$214 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 3/15. 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$532
Montego Bay
Montego Bay2 stops$480
Santo Domingo
Santo Domingo2 stops$532
Montego Bay
Montego Bay2 stops$480

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

Tue, Jan 6 - Tue, Jan 13
United Airlines Logo
7:00 am - 4:36 pm
MAF
-
SJU
7h 36m1 stop
United Airlines Logo
3:46 pm - 9:54 pm
SJU
-
MAF
8h 08m1 stop
$409United Airlines
Sun, Mar 15 - Wed, Mar 25
American Airlines Logo
6:20 pm - 11:24 am
MAF
-
MBJ
17h 04m2 stops
American Airlines Logo
3:04 pm - 10:49 pm
MBJ
-
MAF
7h 45m1 stop
$480American Airlines
Sat, Jan 24 - Sat, Jan 31
American Airlines Logo
12:41 pm - 11:33 am
MAF
-
MBJ
21h 52m2 stops
American Airlines Logo
4:22 pm - 10:07 am
MBJ
-
MAF
18h 45m2 stops
$510American Airlines
Sat, Jan 24 - Sat, Jan 31
American Airlines Logo
10:37 am - 3:16 pm
MAF
-
MBJ
27h 39m1 stop
American Airlines Logo
4:14 pm - 10:54 pm
MBJ
-
MAF
7h 40m1 stop
$512American Airlines
Tue, Jan 6 - Mon, Jan 12
United Airlines Logo
7:00 am - 12:36 am
MAF
-
SJU
15h 36m2 stops
United Airlines Logo
2:05 am - 9:54 pm
SJU
-
MAF
21h 49m2 stops
$519United Airlines
Fri, Feb 27 - Fri, Mar 6
United Airlines Logo
5:00 pm - 1:41 pm
MAF
-
SDQ
18h 41m2 stops
United Airlines Logo
6:00 am - 6:15 pm
SDQ
-
MAF
14h 15m2 stops
$532United Airlines
Fri, Feb 27 - Sat, Mar 7
United Airlines Logo
5:00 pm - 1:41 pm
MAF
-
SDQ
18h 41m2 stops
United Airlines Logo
6:00 am - 6:15 pm
SDQ
-
MAF
14h 15m2 stops
$542United Airlines
Sun, Mar 15 - Wed, Mar 25
American Airlines Logo
8:34 pm - 2:04 pm
MAF
-
MBJ
17h 30m1 stop
American Airlines Logo
3:04 pm - 12:06 am
MBJ
-
MAF
9h 02m1 stop
$636American Airlines
Sat, Jan 17 - Wed, Jan 21
United Airlines Logo
1:45 pm - 1:41 pm
MAF
-
SDQ
21h 56m2 stops
United Airlines Logo
6:00 am - 9:54 pm
SDQ
-
MAF
17h 54m2 stops
$642United Airlines
Sun, Dec 21 - Thu, Dec 25
United Airlines Logo
5:15 pm - 8:09 pm
MAF
-
SJU
24h 54m2 stops
United Airlines Logo
7:45 am - 3:04 pm
SJU
-
MAF
9h 19m1 stop
$771United 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 February and July, when the average cost of round-trip tickets is $825 and $780 respectively.

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

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

When flying from Midland to Caribbean, you should consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Midland, you’ll find the best rates on Thursdays and the most expensive ones on Saturdays.

Good to know

Low seasonOctober
Cheapest flight$214
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Midland to Montego Bay

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.

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

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $570 on average. Morning departures are around 40% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $919.

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.
7.9
SouthwestOverall score based on 4252 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

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.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

A little bit more leg room in premium economy. I am 6’4”.

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

I have a gluten allergy so did have any food

We were very rushed by a staff member at the gate when transferring from American Airlines to Fijian. Then the plane stayed put for ages anyhow! The plane was delayed and my bag sent to San Francisco instead of Fiji

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

The only thing to like was that we eventually got to our destination

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports