$126 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 5/2. 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$687
Oranjestad
Oranjestad1 stop$751
Santo Domingo
Santo Domingo2 stops$687
Oranjestad
Oranjestad1 stop$751

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, May 2 - Thu, May 7
American Airlines Logo
6:16 pm - 9:13 am
MAF
-
SJU
13h 57m
2 stops
American Airlines Logo
11:59 pm - 1:45 pm
SJU
-
MAF
14h 46m
1 stop
$318American Airlines
Sat, May 2 - Thu, May 7
American Airlines Logo
8:26 pm - 4:32 am
MAF
-
SJU
7h 06m
1 stop
American Airlines Logo
11:59 pm - 9:42 am
SJU
-
MAF
10h 43m
1 stop
$330American Airlines
Tue, Apr 28 - Thu, Apr 30
United Airlines Logo
9:41 am - 11:50 pm
MAF
-
SJU
13h 09m
2 stops
United Airlines Logo
7:00 am - 1:32 pm
SJU
-
MAF
7h 32m
1 stop
$342United Airlines
Fri, Apr 24 - Tue, Apr 28
American Airlines Logo
8:26 pm - 2:42 pm
MAF
-
SJU
17h 16m
1 stop
American Airlines Logo
3:44 pm - 8:45 am
SJU
-
MAF
18h 01m
2 stops
$358American Airlines
Tue, Apr 28 - Thu, Apr 30
United Airlines Logo
9:41 am - 11:50 pm
MAF
-
SJU
13h 09m
2 stops
United Airlines Logo
7:00 am - 4:17 pm
SJU
-
MAF
10h 17m
1 stop
$382United Airlines
Sat, May 2 - Thu, May 7
Southwest Logo
5:30 am - 3:35 pm
MAF
-
SJU
9h 05m
2 stops
Southwest Logo
10:00 am - 6:00 pm
SJU
-
MAF
9h 00m
2 stops
$400Southwest
Fri, Jul 17 - Thu, Jul 23
American Airlines Logo
8:23 pm - 4:39 am
MAF
-
SJU
7h 16m
1 stop
American Airlines Logo
12:58 am - 8:50 am
SJU
-
MAF
8h 52m
1 stop
$420American Airlines
Tue, Apr 28 - Thu, Apr 30
United Airlines Logo
7:20 am - 11:50 pm
MAF
-
SJU
15h 30m
2 stops
United Airlines Logo
7:00 am - 4:17 pm
SJU
-
MAF
10h 17m
1 stop
$422United Airlines
Fri, Apr 24 - Tue, Apr 28
American Airlines Logo
8:26 pm - 2:42 pm
MAF
-
SJU
17h 16m
1 stop
American Airlines Logo
6:45 am - 6:58 pm
SJU
-
MAF
13h 13m
1 stop
$424American Airlines
Tue, Apr 28 - Wed, Apr 29
United Airlines Logo
9:41 am - 11:50 pm
MAF
-
SJU
13h 09m
2 stops
United Airlines Logo
1:00 am - 4:17 pm
SJU
-
MAF
16h 17m
2 stops
$426United 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.

Good to know

Low seasonOctober
Cheapest flight$126
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 11% lower on average.
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 4319 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Terrible because it was cancelled due to volcanic ash clouds in Guatemala while all other airlines kept flying. Had to pay for a hotel to stay overnight in Houston and try to fly next day.

Overall we had a good experience during our flight from San Francisco to Houston.

Airport terminal was outdated, flight was on a small jet with no wifi

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

The power at the seat didn't work and the seat itself was difficult to adjust - this was a business class seat. Flight attendant gave me miles to compensate. The attendant was very professional and on top of his game the entire flight.

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

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Poor communication ahead of time about flight delays and old planes/other equipment.

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

The crew was excellent and overall the flight was good. No complaints.

Like all of the flights I took to get down to Dallas. They were delayed

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports