$231 Find Cheap Flights from Midland 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 Midland to Caribbean departing on 6/13. 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

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Cheap Flights from Midland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Santo Domingo
Santo Domingo2 stops$689
Montego Bay
Montego Bay1 stop$524
Oranjestad
Oranjestad2 stops$742
Santo Domingo
Santo Domingo2 stops$689
Montego Bay
Montego Bay1 stop$524
Oranjestad
Oranjestad2 stops$742

Book Cheap Midland 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 Midland 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 Midland to Caribbean

Mon, May 4 - Fri, May 8
United Airlines Logo
12:02 pm - 8:38 pm
MAF
-
SJU
7h 36m
1 stop
United Airlines Logo
7:20 am - 10:55 pm
SJU
-
MAF
16h 35m
2 stops
$260United Airlines
Mon, Mar 2 - Wed, Mar 4
United Airlines Logo
12:07 pm - 9:26 pm
MAF
-
SJU
7h 19m
1 stop
United Airlines Logo
8:30 am - 10:03 pm
SJU
-
MAF
15h 33m
2 stops
$280United Airlines
Mon, Mar 2 - Wed, Mar 4
United Airlines Logo
7:40 am - 6:25 pm
MAF
-
SJU
8h 45m
1 stop
United Airlines Logo
3:46 pm - 9:44 pm
SJU
-
MAF
7h 58m
1 stop
$350United Airlines
Mon, Mar 2 - Wed, Mar 4
Southwest Logo
2:55 pm - 12:40 am
MAF
-
SJU
7h 45m
2 stops
Southwest Logo
5:40 am - 4:15 pm
SJU
-
MAF
12h 35m
2 stops
$352Southwest
Mon, May 4 - Fri, May 8
Southwest Logo
1:00 pm - 11:25 pm
MAF
-
SJU
9h 25m
2 stops
Southwest Logo
6:50 am - 9:45 pm
SJU
-
MAF
15h 55m
2 stops
$373Southwest
Fri, Feb 27 - Mon, Mar 2
American Airlines Logo
8:29 pm - 3:13 pm
MAF
-
SJU
16h 44m
1 stop
American Airlines Logo
7:01 pm - 8:48 am
SJU
-
MAF
15h 47m
2 stops
$596American Airlines
Fri, Feb 13 - Tue, Feb 17
Southwest Logo
3:25 pm - 1:35 am
MAF
-
SJU
8h 10m
2 stops
Southwest Logo
5:35 am - 1:50 pm
SJU
-
MAF
10h 15m
2 stops
$631Southwest
Fri, Feb 27 - Mon, Mar 2
American Airlines Logo
8:29 pm - 3:13 pm
MAF
-
SJU
16h 44m
1 stop
American Airlines Logo
4:01 pm - 8:48 am
SJU
-
MAF
18h 47m
1 stop
$641American Airlines
Sat, May 30 - Sat, Jul 18
American Airlines Logo
6:00 am - 10:59 pm
MAF
-
SDQ
15h 59m
2 stops
American Airlines Logo
7:00 am - 12:12 am
SDQ
-
MAF
18h 12m
2 stops
$689American Airlines
Sat, Feb 14 - Sat, Feb 21
American Airlines Logo
9:18 am - 10:07 am
MAF
-
MBJ
23h 49m
2 stops
American Airlines Logo
2:33 pm - 9:42 am
MBJ
-
MAF
20h 09m
2 stops
$712American Airlines
Booking Insights

KAYAK's insights & trends for Midland to Caribbean flights

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

What is the cheapest month to fly from Midland to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Midland to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Midland to Caribbean is April, when tickets cost $395 (return) on average. On the other hand, the most expensive months are July and February, when the average cost of round-trip tickets is $780 and $764 respectively.

Good to know

Low seasonOctober
Cheapest flight$231
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Midland to San Juan

FAQs - booking Caribbean flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Midland 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 Midland 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 Midland 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 Midland 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 Midland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Midland to Caribbean

 
Need help choosing which airline to fly with from Midland 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.
8.0
SouthwestOverall score based on 4267 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Delayed, toilets did not flush, pilot parked to far away from Gate

I like flying first class, and United has a nice one

Unbelievably poor service from flight attendants. They didn’t even do water service on a four hour flight. Just disrespectful.

Seats had less pitch than a regional jet. Food was OK. Have to buy alcohol on US based carriers flying international. Boarding was a mess. Did not have bags but overhead space was gone quick. Would like to see the airlines enforce the one bag over and one bag under policy

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Crew was excellent. This was a relatively long flight though and had very little leg room, and no entertainment.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

Plane was crowded and even when we hit altitude, the plane was hot, not enough air flow.

Flight was delayed and missed my connection Lufthansa didn’t respond.

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

The seat cushions were very worn so they were extremely uncomfortable.

Delayed, no updates, had a rewards number but was not working

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The professionals have excellent customer service, the seats don´t have enough space.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports