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

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

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

Prices for flights from Midland Intl Airport to Caribbean are refreshed on a daily basis.

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

As of September 2026, there are 2 operators available to choose from for flights from Midland Intl Airport to Caribbean.

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

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.

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

The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$203 Cheap Flights from Midland to Caribbean in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Midland to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

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

9h 42m1 stop Houston George Bush Intcntl

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

9h 29m1 stop Houston George Bush Intcntl

$354United Airlines

Tue, Oct 20 - Wed, Oct 21

7:30 am - 11:50 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

15h 20m2 stops Denver Intl Newark

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

8h 58m1 stop Denver Intl

$354United Airlines

Tue, Oct 20 - Wed, Oct 21

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

9h 42m1 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

$364United Airlines

Tue, Oct 20 - Wed, Oct 21

7:30 am - 11:50 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

15h 20m2 stops Denver Intl Newark

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

8h 58m1 stop Denver Intl

$364United Airlines

Tue, Oct 20 - Wed, Oct 21

8:30 am - 5:25 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

6h 55m1 stop Houston Hobby

5:40 am - 1:20 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

9h 40m2 stops Orlando Dallas Love Field

$367Southwest

Sat, Nov 7 - Tue, Nov 10

10:45 am - 9:20 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

8h 35m2 stops Dallas Love Field Tampa

5:40 am - 1:20 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

9h 40m2 stops Orlando Dallas Love Field

$367Southwest

Sat, Nov 7 - Tue, Nov 10

1:55 pm - 12:25 amMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

9h 30m2 stops Austin Bergstrom Orlando

12:35 pm - 11:15 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

11h 40m2 stops Orlando Dallas Love Field

$381Southwest

Fri, Oct 23 - Mon, Oct 26

8:10 pm - 4:09 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

17h 59m1 stop Dallas/Fort Worth

7:30 am - 7:45 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

14h 15m2 stops Miami Dallas/Fort Worth

$390American Airlines

Fri, Nov 6 - Wed, Nov 11

8:10 pm - 4:09 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

17h 59m1 stop Dallas/Fort Worth

1:00 pm - 9:32 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

10h 32m2 stops Miami Dallas/Fort Worth

$430American Airlines

Fri, Nov 6 - Wed, Nov 11

7:55 am - 10:02 pmMAF Midland Intl-SJU San Juan Luis Munoz Marin Intl

13h 07m2 stops Dallas/Fort Worth Miami

6:00 am - 9:34 pmSJU San Juan Luis Munoz Marin Intl-MAF Midland Intl

16h 34m1 stop Dallas/Fort Worth

$483American Airlines

Mon, Oct 5 - Fri, Oct 9

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Southwest flights from Midland to Caribbean

Our best Southwest deals on Midland to Caribbean flight tickets

Southwest

Nov 7

MAF10:45 amMidland Intl

8h 35m

2 stops

SJU9:20 pmSan Juan Luis Munoz Marin Intl

Nov 10

SJU5:40 amSan Juan Luis Munoz Marin Intl

9h 40m

2 stops

MAF1:20 pmMidland Intl

$367

Southwest

Oct 23

MAF1:55 pmMidland Intl

9h 30m

2 stops

SJU12:25 amSan Juan Luis Munoz Marin Intl

Oct 26

SJU12:35 pmSan Juan Luis Munoz Marin Intl

11h 40m

2 stops

MAF11:15 pmMidland Intl

$381

Southwest

Nov 5

MAF11:10 amMidland Intl

11h 50m

2 stops

SJU1:00 amSan Juan Luis Munoz Marin Intl

Nov 10

SJU5:40 amSan Juan Luis Munoz Marin Intl

9h 40m

2 stops

MAF1:20 pmMidland Intl

$396

American Airlines flights from Midland to Caribbean

Our best American Airlines deals on Midland to Caribbean flight tickets

American Airlines

Nov 6

MAF8:10 pmMidland Intl

17h 59m

1 stop

SJU4:09 pmSan Juan Luis Munoz Marin Intl

Nov 11

SJU7:30 amSan Juan Luis Munoz Marin Intl

14h 15m

2 stops

MAF7:45 pmMidland Intl

$390

American Airlines

Oct 5

MAF5:00 amMidland Intl

16h 02m

2 stops

SJU10:02 pmSan Juan Luis Munoz Marin Intl

Oct 9

SJU12:21 pmSan Juan Luis Munoz Marin Intl

12h 38m

2 stops

MAF11:59 pmMidland Intl

$483

American Airlines

Oct 23

MAF8:07 pmMidland Intl

18h 16m

1 stop

SJU3:23 pmSan Juan Luis Munoz Marin Intl

Oct 26

SJU6:00 amSan Juan Luis Munoz Marin Intl

17h 37m

1 stop

MAF10:37 pmMidland Intl

$496

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 10/20

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Wed 10/21

2:55 pm-11:24 pm

1 stop9h 29m

$354

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Tue 10/20

7:30 am-11:50 pm

2 stops15h 20m

San Juan Luis Munoz Marin Intl

Wed 10/21

2:00 pm-9:58 pm

1 stop8h 58m

$354

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Tue 10/20

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Wed 10/21

2:00 pm-9:58 pm

1 stop8h 58m

$364

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Tue 10/20

7:30 am-11:50 pm

2 stops15h 20m

San Juan Luis Munoz Marin Intl

Wed 10/21

2:00 pm-9:58 pm

1 stop8h 58m

$364

Quickest round-trip

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Sat 11/7

8:30 am-5:25 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Tue 11/10

5:40 am-1:20 pm

2 stops9h 40m

$367

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Sat 11/7

10:45 am-9:20 pm

2 stops8h 35m

San Juan Luis Munoz Marin Intl

Tue 11/10

5:40 am-1:20 pm

2 stops9h 40m

$367

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Fri 10/23

1:55 pm-12:25 am

2 stops9h 30m

San Juan Luis Munoz Marin Intl

Mon 10/26

12:35 pm-11:15 pm

2 stops11h 40m

$381

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Fri 11/6

8:10 pm-4:09 pm

1 stop17h 59m

San Juan Luis Munoz Marin Intl

Wed 11/11

7:30 am-7:45 pm

2 stops14h 15m

$390

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Fri 11/6

8:10 pm-4:09 pm

1 stop17h 59m

San Juan Luis Munoz Marin Intl

Wed 11/11

1:00 pm-9:32 pm

2 stops10h 32m

$430

MidlandSan Juan

MAF Midland Intl - SJU San Juan Luis Munoz Marin Intl

MAFSJU

Midland Intl

Mon 10/5

7:55 am-10:02 pm

2 stops13h 07m

San Juan Luis Munoz Marin Intl

Fri 10/9

6:00 am-9:34 pm

1 stop16h 34m

$483

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first

How to get the cheapest flight ticket from Midland to Caribbean

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?

In general, October is the cheapest month to fly from Midland to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $430. If you don’t want to visit Caribbean in October, then you should wait until August to fly from Midland, when ticket prices are also cheap, with an average price of $435.

Can stopping save me money on Midland to Caribbean flights?

You could potentially save up to 47% on your flight if you consider stops on a Midland to Caribbean flight.

Cheap Midland to Caribbean flight deals and tips

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

Best Price Found	$203
Fastest flight time	7h 28m
Direct flights	None

The best one-way flight to Caribbean from Midland in the past 72 hours is $203. The best round-trip flight deal from Midland to Caribbean found on momondo in the last 72 hours is $354.

The fastest flight from Midland to Caribbean takes 7h 28m

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

Search flight deals

Frequently asked questions about flying from Midland to Caribbean

When did momondo last update prices for flights from Midland Intl Airport to Caribbean?
Prices for flights from Midland Intl Airport to Caribbean are refreshed on a daily basis.
How many operators does momondo search for flights from Midland Intl Airport to Caribbean?
As of September 2026, there are 2 operators available to choose from for flights from Midland Intl Airport to Caribbean.
How old do you have to be to fly from Midland Intl Airport to Caribbean?
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.
What documentation or ID do you need to fly to Caribbean?
The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Midland to Caribbean

Compare and see reviews for airlines that fly from Midland to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $232	Free Cancellation	Rating 7.4 10,224 reviews		Search United Airlines flights
Southwest	PriceFrom $370	Free Cancellation	Rating 8.0 4,192 reviews		Search Southwest flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Midland to Caribbean. momondo saves you time and could save you money on your trip.

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

Yes. momondo enables you to select and highlight flights to Caribbean from Midland with this policy.

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

momondo helps you find the best flight between Midland and Caribbean by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are not ready to book a flight from Midland to Caribbean now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean and let you know when they change.