Find cheap flights from the Cayman Islands to New Windsor

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Boston (BOS)
New Windsor Stewart
Tue 11/24
Tue 12/1
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  • Looking for cheap airfare to New Windsor? 25% of our users found tickets to New Windsor for the following prices or less: From Ottawa $143 one-way - $143 round-trip, from Santiago de Compostela $304 one-way - $304 round-trip, from Traverse City $226 one-way - $322 round-trip
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Top airline flying Cayman Islands to New Windsor Stewart

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 44,867 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.8
Entertainment
6.7
Food
Airline reviews

Cons: "Ask the ticket agent and flight attendants about changing seats and they weren’t helpful. Also their response was abrasive. Didn’t appreciate it!"

Pros: "The crew was respectful and friendly, the seat was comfortable"

Pros: "Crew very friendly."
Cons: "I could not get wifi. Had it from GCM to SAV with no problems."

Cons: "Sat on runway for 30 Minutes at the end of the flight."

Pros: "Quick boarding"
Cons: "American's coach seats are NOT that comfy"

Pros: "How quick American Airlines moves to keep people on time."
Cons: "Nothing"

Pros: "Flight attendant Louis was great. He was very nice and friendly. Calmed me down when I was nervous about turbulent. Great staff overall!"

Cons: "Why do I continue to subject myself to American Airlines and their horrid equipment, late, delayed or cancelled flights? The ABSOLUTE worst carrier in the country. Without question."

Pros: "Good crew. Good movie selection."
Cons: "Seat 20D stereo plug on screen was very finicky, lost audio until I twisted the plug. Happened any time I moved the headset cord."

Pros: "Easy in easy out"
Cons: "Lack of entertainment"

Pros: "We got to our destination safely and sooner than expected!"

Pros: "The air hostess didn’t smile while offering cookies, but she wasn’t rude. She later asked my fellow passenger to move to another window seat and I had the comfort of 2 seats."

Pros: "Quick flight good crew"
Cons: "More entertainment and snack selection"

Cons: "seat back tv"

Pros: "The only good thing on that plane was the crew. We where grounded in board for three hours because of a water leak in the kitchen... My seat had a hole were the ashtray used to be filled with garbage, the tray was filthy when I pulled it open, the overhead light didn't work"

Cons: "My original flight was delayed then we had to spend the night in Dallas."

Cons: "We were delayed, while the board continued to show on time. After about half hour of being delayed received an email saying the flight would be delayed half an hour, it then proceeded to be delayed more. Also were standing at the assigned gate at boarding time, only to overehear other passengers saying that the gate was moved. Asked the gate staff at the assigned gate and the"

Cons: "My son and I had seats in different places and they asked him to move forward several rows because of weight and the seat beside him was empty so I asked if I could sit next to him and they said no without giving any explanation. That kind of upset me. Just a short explanation would be fine."

Pros: "I took two connecting flights on American Airlines between Los Angeles and Lisbon period on the website American claims to have charging and or electrical ports in every row. There were none on either flight. To make matters worse, when my tablet and phone batteries both died before the end of the first flight, there was no inflight entertainment, other than 1 ridiculous thing available, on either flight. American has switched to BYOD for entertainment, but forgot to provide a way to charge our own devices. Incredibly stupid."
Cons: "On top of that, one of the flight attendants on the Philadelphia to Lisbon run was a hella snarky guy with a bad attitude all the way through. I would be surprised if I am the first person to complain about him."

Pros: "Flight was okay."

Pros: "Fun attendants"
Cons: "We boarded late, and due to technical issues had us stay on the plane for 30 minutes with no AC and delayed us for over 2 hours. I had a meeting and missed it. I’m also an American Airlines member and am horrified by this experience!"

Cons: "charged a surprise of $175 for my third bag although Kayak mentioned i should be charged $75 at the time of booking. AA says it is due to Jordanyan Airlines, why was I surprised by this extra charge?!"

Cons: "Confusion when boarding. Uncomfortable seat. No entertainment on a international flight! What kind of person thinks that is a good idea? I thought I will be flying British Airway for the flight back home that is why I bought this whole flight ticket. If I had known it will be AA flying back, I would fun as far away as possible."

Cons: "The Avianca flight was canceled a month ago, and kayak failed to notify me."

Pros: "Nice newer model plane"
Cons: "The usual...cramped seating. Boarding was very slow."

Pros: "Boarding eas good and crew was very good."
Cons: "The three hour delay and the terrible food served."

Pros: "Plenty of overhead storage. Loved USB and AC outlets. Comfortable and expeditious trip."
Cons: "Inboard video sound system stunk. Movie audio was inaudible, particularly dialog, and to make matters worse, choosing subtitles obliterated the rest of the audio. Love Cayman but departure gates are crowded and chaotic."

Pros: "Nothing"
Cons: "Everything."

Pros: "It made for a interesting Christmas but not a very jolly one."
Cons: "The flight staff skipped my aile a few times on accident. The touchscreen didnt worl very well, they offed free headphones but my headphone jack was broke and all of the usb charger ports didnt work in my row there werent many new choices for entertainment. And the food was interesting I'll give it that."

Pros: "Just flying AA excellent flight"
Cons: "No wifi. Pay only"

Pros: "Horrible hospitality. The flight was initially delayed for computer issues which understandably happens. However, we were later switch to another plane 4 hr later, boarded, de iced, taxied, then notified he flight was cancelled at 1 am because the crew hit their maximum work time. We were de-boarded. There was no organization to get vouchers passed out. The hotel ran out of rooms for passengers. The whole trip was 16 hrs delayed and no customer service provided."

Pros: "Nothing"
Cons: "Food was 100% inedible, I didn’t even bother with the breakfast because the main meal was really really disgusting No in seat entertainment The electrical outlet was not turned in for that section of aircraft"

Cons: "Getting to the airport early and waiting an additional ten minutes on the tarmac."

Pros: "Friendly staff"
Cons: "Rickity old plane. Needs updates badly. No drink service options. Cash only bar? Hello, this is the 21st century calling the 20th... You can have your plane and payment methods beck."

Cons: "Seat space very narrow and uncomfortable seats"

Pros: "The price"
Cons: "We were delayed almost two hours for weather and then when I finally boarded, myself and a few other people were pulled aside to be asked new security questions and have new boarding passes printed. The people at the desk let us know that it was because we checked in online. I don't mind being asked questions but they could have done that part of the process in the two hours that we were waiting to board so as not to further delay the boarding process."

Pros: "i like the wifi internet that AA provided. Great movies"
Cons: "The flight attendants were highly rude and i felt as if i was discriminated on. I was sitting in the back and the flight attendant who was suppose to assist us made us feel like i was a bother to her. First of all she just rudly dropped biscuits on my table didnt ask if i wanted and then I had to ask her for coffee, she didnt ask me if i wanted something to drink. Finally she brought my daughter and I some coffee. i ask for sugar and she said im very busy you have to wait....eventually she gave me one packet of sugar. I had to ask for another sugar for my daughter , so when i ask she gets upset and tells me i have to wait but there as a white who ask for assistance and she was very polite to her."

Cons: "a little delay in the departure connection flight ."

Pros: "We hit a very bad bout of turbulence. They were concerned as to our wellbeing and comfort throughout the flight."

Pros: "Great entertainment my second leg with personal TVs and great selection of movies and games. Also got great exit row seating for no additional price!"

Pros: "There was a lot of extra room on the flight so it was comfortable. The meals were tasty. I was glad they gave us a few snacks in addition to the main meal and the dinner snack with the tart and the sponge taper very good."
Cons: "The monitors were very difficult to use. I had to press them multiple times to change the screen"

Pros: "They were able to arrange for a seat for my daughter who was technically a lap child. The crew were courteous and helpful. The flight arrived early."
Cons: "Nothing."

Cons: "The flight left almost 6 hours late, and the delay was not directly due to weather. Another flight from and to the same airports left as scheduled 3 hours before this one finally left."

Cons: "Flight delayed going to and from my destination with no compensation. My bag I had to wait for it to come on the next flight and had to wait 2 hours for it."

Pros: "Avianca personnel helped as much as posssible because I am a frequent flyer in Star Alliance but there was only so much they could do"
Cons: "The itinerary I selected from Kayak site was impossible to accomplish especially with checked luggage because they would not transfer my bag from one airline to the next. Although I got my luggage quickly and got to the check in counter right away, the flight had closed and I had to wait for the next flight."

Pros: "Smooth flight home from Cancun."
Cons: "Late arrival."

Cons: "As I boarded the plane, they were trying to get me to check my carry on item when my bag fit the dimensions. It clearly fit in the luggage sizer, but the representative was quick to want to take my bag."

Pros: "Same"
Cons: "Same"

Pros: "Love the movies!!!"
Cons: "Passengers are allowed to take too much on the plane, which makes boarding & getting off take WAY TO LONG. If American would follow Southwest and allow 1 free bag, this problem would end. E"

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from the Cayman Islands to New Windsor

Airlines flying from the Cayman Islands to New Windsor 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

Mandatory masks

Masks required on board, masks provided

Social distancing seating

Middle seats unavailable to book

Pre-flight testing

Testing for antibodies, testing for symptoms

Book cheap flights from Cayman Islands to New Windsor

Recent round-trip flight deals

1/26
Tue
2 stops
American Airlines
28h 17m
GCM - SWF
1/28
Thu
2 stops
American Airlines
19h 55m
SWF - GCM
2/6
Sat
2 stops
American Airlines
28h 17m
GCM - SWF
2/10
Wed
2 stops
American Airlines
19h 55m
SWF - GCM
2/6
Sat
1 stop
American Airlines
9h 08m
GCM - SWF
2/10
Wed
2 stops
American Airlines
19h 55m
SWF - GCM

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