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Cheap flight deals from Maryland to Caribbean

Round-trip from	$133 (CheapOair)
One-way from	$58 (Cheapflightsfares)
Popular in	December
Cheapest in	September
Average price	$326
Good round-trip deal	$191 or less
Good one-way deal	$114 or less

From Maryland to Caribbean

One-way flight from Maryland to Caribbean

Highest demand for flights based on searches. 10% potential increase in price ($43 potential increase over avg. RT price).

Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).

Average for round-trip flights in February 2025

Price to beat on a round-trip flight from Maryland to Caribbean.

Price to beat on a one-way flight from Maryland to Caribbean.

Best time to book a flight from Maryland to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Maryland with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Maryland to Caribbean

Get recent, data-driven insights about flights from Maryland to Caribbean including ideal travel times, pricing trends, and more.

Rainfall in Caribbean by month

Temperature in Caribbean by month

Reviews of airlines servicing Caribbean

8.1

Very good

Reviews

1 / 20

2.0

Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

8.1

Very good

8.1

Very good

Reviews

1 / 20

2.0

Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

8.0

Very good

8.1

Very good

Reviews

1 / 20

2.0

Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines

8.0

Very good

8.1

Very good

Reviews

1 / 20

2.0

Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

7.6

Good

8.1

Very good

Reviews

1 / 20

2.0

Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Maryland to Caribbean

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Complete your trip

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Find a return flight route from Caribbean

Luis Munoz Marin Intl to Philadelphia flights

Luis Munoz Marin Intl to Dulles Intl flights

Luis Munoz Marin Intl to Reagan-National flights

Luis Munoz Marin Intl to Baltimore flights

Santo Domingo to Philadelphia flights

Santo Domingo to Dulles Intl flights

Punta Cana to Philadelphia flights

Santo Domingo to Reagan-National flights

Port of Spain to Dulles Intl flights

Montego Bay to Dulles Intl flights

Montego Bay to Baltimore flights

Santo Domingo to Baltimore flights

Port of Spain to Reagan-National flights

Nassau to Reagan-National flights

Punta Cana to Dulles Intl flights

Punta Cana to Baltimore flights

Nassau to Dulles Intl flights

Montego Bay to Philadelphia flights

Port of Spain to Baltimore flights

Saint Thomas Island to Dulles Intl flights

Kingston to Baltimore flights

Oranjestad to Dulles Intl flights

Montego Bay to Reagan-National flights

Simpson Bay to Dulles Intl flights

Aguadilla to Reagan-National flights

Punta Cana to Reagan-National flights

Kingston to Philadelphia flights

Kingston to Dulles Intl flights

Nassau to Baltimore flights

Kingston to Reagan-National flights

Saint Thomas Island to Reagan-National flights

Saint Thomas Island to Baltimore flights

Santiago de los Caballeros to Dulles Intl flights

Simpson Bay to Baltimore flights

Santiago de los Caballeros to Philadelphia flights

Bridgetown to Dulles Intl flights

Simpson Bay to Reagan-National flights

Christiansted to Dulles Intl flights

Oranjestad to Baltimore flights

Port of Spain to Philadelphia flights

Oranjestad to Reagan-National flights

Santiago de los Caballeros to Reagan-National flights

Bridgetown to Reagan-National flights

Saint Thomas Island to Philadelphia flights

Nassau to Philadelphia flights

Santiago de los Caballeros to Baltimore flights

Bridgetown to Baltimore flights

Oranjestad to Philadelphia flights

Christiansted to Reagan-National flights

Christiansted to Baltimore flights

Simpson Bay to Philadelphia flights

George Town to Baltimore flights

Freeport to Baltimore flights

Aguadilla to Philadelphia flights

George Town to Dulles Intl flights

Castries to Philadelphia flights

Aguadilla to Baltimore flights

Ponce to Dulles Intl flights

Providenciales to Dulles Intl flights

St. John's to Philadelphia flights

Aguadilla to Dulles Intl flights

George Town to Reagan-National flights

Castries to Baltimore flights

Vieques to Philadelphia flights

Cap Haitien to Reagan-National flights

Port Au Prince to Philadelphia flights

St. John's to Reagan-National flights

Basseterre to Philadelphia flights

Port Au Prince to Baltimore flights

Christiansted to Philadelphia flights

Cap Haitien to Baltimore flights

Port Au Prince to Dulles Intl flights

Mayagüez to Philadelphia flights

Freeport to Reagan-National flights

Roseau to Philadelphia flights

St. George's to Reagan-National flights

Havana to Reagan-National flights

Mayagüez to Reagan-National flights

Port Au Prince to Reagan-National flights

Ponce to Reagan-National flights

Castries to Reagan-National flights

Cap Haitien to Dulles Intl flights

Willemstad to Dulles Intl flights

Freeport to Dulles Intl flights

Maryland to Caribbean flights

Philadelphia to Luis Munoz Marin Intl flights

Dulles Intl to Luis Munoz Marin Intl flights

Baltimore to Luis Munoz Marin Intl flights

Reagan-National to Luis Munoz Marin Intl flights

Dulles Intl to Punta Cana flights

Philadelphia to Punta Cana flights

Baltimore to Punta Cana flights

Dulles Intl to Montego Bay flights

Dulles Intl to Oranjestad flights

Dulles Intl to Saint Thomas Island flights

Baltimore to Montego Bay flights

Reagan-National to Punta Cana flights

Philadelphia to Oranjestad flights

Philadelphia to Montego Bay flights

Reagan-National to Montego Bay flights

Dulles Intl to Nassau flights

Reagan-National to Nassau flights

Baltimore to Oranjestad flights

Reagan-National to Saint Thomas Island flights

Baltimore to Saint Thomas Island flights

Dulles Intl to Providenciales flights

Philadelphia to Nassau flights

Reagan-National to Oranjestad flights

Baltimore to Nassau flights

Dulles Intl to Simpson Bay flights

Philadelphia to Saint Thomas Island flights

Reagan-National to Providenciales flights

Baltimore to Providenciales flights

Philadelphia to Santo Domingo flights

Philadelphia to Providenciales flights

Baltimore to Simpson Bay flights

Dulles Intl to Castries flights

Baltimore to Santo Domingo flights

Dulles Intl to Santo Domingo flights

Philadelphia to Simpson Bay flights

Dulles Intl to Willemstad flights

Reagan-National to Simpson Bay flights

Baltimore to Castries flights

Baltimore to Bridgetown flights

Philadelphia to Castries flights

Reagan-National to Christiansted flights

Reagan-National to Santo Domingo flights

Dulles Intl to Bridgetown flights

Baltimore to Willemstad flights

Dulles Intl to Christiansted flights

Reagan-National to Castries flights

Reagan-National to Bridgetown flights

Baltimore to Christiansted flights

Baltimore to George Town flights

Dulles Intl to George Town flights

Reagan-National to Willemstad flights

Philadelphia to Bridgetown flights

Dulles Intl to Port of Spain flights

Reagan-National to George Town flights

Dulles Intl to Kingston flights

Reagan-National to St. George's flights

Dulles Intl to St. George's flights

Reagan-National to Kingston flights

