$176 Find Cheap Flights from Portland to the Cayman Islands - Compare and Save

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Price, demand and travel trends for Portland 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.

What are the cheapest fares from Portland to the Cayman Islands right now?

The cheapest fare from Portland to the Cayman Islands in the last week was $422 round-trip, to George Town Owen Roberts Intl (GCM).

Which airport in the Cayman Islands is the cheapest to fly to from Portland?

All flights from Portland to the Cayman Islands arrive at George Town Owen Roberts Intl (GCM). On average, round-trip fares are around $586.

What’s the cheapest day to fly from Portland to the Cayman Islands?

Wednesday tends to be the cheapest day to fly from Portland to the Cayman Islands, while Friday is the most expensive. Fares run about 54% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Portland to the Cayman Islands?

Data from the past 12 months shows it's cheapest to fly to the Cayman Islands during the evening with average prices of $341. The afternoon is the most expensive time to fly, with average prices of $684.

Key details for Portland to the Cayman Islands flights

Low season

October

Cheapest flight

$176
Beat the crowds with an average 70% drop in travelers.
The most popular month to fly with an average 99% increase in travelers.
One-way flight from Portland to George Town

Your Portland 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 Portland to the Cayman Islands?

    Yes. Fares from Portland to the Cayman Islands are low right now. As a rule of thumb, a round-trip under $468 (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 Portland to the Cayman Islands?

    Over the past 12 months, round-trip fares from Portland to the Cayman Islands have ranged from $468 to $677.

  • What airlines fly nonstop from Portland to the Cayman Islands?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Portland to the Cayman Islands. One-stop options include:

    • Delta
    • American Airlines
    • United Airlines

  • Which cabin classes are available on flights from Portland to the Cayman Islands?

    On flights from Portland to the Cayman Islands you can only book Economy Class.

Your guide to booking Portland to the Cayman Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for June when flights are typically cheapest and avoid August when prices are at their highest.
  • Flying on Wednesday is usually the cheapest. Flights on Friday cost about 54% more on average, so being flexible with your travel dates could help you save.
  • 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 3 airlines serving from Portland to the Cayman Islands

 
Need help choosing which airline to fly with from Portland 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.
7.8
DeltaOverall score based on 8692 reviews
8.1Boarding
7.8Entertainment
7.2Food
7.8Comfort
8.5Crew
Airline reviews

We experienced delays in small increments that added up to more than an hour. At the gate, staff showed little concern and compared our delay with the inbound flight’s two-hour tarmac wait, which didn’t address our situation. Once onboard, the flight attendants seemed tired and unfriendly. I understand delays are frustrating for everyone, but passengers shouldn’t feel blamed for them. During the flight, a bright light above the emergency exit stayed on. It was concerning, and no one explained it or offered passengers the option to move. After landing, we waited about 30 minutes on the tarmac for a gate, then waited again for an agent to connect the plane to the terminal. From the Reagan gate staff to the cabin crew and RDU personnel, the service felt dismissive throughout. Overall, this was a stressful trip and a very disappointing customer-service experience

4.0 OkayRonald, Oct 2026
Read more Delta reviews

We experienced delays in small increments that added up to more than an hour. At the gate, staff showed little concern and compared our delay with the inbound flight’s two-hour tarmac wait, which didn’t address our situation. Once onboard, the flight attendants seemed tired and unfriendly. I understand delays are frustrating for everyone, but passengers shouldn’t feel blamed for them. During the flight, a bright light above the emergency exit stayed on. It was concerning, and no one explained it or offered passengers the option to move. After landing, we waited about 30 minutes on the tarmac for a gate, then waited again for an agent to connect the plane to the terminal. From the Reagan gate staff to the cabin crew and RDU personnel, the service felt dismissive throughout. Overall, this was a stressful trip and a very disappointing customer-service experience

My flight from Atlanta to Oklahoma City was delayed multiple times. I ended up arriving in Oklahoma City nearly two hours later at around 1:50 am the following morning. This was a highly disappointing experience.

