What airlines fly to Caribbean?

American Airlines, United Airlines and Southwest 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 49% 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.

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 January 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.

$231 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.

12:02 pm - 8:38 pm

MAF

SJU

7h 36m

1 stop

7:20 am - 10:55 pm

SJU

MAF

16h 35m

2 stops

$260United Airlines

lun., may. 4 - vie., may. 8

12:07 pm - 9:26 pm

MAF

SJU

7h 19m

1 stop

8:30 am - 10:03 pm

SJU

MAF

15h 33m

2 stops

$280United Airlines

lun., mar. 2 - mié., mar. 4

9:43 am - 9:26 pm

MAF

SJU

9h 43m

1 stop

3:46 pm - 11:15 pm

SJU

MAF

9h 29m

1 stop

$350United Airlines

lun., mar. 2 - mié., mar. 4

2:55 pm - 12:40 am

MAF

SJU

7h 45m

2 stops

5:40 am - 4:15 pm

SJU

MAF

12h 35m

2 stops

$352Southwest

lun., mar. 2 - mié., mar. 4

1:00 pm - 11:25 pm

MAF

SJU

9h 25m

2 stops

6:50 am - 9:45 pm

SJU

MAF

15h 55m

2 stops

$373Southwest

lun., may. 4 - vie., may. 8

2:35 pm - 12:25 am

MAF

SJU

8h 50m

1 stop

5:00 am - 3:20 pm

SJU

MAF

11h 20m

2 stops

$464Southwest

vie., jun. 12 - jue., jun. 18

8:29 pm - 3:13 pm

MAF

SJU

16h 44m

1 stop

7:01 pm - 8:48 am

SJU

MAF

15h 47m

2 stops

$596American Airlines

vie., feb. 27 - lun., mar. 2

6:00 am - 10:59 pm

MAF

SDQ

15h 59m

2 stops

7:00 am - 12:12 am

SDQ

MAF

18h 12m

2 stops

$689American Airlines

sáb., may. 30 - sáb., jul. 18

9:18 am - 10:07 am

MAF

MBJ

23h 49m

2 stops

2:33 pm - 9:42 am

MBJ

MAF

20h 09m

2 stops

$712American Airlines

sáb., feb. 14 - sáb., feb. 21

6:20 pm - 2:04 pm

MAF

MBJ

19h 44m

1 stop

3:04 pm - 6:11 pm

MBJ

MAF

27h 07m

1 stop

$834American Airlines

sáb., mar. 14 - lun., mar. 30

Southwest flights from Midland to Caribbean

Our best Southwest deals on Midland to Caribbean flight tickets

Southwest

Mar 2

MAF2:55 pmMidland Intl

7h 45m

2 stops

SJU12:40 amSan Juan Luis Munoz Marin Intl

Mar 4

SJU5:40 amSan Juan Luis Munoz Marin Intl

12h 35m

2 stops

MAF4:15 pmMidland Intl

$352

Southwest

May 4

MAF1:00 pmMidland Intl

9h 25m

2 stops

SJU11:25 pmSan Juan Luis Munoz Marin Intl

May 8

SJU6:50 amSan Juan Luis Munoz Marin Intl

15h 55m

2 stops

MAF9:45 pmMidland Intl

$373

Southwest

Jun 12

MAF2:35 pmMidland Intl

8h 50m

1 stop

SJU12:25 amSan Juan Luis Munoz Marin Intl

Jun 18

SJU5:00 amSan Juan Luis Munoz Marin Intl

11h 20m

2 stops

MAF3:20 pmMidland Intl

$464

United Airlines flights from Midland to Caribbean

Our best United Airlines deals on Midland to Caribbean flight tickets

United Airlines

May 4

MAF12:02 pmMidland Intl

7h 36m

1 stop

SJU8:38 pmSan Juan Luis Munoz Marin Intl

May 8

SJU7:20 amSan Juan Luis Munoz Marin Intl

16h 35m

2 stops

MAF10:55 pmMidland Intl

$260

United Airlines

Mar 2

MAF12:07 pmMidland Intl

7h 19m

1 stop

SJU9:26 pmSan Juan Luis Munoz Marin Intl

Mar 4

SJU8:30 amSan Juan Luis Munoz Marin Intl

15h 33m

2 stops

MAF10:03 pmMidland Intl

$280

United Airlines

Mar 2

MAF9:43 amMidland Intl

9h 43m

1 stop

SJU9:26 pmSan Juan Luis Munoz Marin Intl

Mar 4

SJU3:46 pmSan Juan Luis Munoz Marin Intl

9h 29m

1 stop

MAF11:15 pmMidland Intl

$350

Fly from

Fly to

Route

Depart

Return

Price

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

lun. 5/4

12:02 pm-8:38 pm

1 stop7h 36m

San Juan Luis Munoz Marin Intl

vie. 5/8

7:20 am-10:55 pm

2 stops16h 35m

$260

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

lun. 3/2

12:07 pm-9:26 pm

1 stop7h 19m

San Juan Luis Munoz Marin Intl

mié. 3/4

8:30 am-10:03 pm

2 stops15h 33m

$280

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

lun. 3/2

9:43 am-9:26 pm

1 stop9h 43m

San Juan Luis Munoz Marin Intl

mié. 3/4

3:46 pm-11:15 pm

1 stop9h 29m

$350

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

lun. 3/2

2:55 pm-12:40 am

2 stops7h 45m

San Juan Luis Munoz Marin Intl

mié. 3/4

5:40 am-4:15 pm

2 stops12h 35m

$352

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

lun. 5/4

1:00 pm-11:25 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

vie. 5/8

6:50 am-9:45 pm

2 stops15h 55m

$373

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

vie. 6/12

2:35 pm-12:25 am

1 stop8h 50m

San Juan Luis Munoz Marin Intl

jue. 6/18

5:00 am-3:20 pm

2 stops11h 20m

$464

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

vie. 2/27

8:29 pm-3:13 pm

1 stop16h 44m

San Juan Luis Munoz Marin Intl

lun. 3/2

7:01 pm-8:48 am

2 stops15h 47m

$596

MidlandSanto Domingo

MAF - SDQ

MAFSDQ

Midland Intl

sáb. 5/30

6:00 am-10:59 pm

2 stops15h 59m

Santo Domingo Las Americas

sáb. 7/18

7:00 am-12:12 am

2 stops18h 12m

$689

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

sáb. 2/14

9:18 am-10:07 am

2 stops23h 49m

Montego Bay Sangster Intl

sáb. 2/21

2:33 pm-9:42 am

2 stops20h 09m

$712

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

sáb. 3/14

6:20 pm-2:04 pm

1 stop19h 44m

Montego Bay Sangster Intl

lun. 3/30

3:04 pm-6:11 pm

1 stop27h 07m

$834

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

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, April 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 $395. If you don’t want to visit Caribbean in April, then you should wait until October to fly from Midland, when ticket prices are also cheap, with an average price of $456.

Can stopping save me money on Midland to Caribbean flights?

You could potentially save up to 54% 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	7h 36m
Direct flights	None

The fastest flight from Midland to Caribbean takes 7h 36m

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

Search flight deals

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 January 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
American Airlines	PriceFrom $307	Free Cancellation	Rating 7.2 11,205 reviews	Search American Airlines flights
United Airlines	PriceFrom $353	Free Cancellation	Rating 7.4 9,215 reviews	Search United Airlines flights
Southwest	PriceFrom $520	Free Cancellation	Rating 8.0 4,267 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.