$155 Find Cheap Flights from Caribbean to Reagan Washington National Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Reagan-National departing on 8/20. 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.
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1 adult, Economy, 0 bags

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Cheap Flights from Caribbean to Reagan-National

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Reagan-National that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Reagan-National

Fri, Sep 11 - Tue, Sep 22
JetBlue Logo
6:07 pm - 9:58 pmSJU  San Juan Luis Munoz Marin Intl-DCA Washington, D.C. Reagan-National
3h 51mnonstop
JetBlue Logo
8:00 am - 11:52 amDCA  Washington, D.C. Reagan-National-SJU San Juan Luis Munoz Marin Intl
3h 52mnonstop
$285JetBlue
Wed, Sep 16 - Sat, Sep 19
JetBlue Logo
6:07 pm - 9:58 pmSJU  San Juan Luis Munoz Marin Intl-DCA Washington, D.C. Reagan-National
3h 51mnonstop
JetBlue Logo
8:00 am - 11:52 amDCA  Washington, D.C. Reagan-National-SJU San Juan Luis Munoz Marin Intl
3h 52mnonstop
$285JetBlue
Wed, Oct 14 - Mon, Oct 19
American Airlines Logo
6:30 am - 2:49 pmSJU  San Juan Luis Munoz Marin Intl-DCA Washington, D.C. Reagan-National
8h 19m1 stop Miami
American Airlines Logo
1:29 pm - 10:57 pmDCA  Washington, D.C. Reagan-National-SJU San Juan Luis Munoz Marin Intl
9h 28m1 stop Philadelphia
$296American Airlines
Sun, Sep 20 - Fri, Sep 25
American Airlines Logo
2:58 pm - 12:31 amSJU  San Juan Luis Munoz Marin Intl-DCA Washington, D.C. Reagan-National
9h 33m1 stop Miami
American Airlines Logo
7:06 pm - 11:00 amDCA  Washington, D.C. Reagan-National-SJU San Juan Luis Munoz Marin Intl
15h 54m1 stop Miami
$296American Airlines
Wed, Feb 3 - Tue, Feb 16
Southwest Logo
5:45 am - 3:00 pmSJU  San Juan Luis Munoz Marin Intl-DCA Washington, D.C. Reagan-National
10h 15m2 stops Orlando Chicago Midway
Southwest Logo
2:00 pm - 10:40 pmDCA  Washington, D.C. Reagan-National-SJU San Juan Luis Munoz Marin Intl
7h 40m1 stop Tampa
$296Southwest
Sat, Sep 5 - Sat, Sep 12
Southwest Logo
2:50 pm - 9:55 pmSJU  San Juan Luis Munoz Marin Intl-DCA Washington, D.C. Reagan-National
7h 05m1 stop Orlando
Southwest Logo
6:00 am - 4:40 pmDCA  Washington, D.C. Reagan-National-SJU San Juan Luis Munoz Marin Intl
10h 40m2 stops Nashville Intl Orlando
$296Southwest
Sat, Sep 5 - Mon, Sep 7
United Airlines Logo
7:00 am - 9:09 pmSJU  San Juan Luis Munoz Marin Intl-DCA Washington, D.C. Reagan-National
14h 09m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
United Airlines Logo
6:00 am - 1:45 pmDCA  Washington, D.C. Reagan-National-SJU San Juan Luis Munoz Marin Intl
7h 45m1 stop Newark
$316United Airlines
Thu, Sep 3 - Mon, Sep 7
United Airlines Logo
7:00 am - 4:04 pmSJU  San Juan Luis Munoz Marin Intl-DCA Washington, D.C. Reagan-National
9h 04m1 stop Houston George Bush Intcntl
United Airlines Logo
2:59 pm - 11:50 pmDCA  Washington, D.C. Reagan-National-SJU San Juan Luis Munoz Marin Intl
8h 51m1 stop Newark
$316United Airlines
Sat, Oct 31 - Mon, Nov 16
Air Canada Logo
2:40 pm - 4:24 pmSXM  Simpson Bay Princess Juliana-DCA Washington, D.C. Reagan-National
25h 44m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
6:59 am - 3:45 pmDCA  Washington, D.C. Reagan-National-SXM Simpson Bay Princess Juliana
7h 46m1 stop Toronto Pearson Intl
$337Air Canada
Thu, Sep 10 - Thu, Sep 17
Air Canada Logo
2:20 pm - 12:14 pmNAS  Nassau Intl-DCA Washington, D.C. Reagan-National
21h 54m2 stops Montreal Pierre Elliott Trudeau Intl Ottawa
Air Canada Logo
6:00 am - 1:25 pmDCA  Washington, D.C. Reagan-National-NAS Nassau Intl
7h 25m1 stop Montreal Pierre Elliott Trudeau Intl
$338Air Canada
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Good to know

Low season

February

Cheapest flight

$155
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from San Juan to Reagan Washington National Airport

FAQs for booking Caribbean to Reagan Washington National Airport flights

  • How does KAYAK find such low prices on flights from Caribbean to Reagan Washington National Airport?

    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 Caribbean to Reagan Washington National Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to Reagan Washington National Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Reagan Washington National Airport from Caribbean 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 Caribbean to Reagan Washington National Airport?

    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 Reagan Washington National Airport with an airline and back to Caribbean with another airline.

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

    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 Reagan Washington National Airport from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Caribbean to Reagan-National

 
Need help choosing which airline to fly with from Caribbean to Reagan-National? 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.
8.0
SouthwestOverall score based on 4218 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

8.0 ExcellentDavid, Aug 2026
Read more Southwest reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

Flight time kept changing and so did the gate. It was very frustrating

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

The flight was delayed about 20 minutes, but this was an evening flight, so it comes as no surprise. This flight came a good 1.5 days ahead of hurricane Helene which was still far out in the gulf. However, the flight never removed the seated buckle light. The staff announced from the beginning that due to the bad weather (I suppose the hurricane a day and a half away) they would have to do an abbreviated service with water and a snack. I am fine with their water and snack offering, but this was one of the smoothest flights I've had in years. If Southwest believes a flight like this requires everyone to remain seated, then all of their flights should remain buckled for the entire flight. I cannot help but wonder if things like this are a sneaky way to cut back on expenses since the airline is currently under a lot of pressure to reduce costs.

Although the flight was delayed, but the crew was amazing. They did the best they could to make the time enjoyable.

My experience was find with Southwest. The only issue I have is...at the exact time for me to check in...I don't understand how I always end up in C.

Stewardess was not accommodating when I requested a second drink.

Some of the passengers are coming on board with luggage so overstuffed and/or too large that have no business going into the overhead bins.

I am in a wheelchair The gate agent knew exactly how to boarding A wheelchair first also the flight attendant knew exactly what she was doing

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

Flight delayed due to ground hold. Republic airways did a great job.

The flight was smooth, the crew was great but the plane was quite old

Flight was warm for first few hours and quite rough

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

1st flight had mechanical issues after we boarded and almost took off. They tried to fix on runway but couldn’t do we went back to the gate. They couldn’t fix it there either. So we had to deplane and board another plane 2 hrs later. All in all our flight was delayed 4 hrs so we had to cancel some business meeting we had in London for the morning since we were supposed to arrive at 7am and did not arrive until 11:45am. Also, the 2nd plane had mechanical issues as well but fortunately they were able to fix on runway.

The flight to America was freezing. The overnight flight back to the UK was boiling hot and the cabin stank of toilet or occasionally perfume, even though I was several rows back from either bathroom. Food was tiny portions. Two small pieces of tough and dry beef in random gravy with pretend mashed potato raking up most of it. Very little veg. Salad was ok. Wooden cutlery broke within minutes of using. Lots of old films for entertainment. Some new ones. Generally a bit rubbish.

Entertainment center did not work and no electric available at seat for 11 hour flight. Didn’t have access to overhead light or call button. Food was tasteless and had a high salt (27 %) of recommended daily salt intake

What would be infinitely better if for Kayak to not offer this flight as if it was completely different airlines rather than United and then filtering me through some creepy discount site.

Our flight gor canceled and there was no one to help us but told us to scan the qr code and fill the forms on-line. Very poor service especially we are tourists traveling to Washington DC for the 1st time.

Our flight was great with an unexpected upgrade. However, four days into our travel we are still without a piece of luggage. The bag tracker has not been accurate, the airline is not communicating with me or the luggage delivery service and no one is willing to take responsibility or guarantee any kind of support or reimbursement. Unfortunately, we do not have the option to easily shop to replace items as we are currently on a cruise. I have been very disappointed by United Airlines response.

The flight was canceled. I couldn't get on another flight. Meal voucher wouldn't work. The whole experience was a clusterfuck.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Plane left & arrived early- 5 Crew great. Wi fi - paid for 2, only 1 worked - so so. Waste of $. Coolie was good

The entertainment wasn’t playing in the app or online.

My wife has a scooter and they where supposed to send from departure to destination and had it go to connecting flight,not good.Nobody has knowledge of the scooters or the battery's.

The flight was over an hour delayed. The problem was they had the wrong aircraft at the gate, Joe in the world does that happen?

On time departure & early arrival. Made a long day much better.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

Crew and agents misguiding on tight connections, and lack of connecting crew looking for inbound planes. A very avoidable missed connection as a result.

My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.

American Airlines changed are gate no fewer than four times. Walking back and forth from one concourse to another was exhausting, especially after all the flight delays.

Hydraulic leak caused the flight to be cancelled. Auto system scheduled us on a 3 am flight. Wevhsedvrebook on the app and hit schedules later in the afternoon. Our luggage per gate and ticket agent would be rescanned and put in our new flight. Did not happen. Our luggage stayed in hsv. Baggage claim in wash dc unable to help. We filed a claim. Several emails about our luggage were in conflict with one another. Called as baggage and was on hold 30 minutes. Oscar said one of 2 was out fir delivery then cancelled. About 45 minutes later both pieces were delivered. Their system is suspect

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

It was great. Smooth flight, comfortable, left on time and landed on time.

We were several hours delayed due to confusion during boarding. Evidently the crew could not match the manifest with the boarded customers. After significant time trying to find individuals on board, a crew member walked through the entire plane re-scanning each of our boarding passes. Then we had to wait for a new slot to depart, and when we landed, our gate was not ready. It was a complete goat rodeo from start to finish.

My checked in luggage cost was $59, almost ticket price. The first 13 rows were empty, but fly attendant did not alow women with little boy change her middle sit, sweet boy was crying, I am so sorry for mother and passengers. At the end of the flight the cabin became impossible cold. Only good was timing of departure and early landing, but it suppose to be normal.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

Flight was quick, less time than expected, and the attendants all friendly and helpful. We had paid extra for more leg room and were very comfortable. Haven't flown JetBlue in quite a while. Glad to be back!

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Both flights were significantly delayed. The flight experience itself was great.

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

The free wi-fi was great. But, the flight delay was not sustainable. It definitely impacted people schedules and JetBlue didn’t do anything to compensate clients for it

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Old plane. No outlets for laptop or phone. Seats worn out. Area around seat dirty.

Traveling to a place near Reagan-National?

Book flights to Reagan-National if you plan to visit one of these locations
Linthicum Heights
Hanover
Springfield
Gaithersburg
Towson
Oxon Hill
Owings Mills
Greenbelt
Glen Burnie
Edgewood
Chesapeake Beach
Ellicott City
Camp Springs
Pikesville
Colonial Beach
Hunt Valley
Lutherville Timonium
Capitol Heights
Westminster
Stevensville

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