$332 Find Cheap Flights from Midland to Caribbean

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midland to Caribbean departing on 9/20. 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 Midland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Santo Domingo
Santo Domingo2 stops$475
Oranjestad
Oranjestad2 stops$600
Santo Domingo
Santo Domingo2 stops$475
Oranjestad
Oranjestad2 stops$600

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

Sat, Sep 20 - Tue, Sep 23
American Airlines Logo
6:39 pm - 12:50 pmMAF-SJU
17h 11m2 stops
American Airlines Logo
6:10 am - 11:04 pmSJU-MAF
17h 54m2 stops
$332American Airlines
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Mon, Aug 18 - Sat, Aug 23
United Airlines Logo
7:08 pm - 5:30 amMAF-SJU
9h 22m1 stop
United Airlines Logo
7:00 am - 2:02 pmSJU-MAF
8h 02m1 stop
$417United Airlines
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Sat, Sep 20 - Tue, Sep 23
American Airlines Logo
6:01 am - 2:15 pmMAF-SJU
7h 14m1 stop
American Airlines Logo
6:10 am - 11:04 pmSJU-MAF
17h 54m2 stops
$420American Airlines
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Mon, Aug 18 - Sat, Aug 23
American Airlines Logo
6:01 am - 2:25 pmMAF-SJU
7h 24m1 stop
American Airlines Logo
7:05 pm - 9:42 amSJU-MAF
15h 37m2 stops
$440American Airlines
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Sat, Sep 20 - Tue, Sep 23
United Airlines Logo
9:46 am - 8:38 pmMAF-SJU
9h 52m1 stop
United Airlines Logo
2:55 pm - 9:55 pmSJU-MAF
8h 00m1 stop
$459United Airlines
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Tue, Sep 2 - Sat, Sep 6
American Airlines Logo
7:36 am - 11:59 pmMAF-SJU
15h 23m2 stops
American Airlines Logo
7:05 pm - 10:47 amSJU-MAF
16h 42m2 stops
$460American Airlines
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Thu, Sep 18 - Mon, Sep 22
Delta Logo
5:21 pm - 1:24 pmMAF-SDQ
19h 03m2 stops
Delta Logo
7:40 pm - 11:53 amSDQ-MAF
17h 13m2 stops
$475Delta
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Fri, Nov 14 - Sat, Nov 22
Southwest Logo
11:45 am - 12:35 amMAF-SJU
10h 50m2 stops
Southwest Logo
5:55 pm - 12:25 amSJU-MAF
8h 30m1 stop
$499Southwest
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Thu, Sep 18 - Mon, Sep 22
Delta Logo
5:21 pm - 1:24 pmMAF-SDQ
19h 03m2 stops
Delta Logo
7:40 pm - 11:53 amSDQ-MAF
17h 13m2 stops
$539Delta
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Sat, Dec 20 - Sun, Dec 28
Southwest Logo
5:45 am - 6:20 pmMAF-SJU
10h 35m2 stops
Southwest Logo
5:35 am - 3:05 pmSJU-MAF
11h 30m2 stops
$1,105Southwest
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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 January, when tickets cost $443 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $834 and $775 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 seasonNovember
Cheapest flight$332
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 35% 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.

  • 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.
8.0
SouthwestOverall score based on 4241 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

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”.

Overall it was good. I missed my connection but I was put on another flight.

Although the flight was delayed the crew and the flight itself were very good. Couldn't fault anything and after the disappointment of being abandoned in the US by BA it was a welcome relief to travel with United

Gate agent did not hold flight for connection, provided no assistance to get new flight

Boarding experience was smooth. Flight attendants were friendly and helpful. Entertainment system on the Houston-Edmonton flight did not function for passengers on the left side of the aisle. On the bird's eye flight from Quito to Houston, they should not serve a meal. No one needs to eat after midnight and it is disturbing for those passengers trying to sleep.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

My suitcase was completed destroyed. The top part is broken and unusable now.

We boarded but then sat there waiting on some missed connection people to get on so we sat for about 15 minutes for that. Then we sat again because the passenger manifest was wrong and they had to figure it out before we could leave. That took about another 20 minutes or so. The crew was working hard to figure it out so it’s not their fault. It ended up being a system glitch where someone was upgraded to first class while another person was also in the same seat and it just created a mess that took a little while to figure out. They literally went to every person on the plane asking their names to see who was sitting in the wrong seat. I also hate the entertainment that must be watched on your phone or tablet. Just give us setback screens. It’s so much better. Almost every Delta flight has this now and it is so nice to have them. The crew did a great job. I have no complaints from them. They were very hard working, even with the mishap and a disgruntled passenger.

Very poor delay in dfw was really bad n long

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Flight was delayed again and again ultimately almost three hours getting us to our location at close to midnight by the time we got in and out of airport to destination. I had taken time off work to enjoy an evening at destination and that was now wasted

The flight delay in Dallas created a domino effect that impacted all of the connecting flights. It also increased the number of connections. I missed my flight from Casablanca to Marrakech because of the tight turnaround when landing in Casablanca. . CMN airport was understaffed. Only one person could help while other employees were just watching him. It was an extremely frustrating situation. People were crying and slamming their palms on the counter when speaking to the customer service provider, Allabough (man’s name?). Allabough couldn’t change my flight in the system. simultaneously, I was on the call with America. Airlines customer service rep named Solomon that said he couldn’t change it either. So, I took a ONYA voyages train to from Casablanca to Marrakech to get there on Friday June 26. This was unpredictable trip.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

At the beginning of the flight there was some turbulence and the announcement was made that there would be no beverage service. The turbulence only last about 5 minutes then it was smooth sailing. I noticed that first class got their service, but the rest of us did not.

Update departure times in a more timely manner. We are not boarding on time if the plane isn’t arriving until after our scheduled departure time.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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