$343 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 12/23. 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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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$611
Montego Bay
Montego Bay1 stop$556
Punta Cana
Punta Cana2 stops$611
Montego Bay
Montego Bay1 stop$556

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

Sun, Feb 22 - Thu, Feb 26
American Airlines Logo
7:51 pm - 2:43 pmGPT-SJU
16h 52m1 stop
American Airlines Logo
5:41 am - 9:36 pmSJU-GPT
17h 55m2 stops
$473American Airlines
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Mon, Nov 10 - Wed, Nov 12
United Airlines Logo
7:00 am - 4:36 pmGPT-SJU
7h 36m1 stop
United Airlines Logo
2:05 am - 1:20 pmSJU-GPT
13h 15m2 stops
$475United Airlines
Find Deal
Mon, Nov 10 - Thu, Nov 13
American Airlines Logo
5:26 pm - 1:43 pmGPT-SJU
18h 17m2 stops
American Airlines Logo
2:47 pm - 11:57 pmSJU-GPT
11h 10m2 stops
$485American Airlines
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Sun, Feb 22 - Thu, Feb 26
Delta Logo
10:30 am - 8:30 pmGPT-SJU
8h 00m1 stop
Delta Logo
6:15 am - 1:37 pmSJU-GPT
9h 22m1 stop
$525Delta
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Sun, Feb 22 - Thu, Feb 26
American Airlines Logo
7:51 pm - 4:55 amGPT-SJU
7h 04m1 stop
American Airlines Logo
8:04 am - 10:15 pmSJU-GPT
16h 11m1 stop
$551American Airlines
Find Deal
Thu, Jan 8 - Thu, Jan 15
American Airlines Logo
6:32 am - 3:04 pmGPT-MBJ
7h 32m1 stop
American Airlines Logo
4:48 pm - 10:47 pmMBJ-GPT
6h 59m1 stop
$556American Airlines
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Thu, Jan 8 - Thu, Jan 15
American Airlines Logo
5:41 pm - 2:13 pmGPT-MBJ
19h 32m2 stops
American Airlines Logo
4:48 pm - 10:47 pmMBJ-GPT
6h 59m1 stop
$561American Airlines
Find Deal
Tue, Dec 23 - Thu, Jan 8
Multiple Airlines Logo
10:05 am - 8:27 pmGPT-SJU
8h 22m1 stop
Multiple Airlines Logo
10:59 am - 9:00 amSJU-GPT
24h 01m2 stops
$593Multiple Airlines
Find Deal
Sun, Apr 5 - Tue, Apr 7
Delta Logo
6:00 pm - 12:25 pmGPT-PUJ
17h 25m2 stops
Delta Logo
1:45 pm - 9:41 amPUJ-GPT
20h 56m2 stops
$611Delta
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Tue, Dec 23 - Thu, Jan 8
Multiple Airlines Logo
10:05 am - 8:27 pmGPT-SJU
8h 22m1 stop
Multiple Airlines Logo
5:45 am - 9:00 amSJU-GPT
29h 15m1 stop
$787Multiple Airlines
Find Deal
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 $370, prices are generally cheapest when you fly direct.

What’s the cheapest day of the week to fly from Gulfport to Caribbean Islands?

The average price of all round-trip flights from Gulfport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

For Gulfport to Caribbean Islands, Monday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Caribbean Islands back to Gulfport, the best deals are generally found on Tuesday, with Thursday being the most expensive.

Good to know

Low seasonSeptember
Cheapest flight$343
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly with an average 11% 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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $380 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $589.

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 7981 reviews
7.9Entertainment
8.2Boarding
8.5Crew
7.3Food
7.9Comfort
Airline reviews

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

6.0 GoodDavid, Oct 2025JFK - KEF
Read more Delta reviews

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Delayed delayed delayed and no offer for food or vouchers

Disliked having to wait a little longer to disembark from the plan when we landed in London

Typically flights with AA are good. The staff are pleasant, welcoming, and efficient.

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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