Find cheap flights from Oregon to the Cayman Islands

Find cheap flights from Oregon to the Cayman Islands

Round-trip
Economy
Boston (BOS)
Cayman Islands
Thu 3/4
Thu 3/11
Any month
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Good to know

Low season

September Best time to beat the crowds with an average 3% drop in price.

High season

December Most popular time to fly with an average 8% increase in price.

Average price round-trip

$630 (avg. price over the last 2 weeks)

Good deal round-trip

$184 or less

Good deal one-way

$71 or less

FAQs for booking flights from Oregon to the Cayman Islands

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Top airlines flying from Oregon to the Cayman Islands

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 45,160 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.8
Entertainment
6.7
Food
Airline reviews

Pros: "Enough leg and seat space for coach. Timely, easy boarding, clean airplane."
Cons: "Entertainment screens (though good selection for iPhone entertainment) , ability to charge phone."

Pros: "Very friendly and accommodating."
Cons: "tv screens on the back of seats"

Pros: "Leg room"
Cons: "Plane was late for takeoff and we arrived 30 minutes after scheduled time. They didn’t announce a delay or apologize."

Pros: "Everything"
Cons: "Nothing"

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

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 most cramped seats ever"

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: "Seats were comfortable, but stiff"
Cons: "Plane was way too hot inside and no eye masks or earplugs were handed out afaik. There was no beverage service, but this may have been due to turbulence."

Pros: "We got to our destination aver 12 hours late."
Cons: "In addition to being rebooked approximately 12 hours after our original flight, this flight left about 40 minutes late."

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!"

Cons: "Seats are really uncomfortable. My lower back hurt by arrival time."

Pros: "Quick boarding"
Cons: "Flight attendant was very brash. Guy next to me smelled like an ashtray which made everything worse."

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"

Pros: "TSA PRE√ went fast and easy."
Cons: "Seats are miserable to try to sleep on an overnighter."

Cons: "Coach seating is too tight"

Cons: "Seats smaller than before."

Pros: "Flight was one time. Flight crew was also polite and attentive."
Cons: "Plane was more cramped than the flight to Portland, even though both planes were 737's."

Pros: "Overall solid flight"

Pros: "Nice flight once we finally boarded!"
Cons: "Flight was late causing me to run for my connecting international flight in LAX."

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: "Once in the air things went well."
Cons: "We spent more time on the tarmac than in the air. The plane was unusually noisy on landing. There was little room"

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

Pros: "The in flight entertainment was perfect, new, and relevant. I also had an empty seat between myself and another passenger so my legs weren't as cramped."

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)."

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: "."

Pros: "Timeliness"
Cons: "Nothing"

Pros: "Entertainment and great beverage options"

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

Pros: "The switch up w amaerican air Can't find flight for check in no one is on the phone over night. Finally figured out the prob. Did like amer air And all the shuttling. Chaos"

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"

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: "Flight was delayed"

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

Cons: "WiFi"

Cons: "Lol, it's United. What do you expect?"

Pros: "New plane with great overhead bins and comfortable seats and pretty empty!"

Cons: "United's hidden fees"

Pros: "No delays or cancellations occured!"
Cons: "Plane space for feet is terrible. I'm a small person and it is crammed, very uncomfortable seats. Also, electrical outlets didn't work most of the time"

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

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

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

Pros: "It was fine."

Pros: "Friendliness of staff"
Cons: "I booked the flights for both my sister and I and we were never put in seats next to each other"

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."

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: "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"

Pros: "Friendly, comfortable service"

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

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: "Liked that we landed safely and I was treated like a human being not just a seat but the accommodation s were a little under what I expected"

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"

Cons: "Delayed by an hour and a half"

Pros: "Comfortable seats with plenty legroom."
Cons: "No complaints!"

Pros: "Boarded on time."
Cons: "Cramped seats."

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

Cons: "Can't fit in seat"

Pros: "The plane was new"
Cons: "Could not be helped but a delay of a little over an hour."

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

Pros: "Free Upgrade"
Cons: "What wasn't there to like"

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from Oregon to the Cayman Islands

Airlines flying from Oregon 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 Oregon to the Cayman Islands

Mandatory masks

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

Social distancing seating

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

Pre-flight testing

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

Book cheap flights from Oregon to Cayman Islands

Recent round-trip flight deals

5/26
Wed
1 stop
United Airlines
12h 50m
PDX - GCM
6/1
Tue
1 stop
United Airlines
10h 05m
GCM - PDX
5/26
Wed
1 stop
United Airlines
12h 50m
PDX - GCM
6/1
Tue
2 stops
United Airlines
19h 20m
GCM - PDX
5/27
Thu
2 stops
United Airlines
25h 10m
PDX - GCM
6/1
Tue
1 stop
United Airlines
10h 05m
GCM - PDX
5/27
Thu
1 stop
United Airlines
24h 45m
PDX - GCM
6/1
Tue
1 stop
United Airlines
10h 05m
GCM - PDX
6/12
Sat
2 stops
United Airlines
21h 23m
EUG - GCM
6/15
Tue
2 stops
United Airlines
21h 53m
GCM - EUG
6/12
Sat
2 stops
United Airlines
21h 23m
EUG - GCM
6/15
Tue
2 stops
United Airlines
43h 38m
GCM - EUG
5/27
Thu
2 stops
American Airlines
12h 10m
PDX - GCM
6/1
Tue
3 stops
American Airlines
13h 04m
GCM - PDX
5/27
Thu
2 stops
American Airlines
12h 10m
PDX - GCM
6/1
Tue
3 stops
American Airlines
13h 04m
GCM - PDX
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