Find cheap flights from Winnipeg to Caribbean

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YWG — Caribbean
24 Jun — 1 Jul1
Return
1 adult
Economy
0 bags
From?
To?
Fri 24/6
Fri 1/7

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Good to know

Low season

January

High season

December

Cheapest flight

C$ 418

Average price round-trip

C$ 1,039

Good deal round-trip

C$ 720

Good deal one-way

C$ 193
Best time to beat the crowds (5% less expensive on average)
Most popular time to fly (13% more expensive on average)
Flight from Winnipeg to Puerto Plata La Union
(avg. price over the last 2 weeks)
or less
or less

Top tips for finding cheap flights to Caribbean

  • Book at least 1 week 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 Caribbean is September.
  • Morning departure is around 92% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Caribbean flights

Top 4 airlines serving Winnipeg to Caribbean

Scores according to KAYAK customer reviews
7.9
DeltaOverall score based on 30768 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.5Food
Airline reviews

This is another disease as if you have the Internet, you are ordinary deceivers!

Read more about Delta

This is another disease as if you have the Internet, you are ordinary deceivers!

The flight was on time. The snacks could be better

Flight was cancelled by the airlines

Mika, was outstanding. Always available when needed by passes gers. She's very hospitable.

Missed our flight the first time because security and customs in Paris were out of control and took us an hour to get through. Arrived at the gate and had to reschedule. Was informed it was our fault we missed the plane, they did rebook us, but for a flight almost 11 hours later.

Cons: "The audio jack of the movie is not good It's on & off seems loose"
Cons: "Great crew!"
Pros: "Crew not so much!"
Cons: "A bit friendlier ...had no ice??"
Pros: "Maria in Winnipeg tried to find me decent connections. She did book me into a hotel in Boston as I missed connection 3 times!!!!"
Cons: "Flights that arrive and leave on time. How can one plan a trip if flights are continually cancelled or delayed. Very frustrating and a very unhappy customer."
Pros: "New plane, friendly crew."
Cons: "Departure time"
Pros: "The poor cabin stewardess was working the whole time as it was a short flight."
Cons: "This is a horrible route, they charge you more than flying to Europe and give you a one hour ride in a cramped plane where you can't even bring in a carry-on. The cost is insane but is one of the reasons Wall Street loves Delta as they are racking in the profits for very little service."
Pros: "Food was great. Movie selection was good."
Cons: "When we booked our flight, we were not informed by KAYAK that we have to pay for our luggage! I t was very unpleasant surprise both ways."
Pros: "Great crew, snacks, comfortable flight."
Cons: "Late departure"
Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."
Pros: "Crew was nice, food and entertainment was nice."
Cons: "Seats could’ve been more comfortable."
Pros: "It was delayed"
Pros: "Super comfortable seats. Lots of movie options."
Cons: "Food was not very good"
Pros: "The stewards did an awesome job leaving me a chocolate snack and an chicken wrap while I was sleeping!! Definitely a pleasant surprise to wake up to"
Pros: "Staff were friendly. Nothing they could do about the maintenance issue that we experienced."
Cons: "Hour delay due to a maintenance issue. This was a hassle in and of itself, but the flight was also on New Year's Eve and ended up getting us to Buffalo about 20 minutes before midnight, which was a bit disappointing when I had made previous plans for the night. Also, I found the cabin to be very cold during the flight, but it was pretty short so I didn't complain."
Cons: "Turbulence but no one can help that"
Pros: "It is a busy travel day and this flight was unbelievably smooth. The entire crew was competent and friendly."
Pros: "Insane turbulence with no explanation of cause. Also, the jack for my earphones did not function properly."
Cons: "Insane turbulence with no explanation of cause. Also, the jack for my earphones did not function properly."
Pros: "Great service. Smooth flight. Funny flight attendants. No issues boarding or deplaning."
Cons: "Food wasn’t great. What’s new?"
Pros: "The last time we flew Delta, we were underwhelmed. Our flight was delayed several hours and there was nothing exceptional about it when it did finally leave. That was 5 years ago, and there's been a lot of changes. There I'd now in-flight entertainment, reasonably comfortable seats, and everything was on time."
Cons: "Virtually no food options."
Cons: "The crew was great and the flight came in early. I wish there was a better food selection."
Cons: "Friday when I supposed to depart at 7:21 am my flight was delayed to 6:00 pm and yesterday when I supposed to depart from New York at 7:21 pm my flight was delayed until 11:20 pm was horrible! I never again i would took Delta because I call a day before my departure to see if they would help me changing my flight by morning and they couldn’t they told me that i have to pay $300 dollars."
Pros: "nothing"
Cons: "the flight attendant gets the order starting from the back and by the time she gets to the front there's no more selection for breakfast except for what is left that nobody like."
Cons: "Flight was 30 minutes late because the gate was understaffed. During the flight, the crew told us they couldn’t serve us because of turbulence, but then served first class."
Pros: "Good movie selection"
Cons: "Just about everything else was mediocre"
Pros: "Nice flight attendants"
Pros: "Quick service, good information."
Cons: "Not applicable, it was a good flight."
Pros: "Friendly staffs and on time flights"
Pros: "Fast boarding, we even left early! Very kind crew. Flight was WAY shorter than it said on our itinerary!"
Cons: "No TVs and couldn’t get wifi to work. Small plane, slightly uncomfortable."
Pros: "Tons of free entertainment on the screen in front of your seat! Movies, games, and details on your flight, all available on your touch screen. USB charging is also available."
Cons: "No one told us they wanted everyone with a roller carry-on to.check their bags. An attendant told my sister that her bag needed to be checked. We did not receive this notification until we were at the gate, boarding."
Cons: "Flight was delayed ... wish I had received text notice instead of email so I could have enjoyed the extra hours of vacation instead of sitting at airport."
Cons: "Food .gate changes"
Pros: "Pilot flew flawless crew kind and helpful it was a full flight and impressed helpful passengers to get on board was."
Cons: "Disappointed airplane not equipped with free movies. I bought ear buds on return flight for that purpose"
Pros: "We stood on the ground due to weather, which had nothing to do with the airline itself. Keeping this from jading my point of view, the airline stood within the standard of what is expected of a good trip. Food was good, and the choice of movies, shows, and games helped the time pass. Staff was friendly, and checked bags were ready rather quickly."
Cons: "The number of updates telling us we are going nowhere, was a bit excessive."
Cons: "The plane was about 10 minutes late departing (not too bad), but the Entertainment System was down for the flight, meaning that in addition to entertainment, the USB and outlet charging was not working and you couldn't see current flight status."
Pros: "flight was on time, food was good"
Cons: "entertainment was not working, not enough legroom"
Pros: "The organization, the shortening of the flight time."
Cons: "At the Orlando airport, the LACK OF SEATING BY the gate!"
Pros: "Smooth"
Cons: "Delayed because the airline misschdduled the pilots!! We had to wait for pilots to come to the plane... while one the plane"
Pros: "Flight was very comfortable and had a lot of space to move around"
Cons: "The gentleman indicating on the loud speakers what zones will be loading first was very rude."
Cons: "Late taking off, and then unable to get to gate on arrival"
Pros: "Great Service and amenities for a great price!"
Cons: "Nothing"
Pros: "This was a 767 and we flew first class, so we had the more private, reclining seats with the advanced electrical and USB outlets. The flight attendants were excellent and I had a special meal request, which they confirmed and served me well."
Cons: "Nothing. the flight was great!"
Pros: "Plenty of complimentary drinks and snacks. Even complimentary Earbud Style HEAD-SETS !"
Pros: "The in flight entertainment was great with live tv and a assortment of current movies to chose from."
Cons: "Nothing at all"
Cons: "Family of 6 with 3 minors. Could not sit any of us together."
Pros: "Everything was great"
Cons: "Nothing"
Pros: "Very efficient boarding and great crew!!"
Pros: "The crew was good."
Cons: "Seats where uncomfortable. They didn't have the adjustable padded headrest even though we did coming to Winnipeg. You can no longer change your seat selection 24 hrs before you're flight without a fee. There was also no entertainment coming from Winnipeg even though there was entertainment going to Winnipeg."
Pros: "Fantastic crew!"
Pros: "They were very helpful and polite."
Cons: "Times have changed and they offer very little such as entertainment food options. but it was short trip and people need to adjust."
Pros: "The crew was very nice"
Cons: "Seats are uncomfortable and there’s no tv for entertainment."
Pros: "Yes"
Pros: "Crew was great. Seats were not comfortable."
Cons: "Slightly wider seats."
Pros: "Average"
Cons: "Two of the most important things to me in travelling by air are getting through security as quick it’s possible ie the priory line; and a lounge. Traveling and paying for Plus provides neither. Back to Air Canada Business Class or AC Rouge Premium. Going to have to pick up your game WestJet"
Cons: "Missed my connection"
Cons: "Flight was delayed an hour which isnt horrible but then had to sit on the plane an additional hour waiting for take off. I barely made my connecting flight in Calgary. They should have held that plane because i know the elderlt women next to didnt make it. Staff were not attentive enough. Buzzed them servial times and no response."
Cons: "Early on first flight on arrival but late departing by 30 mins due to westjet delay of crew"
Pros: "Flight was smooth no problems"
Cons: "Being 40 minutes late Cost to me $234.00"
Cons: "no refund at all worst outcome"
Cons: "WestJet seems unable to stick to a schedule. Three of my four flights were delayed and a connector flight through Toronto was cancelled altogether just after midnight, leaving me stranded at Pearson Airport. The ground crew were disorganized and unable to provide clear answers – other than their complete assurance that WestJet bore no responsibility for providing hotel accommodation."
Pros: "I’ve always liked WestJet and it’s services. They are my always my first airline I go to check flights."
Pros: "Fun crew. Short flight"
Cons: "Flight was late leaving. Our connecting flight was already boarding when we arrived. I would have liked the 25 mins we were supposed to have."
Cons: "I had to travel with a wedding dress. Westjet does will NOT replace lost Wedding dresses therefore they MUST be carried onto the plane. once on the plane there is no where to hang the wedding dress. The flight attendant was kind enough to take it from me and STUFF it in the over head compartment :( I was furious!"
Pros: "The flight staff were very friendly and helpful upon boarding. Once landed even the pilot was standing in view and say good bye. Thanks again!"
Pros: "Flight crew very friendly."
Cons: "Entertainment app. is terrible, movies really old."
Cons: "First flight on WestJet in 3 Years. Didn’t like not knowing I needed a tablet or laptop and an app to watch tv. Offered a drink and asked for water. Received about 2 ounces. Every body around me ordered soft drinks and got a 10 ounce can"
Pros: "Everyone was very nice"
Cons: "It was cold on the plane!"
Cons: "Cramped seating configuration."
Cons: "Thanks"
Cons: "The stewardess (Stephanie was her name I think) grabbed my arm and pushed it out of her way rather than asking me to move. While it may sound dramatic, I am certainly not accustomed to a stranger putting their hands on me and it was hugely inappropriate and ruined my flight. This was my first WestJet flight after flying countless times with Air Canada. The whole experience was soured and I will never look at WestJet the same again."
Cons: "Non comfortable cold sensation."
Pros: "GREAT CREW"
Cons: "BOARDING FROM OUTSIDE-VERY COLD OUT IF I KNEW I WAS BOOKED ON A PROP PLANE I WOULD HAVE BOOKED DIRECT SEAT SIZE-CRAMPPED-I ASK THE GUY BESIDE ME IF HE WANTED THE AILSE BECAUSE HE WAS TALL AND SQUISHED CALL ME ANYTIME 306-551-3251 THAT WAY I WILL KNOW THE VALUE OF THIS SURVEY"
Pros: "Absolutely nothing."
Cons: "Upon my arrival in Calgary I had missed the last shuttle to Banff (my final destination) and no one at the customer service desk would do anything to help me in my stranded situation."
Pros: "Got away a little late (full flight and de-icing) but still managed to get in to Phoenix well ahead of the scheduled arrival time."
Pros: "West jet employees worked hard to fix the mess they caused. Eventually getting me a ticket for another airline."
Cons: "Changed my flights with less than 3h notice. I’d payed extra to reduce wait times as I was flying with a child just over 2. Originally had me coming in to Vancouver at 9 am and leaving at 5:40pm. Not cool with a young child. Allmost missed the 1st flight getting it fixed, they also didn’t book my child in adjacent seats, despite pre-booking the seats on the flight days before."
Pros: "The pilot was awesome and the crew."
Pros: "Getting on in Palm springs and getting off in Winnipeg. Thanks WestJet"
Cons: "Not knowing to download The app until I was on the plane"
Pros: "The professionalism of the crew and the spacious plane."
Pros: "Quick boarding, good customer service, and friendly staff."
Cons: "When I booked online it was a little unclear that I would have to pay extra to check a bag. No problem but would make a better customer experience if I had been aware of this"
Cons: "Some more food options"
Cons: "Wi fi didn't work"
Pros: "Cabin crew was good,"
Cons: "The seats where not compfie"
Pros: "The roominess, service, food.....all excellent"
Cons: "It would have been so much better if there was a foot rest."
Pros: "Again, staff was friendly and approachable attitude."
Cons: "Toronto airport needs proper signage. I got lost and wasted my half an hour to just find a transist to downtown."
Pros: "Comfortable seat with lots of leg room"
Pros: "It was a great flight . It wasn't full so there was a lot of room . It was on time and the Crew was very friendly"
Pros: "Fight left on time, crew was friendly, entertainment system worked."
Cons: "Cramped seats made worse by reclining passengers seated in front of me. Couldn't pre-order my meal even though I tried 24 hrs before ( 2 days is apparently the requirement)."
Cons: "I was able to download the WestJet Connect app on my phone which gives you access to tv shows and movies to watch on your own device during the flight. The app was free and easy to use and there was a decent selection. However, the wifi on board is not free so even though you could watch the tv show/movie - the sound did not work unless you paid for it. There are many other airlines that offers everything for free - it would have been a more pleasant if we were able to actually utilize the service."
Pros: "On time"
Cons: "Tight seats"
Pros: "Everything was excelente very nice personal."
Cons: "It was as if the baggage fell of somewhere from the plane and came in contact with water."
Cons: "Flight was late leaving ywg"
Pros: "The crew and staff as a whole were very accommodating"
Cons: "Nothing to be honest was a great experience"
Pros: "I liked the entertainment application, and the selection of movies. The crew was courteous."
Cons: "The price was high for the calibre of flight, and the luggage overage charges are just silly."
Pros: "Friendly flight attendants and a smooth ride and landing"

Check in baggage lady had a horrible attitude. Was not helpful at all.

Flight attendants were efficient and friendly. Flight was delayed 1.5hrs then no ground personnel at destination in Toronto. Over 2 hours late!!

4 hours late

Pros: "Got there"
Cons: "Way too expensive"
Pros: "Service"
Cons: "All was as good as expected"
Pros: "I like the app to tell me where is my baggage. Thanks"
Cons: "More drinks, snacks"
Pros: "On time, great cabin crew"
Cons: "Q400 is cramped, noisy and awful overhead storage"
Pros: "On time, crew was cheery!"
Pros: "It was canceled"
Pros: "Comfortable seat - great service"
Cons: "Delays"
Pros: "Crew was friendly"
Pros: "Staff were pleasant"
Pros: "It was on time, both going and return."
Cons: "Food was terrible, the worst I had in flying with air Canada."
Cons: "flight was cancelled. poor communication."
Pros: "Business class was comfortable."
Cons: "Flight was delayed 2 hours."
Cons: "I don’t like the head games air Canada plays when they know the flight is probably not going to leave for three hours and they purposely don’t update the flight details. Only update every 20 minutes for a three hour delay...."
Pros: "Plesant ride"
Cons: "Flight took longer to depart due to boarding and de-icing"
Pros: "Size of seats and entertainment"
Cons: "Late leaving, slow baggage claim"
Pros: "Everyone and everything was outstanding! Completely opposite of every experience I've ever had with Air Canada! They finally get it! Treated us like we were people and valued customers! Amazing!"
Pros: "Everything I will definately be back"
Pros: "The crew was professional and polite"
Pros: "Nothing because it didn't happen"
Cons: "When I got to the airport, the attendant notified me that my flight had been exchanged. No one notified me of this and I was still under the impression that my flight was scheduled as my itenerary in my latest email. It took two hours to figure out that United had changed my flight and booked me on a different one. Once again, without notifying me. Thank god they changed my flight to a later one or I would have missed it. By the time we figured out what flight I was on, I had to sprint to a different terminal because check in was closing in 20 mins. I arrived at the check in kiosk with less than 5 mins to spare. The experience was terrible and customer service from each Kayak, United and Air Canada. I also injured my back while sprinting between terminals wearing a heavy backpacking backpack. Would not book through Kayak again."
Pros: "Nothing"
Cons: "Every part of the experience was horrible from the lady who checked us in to the flight being cancelled after we were are the airport waiting for delayed flight. They did nothing to help us after and didn't rebook for almost 24hrs later when there were much better options to get us to our destination in time for the wedding we were going to. Horrible experience"
Pros: "The crew were helpful and professional."
Cons: "The options for movies and music for the inflight entertainment were not that good. The AirCanada app for mobile devices was not as user-friendly as I expected it to be."
Pros: "Overall it was a quick and painless flight. The crew was friendly and we had no problems!"
Pros: "Great movie selection"
Cons: "Late departing and on arrival the ground crew wasn't available so we were stuck on the plane awaiting their arrival. I can't understand scheduling issues that end up leaving jets stranded."
Pros: "No problems, clean, friendly staff, comfortable chairs with the head rest that folds up towards your ears."
Cons: "No complaints."
Cons: "The flight left almost 1 hour late because paperwork wasn't signed off"
Cons: "Nothing it was fine"
Pros: "People that helped us were personable"
Cons: "The flight was delayed 40 and then 50 minutes. No announcements were made, the screen just changed. I'm glad I went up to ask about my connecting flight to Athens; if I had waited and got on the flight, I would have missed my connection. The people at the AirCanada desk were nice, and were able to find us other seats. However, we were promised seats on the 7:30 flight, but instead were put on the 5:45 flight. We asked for the AirCanada person to call back and change our flight, but she said we would have time (at this point, 1 hour and 20 minutes before the flight left), even though I showed her that there was a lot of traffic between LGA and JFK and we probably would not make it. We had to leave LGA, find our bags and wait in a long taxi line to sit in traffic in a cab we had to pay for our of pocket, and could not make the 5:45 flight. I then had to call AirCanada and wait for 15 minutes for the lady to switch us to the 7:30 flight. In all, we also lost 2 full hours in Athens."
Pros: "The food on Air Canada is horrendous. Bring your own food! The crew was very nice."
Cons: "The Montreal airport is a zoo. I hoped it would be better than other places because it's smaller, but it wasn't. And I didn't fill out the correct customs form. The crew said that we should request a form from the USA if we were Americans, so I did. I have filled out that form many times, so I felt fine--until I got into the Customs area of the airport and learned that I needed to fill out a Canadian form too. So I had to do that before picking up my luggage. You would think that an Air Canada crew would know which forms I had to fill out and give them to me or at least ask questions so that I could be prepared when I went into the incredibly complicated maze to go through customs."
Cons: "2h and 4h30 h late"
Cons: "I was in the middle seat, and the man on my right elbowed me and did not give me room. But the worst thing, besides the awful food, was that my suitcase did not arrive! I hope it arrives today."
Pros: "Seating was fine on their "normal" flights."
Cons: "Regarding Air Canada Rouge service: If you are over 6' in height your knees will not fit in the assigned space."
Cons: "Did not like the idea that we had to pay for use of Ipad to watch shows , especially since I didnt have my own."
Pros: "I liked having the pillow and blanket giving to us. So great!"
Pros: "Entertainment system did not work"
Cons: "Crew provided a card to contact air Canada for compensation"
Pros: "Great crew and service. Seats were comfortable for tall people."
Cons: "Delays for both international flights. Food made us sick."
Pros: "Seat availability (lots of empty seats) Entertainment system had lots of movies & music Friendly flight attendants"
Cons: "Flight attendants could be more aware of his/her surroundings. For example, I was either stepped on (as a result, being woken up) or my backpack was stepped on several times when an attendant was walking down the aisle, and neither of those things were sticking out into the aisle. This has rarely happened to me on trans-Pacific flights (more crowded, longer flights) so I can only attribute it to the carelessness of the attendants and/or the aisle width but since I think aisle width follows international standards it's more likely the former."
Pros: "I liked the service. I dont like flying much but the stewdardes made me feel comfortable so it was a good flight"
Cons: "* Worst food I have ever had on a plane. The crew did not even know what was in some of the food, which is not comforting if you have allergies. * Entertainment system earphones were so bad they were unusable."
Pros: "cruising slightly high to avoid turbulence, the way from Toronto to Winnipeg we were flying on altitude 26,000 and then 30,000 feet. on west jet we were flying on altitude 39,000 feet with less turbulence. thanks"
Pros: "Leg room is comfortable"
Cons: "Flight had one and half hour delay. I did not get E-mail reminder for Check-in, for my return flight from Toronto."
Cons: "Same movies"
Pros: "Entertainment was good."
Cons: "My partner had injured his knee and it was quite swollen. When we phoned and also went to an AC agent at the airport, we were told there was nothing they could really do as far as leg room; Heathrow reps were kind enough to offer a wheelchair when we arrived. The frustrating part was when we were on the flight, there were multiple rows which only had 1 person seated. There did not seem to be any empathy, understanding or patience for our situation and it did not feel great to be treated with annoyance and disdain."
Pros: "The saftey"
Cons: "Food"
Pros: "Check in was excellent"
Cons: "Flight was 4 and half hours late for weather and mechanical reasons. Airline responded very well but such a long delay is annoying"
Pros: "No real issues...nice direct flight...on time too! Good movie selection."
Cons: "Connection of headphones was not good...monophonic sound"

Boarding

Pros: "The crew was responsive and very friendly."
Pros: "We arrived early. :)"
Cons: "A safe, quiet set of flights. Nothing really unusual, which is a good thing. US airlines suck badly in cuisine and this trip reinforcedji"
Cons: "Only bathroom on the plane was closed due to issues. Plane was cold and cramped."
Cons: "Flight was on an older CRJ 200, which was a little cramped and grungy-appearing."
Pros: "Great crew!"
Cons: "Everything was pleasant."
Pros: "Upgrade to economy plus"
Cons: "Norhing"
Cons: "The United App for entertainment would not work. It kept closing. The cabin was cold."
Pros: "I didn’t die."
Cons: "I researched United’s, FAA, and my car seat company website before trying to board with it. I was told by flight attendant that I could only bring the car seat on board if it had a sticker? I don’t know what sticker she was referring to and it’s tough to keep a toddler safe with just a lap belt"
Cons: "Charge for baggage. Pretzels - ugh!"
Pros: "Stroopwaffles, TVs"
Cons: "They made me check my bag which was ridiculous. It’s been on numerous flights and was smaller than any other bag in the overhead bins"
Cons: "3 hour mechanical delay"
Cons: "seats a little small"
Cons: "No entertainment on this flight"
Pros: "Frequent visits by cabin crew, food options were good and healthy, wide array of entertainment options,"
Cons: "Seat screens are very small, purser was pretty gruff"
Pros: "The crew was very friendly on board. The gate crew were a little curt, but it was a full flight and they were really trying to get everyone on board quickly so I can't be too upset about that."
Cons: "Few entertainment options - direct TV unavailable for about half the flight, WiFi also unavailable for the same."
Pros: "Good average flight, everything was efficient, comfortable, reasonable value but not outstanding."
Pros: "The transportation..."
Cons: "There's absolutely no leg room it's the smallest amount of room I have ever experienced on a plane - even the first class is eh - mediocre at best. I am slim and fit and I had very little to no room. Consider someone overweight and they would have to buy 2 seats... united is definitely not my favorite airline..."
Cons: "Video controller was not working properly."
Cons: "There was no in-flight entertainment option on this leg of my journey, which makes a four-hour flight seem long."
Pros: "Quick easy trip"
Cons: "I couldn't put my Cary on luggage in cabin.."
Pros: "we were on time, and the crew was nice."
Cons: "Boarding goes from the front of the plane to the back. When you're sitting towards the back, it's not ideal to have to trip over fellow passengers who are already seated in the front. Why not board from the back to the front like other airlines?"
Pros: "I like the United app for ease of checkin"
Cons: "Flying itself is a terrible experience. Cramped seats, food is nonexistent, no wifi"
Pros: "All went well on on time and service was good."
Pros: "Nothing about this flight did my husband enkoy, we have been apart 3 months, and he never made it in he had to turn around and go back to hawaii, he has a bad leg, and they layover in Newark was gonna be extensive"
Cons: "The entire flight to lax, when he had to get a flight back to Hilo"
Pros: "On time."
Cons: "Flight attendants brought a few people drinks and then disappeared leaving the rest of us thirsty"
Pros: "It was a mess ."
Pros: "Nice crew"
Cons: "Lost luggage twice!!"
Cons: "They cancelled my return flight when I rebooked through united online."
Cons: "No food on plane only a tiny bag of snacks"
Pros: "Nothing"
Cons: "UNITED employees are always rude"
Pros: "United is old school &, I'd forgotten what that meant. The crew was nice, the flight itself was fine, a bit bumpy, but that's weather, not the pilot. The in flight entertainment was good, and had many choices."
Cons: "One tiny bag of snacks, paying for Wi-Fi so I could get work done? Sitting in a seat that wouldn't tip back correctly (that I upgraded to the night before +$109)"
Pros: "Seat had room"
Cons: "Could not lay back"
Cons: "It would have been helpful to tell me when I was picking that seat"
Pros: "On-board WiFi was a nice touch, but redundant as there was no way to charge your electronic devices"
Cons: "Felt herded like cattle. Had to bring your own headphones... WTF? Children's meals requested for my 6-year-old were practically inedible. "Breakfast" consisted a stale, chewy croissant (which I believe I am still trying to digest a week later...) and yogurt. No USB port to charge electronic devices"
Pros: "It was delayed by 2.5 hrs and I ended up rebooking to another flight."
Cons: "Not enough room for my carry on and they checked it. I did not have a secure bag to check with lock and was upset."
Pros: "It was an ok flight. We missed our flight by 10 mins but got the next one at no charge."
Cons: "Nothing"
Cons: "United rerouted us and added another leg to our trip. We never flew Richmond to Denver. We ended up going Richmond -> Chicago -> Denver -> Santa Barbara. This caused us to miss a post-wedding brunch with family that we're only able to see about once every three years. All this after changing our flight out to the east coast the day of the flight (my 8:55pm flight was changed to 5:23pm, and I was notified after 3pm - meaning I had to run out of work early, costing me money, run home to pack, and rush to the airport, only to wait 3 hours for a now delayed flight). The also added another leg to that trip as well (at 3pm, day of). This was a red-eye flight and the last thing we wanted to do was get on and off the plane all night. I will not be flying with United after this trip."
Cons: "The food was not satisfactory. Soon after take-off everyone received a skimpy packet of breadsticks. A while later a meal (lunch) was served. It was very good. Many hours later everyone received a packet of pretzels, etc. About an hour before arrival everyone received a sandwich in a plastic wrap. It was close to inedible. Beverage service was very good. However, the amount of food served was unacceptable. This seemed like a budget flight. Very different from the flight to Europe on a Lufthansa plane. This was on a United plane. Will make me think twice about flying to Europe on a United plane."
Pros: "Nothing"
Cons: "Every flight was delayed. I missed a major meeting due to these delays. Most of all the flight attendants where horrible and UNSAFE."
Cons: "Seats were uncomfortable. Husband who is 6'1" had pain in his knees after flight."
Pros: "The staff was friendly and accommodating. The flight was smooth."
Cons: "Nothing"
Pros: "Absolutely noting."
Cons: "I purchased a return ticket from Port of Spain, Trinidad to Newark, NJ with United. I also purchased the insurance on this flight because it's good sense to be prepared. Unfortunately, I couldn't make the flight because of medical reasons and had to cancel. When I called United to purchase a new ticket, they were charging me a $200 rebooking fee plus a $30 processing fee. That's almost the price of the ticket! This is an absolutely horrible policy and very unfair. I had to rebook a new ticket with JetBlue which is 100% better, reasonable and understanding than United. Not to mention I lost the credit with united because with the rebooking and processing fee, it's almost the same price as the ticket. Because of this atrocious experience, United will never get my business again."
Pros: "Okay crew."
Cons: "Cramped, uncomfortable seating. Departure time and gate changes."
Pros: "The landing was not good as we had turbulance. Other than that, everything was good."
Pros: "Easy flight"
Cons: "Very bumpy!"
Pros: "Nothing"
Cons: "The service by the crew was awful! Airlines forget that customers pay for transportation. Sometimes hundreds to thousands of dollars. Will never use them again"
Pros: "The tvs were just frozen the whole time. No movies, no maps, nothing. Wifi wouldn't connect. The crew was wonderful though - they made up for it as best they could."
COVID-19 information

Safety measures for airlines flying from Winnipeg to Caribbean

Airlines flying from Winnipeg to Caribbean have enacted additional safety measures and adjusted policies to better accommodate travellers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Winnipeg to Caribbean

Mandatory masks

Masks required on board, masks provided on flights from Winnipeg to Caribbean

Social distancing seating

Middle seats unavailable to book on flights from Winnipeg to Caribbean

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Winnipeg to Caribbean

Flexible cancellations

Waiving of change fees. Search flexible flights from Winnipeg to Caribbean

Book cheap flights from Winnipeg to Caribbean

Recent round-trip flight deals

27/9Tue
2 stopsDelta
23h 54mYWG-AUA
7/10Fri
2 stopsDelta
24h 37mAUA-YWG
C$ 673
31/10Mon
1 stopWestJet
19h 58mYWG-NAS
8/11Tue
1 stopWestJet
7h 32mNAS-YWG
C$ 703
31/10Mon
1 stopAir Canada
16h 45mYWG-NAS
8/11Tue
1 stopAir Canada
9h 55mNAS-YWG
C$ 706
3/8Wed
1 stopWestJet
19h 50mYWG-SXM
18/9Sun
1 stopWestJet
9h 22mSXM-YWG
C$ 716
26/10Wed
1 stopAir Canada
15h 50mYWG-NAS
9/11Wed
1 stopAir Canada
21h 55mNAS-YWG
C$ 733
31/10Mon
2 stopsWestJet
21h 18mYWG-NAS
10/11Thu
1 stopWestJet
7h 32mNAS-YWG
C$ 734
17/10Mon
3 stopsMultiple Airlines
41h 04mYWG-PUJ
24/10Mon
1 stopMultiple Airlines
18h 25mPUJ-YWG
C$ 737
6/8Sat
1 stopWestJet
19h 50mYWG-SXM
18/9Sun
2 stopsWestJet
27h 57mSXM-YWG
C$ 746
26/10Wed
1 stopAir Canada
21h 10mYWG-NAS
10/11Thu
1 stopAir Canada
7h 55mNAS-YWG
C$ 762
29/10Sat
2 stopsWestJet
21h 03mYWG-NAS
5/11Sat
1 stopWestJet
7h 33mNAS-YWG
C$ 763
26/10Wed
2 stopsMultiple Airlines
44h 43mYWG-NAS
7/11Mon
1 stopMultiple Airlines
27h 25mNAS-YWG
C$ 776
25/10Tue
1 stopAir Canada
20h 15mYWG-NAS
5/11Sat
1 stopAir Canada
22h 55mNAS-YWG
C$ 812
6/10Thu
2 stopsMultiple Airlines
18h 05mYWG-NAS
9/10Sun
2 stopsMultiple Airlines
29h 05mNAS-YWG
C$ 828
26/10Wed
1 stopAir Canada
29h 05mYWG-NAS
6/11Sun
1 stopAir Canada
27h 25mNAS-YWG
C$ 843
31/10Mon
2 stopsDelta
29h 49mYWG-NAS
8/11Tue
2 stopsDelta
9h 46mNAS-YWG
C$ 848
6/11Sun
2 stopsMultiple Airlines
33h 05mYWG-NAS
13/11Sun
3 stopsMultiple Airlines
30h 15mNAS-YWG
C$ 863
29/10Sat
2 stopsDelta
8h 52mYWG-NAS
8/11Tue
2 stopsDelta
9h 46mNAS-YWG
C$ 865
6/11Sun
2 stopsMultiple Airlines
28h 00mYWG-NAS
13/11Sun
2 stopsMultiple Airlines
28h 45mNAS-YWG
C$ 880
27/10Thu
2 stopsDelta
22h 30mYWG-NAS
6/11Sun
2 stopsDelta
21h 28mNAS-YWG
C$ 935
28/10Fri
2 stopsEndeavor Airlines
28h 20mYWG-NAS
7/11Mon
2 stopsEndeavor Airlines
21h 42mNAS-YWG
C$ 1,494

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Recent one-way flight deals

13/6Mon
1 stopAir Canada
17h 45mYWG-POP
C$ 418
13/6Mon
2 stopsAir Canada
44h 55mYWG-POP
C$ 445
13/6Mon
3 stopsMultiple Airlines
42h 45mYWG-POP
C$ 576

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Winnipeg - Caribbean Flights

Departure:

Winnipeg (YWG)Canada

Return flight deals:

Caribbean - Winnipeg

Cabin classes:

C$ 2,737
C$ 484

Browse origins:

C$ 603

Browse destinations:

C$ 673
C$ 603
C$ 2,866
C$ 1,245
C$ 2,032
C$ 1,052
C$ 1,116
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