$142 Find Cheap Flights from Reagan Washington National Airport to Cayman Islands - Compare and Save

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Price, demand and travel trends for Washington, D.C. Reagan-National Airport to the Cayman Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Washington, D.C. Reagan-National Airport to the Cayman Islands cheaper or more expensive than last year?

Fares from Washington, D.C. Reagan-National Airport to the Cayman Islands are running about 14% lower than they were around this time last year, averaging $518 round-trip.

What are the cheapest fares from Washington, D.C. Reagan-National Airport to the Cayman Islands right now?

The cheapest fares from Washington, D.C. Reagan-National Airport to the Cayman Islands on KAYAK in the last week were to George Town Owen Roberts Intl (GCM) from $390 round-trip, and to Cayman Brac Gerrard-Smith (CYB) from $1,270 round-trip.

What’s the cheapest month to fly from Washington, D.C. Reagan-National Airport to the Cayman Islands?

January is the cheapest time of year to fly, with average fares of $349. Prices are highest in November, when average flight costs increase to around $642.

When is the best time to book flights from Washington, D.C. Reagan-National Airport to the Cayman Islands?

Book your flights 20 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 26% compared to booking last-minute (within 2 weeks of departure).

Which airport in the Cayman Islands is the cheapest to fly to from Washington, D.C. Reagan-National Airport?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into the Cayman Islands are:

• George Town Owen Roberts Intl (GCM) from $500
• Cayman Brac Gerrard-Smith (CYB) from $899

What’s the cheapest day to fly from Washington, D.C. Reagan-National Airport to the Cayman Islands?

Tuesday tends to be the cheapest day to fly from Washington, D.C. Reagan-National Airport to the Cayman Islands, while Sunday is the most expensive. Fares run about 28% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Washington, D.C. Reagan-National Airport to the Cayman Islands?

Data from the past 12 months shows it's cheapest to fly to the Cayman Islands during the night with average prices of $471. The evening is the most expensive time to fly, with average prices of $899.

Key details for Washington, D.C. Reagan-National Airport to the Cayman Islands flights

Low season

October

Cheapest flight

$142
Beat the crowds with an average 59% drop in travelers.
The most popular month to fly with an average 59% increase in travelers.
One-way flight from Washington, D.C. Reagan-National Airport to George Town

Your Washington, D.C. Reagan-National Airport to the Cayman Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Washington, D.C. Reagan-National Airport to the Cayman Islands?

    Yes. Fares from Washington, D.C. Reagan-National Airport to the Cayman Islands are low right now. As a rule of thumb, a round-trip under $415 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Washington, D.C. Reagan-National Airport to the Cayman Islands?

    Over the past 12 months, round-trip fares from Washington, D.C. Reagan-National Airport to the Cayman Islands have ranged from $415 to $627.

  • What are the main airports serving the Cayman Islands?

    Flights to the Cayman Islands use two main airports, George Town Owen Roberts Intl (GCM) and Cayman Brac Gerrard-Smith (CYB).

  • What airlines fly nonstop from Washington, D.C. Reagan-National Airport to the Cayman Islands?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Washington, D.C. Reagan-National Airport to the Cayman Islands. One-stop options include:

    • American Airlines
    • Delta
    • Southwest

  • Which cabin classes are available on flights from Washington, D.C. Reagan-National Airport to the Cayman Islands?

    On flights from Washington, D.C. Reagan-National Airport to the Cayman Islands you can book Economy Class or First Class.

Your guide to booking Washington, D.C. Reagan-National Airport to the Cayman Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 20 weeks before your trip. KAYAK data shows fares in this window are around 26% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for January when flights are typically cheapest and avoid November when prices are at their highest.
  • Flying on Tuesday is usually the cheapest. Flights on Sunday cost about 28% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, George Town Owen Roberts Intl (GCM) is the cheapest airport to fly into from Washington, D.C. Reagan-National Airport. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in George Town, which is the most popular destination in the Cayman Islands. From there, it's easy to continue on to other popular destinations such as West Bay, East End and North Side.

Reviews of the top airlines flying from Reagan-National to the Cayman Islands

 
Need help choosing which airline to fly with from Reagan-National to the Cayman 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 10332 reviews
6.7Food
7.1Entertainment
7.7Boarding
7.3Comfort
8.1Crew
Airline reviews

The flight from Frankfurt to Pisa was cancelled and we were rebooked to route through London. The flight to London was delayed for maintenance issues and we missed our connection flight. Lufthansa automatically rebooked my wife on the next flight but I was not rebooked. I spent over an hour trying to get onto the flight. Ultimately my wife’s gate checked bag from Washington did not arrive in Pisa and remained in London. Very bad experience overall.

2.0 MediocreAndrew, Oct 2026
Read more United Airlines reviews

The flight from Frankfurt to Pisa was cancelled and we were rebooked to route through London. The flight to London was delayed for maintenance issues and we missed our connection flight. Lufthansa automatically rebooked my wife on the next flight but I was not rebooked. I spent over an hour trying to get onto the flight. Ultimately my wife’s gate checked bag from Washington did not arrive in Pisa and remained in London. Very bad experience overall.

Flight attendant incredibly rude. Stuck her finger in my drink and didn’t even have the courtesy to apologize.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Never nice, United Express partners always do an amazing job.

Being stick waiting for gate at ORD cause me to almost miss my connecting flight…being deaf United made no no effort to keep me updated as I couldn’t hear the PA

The flight was on time and the crew were great.

I was forced to gate check my carry on luggage. Somehow it did not arrive at my destination. I still have yet to receive my bag r days after arrival.

Boarding area is a mess. Lines not bounded and gate area too small. Food options (on this specific flight) were poor and you couldn’t pick part of it since it was like a mash of chicken and other unrecognisable stuff. Comfort of seats along with child noise made it difficult to get a good sleep. Last, the flight attendant that served my aisle was rude (others seemed fine) towards me and others.

Flight was delayed which isn’t the airline’s fault, but the communication around it was terrible. I left the lounge to show up at the gate to board at the time in my app, and the flight in front of mine was still boarding and the inbound plane hadn’t even taken off yet. Delays were slow to show up in my app. Improved communication could have let me have a more pleasant experience in the lounge vs waiting 1.5 hours at the gate.

Wifi was good on the flight from DCA to Dallas and terrible on the flight from Dallas to Tucson. The forward head in the flight from Dallas to Tucson was putrid smelling entirely urine soaked. The flight from DCA to Dallas was delayed by almost 30 min with a plane change.

Sat on tarmac at arrival at DFw for more than 30 min waiting for a gate.

Business Class layout was excellent. The seats were not nearly as comfortable as UA, Delta or Air New Zealand (the best). Nor were the controls as flexible. Food was okay but not great. Breakfast pancakes were like cardboard.

I am Plstinum Pro snd was standby on earlier flight. They gave seats to people that asked rather than follow standby order. When realized what was happening was too late to get on as no seats left. My scheduled flight was late. Then filled the seat beside me Ruth rude person that they had to move from her original seat

I have yet to come across an AA agent or flight attendant that is friendly. They really inhibit a good experience.

Flight was good, little delayed because of busy plane traffic

Flight was delayed multiple times and rerouted to different concourses in the airport because of all of American's delays. App/boarding pass would not update with changed gate information.

Did not know that they didn’t have screens for entertainment. I didn’t have headphones so I couldn’t watch anything on my phone.

Disorganized boarding. Mandatory to gate check bags. Curt flight staff. No space for cabin bag, even when I was in first class.

More options for your flight from Reagan-National to the Cayman Islands

Complete your trip to the Cayman Islands with a hotel stay or car rental