Find cheap flights from Portland to the Cayman Islands

Find cheap flights from Portland to the Cayman Islands

Search hundreds of travel sites at once for deals on flights to the Cayman Islands

Round-trip
Economy
Portland (PDX)
Cayman Islands
Wed 4/21
Wed 4/28
Any month
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There are travel restrictions to Cayman Islands. Learn more
Stay informed and receive email updates for when travel restrictions ease for Cayman Islands.

Good to know

Low season

JanuaryBest time to beat the crowds with an average 4% drop in price.

High season

DecemberMost popular time to fly with an average 6% increase in price.

Average price round-trip

$624(avg. price over the last 2 weeks)

Good deal round-trip

$442or less

Good deal one-way

$229or less

Top tips for finding cheap flights to the Cayman Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to the Cayman Islands is March.

FAQs - booking Cayman Islands flights

Are there Cayman Islands travel restrictions currently due to Coronavirus?

How does KAYAK find such low prices on flights to the Cayman Islands?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to the Cayman Islands?

What is the Hacker Fare option on flights to the Cayman Islands?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to the Cayman Islands?

Top 3 airlines serving Portland to Cayman Islands

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,464 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Cons: "They delayed the flight because of a mechanical issue now I have layover for 12 hours"

Cons: "Too long to get “maintenance sign off”"

Pros: "One stewardess was pretty rude and impatient. Other staff excellent"
Cons: "Stewardess should speak slower, enunciate and smile."

Pros: "The crew was great!"
Cons: "The TV reception was terrible There were 3 cats on the plane and I have a terrible allergy to cats. Miserable 2+ hours"

Pros: "Great crew"

Cons: "I never went on this trip. Why are you asking me to rate it??"

Pros: "Easy flight left and arrived early even!"

Pros: "Crew was very friendly, on-boarding was easy and fast, everything was clean, and there were nice touches like a sleep mask and ear plugs on every seat."
Cons: "The leg room was better than in other flights, but that's not saying much and the seats were very uncomfortable and for such a long flight, it was deeply uncomfortable overall. My knee joints still hurt two days later."

Pros: "Not much other than an easy boarding."
Cons: "I want to complain about my experience on your Flight #1206 from PDX to JFX the plane is severely outdated. It doesn’t even look like a JetBlue plane. My tv doesn’t work as did a few others on board. We were told by the steward they were already reset and they just don’t work. That’s really unacceptable and a-shame. I could of flown whatever airline if I wanted to be uncomfortable for a 5 hour flight. I’m very disappointed with this. I have tried to go through your website to voice the issue but conveniently it doesn’t process after I fill out the required information. Your Twitter help team offered me $15 credit for my inconvenience wow what a way to help a customer what’s that not even a checked bag on one of your flights. What a joke. Very unhappy and I fly JetBlue often. Sad."

Pros: "Quick boarding and great service"

Pros: "Flight attendants super friendly quick flight good tailwind 4hr 40min another homerun JetBlue see you again soon"

Pros: "Focus on customer service, spacious and comfortable seating, courtesy with respect to my disability, and general availability of Wi-Fi without charge."
Cons: "Where I am on a long business trip, I did not appreciate being charged $150, above the $30 baggage fee, due to being 8 pounds overweight with my luggage."

Pros: "Light snacks and water bottles for free were nice. They kept it dark for most of our overnight flight. Flight attendants were helpful and competent."
Cons: "My tv would not turn off. Had to cover it so I could sleep."

Pros: "Effecient! Nice plane. Great flight and ground crew"

Pros: "The in-flight entertainment did not work."

Pros: "Plane loaded a few minutes late, but efficiently on the return leg. Flight Attendants were courteous, and attentive on both. Did those of you who don't know how to turn the TV off, lower the 'Brightness' to zero."

Pros: "The seat had a bit more cushion/comfort than the non-JetBlue flight I took recently, although overall comfort minimal in economy. Staff were friendly and efficient. I took a red-eye flight and the complimentary eye masks and ear plugs were a nice touch."
Cons: "My tv screen and the channel buttons and volume were glitchy but I didn't ask about fixing them. I did miss the phone charging port that is available on other airlines."

Pros: "It was a joy"

Cons: "Bumpy ride"

Pros: "Free wifi"
Cons: "Flight was late; incoming aircraft was running late all day. Upon landing, there was no gate available. Plane got uncomfortably warm while waiting for one."

Pros: "Quick on and off of the plane. A little tie up in Long Beach, but we arrived early."
Cons: "The TV's were not working properly. Could not view the World Cup match between Brazil and Mexico."

