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Cheap flights from Midland to Caribbean Islands from $123

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Midland to Caribbean Islands departing on 2/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Midland to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
12:03 pm - 8:38 pm
MAF
-
SJU
7h 35m1 stop
United Airlines Logo
2:55 pm - 9:38 pm
SJU
-
MAF
7h 43m1 stop
$469United Airlines
Sat, May 2 - Tue, May 5
United Airlines Logo
7:00 am - 3:42 pm
MAF
-
SJU
7h 42m1 stop
United Airlines Logo
1:00 am - 10:03 pm
SJU
-
MAF
22h 03m2 stops
$479United Airlines
Sat, May 2 - Mon, May 4
United Airlines Logo
7:00 am - 4:36 pm
MAF
-
SJU
7h 36m1 stop
United Airlines Logo
2:05 am - 1:54 pm
SJU
-
MAF
13h 49m2 stops
$485United Airlines
Sat, Jan 10 - Tue, Jan 13
United Airlines Logo
7:00 am - 12:36 am
MAF
-
SJU
15h 36m2 stops
United Airlines Logo
3:46 pm - 9:54 pm
SJU
-
MAF
8h 08m1 stop
$488United Airlines
Fri, Feb 6 - Tue, Feb 10
United Airlines Logo
9:38 am - 11:50 pm
MAF
-
SJU
13h 12m2 stops
United Airlines Logo
7:20 am - 9:38 pm
SJU
-
MAF
15h 18m2 stops
$519United Airlines
Sat, May 2 - Tue, May 5
American Airlines Logo
9:11 am - 10:26 pm
MAF
-
SJU
11h 15m1 stop
American Airlines Logo
7:07 am - 10:54 pm
SJU
-
MAF
17h 47m1 stop
$523American Airlines
Fri, Feb 6 - Tue, Feb 10
Southwest Logo
11:35 am - 12:40 am
MAF
-
SJU
11h 05m2 stops
Southwest Logo
12:10 pm - 9:35 pm
SJU
-
MAF
11h 25m2 stops
$562Southwest
Fri, Feb 6 - Tue, Feb 10
American Airlines Logo
8:28 pm - 1:00 pm
MAF
-
MBJ
16h 32m2 stops
American Airlines Logo
5:05 pm - 11:43 pm
MBJ
-
MAF
6h 38m1 stop
$571American Airlines
Tue, Jun 16 - Sat, Jun 20
American Airlines Logo
4:55 pm - 10:48 am
MAF
-
SJU
15h 53m2 stops
American Airlines Logo
6:00 am - 4:25 pm
SJU
-
MAF
12h 25m2 stops
$585American Airlines
Sat, Jan 10 - Wed, Jan 14
American Airlines Logo
8:28 pm - 1:00 pm
MAF
-
MBJ
16h 32m2 stops
American Airlines Logo
10:55 am - 10:34 pm
MBJ
-
MAF
11h 39m2 stops
$599American Airlines
Tue, Jun 16 - Sat, Jun 20

American Airlines flights from Midland to Caribbean Islands

Our best American Airlines deals on Midland to Caribbean Islands flight tickets
American Airlines
Feb 6
MAF9:11 amMidland Intl
11h 15m
1 stop
SJU10:26 pmSan Juan Luis Munoz Marin Intl
Feb 10
SJU7:07 amSan Juan Luis Munoz Marin Intl
17h 47m
1 stop
MAF10:54 pmMidland Intl
$523
Find similar
American Airlines
Jun 16
MAF8:28 pmMidland Intl
16h 32m
2 stops
MBJ1:00 pmMontego Bay Sangster Intl
Jun 20
MBJ5:05 pmMontego Bay Sangster Intl
6h 38m
1 stop
MAF11:43 pmMidland Intl
$571
Find similar
American Airlines
Jan 10
MAF4:55 pmMidland Intl
15h 53m
2 stops
SJU10:48 amSan Juan Luis Munoz Marin Intl
Jan 14
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 25m
2 stops
MAF4:25 pmMidland Intl
$585
Find similar

United Airlines flights from Midland to Caribbean Islands

Our best United Airlines deals on Midland to Caribbean Islands flight tickets
United Airlines
May 2
MAF12:03 pmMidland Intl
7h 35m
1 stop
SJU8:38 pmSan Juan Luis Munoz Marin Intl
May 5
SJU2:55 pmSan Juan Luis Munoz Marin Intl
7h 43m
1 stop
MAF9:38 pmMidland Intl
$469
Find similar
United Airlines
May 2
MAF7:00 amMidland Intl
7h 42m
1 stop
SJU3:42 pmSan Juan Luis Munoz Marin Intl
May 4
SJU1:00 amSan Juan Luis Munoz Marin Intl
21h 38m
2 stops
MAF9:38 pmMidland Intl
$479
Find similar
United Airlines
Jan 10
MAF7:00 amMidland Intl
7h 36m
1 stop
SJU4:36 pmSan Juan Luis Munoz Marin Intl
Jan 13
SJU2:05 amSan Juan Luis Munoz Marin Intl
13h 49m
2 stops
MAF1:54 pmMidland Intl
$485
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Midland to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 27, 2025.
Use the filters below to find and compare flights from Midland to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 5/2

12:03 pm-8:38 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Tue 5/5

2:55 pm-9:38 pm

1 stop7h 43m

$469

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 5/2

7:00 am-3:42 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Mon 5/4

1:00 am-10:03 pm

2 stops22h 03m

$479

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 1/10

7:00 am-4:36 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

Tue 1/13

2:05 am-1:54 pm

2 stops13h 49m

$485

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Fri 2/6

7:00 am-12:36 am

2 stops15h 36m

San Juan Luis Munoz Marin Intl

Tue 2/10

3:46 pm-9:54 pm

1 stop8h 08m

$488

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 5/2

9:38 am-11:50 pm

2 stops13h 12m

San Juan Luis Munoz Marin Intl

Tue 5/5

7:20 am-9:38 pm

2 stops15h 18m

$519

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Fri 2/6

9:11 am-10:26 pm

1 stop11h 15m

San Juan Luis Munoz Marin Intl

Tue 2/10

7:07 am-10:54 pm

1 stop17h 47m

$523

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Fri 2/6

11:35 am-12:40 am

2 stops11h 05m

San Juan Luis Munoz Marin Intl

Tue 2/10

12:10 pm-9:35 pm

2 stops11h 25m

$562

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Tue 6/16

8:28 pm-1:00 pm

2 stops16h 32m

Montego Bay Sangster Intl

Sat 6/20

5:05 pm-11:43 pm

1 stop6h 38m

$571

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sat 1/10

4:55 pm-10:48 am

2 stops15h 53m

San Juan Luis Munoz Marin Intl

Wed 1/14

6:00 am-4:25 pm

2 stops12h 25m

$585

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Tue 6/16

8:28 pm-1:00 pm

2 stops16h 32m

Montego Bay Sangster Intl

Sat 6/20

10:55 am-10:34 pm

2 stops11h 39m

$599

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Midland to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of April is, on average, the cheapest month to fly to Caribbean Islands from Midland, with most prices found around $395. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Midland averaging around $436.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Midland to Caribbean Islands in the evening for as low as $570. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the afternoon because they tend to be around $919. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Midland to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Midland to Caribbean Islands.

Cheap Midland to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Midland to Caribbean Islands

Fastest flight time

7h 36m

Direct flights

None
The fastest flight from Midland to Caribbean Islands takes 7h 36m
There are no direct flights from Midland to Caribbean Islands. There are no popular flight routes from Midland to Caribbean Islands.
Search flight deals

  • When did momondo last update prices for flights from Midland Intl Airport to Caribbean Islands?

    Prices for flights from Midland Intl Airport to Caribbean Islands refresh daily.

  • How many operators does momondo search for flights from Midland Intl Airport to Caribbean Islands?

  • How old do you have to be to fly from Midland Intl Airport to Caribbean Islands?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Midland Intl Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Midland to Caribbean Islands?

Best airlines flying from Midland to Caribbean Islands

Compare and see reviews for airlines that fly from Midland to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $307Free CancellationRating
7.2
11,067 reviews
Search American Airlines flights
United AirlinesPriceFrom $370Free CancellationRating
7.4
9,116 reviews
Search United Airlines flights
SouthwestPriceFrom $520Free CancellationRating
8.0
4,257 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Midland to Caribbean Islands?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Midland to Caribbean Islands for you.

Can I find flights from Midland to Caribbean Islands with flexible booking policies on momondo?

momondo does allow users to show only those flights to Caribbean Islands from Midland which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Midland to Caribbean Islands?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Midland to Caribbean Islands.

I’m not ready to book a flight from Midland to Caribbean Islands right now. Can momondo alert me if prices change?

Price alerts on flights to Caribbean Islands from Midland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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