What airlines fly to Caribbean Islands?

American Airlines, Southwest and United Airlines are the top three most popular airlines that fly to Caribbean Islands from Midland according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 3 different airlines that fly to Caribbean Islands 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 Islands?

United Airlines, American Airlines, and Southwest 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 March 2026, there are 3 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.

$165 Cheap Flights from Midland to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

6:16 pm - 9:13 am

MAF

SJU

13h 57m

2 stops

7:00 pm - 9:42 am

SJU

MAF

15h 42m

2 stops

$332American Airlines

Mon, May 4 - Tue, May 5

2:15 pm - 11:02 pm

MAF

SJU

7h 47m

1 stop

11:59 pm - 9:42 am

SJU

MAF

10h 43m

1 stop

$337American Airlines

Mon, May 4 - Sat, May 9

9:41 am - 8:38 pm

MAF

SJU

9h 57m

1 stop

1:00 am - 12:52 pm

SJU

MAF

12h 52m

2 stops

$350United Airlines

Sun, Apr 12 - Fri, Apr 17

8:23 pm - 4:14 pm

MAF

MBJ

19h 51m

1 stop

12:47 pm - 11:59 pm

MBJ

MAF

11h 12m

1 stop

$358American Airlines

Fri, Jul 31 - Thu, Aug 6

8:23 pm - 4:14 pm

MAF

MBJ

19h 51m

1 stop

3:20 pm - 9:56 am

MBJ

MAF

18h 36m

2 stops

$363American Airlines

Fri, Jul 31 - Thu, Aug 6

7:00 am - 1:30 pm

MAF

MBJ

6h 30m

1 stop

2:40 pm - 11:15 pm

MBJ

MAF

8h 35m

1 stop

$391United Airlines

Sun, May 3 - Sun, May 10

12:46 pm - 11:02 pm

MAF

SJU

9h 16m

1 stop

6:45 am - 12:06 am

SJU

MAF

18h 21m

1 stop

$400American Airlines

Sun, Apr 12 - Sat, Apr 18

9:41 am - 8:38 pm

MAF

SJU

9h 57m

1 stop

1:40 pm - 10:15 pm

SJU

MAF

9h 35m

1 stop

$420United Airlines

Mon, May 4 - Wed, May 6

1:00 pm - 11:55 pm

MAF

SJU

9h 55m

2 stops

11:15 am - 9:00 pm

SJU

MAF

10h 45m

2 stops

$440Southwest

Mon, May 4 - Sat, May 9

12:25 pm - 11:45 pm

MAF

SJU

10h 20m

2 stops

6:25 am - 4:00 pm

SJU

MAF

10h 35m

2 stops

$493Southwest

Sun, Apr 12 - Sat, Apr 18

United Airlines flights from Midland to Caribbean Islands

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

United Airlines

Apr 12

MAF9:41 amMidland Intl

9h 57m

1 stop

SJU8:38 pmSan Juan Luis Munoz Marin Intl

Apr 17

SJU1:00 amSan Juan Luis Munoz Marin Intl

12h 52m

2 stops

MAF12:52 pmMidland Intl

$350

United Airlines

May 3

MAF7:00 amMidland Intl

6h 30m

1 stop

MBJ1:30 pmMontego Bay Sangster Intl

May 10

MBJ2:40 pmMontego Bay Sangster Intl

8h 35m

1 stop

MAF11:15 pmMidland Intl

$391

United Airlines

May 4

MAF9:41 amMidland Intl

9h 57m

1 stop

SJU8:38 pmSan Juan Luis Munoz Marin Intl

May 6

SJU1:40 pmSan Juan Luis Munoz Marin Intl

9h 35m

1 stop

MAF10:15 pmMidland Intl

$420

American Airlines flights from Midland to Caribbean Islands

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

American Airlines

May 4

MAF6:16 pmMidland Intl

13h 57m

2 stops

SJU9:13 amSan Juan Luis Munoz Marin Intl

May 5

SJU7:00 pmSan Juan Luis Munoz Marin Intl

15h 42m

2 stops

MAF9:42 amMidland Intl

$332

American Airlines

May 4

MAF6:16 pmMidland Intl

13h 57m

2 stops

SJU9:13 amSan Juan Luis Munoz Marin Intl

May 9

SJU11:59 pmSan Juan Luis Munoz Marin Intl

9h 46m

1 stop

MAF8:45 amMidland Intl

$337

American Airlines

Jul 31

MAF8:23 pmMidland Intl

19h 51m

1 stop

MBJ4:14 pmMontego Bay Sangster Intl

Aug 6

MBJ12:47 pmMontego Bay Sangster Intl

11h 12m

1 stop

MAF11:59 pmMidland Intl

$358

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 5/4

6:16 pm-9:13 am

2 stops13h 57m

San Juan Luis Munoz Marin Intl

Tue 5/5

7:00 pm-9:42 am

2 stops15h 42m

$332

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 5/4

2:15 pm-11:02 pm

1 stop7h 47m

San Juan Luis Munoz Marin Intl

Sat 5/9

11:59 pm-9:42 am

1 stop10h 43m

$337

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sun 4/12

9:41 am-8:38 pm

1 stop9h 57m

San Juan Luis Munoz Marin Intl

Fri 4/17

1:00 am-12:52 pm

2 stops12h 52m

$350

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Fri 7/31

8:23 pm-4:14 pm

1 stop19h 51m

Montego Bay Sangster Intl

Thu 8/6

12:47 pm-11:59 pm

1 stop11h 12m

$358

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Fri 7/31

8:23 pm-4:14 pm

1 stop19h 51m

Montego Bay Sangster Intl

Thu 8/6

3:20 pm-9:56 am

2 stops18h 36m

$363

Quickest round-trip

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Sun 5/3

7:00 am-1:30 pm

1 stop6h 30m

Montego Bay Sangster Intl

Sun 5/10

2:40 pm-11:15 pm

1 stop8h 35m

$391

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sun 4/12

12:46 pm-11:02 pm

1 stop9h 16m

San Juan Luis Munoz Marin Intl

Sat 4/18

6:45 am-12:06 am

1 stop18h 21m

$400

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 5/4

9:41 am-8:38 pm

1 stop9h 57m

San Juan Luis Munoz Marin Intl

Wed 5/6

1:40 pm-10:15 pm

1 stop9h 35m

$420

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 5/4

1:00 pm-11:55 pm

2 stops9h 55m

San Juan Luis Munoz Marin Intl

Sat 5/9

11:15 am-9:00 pm

2 stops10h 45m

$440

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Sun 4/12

12:25 pm-11:45 pm

2 stops10h 20m

San Juan Luis Munoz Marin Intl

Sat 4/18

6:25 am-4:00 pm

2 stops10h 35m

$493

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 April is, on average, the cheapest month to fly to Caribbean Islands from Midland, with most prices found around $395. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Midland averaging around $456.

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

You could potentially save up to 27% on your flight if you consider stops on a Midland to Caribbean Islands flight.

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	9h 40m
Direct flights	None

The fastest flight from Midland to Caribbean Islands takes 9h 40m

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?
As of March 2026, there are 3 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 20.70% of the total bookings. Other popular models include Boeing 737 MAX 8 with 12.42%, Boeing 737-800 with 10.83%, and Canadair (Bombardier) Regional Jet 700 with 8.92%.

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 9,467 reviews	Search United Airlines flights
American Airlines	PriceFrom $307	Free Cancellation	Rating 7.1 11,492 reviews	Search American Airlines flights
Southwest	PriceFrom $461	Free Cancellation	Rating 8.0 4,328 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.