Baltimore to Kingston flights

Reagan-National to Port of Spain flights

Reagan-National to Puerto Plata flights

Philadelphia to George Town flights

Philadelphia to Christiansted flights

Baltimore to Port of Spain flights

Dulles Intl to Puerto Plata flights

Dulles Intl to St. John's flights

Philadelphia to Willemstad flights

Baltimore to Puerto Plata flights

Baltimore to St. John's flights

Baltimore to Santiago de los Caballeros flights

Baltimore to St. George's flights

Dulles Intl to Santiago de los Caballeros flights

Philadelphia to Kingston flights

Philadelphia to Santiago de los Caballeros flights

Dulles Intl to Road Town flights

Reagan-National to St. John's flights

Reagan-National to Road Town flights

Philadelphia to Puerto Plata flights

Philadelphia to St. John's flights

Dulles Intl to Marsh Harbour flights

Reagan-National to Santiago de los Caballeros flights

Reagan-National to Marsh Harbour flights

Dulles Intl to Roseau flights

Baltimore to Freeport flights

Baltimore to Road Town flights

Dulles Intl to The Valley flights

Dulles Intl to Basseterre flights

Dulles Intl to Kralendijk flights

Reagan-National to Gregory Town flights

Baltimore to Kralendijk flights

Baltimore to Gregory Town flights

Baltimore to Georgetown flights

Reagan-National to Freeport flights

Philadelphia to Georgetown flights

Baltimore to Roseau flights

Dulles Intl to Georgetown flights

Philadelphia to Basseterre flights

Philadelphia to Freeport flights

Reagan-National to Kralendijk flights

Philadelphia to Gregory Town flights

Philadelphia to Port of Spain flights

Baltimore to Basseterre flights

Philadelphia to St. George's flights

Philadelphia to Castries flights

Reagan-National to Basseterre flights

Reagan-National to Aguadilla flights

Reagan-National to Kingstown flights

Philadelphia to Road Town flights

Dulles Intl to Freeport flights

Baltimore to The Valley flights

Reagan-National to Georgetown flights

Reagan-National to Ponce flights

Philadelphia to Kingstown flights

Reagan-National to The Valley flights

Dulles Intl to Kingstown flights

Baltimore to Kingstown flights

Philadelphia to The Valley flights

Baltimore to Cap Haitien flights

Baltimore to Marsh Harbour flights

Dulles Intl to Pointe-à-Pitre flights

Dulles Intl to Gustavia flights

Philadelphia to Kralendijk flights

Philadelphia to Ponce flights

Reagan-National to Pointe-à-Pitre flights

Philadelphia to Roseau flights

Baltimore to Castries flights

Reagan-National to Port Au Prince flights

Philadelphia to Cap Haitien flights

Philadelphia to Gustavia flights

Baltimore to Gustavia flights

Reagan-National to Gustavia flights

Philadelphia to Marsh Harbour flights

Baltimore to Aguadilla flights

Philadelphia to Aguadilla flights

Reagan-National to Culebra flights

Philadelphia to Newcastle flights

Reagan-National to Governor’s Harbour flights

Reagan-National to Vieques flights

Dulles Intl to La Romana flights

Baltimore to Mayagüez flights

Baltimore to Pointe-à-Pitre flights

Dulles Intl to Fort-de-France flights

Philadelphia to Culebra flights

Philadelphia to Vieques flights

Reagan-National to Mayagüez flights

Dulles Intl to Aguadilla flights

Dulles Intl to Scarborough flights

Baltimore to Havana flights

Reagan-National to Scarborough flights

Dulles Intl to Culebra flights

Dulles Intl to Newcastle flights

Philadelphia to Mayagüez flights

Baltimore to Culebra flights

Baltimore to Newcastle flights

Dulles Intl to Vieques flights

Baltimore to Governor’s Harbour flights

Baltimore to Vieques flights

Reagan-National to Fort-de-France flights

Dulles Intl to Havana flights

Philadelphia to Governor’s Harbour flights

Baltimore to Port Royal flights

Baltimore to Fort-de-France flights

Baltimore to Scarborough flights

Dulles Intl to Port Royal flights

Salisbury to Luis Munoz Marin Intl flights

Dulles Intl to Nagua flights

Dulles Intl to Cap Haitien flights

Dulles Intl to Cayman Brac flights

Dulles Intl to Governor’s Harbour flights

Dulles Intl to Santa Clara flights

Philadelphia to Havana flights

Baltimore to Nagua flights

Baltimore to Port Au Prince flights

Baltimore to Santa Clara flights

Reagan-National to Nagua flights

Reagan-National to Cap Haitien flights

Reagan-National to Havana flights

Dulles Intl to Holguín flights

Philadelphia to Port Royal flights

Philadelphia to Port Au Prince flights

Baltimore to Holguín flights

Baltimore to Saba Island flights

Baltimore to Treasure Cay flights

Reagan-National to Port Royal flights

Reagan-National to Deadman's Cay flights

Reagan-National to Saba Island flights

Reagan-National to Treasure Cay flights

Top 8 airlines flying from Maryland to Caribbean

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$116	Average$339	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$132	Average$392	FlexibilityNo cancel fee	On-time65%
JetBlue	Cheapest$167	Average$370	FlexibilityNo cancel fee	On-time62%
United Airlines	Cheapest$197	Average$565	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$276	Average$635	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$276	Average$544	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$325	Average$677	FlexibilityNo cancel fee	On-time63%
Copa Airlines	Cheapest$352	Average$517	FlexibilityNo cancel fee	On-time70%

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