Pros: "Staff was very courteous, plane was very clean and looked nice. Lots of room in the seats. Boarding was very fast - I got there and went straight on."
Cons: "There was somewhat of a delay on the ground before we took off. It would have been nice to have some more substantial food available, like meals. Also, my neck wasn't comfortable when trying to sleep so I could have used a pillow and it would have been more comfortable in a window seat."

Pros: "The comfort space from the seats"
Cons: "Nothing"

Cons: "I appreciate the commitment to safety but it seemed odd that the entire plane was help up for almost an hour to add a quart of oil to one engine. Otherwise an excellent first experience with Jet Blue. We will be back."

Cons: "delayed"

Pros: "On time and very friendly crew."

Cons: "I received a text when leaving about a 2 hour flight delay with an estimated arrival time ( when the plane would be to the airport before departure. When going home, I received a similar text with a delay warning and a new arrival time. It was the arrival time at the destination airport not the travel airport and I arrived 30 minutes after the flight had left and had to scramble to find a flight a different airline because Jet Blue had no one there and nothing leaving for over 24 hours and that was to NY not Ca. I can say I will not fly Jet Blue again nor use a booking service again, I will take my chances on my own!"

Pros: "Staff on the flight was friendly and helpful"
Cons: "Late departure from Portland created a late arrival in New York- the gate door was closed when I got there. Scheduling connections as tight as you did came very close to leaving me in New York. Jet blue staff in Portland was less than helpful when I expressed my connection concerns ( wanting to rebook to a latter connection before I left Portland). Stop treating people like chattel"

Pros: "Loved the free WiFi but signal wasn’t very strong"

Pros: "Free wifi and comfortable seats"

Pros: "The cheezits were awesome."
Cons: "After departing an hour late because they forgot to fuel the aircraft, we have landed and are currently in the wrong city because they did not onboard the correct amount of fuel. This is awful. In 30 minutes we are told we will have enough fuel to take off again on the second attempt to get to our original “nonstop” destination."

Pros: "JetBlue flights continue to be both comfortable and relaxing. Your upbeat crew are the best."

Pros: "Leg space"
Cons: "My husband and I had to sit apart - even though there were seats together - they just weren’t available unless we paid more"

Cons: "The TVs did not work for the entire flight."

Pros: "I loved everything about this flight"

Pros: "Everything"

Pros: "Half the passengers were sleeping in rows to themselves. I’m 6’5” with a bad back and was stuck in an aisle seat, unable to even rest much less sleep. I get that those seats were available for purchase, but after the doors close it seems ridiculous to not let a customer sit there, ESPECIALLY is taller folks!!!! One could make the argument that it’s less safe as well, seeing how there’s no one IN the exit row to help open the window in the event of an emergency. I like Jetblue but this policy is likely to keep me from flying them if I can fly for just a bit more $ and have comfort."
Cons: "Heartless rule, give the flight attendants power to make customers happy...healthy!"

Pros: "Quick and prompt service at check in. The flight pulled out of the gate on time as well."

Pros: "The attention and the time was great and thanks Kayak for all the help booking my ticket. Walter"

Pros: "Easy on, easy off. I've been flying JetBlue for years, never had a "bad" experience. Reliable NY-based airline with a good network."
Cons: "Seats don't have power, limited food options. Entertainment hasn't been updated in years. Newer aircraft have newer amenities, but upgrades have been slow on the older planes."

Cons: "Flight was delayed by over an hour and we never got an explanation as to why. Just an apology from the pilot once we finally took off."

Cons: "my seat was dirty when I arrived and I had to clean food off of it."

Pros: "Groundstaff at check in were very good. Quick and professional. Legroom was better than average without paying extra. Staff were very attentive and helpful."
Cons: "The system wouldn't let me check in online. I rang JetBlue,very unhelpful, they could find no record even though I gave them confirmation and flight details. They said try checking in with American airlines as the second leg of journey was with them,no good there either."

Pros: "JetBlue is really the only airline that I care to fly anymore. Not only do they get me to my destination on time in comfortable seats but their staff is very accommodating and friendly."

Pros: "Reliable, comfortable, excellent crew"
Cons: "Like all commercial airlines, you have to pay for any little extra. While Jetblue has better legroom space, exit rows now cost extra for long legged people like myself. But overall, a good experience. seamless."

Pros: "N/A"
Cons: "N/a"

Pros: "More leg room than most, friendly staff"
Cons: "After fully boarding, we sat at the gate for over an hour due to paperwork. Nearly half an hour after the scheduled departure time, I got an email alerting me to the delay saying I should still 'arrive on time.'"

