$197 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 8/1. 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$601
Montego Bay
Montego Bay1 stop$442
Punta Cana
Punta Cana2 stops$601
Montego Bay
Montego Bay1 stop$442

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

Thu, Aug 20 - Sun, Aug 23
Multiple Airlines Logo
7:25 pm - 11:06 am
GPT
-
SJU
14h 41m
1 stop
Multiple Airlines Logo
5:15 pm - 7:41 am
SJU
-
GPT
15h 26m
1 stop
$411Multiple Airlines
Tue, Oct 20 - Sat, Oct 24
American Airlines Logo
6:27 pm - 2:35 pm
GPT
-
STT
19h 08m
2 stops
American Airlines Logo
5:40 pm - 5:28 pm
STT
-
GPT
24h 48m
2 stops
$433American Airlines
Sat, Oct 17 - Wed, Oct 21
American Airlines Logo
6:49 pm - 9:05 am
GPT
-
MBJ
14h 16m
1 stop
American Airlines Logo
12:47 pm - 11:05 pm
MBJ
-
GPT
10h 18m
1 stop
$442American Airlines
Tue, Dec 8 - Wed, Dec 16
American Airlines Logo
4:38 pm - 10:35 am
GPT
-
SJU
15h 57m
2 stops
American Airlines Logo
6:00 am - 4:08 pm
SJU
-
GPT
12h 08m
2 stops
$446American Airlines
Sat, Oct 17 - Wed, Oct 21
American Airlines Logo
6:27 pm - 12:40 pm
GPT
-
MBJ
18h 13m
2 stops
American Airlines Logo
5:00 pm - 10:51 am
MBJ
-
GPT
17h 51m
2 stops
$447American Airlines
Sun, Jul 12 - Thu, Jul 16
Multiple Airlines Logo
7:25 pm - 9:43 pm
GPT
-
SJU
25h 18m
1 stop
Multiple Airlines Logo
5:22 pm - 7:41 am
SJU
-
GPT
15h 19m
1 stop
$458Multiple Airlines
Mon, Sep 21 - Mon, Sep 28
American Airlines Logo
5:35 am - 2:45 pm
GPT
-
SJU
8h 10m
1 stop
American Airlines Logo
3:35 pm - 11:24 pm
SJU
-
GPT
8h 49m
1 stop
$486American Airlines
Fri, Oct 9 - Sun, Oct 11
United Airlines Logo
5:14 pm - 1:30 pm
GPT
-
MBJ
20h 16m
1 stop
United Airlines Logo
2:40 pm - 4:12 pm
MBJ
-
GPT
25h 32m
1 stop
$609United Airlines
Sat, Sep 26 - Tue, Sep 29
United Airlines Logo
7:08 am - 3:42 pm
GPT
-
SJU
7h 34m
1 stop
United Airlines Logo
1:00 am - 4:12 pm
SJU
-
GPT
16h 12m
2 stops
$679United Airlines
Mon, Sep 28 - Fri, Oct 2
United Airlines Logo
5:14 pm - 11:43 am
GPT
-
MBJ
18h 29m
2 stops
United Airlines Logo
12:52 pm - 11:18 am
MBJ
-
GPT
46h 26m
2 stops
$700United Airlines
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 $388, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
Cheapest flight$197
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 29% lower on average.
Flight from Gulfport to Montego Bay

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 11705 reviews
7.5Boarding
6.8Entertainment
7.2Comfort
6.4Food
7.9Crew
Airline reviews

Excellent service. Flight attendance like Jessica,, on our flight, is a reason I wouldn’t mind flying through British Airways again. Jessica,, was very courteous and helpful.

10.0 ExcellentShahid Bobby, Jun 2026
ORF - JFK
Read more American Airlines reviews

Excellent service. Flight attendance like Jessica,, on our flight, is a reason I wouldn’t mind flying through British Airways again. Jessica,, was very courteous and helpful.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

Significant delays on my trip to Chicago and my trip back to NY

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Flight had mechanical issues and it was delayed 30 mins - some of us boarded and then had to deplane.

technology worked well and everything ran smoothly. The seats are quite cramped so please don't try to re-engineer the cabin to squeeze more bodies on board.

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

Flight was delayed due to connecting passengers. Lack of snack options bad. Sitting in Aisle, last cart run pulled the cart directly into my knee. Rude awakening.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports