Find flights
Deals
When to book
FAQs & Tips
Airlines

$214 Find cheap flights from Midland to Caribbean Islands

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midland to Caribbean Islands departing on 9/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 7/13
Sat 7/20

Search hundreds of travel sites at once for deals on flights to Caribbean Islands

In the last 7 days travelers have searched 44,148,666 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Montego Bay
Montego Bay2 stops$620

Good to know

Low season

October

High season

June

Cheapest flight

$214
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Midland to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Midland to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Midland to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Midland to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean Islands from Midland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Midland to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Caribbean Islands with an airline and back to Midland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Midland to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Caribbean Islands from Midland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airlines flying from Midland to Caribbean Islands

Need help choosing which airline to fly with from Midland to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 10000 reviews
7.2Comfort
8.1Crew
6.7Food
7.1Entertainment
7.7Boarding
Airline reviews

Lady was a bit rude during boarding and I was being nice to her.

8.0 ExcellentMital, Jun 2024IAH - PUJ
Read more about United Airlines reviews

Lady was a bit rude during boarding and I was being nice to her.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

My seat was broken. WiFi didn’t work. Gate crew at HOU were rude and condescending. Treated all the passengers badly. Bad experience, United.

Food wasn’t very good, old business seating configuration on an old A340

Not a fan of the diagonal partially enclosed business class seats or how they have to be converted to beds manually by crew. I prefer more isolation and user control for switching to lie flat.

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

There was a group of school age passengers that were very loud and unruly with their chaperones were no where to be found.

On time every leg of the journey and exceptional staff at counter, gate, and on board. I haven’t travelled in US for a long time and was genuinely surprised how pleasant this was.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

Nothing, terrible travel experience due to weather and maintenance delays and was left stranded in Austin.

Experience was bad. 3.5 hour delay for a 2.5 hour trip. There was no r Transparency about the reason for the delay and it was done 30 mins at a time.

Everything was great except for the wifi was junk. Crew was super friendly and helpful

The flight was short. However, my bag was delayed and was put on another flight.

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

Flight was cancelled had to move to another gate late again no internet paid for the month and never can use it waste of money

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

Missed the flight because of them and up geting a rental car

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Book cheap flights from Midland to Caribbean Islands

Recent round-trip flight deals

9/6Fri
1 stopAmerican Airlines
7h 40mMAF-SJU
9/12Thu
2 stopsAmerican Airlines
17h 45mSJU-MAF
$214
8/30Fri
2 stopsAmerican Airlines
17h 46mMAF-SJU
9/2Mon
2 stopsAmerican Airlines
17h 38mSJU-MAF
$254
9/6Fri
1 stopAmerican Airlines
7h 40mMAF-SJU
9/12Thu
1 stopAmerican Airlines
8h 06mSJU-MAF
$299
7/12Fri
1 stopAmerican Airlines
9h 36mMAF-SJU
7/18Thu
1 stopAmerican Airlines
15h 46mSJU-MAF
$423
7/12Fri
2 stopsAmerican Airlines
19h 14mMAF-SJU
7/18Thu
1 stopAmerican Airlines
9h 17mSJU-MAF
$424
9/6Fri
2 stopsUnited Airlines
18h 30mMAF-SJU
9/11Wed
2 stopsUnited Airlines
13h 47mSJU-MAF
$530
9/6Fri
1 stopUnited Airlines
9h 19mMAF-SJU
9/11Wed
2 stopsUnited Airlines
16h 06mSJU-MAF
$531
7/9Tue
1 stopUnited Airlines
8h 22mMAF-MBJ
7/16Tue
2 stopsUnited Airlines
31h 17mMBJ-MAF
$744
7/3Wed
2 stopsDelta
14h 14mMAF-SJU
7/7Sun
2 stopsDelta
17h 25mSJU-MAF
$1,024
7/17Wed
2 stopsDelta
14h 13mMAF-SJU
7/21Sun
2 stopsDelta
17h 23mSJU-MAF
$1,054

Search by stops

Search by airline

Search by price

Recent one-way flight deals

11/22Fri
1 stopAmerican Airlines
10h 45mMAF-SJU
$542
11/22Fri
2 stopsDelta
15h 33mMAF-SJU
$607

Search by stops

Search by airline

Search by price

Last minute flights from Midland to Caribbean Islands

Last minute flight, train and bus deals

6/18Tue
multi-stopAmerican Airlines
15h 21mMAF-SJU
6/29Sat
multi-stopAmerican Airlines
11h 53mSJU-MAF
$594
6/18Tue
multi-stopAmerican Airlines
13h 35mMAF-SJU
6/29Sat
multi-stopAmerican Airlines
14h 22mSJU-MAF
$634
6/15Sat
multi-stopAmerican Airlines
15h 39mMAF-SJU
6/17Mon
multi-stopAmerican Airlines
14h 22mSJU-MAF
$688
6/14Fri
multi-stopAmerican Airlines
10h 52mMAF-SJU
6/16Sun
multi-stopAmerican Airlines
10h 58mSJU-MAF
$748
6/14Fri
multi-stopAmerican Airlines
8h 42mMAF-SJU
6/16Sun
multi-stopAmerican Airlines
13h 01mSJU-MAF
$789
6/14Fri
multi-stopAmerican Airlines
17h 46mMAF-SJU
6/16Sun
multi-stopAmerican Airlines
13h 51mSJU-MAF
$814
6/14Fri
multi-stopDelta
14h 15mMAF-SJU
6/16Sun
multi-stopDelta
10h 24mSJU-MAF
$874
6/18Tue
multi-stopUnited Airlines
13h 27mMAF-SJU
6/28Fri
multi-stopUnited Airlines
16h 28mSJU-MAF
$905
6/14Fri
multi-stopUnited Airlines
9h 58mMAF-SJU
6/16Sun
multi-stopUnited Airlines
11h 33mSJU-MAF
$924
6/18Tue
multi-stopUnited Airlines
9h 42mMAF-SJU
6/28Fri
multi-stopUnited Airlines
16h 28mSJU-MAF
$928

Search by stops

Search by airline

Search by price

Midland - Caribbean Islands Flights

Departure:

Midland (MAF)United States

Cabin classes:

$372
$436
$996
$106