Pros: "Good flight was treated well and felt welcome with refreshments and snacks. The way it should be!"

Pros: "flying schedule was on time"

Cons: "Flight was delayed due to weather. That is understandable. However the crew was not helpful in sharing any information with customers about changes to connecting flights. Much time was wasted and I had to reschedule my flight. The staff members that booked my hotel and my new flight were short and brief and not very helpful or accommodating or informative. Overall I didn’t not feel like a welcomed guest and I do not feel enough compensation was offered for such an inconvenience. Not being able to have my bag overnight was a hassle. I had no clean clothes and had to throw out my contacts because I had no solution. I also couldn’t use the meal voucher they gave me because everywhere in the airport was closed by that time. No stipend was given for toiletries or food delivery. Very unimpressed."

Pros: "Amazing crew. Departed and arrived on time."

Pros: "Crew members were okay"
Cons: "Wifi could be better"

Pros: "Crew"
Cons: "Decaf tea"

Pros: "Being relatively on-time was nice for a change."
Cons: "Seats are tight / uncomfortable. Crew could be better at spotting intoxicated passengers and not continuing to serve them."

Pros: "Everything"
Cons: "Nothing"

Pros: "The crew was fantastic and very nicely got us into an earlier flight and allowed my wife and I to sit together for our 10th anniversary"
Cons: "The entertainment apps were difficult to use"

Pros: "Crew seemed friendly and considerate"
Cons: "Flight from SLT was delayed by weather, so our flight left almost one hour late."

Pros: "The crew did a great job."
Cons: "Seating is very uncomfortable."

Pros: "WiFi entertainment system."
Cons: "Hard seats, no arm padding. No power to recharge phone and iPad."

Pros: "amazing seat and awesome crew couldn't ask for more"

Pros: "Arrived early with great service which is most important when flying."
Cons: "Entertainment was not on par with competitors like Delta, especially on a long flight. Movies depended on downloading the gogo app before you boarded which most were not aware of until we were airborne."

Pros: "The seat was cormfortable and the entertainment was dope!"
Cons: "Communication. The pilot did not say when he was landing and considering it was a rough landing it would have been helpful to say. He said we shall be landing like 40minutes before Then quiet"

Cons: "Bigger seat"

Pros: "The free movie"

Pros: "WiFi"
Cons: "Had to take shuttle to other side of airport which took over an hour. Very very poor experience. Also, Seats had no room pull down table."

Pros: "Everything was ok."
Cons: "very little service"

Pros: "Crew is very nice, we were on time and baggage didn't get lost for once."
Cons: "Seats are simply too tight, not enough space for carry-on, and boarding procedures are a joke."

Pros: "The crew was nice and so was the American Airlines customer service office in Phoenix"
Cons: "I didn’t like the male and female check in people in Portland. They sat there and watched me for an hour not telling me I could not use cash to check in my luggage at the gate after they told me it was double the amount to check it in at the gate. The sight u use on the boarding pass u download on the phone is not clear. It says baggage fee +$25.00. I thought it was 25.00 till the women in Phoenix showed me the + sign. She said “it is confusing”. I did not buy the ticket because it was for an unexpected funeral of my sister. My other sister did so I didn’t see all the stuff from Travelocity. After telling me it would be $50.00 the check in male and female at the gate saw me sitting there for an hour and never told me I couldn’t pay cash. By the time it was boarding time if a nice woman did not offer to use her credit card and I have her the $50 cash I would have missed my flight. The manager at the gate in Portland even told me I would miss my flight. The two check in staff at the gate said “well we didn’t know you only had cash” and they weren’t even concerned that I was going to miss my flight. It would of been nice of them to tell me this when I sat there for an hour after they told me They we’re doubling the price. I would of had time to go back through security, only pay $25.00 and the other nice passenger would have not had to use her credit card. Very rude and poor service especially after a sad occasion of burying your sister!"

Pros: "N/a"
Cons: "Flights from PDX to BOS cancelled. Rerouted to PHX. All flights out of BOS, DC, Philly cancelled. I missed my Habitat for Humanity trip, not getting any refunds on flights or hotels. Out thousands and no one is helping me."

Pros: "A nice uneventful trip"

Cons: "Coach seating is too tight"

Cons: "Seats smaller than before."

Pros: "Crew was nice."
Cons: "Ran out of sandwiches on PDX to CLT leg. ☹️"

Cons: "Boarding chaos at Miami airport."

