What is the cheapest airline that flies from Midland Intl to Caribbean Islands?

American Airlines and United Airlines are the most popular carriers operating from Midland Intl to Caribbean Islands

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?

As of August 2026, there are 2 operators available to choose from 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.

$266 Cheap Flights from Midland to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Midland to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 4:09 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

8h 09m1 stop Dallas/Fort Worth

6:28 am - 9:32 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

17h 04m1 stop Dallas/Fort Worth

$310American Airlines

Tue, Nov 3 - Wed, Nov 11

6:00 am - 4:09 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

8h 09m1 stop Dallas/Fort Worth

6:55 pm - 9:43 amSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

16h 48m2 stops Miami Dallas/Fort Worth

$310American Airlines

Tue, Nov 3 - Thu, Nov 12

5:23 pm - 10:44 amMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

15h 21m2 stops Dallas/Fort Worth Miami

6:55 pm - 9:43 amSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

16h 48m2 stops Miami Dallas/Fort Worth

$310American Airlines

Fri, Nov 6 - Tue, Nov 10

12:38 pm - 10:44 amMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

20h 06m2 stops Dallas/Fort Worth Miami

1:18 pm - 10:47 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

11h 29m2 stops Miami Dallas/Fort Worth

$310American Airlines

Fri, Nov 6 - Fri, Nov 13

9:34 am - 8:38 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

10h 04m1 stop Houston George Bush Intcntl

7:00 am - 4:13 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

10h 13m1 stop Houston George Bush Intcntl

$370United Airlines

Fri, Sep 11 - Fri, Sep 18

9:34 am - 8:38 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

10h 04m1 stop Houston George Bush Intcntl

2:00 pm - 9:58 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

8h 58m1 stop Denver Intl

$370United Airlines

Sat, Oct 17 - Wed, Oct 21

9:34 am - 11:50 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

13h 16m2 stops Houston George Bush Intcntl Newark

2:55 pm - 11:24 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

9h 29m1 stop Houston George Bush Intcntl

$370United Airlines

Sat, Oct 17 - Wed, Oct 21

11:00 am - 12:45 amMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

11h 45m2 stops Dallas Love Field Orlando

5:40 am - 2:00 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

10h 20m2 stops Orlando Houston Hobby

$439Southwest

Wed, Nov 4 - Wed, Nov 11

6:45 am - 6:10 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

10h 25m2 stops Dallas Love Field Orlando

2:35 pm - 10:25 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

8h 50m2 stops Orlando Houston Hobby

$453Southwest

Wed, Aug 26 - Fri, Sep 11

6:45 am - 4:25 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

8h 40m2 stops Dallas Love Field Orlando

11:45 am - 7:55 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

9h 10m2 stops Orlando Dallas Love Field

$556Southwest

Wed, Aug 26 - Sat, Aug 29

Cheap last minute flights

Enter your travel dates to find the best prices.

2:00 pm - 11:50 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

8h 50m2 stops Houston Hobby Orlando

2:35 pm - 10:20 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

8h 45m2 stops Orlando Houston Hobby

$582Southwest

Thu, Aug 20 - Thu, Aug 27

2:00 pm - 11:50 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

8h 50m2 stops Houston Hobby Orlando

6:00 am - 1:20 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

8h 20m2 stops Tampa Houston Hobby

$582Southwest

Thu, Aug 20 - Fri, Aug 28

12:25 pm - 10:00 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

8h 35m2 stops Houston Hobby Orlando

1:45 pm - 10:00 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

9h 15m2 stops Orlando Houston Hobby

$582Southwest

Wed, Aug 19 - Tue, Aug 25

5:00 am - 2:54 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

8h 54m1 stop Dallas/Fort Worth

7:24 pm - 9:46 amSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

15h 22m2 stops Miami Dallas/Fort Worth

$600American Airlines

Wed, Aug 19 - Tue, Aug 25

5:00 am - 2:54 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

8h 54m1 stop Dallas/Fort Worth

3:44 pm - 8:51 amSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

18h 07m1 stop Dallas/Fort Worth

$600American Airlines

Wed, Aug 19 - Tue, Aug 25

5:00 am - 3:42 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

9h 42m1 stop Houston George Bush Intcntl

2:20 pm - 9:34 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

8h 14m1 stop Houston George Bush Intcntl

$662United Airlines

Thu, Aug 20 - Thu, Aug 27

7:00 am - 3:42 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

7h 42m1 stop Houston George Bush Intcntl

1:00 am - 1:32 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

13h 32m2 stops Newark Houston George Bush Intcntl

$662United Airlines

Thu, Aug 20 - Wed, Aug 26

9:34 am - 8:38 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

10h 04m1 stop Houston George Bush Intcntl

1:00 am - 1:32 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

13h 32m2 stops Newark Houston George Bush Intcntl

$662United Airlines

Thu, Aug 20 - Thu, Aug 27

9:34 am - 8:38 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

10h 04m1 stop Houston George Bush Intcntl

7:00 am - 4:05 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

10h 05m1 stop Houston George Bush Intcntl

$676United Airlines

Thu, Aug 20 - Fri, Aug 28

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American Airlines flights from Midland to Caribbean Islands