My Delta flight 2423 from Atlanta to Oklahoma City got delayed multiple times. It was originally scheduled to depart at 10:41 pm EST with a 11:58 pm CST arrival in Oklahoma City. However, after multiple delays, the flight finally departed Atlanta at around 12:40 am and arrived in Oklahoma City at around 1:50 am. What was even more disappointing was that none of the crew members acknowledged, let alone apologize, for the delays. These delays were not due to weather and were only due to operational/mechanical issues on the part of Delta. As a former Platinum SkyMiles member, I valued loyalty with Delta. However, after having similar experiences in the recent past, I'll be switching my loyalty over to American Airlines going forward. This was a highly disappointing experience.

Love Delta. I'll take connections to stay on Delta even if another airline has a direct flight.

The main issue was the quantity of the drink. The hostess gave only half cup full of the soft drink. I was thirsty and was expecting full glass like every other time.

Delta always provides stellar service. I am always impressed and will try my best to travel via Delta if I can afford it.

Everything was pretty good. I would like to have more drinks (water) during four hours of the flight.

This flight was the flight we missed due to deltas delay at our first airport going TO Atlanta.

Wi-fi was out for the whole flight. I pay a premium to fly Delta because it has wifi and because it was out I didn’t get to work on anything I wanted to. I’ll have to make it up later this week by spending less time with my family.

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

It was good flight was smooth, little cold on the plane but other wise good.

I need to note that this flight experience was generally fine but the boarding situation was absolutely a mess and there wasn’t any actual priority boarding. I rated the experience poorly because I’m am genuinely so frustrated with the crew on United taking the baggage space in first class. This flight it didn’t happen, but the last few flights (when I ironically don’t get an opportunity to provide feedback) have been spoiled because upon entering the first class cabin as one of the first few seated passengers, the overhead bins are full and ‘crew’’ tags are on the bags of those taking space. I don’t intend to infer some sort of a class or caste system but it’s absolutely ridiculous that the crew takes the overhead storage above and beyond their most loyal and lucrative customers. They should not even have economy space IMO. And I’ve gotten grief when I’ve noted to the crew the ridiculousness of the notion that the crew (who are the last off the plane) should have priority over flyers who pay. I hope you find a way to convey this message to United because it’s happening with increasing frequency and I intend to find a way to expose the specific crew members who are doing this on a flight by flight basis. (And I have a day job)

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

Flight and crew were great. Need more legroom and do not allow seats to recline.

Bathrooms broken, Wifi not working, Direct TV stuck in a United credit card loop for whole flight

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

Both my flight where delayed Had 25min to make it to my transfer flight

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

Flight was good- arrived early ! But ticketing with Underpricer and Kayak was poor at best- unnessacarily difficult due to how the ticket were issued

Flight attendant, forgot her name, was in front cabin, she was great

My overall experience with British Airways was good. The cabin crew were friendly and helpful, and the flight was comfortable. The food was average and could be improved, but overall, I had a pleasant experience.

Cabin staff were very disengaged, spoke with no eye contact, dismissive. Disappointing compared to my United experiences.

Both directions of our trip were befuddled by massive delays, one of which led to our connecting flight being grounded mid air due to storms that we’d have missed if we were on time. The other our originating flight was delayed repeatedly until it arrived at our connecting airport later than our final leg was even supposed to have arrived. American cannot seem to manage rebooking s for a family party… both directions we had to come up with a plan to get to Boston stay overnight only one night each direction was covered by the airline -and take a bus to or from our destination. Missed an entire leg of our trip, hotel cancellation fees, expensive stay in Boston and bus ticket expenses are unlikely to be comped and the meal vouchers are worthless.

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.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Flight left more than 5 hours late. American's policy did not allow flight to be fueled or bags to be loaded due to intermittent lightning. We were on the plane for hours before having to deplane. They then changed the departure time to an earlier than expected time. We re-boarded and had to wait another 1.5 hours on the plane before it finally took off. Flight crew did not serve any food or drinks while airborne.

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

More options for your flight from Portland to the Cayman Islands

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