Pros: "Entertainment Captain Food"

Pros: "Nice clean plane prompt w drinks and food great attendants"
Cons: "Nothing. All was excellent"

Pros: "Entertainment and meals"
Cons: "Crew could of been friendlier"

Pros: "Very efficient crew. Pleasant enough"
Cons: "Bumpy flight, obviously not something that could be helped (tho the pilot came on and said he was hoping to find a smoother altitude, greatly appreciate him trying!)"

Cons: "Holding pattern over Dallas for 45 minutes."

Pros: "Ticket agents at all airports were helpful and very considerate."
Cons: "We were not able to print our boarding passes the day before as expected per the website and purchase docs for the tickets, despite providing passport numbers (several times) and Global Entry registrations. Had to go to a ticket desk at first departure and third departure points to have them printed, with no explanations given. Also not allowed to choose our seats for the third leg. Food was barely edible. Paid extra for roomier seats on one leg, making it more comfortable, but were extremely tight on another leg which had many empty seats scattered throughout the cabin. Cabin attendants seemed more interested in pushing items that generated revenue than providing the ones that came with the ticket (which is never cheap to begin with)."

Pros: "Nothing"
Cons: "Every single bit. Was horrible and the crew was just aweful."

Cons: "Due to mechanical issues our 8am flight kept getting delayed in 30 minute increments until around 9:45 when the front desk attendants told us the necessary part had to be driven from Seattle and wouldn't be available until noon, and that their was no certainty the part would work, and that we should make other arrangements. So we did, but their earliest we could get us into Chicago was 9:30pm (original arrival was 2pm). We booked the arrangements only to find out that our original flight took off at 10:55 and American didn't even attempt to contact us. The cherry on top was that our flight (which was indirect through SFO) got delayed and we're now going to miss our connection in SFO. So currently looking at 10:30pm arrival in Chicago."

Pros: "Fabulous crew and service, absolutely fantastic."
Cons: "Having to get off!"

Pros: "Friendly staff ice landong"
Cons: "No leg room & I am only 5'6' & slim."

Pros: "Snacks"
Cons: "They wouldn't allow me to check my bag at the main gate so I had to go through security and check it at the boarding gate. Souvenirs were confiscated because the bag couldn't be check sooner. Then they tagged my bag with the wrong name and destination. It was 48 hours later before I got my bag."

Pros: "The crew is caring and attentive. AA is upgrading all their planes and the individual monitors so you can watch and/or listen to any entertainment you wants. Plane left on time and arrive early, making transfer less stressful."
Cons: "Nothing."

Pros: "."

Pros: "Timeliness"
Cons: "Nothing"

Pros: "Entertainment and great beverage options"

Pros: "Comfort, convienience. Great service. Will fly again."

Pros: "Entertainment was free."
Cons: "Had to wait for mechanical issues so we were delayed."

Pros: "Comfortable seats"
Cons: "Lack of entertainment and no free WiFi. Also food choice was not the greatest"

Cons: "I used to fly with American Airlines a lot more and every time the staff somehow finds a way to be rude and ruin my day so I try to avoid this airline. On this particular flight it was the very rude asian flight attendant that really set the mood. The attitude of the staff really makes or breaks the experience and it seems like American Airlines doesnt care about the quality of thier employees"

Pros: "Pretty comfortable"

Pros: "I like that they had a TV show showing at no extra cost"
Cons: "The seats were so uncomfortable, I've been on planes before but after an hours I couldn't get comfortable at all."

Cons: "Horrible disorganization at boarding. Board from back to front for goodness sake...its common sense."

Pros: "Nothing"
Cons: "Ticket agent would not let me pay for up grade was first flight for me to fly with my wife she sat in first class while I was at the back of the plane!! And there was a seat available for me in first class he just wouldn't let me have it I would not recommend American to any one"

Cons: "Numerous delays and disappointments. Two delays before boarding. Another long delay after boarding waiting for paperwork to be completed. Long taxi period. Waited over half hour for baggage claim conveyor to start rolling."

Pros: "The in flight attendants were very helpful. They never got upset with anyone when I got walked passed my seat while boarding and had traffic backed up while boarding.Such a pleasant flight. I would rather fly American Airlines than spirit, United."
Cons: "The only thing I can say I didn't like was the vents did not blow the air condition hard enough. .."

Cons: "Airlines are definitely putting profits above passenger safety!! How could they fully book a plane during the COVID pandemic?? Shame on you!!"

Cons: "They lost one of our parties luggage. How do two bags make it to the destination, and one not??"

Cons: "WiFi"

Cons: "A little late getting started, otherwise OK."

Cons: "Bad smell"

Pros: "When we were checking in, the personal service from staff was outstanding."

Cons: "Sitting on tarmac for 30-40 min"

Pros: "Nothing"

Pros: "There wasn't any delays. We even got to destination earlier"

Pros: "It was fine."

Pros: "Good service."
Cons: "The website is pretty bad, not user friendly. Took several times for things to take, and was a frustrating experience. Luftansa's website. Not United."

Pros: "Fast. Easy. Gave me free seat with more room"
Cons: "Such a tiny plane.... crowded. Made you pay for wifi."

Cons: "Both flights were late, seriously late."

Pros: "the soda water was good."
Cons: "It was late, as almost all United flights are. sad."

Pros: "The crew in air Canada is awesome! They were really great and friendly. I'm impressed with their impeccable service even if it was a short flight to Vancouver."
Cons: "Flight was delayed."

Cons: "Plane departed 2 hrs late,taxied 40 min in San Fransisco for lack of access to gate"

Pros: "It was a new plane ...but the same old rules..."

Cons: "When booking through kyak, we were not informed that we were booking basic economy and all of the restrictions that come along with that ticket. We were not happy to have to check our carry on luggage and not be able to choose our seats and would have opted for a more expensive ticket if given the option"

Cons: "Terrible uncaring old waitresses overweight, no room for luggage no room for even walk in the plane, kept asking to turn off devices when it is well known devices don't cause any problem. No free internet. Old tired planes, terrible third world airline."

Pros: "Got everything we needed."
Cons: "No complaints."

Pros: "It was spacious."
Cons: "No free Wi-Fi."

Pros: "WIFI allowed access to imessage"
Cons: ""Free" movies and TV didn't work"

Cons: "Multiple delays"

Pros: "On time"
Cons: "No Free baggage no free food"

Cons: "We had to check our hand luggage and be charged EUR120.00 We should have been aware of this before we obtained the boarding pass..."

Pros: "Friendly, comfortable service"

Cons: "Plane was hot no air and super uncomfortable"

Cons: "Had to circle 3 time before landing due to air traffic."

Pros: "The sunrise"
Cons: "I was on the wrong side of the plane!"

Cons: "Crowded"

Pros: "The exit isles were comfortable"
Cons: "No free food service and the menu was unappealing and extraordinarily overprice! The bathroom was dirty and toilet unflusable...garbage can overflowing and dirty paper towels everywhere !"

Pros: "I liked being so welcomed even though I am scared of flights."

Pros: "Best company"

Pros: "Thanks. On time. No problems"

Pros: "Smooth ride"
Cons: "Snack was a ridiculous cookie. Lame."

Pros: "On time"

Pros: "Comfortable and on time"

Cons: "Check in staff was dismissive and not helpful at all at first."

Pros: "It was great. Absolutely no complaints"

Pros: "No one smiled or looked like they were happy with a plane full of vacationers"

Cons: "Can't fit in seat"

Pros: "Smooth"

Pros: "Everything from check in to breakfast to boarding was smooth and effortless at PDX. The restaurants are layed out in a smart configuration with plenty of options on either side of security. The staff are friendly and the travelers in the airport are generally personable and in a good mood, which is a stark contrast to the majority of the nation's airports."
Cons: "The boarding process at the United gate could have been more expeditated."

Pros: "Was a nice trip"
Cons: "All was good"

Pros: "United transfer me to Alaska Airlines because there was delay that would impacted my layover.. So they gave me non stop with Alaska. I'm pleased with their service!"
Cons: "Nothing"

Pros: "Ok time"
Cons: "Had to check carry on bag"

Pros: "N/A"
Cons: "N/A"

Pros: "I liked the service. It's good in general but, looking for better."
Cons: "I didn't like the service sometimes. Especially the hostesses, they are too old. The plane was too small when I flied from Austin to San Francisco. Thank you"

Pros: "Plenty of personal space. this first leg was actually quite pleasant I would give this leg a 4.5"
Cons: "The spicy snack was awful, I needed water, it took a while to get to me."

Pros: "No delays! First time that's happened in a while! So easy!"

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Portland to the Cayman Islands

Airlines flying from Portland to the Cayman Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Portland to the Cayman Islands

Mandatory masks

Masks required on board, masks provided on flights from Portland to the Cayman Islands

Social distancing seating

Middle seats unavailable to book on flights from Portland to the Cayman Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Portland to the Cayman Islands

Book cheap flights from Portland to Cayman Islands

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