Our best American Airlines deals on Midland to Caribbean Islands flight tickets

American Airlines

Nov 3

MAF6:00 amMidland Intl

8h 09m

1 stop

SJU4:09 pmSan Juan Luis Munoz Marin Intl

Nov 12

SJU6:28 amSan Juan Luis Munoz Marin Intl

13h 45m

1 stop

MAF6:13 pmMidland Intl

$310

American Airlines

Sep 11

MAF6:20 pmMidland Intl

18h 37m

2 stops

SJU1:57 pmSan Juan Luis Munoz Marin Intl

Sep 18

SJU10:16 amSan Juan Luis Munoz Marin Intl

13h 13m

2 stops

MAF10:29 pmMidland Intl

$359

American Airlines

Nov 5

MAF2:16 pmMidland Intl

20h 12m

2 stops

SJU12:28 pmSan Juan Luis Munoz Marin Intl

Nov 10

SJU3:17 pmSan Juan Luis Munoz Marin Intl

20h 26m

2 stops

MAF9:43 amMidland Intl

$454

Southwest flights from Midland to Caribbean Islands

Our best Southwest deals on Midland to Caribbean Islands flight tickets

Southwest

Nov 4

MAF11:00 amMidland Intl

11h 45m

2 stops

SJU12:45 amSan Juan Luis Munoz Marin Intl

Nov 11

SJU5:40 amSan Juan Luis Munoz Marin Intl

10h 20m

2 stops

MAF2:00 pmMidland Intl

$439

Southwest

Aug 26

MAF6:45 amMidland Intl

10h 25m

2 stops

SJU6:10 pmSan Juan Luis Munoz Marin Intl

Sep 11

SJU2:35 pmSan Juan Luis Munoz Marin Intl

8h 50m

2 stops

MAF10:25 pmMidland Intl

$453

Southwest

Aug 27

MAF10:35 amMidland Intl

10h 35m

2 stops

SJU10:10 pmSan Juan Luis Munoz Marin Intl

Aug 31

SJU6:00 amSan Juan Luis Munoz Marin Intl

8h 20m

2 stops

MAF1:20 pmMidland Intl

$579

momondo Fare Finder

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

Cheapest round-trip

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Tue 11/3

6:00 am-4:09 pm

1 stop8h 09m

San Juan Luis Munoz Marin Intl

Wed 11/11

6:28 am-9:32 pm

1 stop17h 04m

$310

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Tue 11/3

6:00 am-4:09 pm

1 stop8h 09m

San Juan Luis Munoz Marin Intl

Thu 11/12

6:55 pm-9:43 am

2 stops16h 48m

$310

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Fri 11/6

5:23 pm-10:44 am

2 stops15h 21m

San Juan Luis Munoz Marin Intl

Tue 11/10

6:55 pm-9:43 am

2 stops16h 48m

$310

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Fri 11/6

12:38 pm-10:44 am

2 stops20h 06m

San Juan Luis Munoz Marin Intl

Fri 11/13

1:18 pm-10:47 pm

2 stops11h 29m

$310

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Fri 9/11

9:34 am-8:38 pm

1 stop10h 04m

San Juan Luis Munoz Marin Intl

Fri 9/18

7:00 am-4:13 pm

1 stop10h 13m

$370

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Sat 10/17

9:34 am-8:38 pm

1 stop10h 04m

San Juan Luis Munoz Marin Intl

Wed 10/21

2:00 pm-9:58 pm

1 stop8h 58m

$370

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Sat 10/17

9:34 am-11:50 pm

2 stops13h 16m

San Juan Luis Munoz Marin Intl

Wed 10/21

2:55 pm-11:24 pm

1 stop9h 29m

$370

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Wed 11/4

11:00 am-12:45 am

2 stops11h 45m

San Juan Luis Munoz Marin Intl

Wed 11/11

5:40 am-2:00 pm

2 stops10h 20m

$439

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Wed 8/26

6:45 am-6:10 pm

2 stops10h 25m

San Juan Luis Munoz Marin Intl

Fri 9/11

2:35 pm-10:25 pm

2 stops8h 50m

$453

Quickest round-trip

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Wed 8/26

6:45 am-4:25 pm

2 stops8h 40m

San Juan Luis Munoz Marin Intl

Sat 8/29

11:45 am-7:55 pm

2 stops9h 10m

$556

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 resultsSorted by cheapest first

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

Prices

Airlines

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Midland, with most prices found around $0. The month of June is another great option to travel to Caribbean Islands, with average flight prices from Midland averaging around $0.

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 42m
Direct flights	None

The fastest flight from Midland to Caribbean Islands takes 7h 42m

There are no direct flights from Midland to Caribbean Islands. There are no popular flight routes from Midland to Caribbean Islands.

Search flight deals

Frequently asked questions about flying from Midland to Caribbean Islands

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?
As of August 2026, there are 2 operators available to choose from 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?
Based on momondo bookings for flights between Midland and Caribbean Islands, the leading plane model is Embraer 175 (Enhanced Winglets), making up 17.61% of the total bookings. Other popular models include Boeing 737 MAX 8 with 13.35%, Canadair (Bombardier) Regional Jet 700 with 9.94%, and Boeing 737-800 with 8.81%.

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
United Airlines	PriceFrom $232	Free Cancellation	Rating 7.4 10,105 reviews		Search United Airlines flights
Southwest	PriceFrom $370	Free Cancellation	Rating 8.0 4,217 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.