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 43% 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?

Southwest 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 May 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.

$205 Cheap Flights from Midland to Caribbean Islands in 2026

1 adult

0 bags

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.

12:25 pm - 10:00 pm

MAF

SJU

8h 35m

2 stops

8:55 pm - 10:55 am

SJU

MAF

15h 00m

2 stops

$442Southwest

Tue, Aug 11 - Fri, Aug 14

5:00 am - 3:42 pm

MAF

SJU

9h 42m

1 stop

7:00 am - 4:12 pm

SJU

MAF

10h 12m

1 stop

$455United Airlines

Tue, Aug 11 - Fri, Aug 14

2:35 pm - 12:30 am

MAF

SJU

8h 55m

1 stop

6:00 am - 1:20 pm

SJU

MAF

8h 20m

2 stops

$473Southwest

Mon, Aug 3 - Mon, Aug 10

6:00 am - 2:54 pm

MAF

SJU

7h 54m

1 stop

6:00 am - 5:00 pm

SJU

MAF

12h 00m

2 stops

$474American Airlines

Tue, Aug 11 - Fri, Aug 14

2:00 pm - 11:50 pm

MAF

SJU

8h 50m

2 stops

5:00 am - 1:00 pm

SJU

MAF

9h 00m

2 stops

$493Southwest

Fri, Aug 14 - Sun, Aug 16

7:00 am - 3:42 pm

MAF

SJU

7h 42m

1 stop

2:20 pm - 9:34 pm

SJU

MAF

8h 14m

1 stop

$526United Airlines

Fri, Aug 14 - Sun, Aug 16

1:30 pm - 12:05 am

MAF

SJU

9h 35m

2 stops

6:00 am - 1:20 pm

SJU

MAF

8h 20m

2 stops

$545Southwest

Mon, Aug 3 - Mon, Aug 10

5:00 am - 11:03 pm

MAF

SJU

17h 03m

1 stop

11:55 am - 11:16 pm

SJU

MAF

12h 21m

2 stops

$556American Airlines

Tue, May 19 - Sat, May 23

5:00 am - 6:10 pm

MAF

SJU

12h 10m

2 stops

11:55 am - 11:16 pm

SJU

MAF

12h 21m

2 stops

$596American Airlines

Tue, May 19 - Sat, May 23

8:23 pm - 1:30 pm

MAF

MBJ

17h 07m

2 stops

12:47 pm - 11:59 pm

MBJ

MAF

11h 12m

1 stop

$637American Airlines

Wed, Jul 1 - Fri, Jul 17

American Airlines flights from Midland to Caribbean Islands

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

American Airlines

Aug 11

MAF6:00 amMidland Intl

7h 54m

1 stop

SJU2:54 pmSan Juan Luis Munoz Marin Intl

Aug 14

SJU6:00 amSan Juan Luis Munoz Marin Intl

12h 00m

2 stops

MAF5:00 pmMidland Intl

$474

American Airlines

May 19

MAF5:00 amMidland Intl

17h 03m

1 stop

SJU11:03 pmSan Juan Luis Munoz Marin Intl

May 23

SJU11:55 amSan Juan Luis Munoz Marin Intl

12h 21m

2 stops

MAF11:16 pmMidland Intl

$556

American Airlines

May 19

MAF5:00 amMidland Intl

12h 10m

2 stops

SJU6:10 pmSan Juan Luis Munoz Marin Intl

May 23

SJU11:55 amSan Juan Luis Munoz Marin Intl

12h 21m

2 stops

MAF11:16 pmMidland Intl

$596

Southwest flights from Midland to Caribbean Islands

Our best Southwest deals on Midland to Caribbean Islands flight tickets

Southwest

Aug 11

MAF12:25 pmMidland Intl

8h 35m

2 stops

SJU10:00 pmSan Juan Luis Munoz Marin Intl

Aug 14

SJU8:55 pmSan Juan Luis Munoz Marin Intl

15h 00m

2 stops

MAF10:55 amMidland Intl

$442

Southwest

Aug 3

MAF2:35 pmMidland Intl

8h 55m

1 stop

SJU12:30 amSan Juan Luis Munoz Marin Intl

Aug 10

SJU6:00 amSan Juan Luis Munoz Marin Intl

8h 20m

2 stops

MAF1:20 pmMidland Intl

$473

Southwest

Aug 14

MAF2:00 pmMidland Intl

8h 50m

2 stops

SJU11:50 pmSan Juan Luis Munoz Marin Intl

Aug 16

SJU5:00 amSan Juan Luis Munoz Marin Intl

9h 00m

2 stops

MAF1:00 pmMidland Intl

$493

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 8/11

12:25 pm-10:00 pm

2 stops8h 35m

San Juan Luis Munoz Marin Intl

Fri 8/14

8:55 pm-10:55 am

2 stops15h 00m

$442

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 8/11

5:00 am-3:42 pm

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Fri 8/14

7:00 am-4:12 pm

1 stop10h 12m

$455

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 8/3

2:35 pm-12:30 am

1 stop8h 55m

San Juan Luis Munoz Marin Intl

Mon 8/10

6:00 am-1:20 pm

2 stops8h 20m

$473

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 8/11

6:00 am-2:54 pm

1 stop7h 54m

San Juan Luis Munoz Marin Intl

Fri 8/14

6:00 am-5:00 pm

2 stops12h 00m

$474

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Fri 8/14

2:00 pm-11:50 pm

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Sun 8/16

5:00 am-1:00 pm

2 stops9h 00m

$493

Quickest round-trip

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Fri 8/14

7:00 am-3:42 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Sun 8/16

2:20 pm-9:34 pm

1 stop8h 14m

$526

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Mon 8/3

1:30 pm-12:05 am

2 stops9h 35m

San Juan Luis Munoz Marin Intl

Mon 8/10

6:00 am-1:20 pm

2 stops8h 20m

$545

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 5/19

5:00 am-11:03 pm

1 stop17h 03m

San Juan Luis Munoz Marin Intl

Sat 5/23

11:55 am-11:16 pm

2 stops12h 21m

$556

MidlandSan Juan

MAF - SJU

MAFSJU

Midland Intl

Tue 5/19

5:00 am-6:10 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Sat 5/23

11:55 am-11:16 pm

2 stops12h 21m

$596

MidlandMontego Bay

MAF - MBJ

MAFMBJ

Midland Intl

Wed 7/1

8:23 pm-1:30 pm

2 stops17h 07m

Montego Bay Sangster Intl

Fri 7/17

12:47 pm-11:59 pm

1 stop11h 12m

$637

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 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 November is, on average, the cheapest month to fly to Caribbean Islands from Midland, with most prices found around $0. The month of October 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?

You could potentially save up to 18% 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	7h 36m
Direct flights	None

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

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 May 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 17.03% of the total bookings. Other popular models include Boeing 737 MAX 8 with 12.64%, Canadair (Bombardier) Regional Jet 700 with 11.36%, and Boeing 737-800 with 9.16%.

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 9,692 reviews	Search United Airlines flights
American Airlines	PriceFrom $307	Free Cancellation	Rating 7.1 11,669 reviews	Search American Airlines flights
Southwest	PriceFrom $428	Free Cancellation	Rating 8.0 4,302 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.