan for life. There is reason people have negative comments about American and I am done supporting them.

Horrible - their gate agents do not care and loyalty means nothing to them. Planes are often late and you are left on your own. Oh, and WiFi - good luck!

Awful! We boarded and then sat on the plane for 50 mins before having to deplane due to a maintenance issue which should have been addressed before boarding. Then we had to change terminals as there was no other plane for us at the current terminal. Then we waited another 2 and a half hours to board again only to wait for 50 mins on the plane again for the snacks to be brought from the broken plane. And once we were on the flight we still only got the complimentary cookie and soda or water. No food vouchers provided even though we had waited over 3 hours for our flight.

There was a 6 hours delay in our departure. And yet, no compensation was offered. A company should be responsible for such a delay.

American Airlines gets worse every time I fly them. This is the 3rd time they lost my bags in a year. I also think their employees do not care when I communicate that I’m unsatisfied with the airlines. I’m a credit card holder, fly first class, and an advantage member but I think that I’m finally going to make the switch to Delta.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports