$278 Find Cheap Flights from Gulfport to Caribbean

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 departing on 9/23. 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

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Cheap Flights from Gulfport to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$533
Montego Bay
Montego Bay1 stop$531
Bridgetown
Bridgetown2 stops$866
Punta Cana
Punta Cana2 stops$533
Montego Bay
Montego Bay1 stop$531
Bridgetown
Bridgetown2 stops$866

Book Cheap Gulfport 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 Gulfport 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 Gulfport to Caribbean

Wed, Nov 19 - Wed, Dec 10
American Airlines Logo
5:26 pm - 11:12 amGPT-SJU
15h 46m2 stops
American Airlines Logo
6:00 am - 5:44 pmSJU-GPT
13h 44m2 stops
$365American Airlines
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Tue, Oct 14 - Tue, Oct 21
American Airlines Logo
5:45 pm - 12:44 pmGPT-SJU
17h 59m2 stops
American Airlines Logo
7:00 am - 11:36 pmSJU-GPT
17h 36m2 stops
$405American Airlines
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Tue, Oct 14 - Tue, Oct 21
American Airlines Logo
1:55 pm - 10:10 pmGPT-SJU
7h 15m1 stop
American Airlines Logo
7:00 am - 10:46 pmSJU-GPT
16h 46m2 stops
$425American Airlines
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Fri, Oct 10 - Sun, Oct 12
Multiple Airlines Logo
6:51 pm - 6:58 pmGPT-SJU
23h 07m1 stop
Multiple Airlines Logo
3:19 pm - 8:59 amSJU-GPT
18h 40m2 stops
$431Multiple Airlines
Find Deal
Wed, Nov 19 - Tue, Dec 9
United Airlines Logo
7:00 am - 10:22 pmGPT-SJU
13h 22m2 stops
United Airlines Logo
2:05 am - 1:20 pmSJU-GPT
13h 15m2 stops
$474United Airlines
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Mon, Jan 5 - Fri, Jan 9
American Airlines Logo
2:32 pm - 12:10 pmGPT-STT
19h 38m2 stops
American Airlines Logo
6:35 pm - 10:01 amSTT-GPT
17h 26m2 stops
$479American Airlines
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Fri, Oct 10 - Sun, Oct 12
Multiple Airlines Logo
6:51 pm - 6:58 pmGPT-SJU
23h 07m1 stop
Multiple Airlines Logo
5:54 pm - 8:59 amSJU-GPT
16h 05m1 stop
$488Multiple 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
7:30 am - 1:37 pmSJU-GPT
8h 07m1 stop
$507Delta
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Wed, Nov 19 - Tue, Dec 9
United Airlines Logo
7:00 am - 4:36 pmGPT-SJU
7h 36m1 stop
United Airlines Logo
2:05 am - 4:02 pmSJU-GPT
15h 57m2 stops
$537United Airlines
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Mon, Jan 5 - Fri, Jan 9
Delta Logo
6:00 am - 4:00 pmGPT-STT
8h 00m1 stop
Delta Logo
3:00 pm - 10:09 pmSTT-GPT
9h 09m1 stop
$579Delta
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Booking Insights

KAYAK's insights & trends for Gulfport to Caribbean flights

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

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

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

If your flying dates are flexible, you should consider flying to Caribbean on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Tuesday is the most expensive day to fly from Gulfport to Caribbean. For your return ticket, we recommend flying on a Tuesday and avoiding Thursdays for the best deals.

Good to know

Low seasonSeptember
Cheapest flight$278
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Gulfport to San Juan

FAQs - booking Caribbean flights

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

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

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

    The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $380 on average. The most expensive time of day to fly to Caribbean 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

 
Need help choosing which airline to fly with from Gulfport 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.
7.9
DeltaOverall score based on 7954 reviews
7.9Comfort
7.9Entertainment
8.5Crew
8.2Boarding
7.3Food
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

The food was terrible especially for a 15 hour international flight. The crew was unpleasant as well.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

Quick check in. Everything went smooth. I don't know what can be done about airline food.

Crew was good. The reservation got mixed up and they didn't have my TSA number. I am also a Silver Medallion and wasn't able to use Sky Priority.

Delta made it easy, comfortable and timely. The crew was fantastic.

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Nothing special. The crew never went out of their way for anything.

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Don’t know they cancelled the flight day before I was to leave. They sent a email at 9:00 pm at night saying they cancelled. That is the smooth way to say we don’t want your business! I think they didn’t have enough people booking so they cancelled the flight! It’s all about the money anymore there is no honesty in business.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

The entertainment package was vast and the selections were very current. Keep updating it was great.

Everything you need to know for your flight to Caribbean

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