$154 Find Cheap Flights from Gulfport to Caribbean Islands

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 4/27. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Gulfport to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Gulfport to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Gulfport to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$569
Montego Bay
Montego Bay2 stops$357
Bridgetown
Bridgetown2 stops$732
Punta Cana
Punta Cana2 stops$569
Montego Bay
Montego Bay2 stops$357
Bridgetown
Bridgetown2 stops$732

Book Cheap Gulfport to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Gulfport to Caribbean Islands 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 Gulfport to Caribbean Islands

Tue, Jul 14 - Tue, Aug 11
American Airlines Logo
6:39 pm - 1:09 pm
GPT
-
MBJ
18h 30m
2 stops
American Airlines Logo
10:25 am - 10:51 am
MBJ
-
GPT
24h 26m
2 stops
$357American Airlines
Thu, May 28 - Fri, Jun 12
Multiple Airlines Logo
7:50 pm - 2:08 am
GPT
-
SJU
29h 18m
1 stop
Multiple Airlines Logo
8:04 pm - 7:10 pm
SJU
-
GPT
48h 06m
2 stops
$441Multiple Airlines
Tue, Jul 14 - Tue, Aug 11
American Airlines Logo
5:00 am - 4:14 pm
GPT
-
MBJ
11h 14m
1 stop
American Airlines Logo
3:20 pm - 10:51 am
MBJ
-
GPT
19h 31m
2 stops
$457American Airlines
Thu, Jul 16 - Wed, Jul 22
Multiple Airlines Logo
7:50 pm - 12:44 am
GPT
-
SJU
51h 54m
2 stops
Multiple Airlines Logo
2:59 am - 7:10 pm
SJU
-
GPT
17h 11m
1 stop
$477Multiple Airlines
Tue, Apr 21 - Sat, May 2
American Airlines Logo
5:00 am - 6:10 pm
GPT
-
SJU
12h 10m
2 stops
American Airlines Logo
10:01 am - 11:58 pm
SJU
-
GPT
14h 57m
2 stops
$486American Airlines
Mon, May 18 - Mon, May 25
American Airlines Logo
5:03 pm - 1:19 pm
GPT
-
MBJ
20h 16m
2 stops
American Airlines Logo
5:17 pm - 7:19 pm
MBJ
-
GPT
26h 02m
2 stops
$492American Airlines
Mon, Apr 27 - Sat, May 2
Delta Logo
2:40 pm - 11:13 pm
GPT
-
SJU
7h 33m
1 stop
Delta Logo
12:55 pm - 10:13 pm
SJU
-
GPT
10h 18m
1 stop
$561Delta
Mon, Apr 27 - Fri, May 1
United Airlines Logo
7:10 am - 3:42 pm
GPT
-
SJU
7h 32m
1 stop
United Airlines Logo
1:00 am - 1:21 pm
SJU
-
GPT
13h 21m
2 stops
$606United Airlines
Tue, May 5 - Fri, May 8
United Airlines Logo
7:07 am - 1:30 pm
GPT
-
MBJ
6h 23m
1 stop
United Airlines Logo
4:12 pm - 4:13 pm
MBJ
-
GPT
24h 01m
2 stops
$628United Airlines
Fri, Apr 17 - Tue, Apr 21
Delta Logo
6:00 am - 2:48 pm
GPT
-
STT
7h 48m
1 stop
Delta Logo
1:59 pm - 10:13 pm
STT
-
GPT
9h 14m
1 stop
$725Delta
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 $398, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$154
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 3% increase in price.
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 airlines 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.
7.9
DeltaOverall score based on 8387 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.9Comfort
7.2Food
Airline reviews

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

10.0 ExcellentRay, Apr 2026
FWA - ATL
Read more Delta reviews

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

there are no options s for snack besides cookies would ve nice to have a salty option n

We did not have enough time to make our connecting flight. As a result, we were put onto a different airline for our second leg. The different airline was NOT comparable to British Airlines, and our arrival was significantly delayed. The actual flight on BA was amazing.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Human interaction. Thought there would be more service-even a smile would have been nice.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports