$330 Find Cheap Flights from Midland to Caribbean Islands - Compare and Save

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 Islands departing on 7/12. 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 Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Santo Domingo
Santo Domingo2 stops$756
Montego Bay
Montego Bay2 stops$377
Oranjestad
Oranjestad2 stops$776
Santo Domingo
Santo Domingo2 stops$756
Montego Bay
Montego Bay2 stops$377
Oranjestad
Oranjestad2 stops$776

Book Cheap Midland 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 Midland 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 Midland to Caribbean Islands

Fri, Aug 21 - Thu, Aug 27
American Airlines Logo
6:26 pm - 1:21 pm
MAF
-
MBJ
18h 55m
2 stops
American Airlines Logo
5:08 pm - 11:19 am
MBJ
-
MAF
18h 11m
2 stops
$377American Airlines
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
6:45 am - 6:10 pm
MAF
-
SJU
10h 25m
2 stops
Southwest Logo
8:20 am - 7:55 pm
SJU
-
MAF
12h 35m
2 stops
$418Southwest
Sat, Aug 29 - Wed, Sep 2
United Airlines Logo
5:00 am - 3:42 pm
MAF
-
SJU
9h 42m
1 stop
United Airlines Logo
2:20 pm - 9:47 pm
SJU
-
MAF
8h 27m
1 stop
$420United Airlines
Fri, Aug 21 - Thu, Aug 27
American Airlines Logo
11:49 am - 4:08 pm
MAF
-
MBJ
28h 19m
1 stop
American Airlines Logo
12:47 pm - 7:42 pm
MBJ
-
MAF
6h 55m
1 stop
$463American Airlines
Mon, Aug 17 - Fri, Aug 21
American Airlines Logo
5:00 am - 9:55 pm
MAF
-
SJU
15h 55m
2 stops
American Airlines Logo
7:24 pm - 9:46 am
SJU
-
MAF
15h 22m
2 stops
$463American Airlines
Thu, Sep 3 - Sun, Sep 6
American Airlines Logo
8:12 pm - 2:54 pm
MAF
-
SJU
17h 42m
1 stop
American Airlines Logo
6:00 am - 5:00 pm
SJU
-
MAF
12h 00m
2 stops
$503American Airlines
Mon, Aug 17 - Thu, Aug 20
United Airlines Logo
5:00 am - 3:42 pm
MAF
-
SJU
9h 42m
1 stop
United Airlines Logo
1:00 am - 12:45 pm
SJU
-
MAF
12h 45m
2 stops
$518United Airlines
Sat, Aug 29 - Wed, Sep 2
United Airlines Logo
7:00 am - 3:42 pm
MAF
-
SJU
7h 42m
1 stop
United Airlines Logo
4:55 pm - 8:51 am
SJU
-
MAF
16h 56m
2 stops
$570United Airlines
Mon, Aug 31 - Thu, Sep 3
United Airlines Logo
2:13 pm - 2:00 pm
MAF
-
AUA
22h 47m
2 stops
United Airlines Logo
3:10 pm - 12:45 pm
AUA
-
MAF
22h 35m
2 stops
$816United Airlines
Thu, Jul 23 - Wed, Jul 29
Southwest Logo
6:35 pm - 12:45 pm
MAF
-
AUA
17h 10m
2 stops
Southwest Logo
1:45 pm - 11:05 pm
AUA
-
MAF
10h 20m
2 stops
$826Southwest
Booking Insights

KAYAK's insights & trends for Midland to Caribbean Islands flights

Get data-powered insights and trends into flights from Midland 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 Midland 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 $453, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Midland to Caribbean Islands, 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 Islands is June, when tickets cost $0 (return) on average. On the other hand, the most expensive months are December and September, when the average cost of round-trip tickets is $1,077 and $950 respectively.

Good to know

Low seasonOctober
Cheapest flight$330
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Midland to San Juan

FAQs - booking Caribbean Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Midland 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 Midland 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 Midland 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 Midland 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 Midland 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 airline flying from Midland to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Midland 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 Midland 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.
7.4
United AirlinesOverall score based on 9938 reviews
6.6Food
7.3Comfort
7.7Boarding
7.1Entertainment
8.1Crew
Airline reviews

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

2.0 MediocreAnonymous, Jun 2026
SAT - ORD
Read more United Airlines reviews

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

They delayed the flight 3 hours because it wasn't full they moved us to 5 different gates probably the worst airline ever not even spirit is this bad.

The entertainment is a bit limited, it would be better if they added some games to play besides the movies and tv shows. But the seats are comfortable and the crew is polite

Flight cancelled instead of leaving Friday am now, maybe, leaving Sunday

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

one of the flight attendants on the Dallas to frankfurt leg was somewhat rude..

Packed flight, which makes it tough on crew and boarding staff (and the customers of course). But this was great boarding, clear instructions, etc. Traveling on the weekends are always fraught with danger as you have families and less frequent flyers thus more confusion. But this flight went as planned.

Boarded early, left early, arrived 40 mins early! A win win for me!

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports