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

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

What airlines fly to Caribbean?

American Airlines, Southwest and United Airlines are the top three most popular airlines that fly to Caribbean from Midland according to our data. American Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 3 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

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 May 2026, there are 3 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.

$288 Cheap Flights from Midland to Caribbean in 2026

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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.

9:55 am - 10:15 pm

MAF

SJU

11h 20m

2 stops

5:00 am - 1:30 pm

SJU

MAF

9h 30m

2 stops

$426Southwest

Fri, Aug 28 - Mon, Aug 31

7:13 pm - 5:29 am

MAF

SJU

9h 16m

1 stop

2:05 am - 8:52 am

SJU

MAF

7h 47m

1 stop

$458United Airlines

Mon, Jun 1 - Wed, Jun 3

5:18 pm - 3:10 pm

MAF

MBJ

21h 52m

2 stops

12:52 pm - 7:39 pm

MBJ

MAF

30h 47m

2 stops

$514United Airlines

Tue, Jun 9 - Tue, Jun 16

5:18 pm - 5:29 am

MAF

SJU

11h 11m

2 stops

2:05 am - 8:52 am

SJU

MAF

7h 47m

1 stop

$524United Airlines

Mon, Jun 1 - Wed, Jun 3

11:35 am - 12:34 pm

MAF

SJU

23h 59m

2 stops

1:00 am - 1:34 pm

SJU

MAF

13h 34m

2 stops

$570United Airlines

Mon, Jun 1 - Wed, Jun 3

8:23 pm - 1:31 pm

MAF

MBJ

17h 08m

2 stops

5:14 pm - 2:09 pm

MBJ

MAF

20h 55m

2 stops

$604American Airlines

Thu, Jul 9 - Mon, Jul 13

8:23 pm - 4:14 pm

MAF

MBJ

19h 51m

1 stop

5:14 pm - 2:09 pm

MBJ

MAF

20h 55m

2 stops

$611American Airlines

Thu, Jul 9 - Mon, Jul 13

10:35 am - 11:25 pm

MAF

SJU

11h 50m

2 stops

6:30 am - 5:25 pm

SJU

MAF

11h 55m

2 stops

$611Southwest

Mon, Jun 1 - Thu, Jun 4

5:31 pm - 9:43 am

MAF

SJU

15h 12m

2 stops

3:44 pm - 8:51 am

SJU

MAF

18h 07m

1 stop

$636American Airlines

Fri, Aug 28 - Mon, Aug 31

8:23 pm - 1:31 pm

MAF

MBJ

17h 08m

2 stops

2:08 pm - 8:51 am

MBJ

MAF

18h 43m

2 stops

$646American Airlines

Mon, Jun 15 - Mon, Jun 22

United Airlines flights from Midland to Caribbean

Our best United Airlines deals on Midland to Caribbean flight tickets

United Airlines

Jun 1

MAF7:13 pmMidland Intl

9h 16m

1 stop

SJU5:29 amSan Juan Luis Munoz Marin Intl

Jun 3

SJU2:05 amSan Juan Luis Munoz Marin Intl

7h 47m

1 stop

MAF8:52 amMidland Intl

$458

United Airlines

Jun 9

MAF5:18 pmMidland Intl

21h 52m

2 stops

MBJ3:10 pmMontego Bay Sangster Intl

Jun 16

MBJ12:52 pmMontego Bay Sangster Intl

30h 47m

2 stops

MAF7:39 pmMidland Intl

$514

United Airlines

Jun 1

MAF5:18 pmMidland Intl

11h 11m

2 stops

SJU5:29 amSan Juan Luis Munoz Marin Intl

Jun 3

SJU2:05 amSan Juan Luis Munoz Marin Intl

7h 47m

1 stop

MAF8:52 amMidland Intl

$524

American Airlines flights from Midland to Caribbean

Our best American Airlines deals on Midland to Caribbean flight tickets

American Airlines

Jul 9

MAF8:23 pmMidland Intl

17h 08m

2 stops

MBJ1:31 pmMontego Bay Sangster Intl

Jul 13

MBJ5:14 pmMontego Bay Sangster Intl

20h 55m

2 stops

MAF2:09 pmMidland Intl

$604

American Airlines

May 11

MAF12:46 pmMidland Intl

14h 46m

1 stop

SJU4:32 amSan Juan Luis Munoz Marin Intl

May 17

SJU11:59 pmSan Juan Luis Munoz Marin Intl

9h 46m

1 stop

MAF8:45 amMidland Intl

$611

American Airlines

Aug 28

MAF5:31 pmMidland Intl

15h 12m

2 stops

SJU9:43 amSan Juan Luis Munoz Marin Intl

Aug 31

SJU3:44 pmSan Juan Luis Munoz Marin Intl

18h 07m

1 stop

MAF8:51 amMidland Intl

$636

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Fri 8/28

9:55 am-10:15 pm

2 stops11h 20m

San Juan Luis Munoz Marin Intl

Mon 8/31

5:00 am-1:30 pm

2 stops9h 30m

$426

Quickest round-trip

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 6/1

7:13 pm-5:29 am

1 stop9h 16m

San Juan Luis Munoz Marin Intl

Wed 6/3

2:05 am-8:52 am

1 stop7h 47m

$458

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Tue 6/9

5:18 pm-3:10 pm

2 stops21h 52m

Montego Bay Sangster Intl

Tue 6/16

12:52 pm-7:39 pm

2 stops30h 47m

$514

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 6/1

5:18 pm-5:29 am

2 stops11h 11m

San Juan Luis Munoz Marin Intl

Wed 6/3

2:05 am-8:52 am

1 stop7h 47m

$524

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 6/1

11:35 am-12:34 pm

2 stops23h 59m

San Juan Luis Munoz Marin Intl

Wed 6/3

1:00 am-1:34 pm

2 stops13h 34m

$570

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Thu 7/9

8:23 pm-1:31 pm

2 stops17h 08m

Montego Bay Sangster Intl

Mon 7/13

5:14 pm-2:09 pm

2 stops20h 55m

$604

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Thu 7/9

8:23 pm-4:14 pm

1 stop19h 51m

Montego Bay Sangster Intl

Mon 7/13

5:14 pm-2:09 pm

2 stops20h 55m

$611

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 6/1

10:35 am-11:25 pm

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Thu 6/4

6:30 am-5:25 pm

2 stops11h 55m

$611

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Fri 8/28

5:31 pm-9:43 am

2 stops15h 12m

San Juan Luis Munoz Marin Intl

Mon 8/31

3:44 pm-8:51 am

1 stop18h 07m

$636

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Mon 6/15

8:23 pm-1:31 pm

2 stops17h 08m

Montego Bay Sangster Intl

Mon 6/22

2:08 pm-8:51 am

2 stops18h 43m

$646

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 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, May 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 $232. If you don’t want to visit Caribbean in May, then you should wait until October to fly from Midland, when ticket prices are also cheap, with an average price of $307.

Can stopping save me money on Midland to Caribbean flights?

You could potentially save up to 13% 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

Fastest flight time	8h 55m
Direct flights	None

The fastest flight from Midland to Caribbean takes 8h 55m

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 May 2026, there are 3 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 9,680 reviews	Search United Airlines flights
American Airlines	PriceFrom $307	Free Cancellation	Rating 7.1 11,673 reviews	Search American Airlines flights
Southwest	PriceFrom $428	Free Cancellation	Rating 7.9 4,307 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.