What airlines fly to Caribbean Islands?

Southwest, Frontier and American Airlines are the top three most popular airlines that fly to Caribbean Islands from Maryland according to our data. Southwest is the first choice among our users, with 36% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 6 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

How many flights depart from Maryland to Caribbean Islands on average per week?

183 flights are operational weekly from Maryland to Caribbean Islands as of June 2026. The most popular departure day for this route is Sat, with 17% of flights per week taking off on this day.

How many flights depart from Maryland to Caribbean Islands on average per day?

The number of flights available between Maryland and Caribbean Islands is 26 per day as of June 2026. The most frequent departure time is 8:00AM, with 77% of daily flights leaving at noon.

What is the cheapest airline that flies from Maryland to Caribbean Islands?

Southwest, JetBlue, and United Airlines are the most popular carriers operating from Maryland to Caribbean Islands

When did momondo last update prices for flights from Maryland to Caribbean Islands?

Prices for flights from Maryland to Caribbean Islands are updated daily.

How many operators does momondo search for flights from Maryland to Caribbean Islands?

The number of operators available for flights from Maryland to Caribbean Islands is 9 as of June 2026.

How old do you have to be to fly from Maryland to Caribbean Islands?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maryland 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.

$90 Cheap Flights from Maryland to Caribbean Islands in 2026

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Find the cheapest flights from Maryland to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:41 am - 3:41 pm

