$182 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 6/8. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$529
Montego Bay
Montego Bay2 stops$317
Punta Cana
Punta Cana2 stops$529
Montego Bay
Montego Bay2 stops$317

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

Mon, May 4 - Sat, May 9
American Airlines Logo
7:38 pm - 3:37 pm
GPT
-
MBJ
19h 59m
2 stops
American Airlines Logo
2:29 pm - 10:33 am
MBJ
-
GPT
20h 04m
2 stops
$317American Airlines
Mon, May 4 - Sat, May 9
American Airlines Logo
7:38 pm - 3:37 pm
GPT
-
MBJ
19h 59m
2 stops
American Airlines Logo
12:56 pm - 10:33 am
MBJ
-
GPT
21h 37m
2 stops
$337American Airlines
Tue, Apr 21 - Tue, Apr 28
American Airlines Logo
5:49 pm - 4:15 pm
GPT
-
STT
21h 26m
2 stops
American Airlines Logo
5:05 pm - 10:33 am
STT
-
GPT
18h 28m
2 stops
$370American Airlines
Wed, Apr 22 - Wed, Apr 29
Delta Logo
2:40 pm - 11:12 pm
GPT
-
SJU
7h 32m
1 stop
Delta Logo
6:15 am - 1:54 pm
SJU
-
GPT
8h 39m
1 stop
$376Delta
Thu, Apr 23 - Thu, Apr 30
American Airlines Logo
11:10 am - 11:02 pm
GPT
-
SJU
10h 52m
1 stop
American Airlines Logo
11:43 am - 11:58 pm
SJU
-
GPT
13h 15m
2 stops
$396American Airlines
Fri, Mar 27 - Sat, Mar 28
Multiple Airlines Logo
6:54 pm - 10:10 am
GPT
-
SJU
14h 16m
1 stop
Multiple Airlines Logo
3:08 am - 6:40 pm
SJU
-
GPT
16h 32m
1 stop
$472Multiple Airlines
Tue, Mar 24 - Tue, Mar 31
Delta Logo
6:00 am - 1:47 pm
GPT
-
STT
6h 47m
1 stop
Delta Logo
3:00 pm - 10:15 pm
STT
-
GPT
8h 15m
1 stop
$490Delta
Fri, Mar 27 - Sat, Mar 28
Multiple Airlines Logo
6:54 pm - 11:49 am
GPT
-
SJU
15h 55m
2 stops
Multiple Airlines Logo
3:08 am - 6:40 pm
SJU
-
GPT
16h 32m
1 stop
$540Multiple Airlines
Mon, May 4 - Thu, May 7
United Airlines Logo
2:00 pm - 1:30 pm
GPT
-
MBJ
23h 30m
1 stop
United Airlines Logo
2:40 pm - 4:13 pm
MBJ
-
GPT
25h 33m
1 stop
$543United Airlines
Sun, Mar 29 - Sat, Apr 4
United Airlines Logo
5:15 pm - 12:30 pm
GPT
-
GCM
19h 15m
1 stop
United Airlines Logo
1:35 pm - 7:53 pm
GCM
-
GPT
6h 18m
1 stop
$993United 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 $411, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$182
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 1% increase in price.
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 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 8239 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

2+hrs delay without any reason provided and a cramped flight

2.0 MediocreYogendra Kumar, Feb 2026
DTW - MDT
Read more Delta reviews

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

Never got on it. Was re-routed through Detroit and am still in airports 12 hours later waiting for my connecting plane to arrive.

Delta has too many delays now days. It is 1:06 am now. I was supposed to land in Norfolk at 10:30 pm. I got re-booked through Detroit and I’m still in Detroit. I hope to be landed in Norfolk by 3am. I’ve been in airports for 12 hours as of right now. There is a weather delay now but most delays lately have been maintenance.

Very Very late. Subsequent flights left an hour before ours

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

I am an AA flyer for a very long time... AA has yet to disappoint.

Flight was delayed. Not much information on when the flight would take off. Eventually we were told it was maintenance. App was not giving updates.

Never ontime and always delays. Long waits for customer service and often app doesn’t work

Arriving plane went to wrong gate. Flight Attendant was late. Was in no Hurry when he arrived. Flight was fine. Plane had to wait 20 minutes to get assigned a gate due to designated gate tied up. barely connected.. Boarded extremely late on final leg of trip.

We arrived 25 minutes early only to be told our gate was occupied and so we sat for close to 30 minutes to pull into a gate. That’s not an early arrival!

Experience was great. The best part is the free Wi-Fi connection which helps me to work on the flight

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

The TSA check in took 1.5 hours to get through in Austin and I missed my flights back to DC

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports