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Find cheap flights from Winnipeg to Simpson Bay

YWG - SXM

Find cheap flights from Winnipeg to Simpson Bay

Round-trip
Economy
Winnipeg (YWG)
Simpson Bay Princess Juliana
Thu. 21/1
Thu. 28/1
Any month
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Good to know

Low season

May Best time to beat the crowds (30% less expensive on average)

High season

September Most popular time to fly (27% more expensive on average)

Average price round-trip

C$ 845 (avg. price over the last 2 weeks)

Good deal round-trip

C$ 559 or less

When to book flights from Winnipeg to Simpson Bay

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 712 or less round-trip.
  • High season is considered to be August, September and October. The cheapest month to fly is May.

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Top airlines flying Winnipeg to Simpson Bay Princess Juliana

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,919 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Fast/ efficient"
Cons: "The little plane is always brutal. I'm not a small guy and sat next to an offensive lineman. It was tight for sure!"

Cons: "Flight delayed for 2 hours"

Cons: "long delay in boarding"

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."

Cons: "Everything"

Pros: "Everything. Always an excellent and professional experience."
Cons: "Nothing"

Pros: "Grateful Delta still has drink and snack service. Also grateful to still be able to bring a carry on on board. Good movie selections."

Pros: "Hands down one of the best flights ever. Great seats, great leg room, amazing crew; I even met some good people on the flight. All around pleasing experience."
Cons: "My only complaint is the food. Some of the other airlines feed us real food, I want to pay for something a bit better. Still a great airline!"

Pros: "Everythg was perfect"
Cons: "Have some headset so people can watch movies in the plane"

Cons: "Plane was way too hot and stuffy, wasn't until about 20 min into flight before started to cool down."

Cons: "Crazy rough, fast landing but not boring!!!"

Pros: "none"
Cons: "ground staff was rude when I asked for clarification because the descripency between app in formation and unclear voice announcements."

Cons: "... on top of that I kindly requested to speak with a supervisor and i was denied it. As a customer I deserved that. I would a ticket with Aerolineas and nowhere it said it was delta. I followed the baggage allowance explained on kayak website and on Aerolineas Argentinas. I took a bicycle which is free and i pay $100 to packed it as Aerolineas wanted. When I arrived it was a Delta flight and they told they don't allow bicycles and that i had to play $150. Aerolineas website and kayak clearly says that bicycles were free on my flight. I show the agent my ticket and that no where it said delta to consider what he was saying since it is an alliance but i was not informed about it. He said no and after wait there for a while before boarding i kindly ask to speak with a supervisor and the denied it and disappeared. I request a refund of my fee to you for providing incorrect information."

Pros: "Quick deboarding process. Attendants also wonderful. Diverse staffing. Attendants were friendly and helpful."
Cons: "Bumpy flight. But it was a short flight and they tend to be bumpier."

Cons: "Flight was delayed."

Cons: "Hassel about getting a visa to Cambodia. Refused to give me a boarding pass for 2nd and 3 rf leg of trip. Korean Air had no problems giving me yhe passes. Otter people had Delta boarding passes shivh they traded for Korran Aiir passes but the got better seats. Food was very good"

Pros: "Nothing"
Cons: "Gate staff was garbage."

Pros: "Everything was great from boarding to landing."

Pros: "Crew was great"
Cons: "No entertainment on flight. No smoking in Minneapolis airport"

Cons: "The leg from Atlanta to Pointe de Pitre had no wifi or even old style entertainment. Bring a book!"

Pros: "food was pretty good."
Cons: "a bit squashy in the seat. Inability to go online and select my seat without having to ring Delta and they do it."

Pros: "The plane was on time, the crew was friendly, no delays, landing was fine. In fact we actually made it a little before the time that we were scheduled. Since the flight was so short, I did not have any food."
Cons: "The seats were a little small."

Pros: "early take off and early landing"
Cons: "crying baby... passengers hanging out in the aisle... also lady sat in my emergency row seat and would not leave so I let her have it. also the lady next to that seat complained the whole time we tried to negotiate that seat. also the flight attendant that gave our section drinks seemed irritated and very rude. Older african american woman that stuck her finger in my face and the person next to me to ask her to stop her question as he picked up snacks that she dropped in the aisle. Kind of rude and kind of uncalled for. And the lady next to me (lauren) is an ER dr that had a layover in Atlanta for 4 hours to vacation with her fiance in the Caribbean..."

Pros: "Very satisfied. Great service"

Pros: "Giid free sandwixh. Very good entertainment system. Good seats."

Pros: "Delta did a really good job as always. Cheaper, more comfortable, and a WAY better experience than Alaska Airlines."
Cons: "Nothing."

Pros: "Outlets to charge your phone and watch movies."
Cons: "It wasnt specified which terminal to go to Aeromexico or delta. Going both ways. I had to pay a 40 dollar taxi to get me to the correct terminal .5 a mile away. And leaving in the early morning it was too dark and they convinced us it was unsafe and a 35 min walk. It’s def would be that long of a walk in Mexico since we had no idea where we were going."

Pros: "Although the flight was delayed, when it was time to board and take off, this was extremely efficient."
Cons: "Delayed flight. However, I know this sometimes out ot the airlines control."

Pros: "Delta and Westjet staff are of great help to me."
Cons: "Not applicable"

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: "Compared to previous flight - this was so much better with upgrade to first class and extra space."

Cons: "Too crowded and seat mate stunk like pot , flight was good because we were 20 minutes late and flight crew very nice"

Pros: "Great service, very comfortable."

Pros: "My wife’s and my headphone connections would not work."

Pros: "I love how attentive the crew was. Food and beverages we’re always available and I even had the chance to rest."

Cons: "After fully boarding the plane, we all had to leave because the air conditioning failed. We've traveled five times on Delta this year and every trip has had a significant delay."

Cons: "Delta delayed our outbound flight causing us to miss our connection."

Pros: "I flew with Delta"
Cons: "Your information was Aeroméxico"

Pros: "Nothing"
Cons: "I'm a frequent flier and was treated poorly, seated in the last seat and last row despite paying more than $1,000 on ticket. Awful."

Cons: "Condition of the airplane"

Cons: "Horrible wait if nearly 30 minutes after landing"

Pros: "Friendly staff"
Cons: "Every flight was delayed"

Pros: "It was wonderful to have a non-stop from Rome to Atlanta. The flight was comfortable and punctual. The in-flight entertainment was very good and helped pass the long flight."
Cons: "I liked the complimentary beverage service and many meal and snack interludes, although the food was sub par, especially the snack. I don't know how you can mess up crackers, but they were terrible, even slathered with the accompanying marinara. Also not sure that I ever met a shortbread cookie I didn't like until this trip; why lace it with artificial strawberry flavor?"

Pros: "Reassuring that the airport desk staff were keeping an eye on my connection from LAX to Columbus. Turned out it was too tight of a squeeze and I missed the connecting airplane's door closing by a few minutes, despite having RUN through LAX to get there."
Cons: "I am disappointed by the lack of communication among Delta staff when we arrived at LAX. Our turn-around was late coming into SMF, thus late leaving. It would have been very helpful if the gate staff at LAX had advised me to not bother to try to make my connection, or called the next gate to tell them we were running over there. RUNNING. Or at least done something to act like they cared. I am disappointed by the lack of initiative. I understand flights cannot wait, and I would have greatly appreciated being saved the trouble of running to a different terminal and instead taking that time to change my travel plans. They may see travelers struggling like this daily, but to each traveler, a hiccup in travel plans trip is stressful and urgent. I ask Delta staff to please consider that when they come to work. Thank you."

Cons: "For the second time in one day, my seat would not recline!!! Very uncomfortable for an even longer flight than the first one!!"

Cons: "See above description"

Pros: "Entertainment options"

Pros: "Good pilot. Decent flight attendants. All good."
Cons: "The price."

Pros: "Length of flight was good, one of the flight attendants was very nice"
Cons: "Flight attendant arguing and having words with a passenger BEFORE the flight even took off was very alarming, the attendant had walked past the seat, we saw her face change, she halted and walked back to the passenger and a very heated and negative exchange ensued, then another flight attendant came out and threatened to evict the passenger from the flight, this was before the flight even took place .... all passengers were like just remove them already ... t his is a short flight and most of use were connecting from a long flight from overseas ...."

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."
Cons: "I wish the entertainment system had had closed captioning, and/or that the inflight wifi had worked."

Cons: "Food is tasteless and it is too crapped. No leg room on planes"

Pros: "Business class was comfortable."
Cons: "Flight was delayed 2 hours."

Cons: "Why did I have to pay to select my seat? Isn't that the point of purchasing a seat at all? Silly."

Pros: "Flight attendants friendly"
Cons: "Food was not as good time"

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: "One of the crewmembers (regrettably, I did not catch his name) was incredibly kind when I moved seats to accommodate a couple that wanted to sit together. He really made this flight great."
Cons: "Seats were comfortable but the row I moved to did not allow me to recline."

Pros: "As we approached Raleigh ~3:15am, over 4.5 hours late, the pilot apologized for the delay, which was thoughtful of him. And we arrived in one piece, so that was good too."
Cons: "While waiting for the flight, I whined on FB about our probable delay, and a friend responded with "I'm guessing that you're crammed at the end of that terminal hallway with about 10 other gates of people with no airplanes, no information, and 2 AC employees." Spot on. Apparently such delays, understaffed gates, and failures to communicate with passengers are par for the course. Friend even predicted the free bagels AC would eventually offer at the restaurant that closed 3 hours before our flight finally left. He didn't predict the multiple announcements about assorted other flights not having functional restrooms so please pee before boarding."

Pros: "The crew was professional and polite"

Cons: "dirt and stuff on floor between floor and wall, bad, never seen that before in a nearly new plane"

Pros: "Overall it was a quick and painless flight. The crew was friendly and we had no problems!"

Pros: "I didn't really like breakfast but I am glad we had it."
Cons: "While the plane was circling in a holding pattern our luggage was left out in the snow for over an hour. My one bag was wet when I got it and my other bag didn't arrive. And because there were no Air Canada workers at the desk in Philly no one could tell me where my bag was. It was a very stressful end to a long series of flights."

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: "Nothing. The only good thing was it was a direct flight."
Cons: "Why when the seats are so close do you allow the seats to recline. Maybe the flight attendants should be more interested in the passengers than selling stuff."

Pros: "The flight attendant Kaldon was amazing. He was friendly, professional, and you could tell he loved his job. He truly made the short flight something special."

Pros: "The plane was nice and spacious. A CA agent stationed by customs helped about five of us get to the front of the line, so we'd make our next flight."
Cons: "1. After playing 20 questions at the check-in kiosk, it was unable to print our documents. 2. So we played 20 questions again and the second machine failed to check us in. 3. The flight was delayed about an hour (due to weather, not your fault), so our connection was tight. We alerted the agent at the gate (along with several others). She didn't help at all. She just told us to go to the gate. Well, we had to go through customs, so that wasn't helpful. What we were asking is if she could alert the gate agents at the next flight that we were running as fast as we could. 4. So five of us get to the next gate as they're paging us that the doors are closing. 5. Our bags didn't make the flight, which wasn't unexpected, but it was worrisome when the agent at our final destination told us she couldn't tell where they were."

Pros: "Flight was well managed, and even though the flight was full, service was on time and pleasant. A great travel experience overall."

Pros: "I thought the overall service was very good. I like how well the crew communicated with the passengers and how smoothly everything went."
Cons: "The food (dinner: chicken with rice, breakfast: eggs) was ok, maybe even a little yummy, but could've been better (eggs where a bit too wet). I also felt like the movie selection was rather disappointing. A lot of not so great hollywood blockbusters."

Cons: "The flight left almost 1 hour late because paperwork wasn't signed off"

Pros: "In flight Game of Thrones!!"
Cons: "The lines at YVR were horrendous."

Pros: "Reaching my destination, that's the only thing I was happy about"
Cons: "The plane is old and seat are close to each others, it wouldn't hirt if they make extra space, afterall it's a long flight!"

Cons: "2h and 4h30 h late"

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: "My one checked bag did not arrive with me. Not sure where the delay was."

Cons: "Never made connecting flight due to delays on first leg of the trip. Airline was generally apathetic to situation."

Cons: "Flight was delayed for hours first without any communication, later with very unclear communication. Spent multiple hours at the airport just to have to fly out next morning at 6:30am. Wasted day, wasted night. Delays can happen, but according to the finally communicated cause this could all have been communicated early on (crew not available in Cleveland, that was two flight legs earlier)."

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: "Nothing"
Cons: "Never happened since the first fligh never landed. Has to be rebooked on a united flight which took me to destination."

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: "Things were very good. Staff was freindly."
Cons: "The internet wasn't working but not a problem for a 1 hour flight."

Cons: "My Mon couldn't fly because I never have noticed that she needed a Canadian Visa. She came from Mexico with her American visa and the experience buying a ticket with this airline was a nightmare."

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"

Cons: "Flight should leave at 8:00.Left around 8:25 because delay loading luggage....Reached LA 20 mins. late and waited 10 mins to taxied to the gate....."

Pros: "This was my first Air Canada flight, and I was beyond impressed with the service overall. The plane was extremely nice and very spacious. The flight crew was very attentive and helpful, and had great attitudes. I had trouble with my entertainment screen early on, and a flight attendant went out of her way to reset and make sure it was working for me. The 12 hour flights both ways were comfortable and enjoyable."
Cons: "I honestly can't say anything negative about this experience!"

Pros: "On time or early"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Winnipeg to Simpson Bay

Airlines flying from Winnipeg to Simpson Bay 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 Simpson Bay

Mandatory masks

Masks required on board, masks provided on flights from Winnipeg to Simpson Bay

Social distancing seating

Middle seats unavailable to book on flights from Winnipeg to Simpson Bay

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Winnipeg to Simpson Bay

Book cheap flights from Winnipeg to Simpson Bay

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26h 01m
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25h 50m
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