PHL

SJU

4h 00mnonstop

2:36 pm - 6:42 pm

SJU

PHL

4h 06mnonstop

$197Frontier

Mon, Aug 31 - Thu, Sep 3

11:59 pm - 3:57 am

PHL

SJU

3h 58mnonstop

2:36 pm - 6:42 pm

SJU

PHL

4h 06mnonstop

$201Frontier

Mon, Aug 31 - Sat, Sep 5

3:11 pm - 11:59 pm

DCA

SJU

8h 48m

1 stop

10:33 am - 10:10 pm

SJU

DCA

11h 37m

1 stop

$271American Airlines

Tue, Sep 1 - Wed, Sep 2

6:10 am - 2:51 pm

IAD

SJU

8h 41m

1 stop

3:47 pm - 10:55 pm

SJU

IAD

7h 08m

1 stop

$276American Airlines

Sat, Aug 22 - Thu, Aug 27

11:55 am - 10:00 pm

DCA

SJU

10h 05m

2 stops

8:20 am - 4:05 pm

SJU

DCA

7h 45m

1 stop

$296Southwest

Tue, Sep 1 - Wed, Sep 2

6:00 am - 1:35 pm

DCA

SJU

7h 35m

1 stop

6:30 am - 2:40 pm

SJU

DCA

8h 10m

2 stops

$301Southwest

Tue, Sep 1 - Thu, Sep 3

8:00 am - 3:27 pm

BWI

PUJ

7h 27m

1 stop

4:41 pm - 11:27 pm

PUJ

BWI

6h 46m

1 stop

$363JetBlue

Fri, Aug 28 - Thu, Sep 3

6:09 am - 12:55 pm

BWI

PUJ

6h 46m

1 stop

2:05 pm - 11:27 pm

PUJ

BWI

9h 22m

1 stop

$369JetBlue

Fri, Aug 28 - Thu, Sep 3

6:45 am - 10:42 am

PHL

PUJ

3h 57mnonstop

1:50 pm - 11:53 pm

PUJ

PHL

10h 03m

1 stop

$399Multiple Airlines

Tue, Jul 14 - Sun, Jul 19

8:03 pm - 8:19 pm

PHL

PUJ

24h 16m

1 stop

1:50 pm - 10:29 pm

PUJ

PHL

8h 39m

1 stop

$403Multiple Airlines

Tue, Jul 14 - Sun, Jul 19

Southwest flights from Maryland to Caribbean Islands

Our best Southwest deals on Maryland to Caribbean Islands flight tickets

Southwest

Aug 22

DCA11:45 amWashington, D.C. Reagan-National

6h 30m

1 stop

SJU6:15 pmSan Juan Luis Munoz Marin Intl

Aug 28

SJU6:30 amSan Juan Luis Munoz Marin Intl

8h 10m

2 stops

DCA2:40 pmWashington, D.C. Reagan-National

$301

Southwest

Aug 12

DCA11:55 amWashington, D.C. Reagan-National

10h 05m

2 stops

SJU10:00 pmSan Juan Luis Munoz Marin Intl

Aug 13

SJU6:00 amSan Juan Luis Munoz Marin Intl

6h 50m

1 stop

DCA12:50 pmWashington, D.C. Reagan-National

$306

Southwest

Aug 10

DCA12:15 pmWashington, D.C. Reagan-National

9h 55m

2 stops

SJU10:10 pmSan Juan Luis Munoz Marin Intl

Aug 14

SJU6:00 amSan Juan Luis Munoz Marin Intl

6h 50m

1 stop

DCA12:50 pmWashington, D.C. Reagan-National

$311

Frontier flights from Maryland to Caribbean Islands

Our best Frontier deals on Maryland to Caribbean Islands flight tickets

Frontier

Aug 31

PHL11:59 pmPhiladelphia

3h 58m

SJU3:57 amSan Juan Luis Munoz Marin Intl

Sep 5

SJU2:36 pmSan Juan Luis Munoz Marin Intl

4h 06m

PHL6:42 pmPhiladelphia

$197

Frontier

Aug 31

PHL11:59 pmPhiladelphia

3h 58m

SJU3:57 amSan Juan Luis Munoz Marin Intl

Sep 5

SJU2:36 pmSan Juan Luis Munoz Marin Intl

4h 06m

PHL6:42 pmPhiladelphia

$201

Frontier

Aug 28

PHL7:47 pmPhiladelphia

4h 10m

SJU11:57 pmSan Juan Luis Munoz Marin Intl

Sep 4

SJU6:45 pmSan Juan Luis Munoz Marin Intl

4h 07m

PHL10:52 pmPhiladelphia

$203

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 8/31

11:41 am-3:41 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 9/3

2:36 pm-6:42 pm

Nonstop4h 06m

$197

Quickest round-trip

PhiladelphiaSan Juan

PHL - SJU

PHLSJU

Philadelphia

Mon 8/31

11:59 pm-3:57 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Sat 9/5

2:36 pm-6:42 pm

Nonstop4h 06m

$201

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 9/1

3:11 pm-11:59 pm

1 stop8h 48m

San Juan Luis Munoz Marin Intl

Wed 9/2

10:33 am-10:10 pm

1 stop11h 37m

$271

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sat 8/22

6:10 am-2:51 pm

1 stop8h 41m

San Juan Luis Munoz Marin Intl

Thu 8/27

3:47 pm-10:55 pm

1 stop7h 08m

$276

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 9/1

11:55 am-10:00 pm

2 stops10h 05m

San Juan Luis Munoz Marin Intl

Wed 9/2

8:20 am-4:05 pm

1 stop7h 45m

$296

Washington, D.C.San Juan

DCA - SJU

DCASJU

Washington, D.C. Reagan-National

Tue 9/1

6:00 am-1:35 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Thu 9/3

6:30 am-2:40 pm

2 stops8h 10m

$301

BaltimorePunta Cana

BWI - PUJ

BWIPUJ

Baltimore/Washington

Fri 8/28

8:00 am-3:27 pm

1 stop7h 27m

Punta Cana

Thu 9/3

4:41 pm-11:27 pm

1 stop6h 46m

$363

BaltimorePunta Cana

BWI - PUJ

BWIPUJ

Baltimore/Washington

Fri 8/28

6:09 am-12:55 pm

1 stop6h 46m

Punta Cana

Thu 9/3

2:05 pm-11:27 pm

1 stop9h 22m

$369

PhiladelphiaPunta Cana

PHL - PUJ

PHLPUJ

Philadelphia

Tue 7/14

6:45 am-10:42 am

Nonstop3h 57m

Punta Cana

Sun 7/19

1:50 pm-11:53 pm

1 stop10h 03m

$399

PhiladelphiaPunta Cana

PHL - PUJ

PHLPUJ

Philadelphia

Tue 7/14

8:03 pm-8:19 pm

1 stop24h 16m

Punta Cana

Sun 7/19

1:50 pm-10:29 pm

1 stop8h 39m

$403

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 Maryland 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

Other information

What is the cheapest month to fly to Caribbean Islands?

The month of August is, on average, the cheapest month to fly to Caribbean Islands from Maryland, with most prices found around $552. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Maryland averaging around $586.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Maryland to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $319. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $425. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is at noon. momondo users have found flights departing from Maryland to Caribbean Islands at noon for as low as $315. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the evening because they tend to be around $406. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Maryland to Caribbean Islands flight route?

Fly from Baltimore/Washington to San Juan Luis Munoz Marin Intl for the best Maryland - Caribbean Islands flight prices

How far in advance should I book a flight from Maryland to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Maryland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $401 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Maryland for as low as $335 on momondo.

What cabin class options are available on Maryland to Caribbean Islands flights?

There are 4 cabin classes available to choose from on Maryland to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

No. A direct flight is the cheapest option for a flight between Maryland to Caribbean Islands.

Cheap Maryland to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maryland to Caribbean Islands

Fastest flight time	2h 30m
Direct flights	Every day
Airports in Caribbean Islands	99 airports

The fastest flight from Maryland to Caribbean Islands takes 2h 30m

Direct flights go from Maryland to Caribbean Islands every day.

There are 99 airports in Caribbean Islands. From Maryland there are direct flights to Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), San Juan Luis Munoz Marin Intl (SJU).

Search flight deals

Frequently asked questions about flying from Maryland to Caribbean Islands

When did momondo last update prices for flights from Maryland to Caribbean Islands?
Prices for flights from Maryland to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Maryland to Caribbean Islands?
The number of operators available for flights from Maryland to Caribbean Islands is 9 as of June 2026.
How old do you have to be to fly from Maryland to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maryland 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 Maryland to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Maryland to Caribbean Islands is Boeing 737 MAX 8, representing 17.86% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 11.01%, Airbus A321neo at 8.79%, and Airbus A320-100/200 at 8.22%.

Best airlines flying from Maryland to Caribbean Islands

Compare and see reviews for airlines that fly from Maryland to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $135	Free Cancellation	Rating 7.9 8,396 reviews	Search Delta flights
JetBlue	PriceFrom $146	Free Cancellation	Rating 7.1 2,977 reviews	Search JetBlue flights
Frontier	PriceFrom $160	Free Cancellation	Rating 5.6 2,906 reviews	Search Frontier flights
United Airlines	PriceFrom $172	Free Cancellation	Rating 7.4 9,780 reviews	Search United Airlines flights
American Airlines	PriceFrom $225	Free Cancellation	Rating 7.1 11,642 reviews	Search American Airlines flights
Southwest	PriceFrom $376	Free Cancellation	Rating 7.9 4,251 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Maryland to Caribbean Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Maryland to Caribbean Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Maryland to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean Islands from Maryland with this policy.

How can momondo help me find flights from Maryland to Caribbean Islands?

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Maryland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Maryland to Caribbean Islands right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Maryland to Caribbean Islands flights. All you need is a valid email address and we will do the rest; it is that quick and easy.