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Find cheap flights from Winnipeg to Massachusetts from $203

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Winnipeg to Massachusetts departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 6/19
Wed 6/26

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Best Massachusetts Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Boston2 stops$356
Albany
Albany2 stops$598

Good to know

Low season

November

High season

June

Cheapest flight

$203
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Winnipeg to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Winnipeg to Massachusetts?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Winnipeg to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Winnipeg to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Massachusetts from Winnipeg is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Winnipeg to Massachusetts?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Massachusetts with an airline and back to Winnipeg with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Winnipeg to Massachusetts?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Massachusetts from Winnipeg up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Massachusetts

  • Morning departure is around 25% 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

Top 3 airlines serving from Winnipeg to Massachusetts

 
Need help choosing which airline to fly with from Winnipeg to Massachusetts? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.5
Korean AirOverall score based on 1166 reviews
8.6Boarding
8.3Comfort
8.8Crew
8.2Entertainment
8.1Food
Airline reviews

The flight crews were extremely professional, helpful, and courteous. Departure and arrival times were accurate. No delay. I will use K airline again. Thanks

10.0 ExcellentAnonymous, Apr 2024IAD - ICN
Read more about Korean Air reviews

The flight crews were extremely professional, helpful, and courteous. Departure and arrival times were accurate. No delay. I will use K airline again. Thanks

Not very comfortable seated in the back plane due to turbulence

Ford not that great the seat not to big for leg room like other airline

Great crew, decent food Charging plugs were broken on both seats next to me. Only the USB port was available, and that charges, very, very slowly. Seat was also broken, it would not lock into position when reclining.

New plane. Perfect gluten free meal Very flawless procedures from check-in to the landing. Taking off on time and landing even earlier and the luggages are already there after shortest arrival report.

It was ok. Not good and not a bad experience

not too bad but not too great either. Service on all airlines declined ever since covid. Your Delta Stewardess are not that friendly at all. :-(

I like your stewardess, they are nice. However, your food could have been better and wheres your dessert? You do not offer beer or scotch. I do not drink alcohol biut my husband can have one or two, he has to ask if he can have one. during dinner or lunch, it should be offerred. Also, you do not have the most famous drinks ginger ale

Not accommodating ground staff On board slow service Crew members not very friendly

lunch was good; breakfast was kinda meh cabin temprature was way too high new entertainment system but somewhat limited content

Was the longest flight I have ever taken to Orlando. Not Westjet’s fault necessarily. There was a traffic issue in Orlando. We sat in the airplane for about 2 hrs before leaving Calgary on a 5 hour flight was just a little long to be stuck in the plane. Once we arrived in Orlando we were stuck in traffic on the ground for another 30min. I guess maybe the flight could be delayed so boarding would have been later so we wouldn’t have to have the discomfort of being on the plane so long.

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

Nothing to like about flying in the Dash 8s. With very small seats, little legroom, and a very noisy plane, nothing about such trips is enjoyable.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Difficult to say. Over crowded but that is the fault of the airplane not WestJet

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

Check in was seamless , crew very polite , arrived on time!

Flight arrived early even after leaving late. Bag drop was a zoo, very slow even after using pre-checkin and airport kiosk.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Seriously need to improve the time schedule and the plans

Great TV, easy boarding, wonderful ground crew and flight crew.

Pretty good service and US Migratory officers providing services in Canada was awesome, because the arrival was quick and smooth

Rude Customer Service at checkin, 90 minute limit in flight check in is too strict. I was in line for 30 minutes because of slow/insufficient workers. Somewhere I got to the the counter of course the employee warned me about the 90 minutes. People were cutting the lines. No one did anything.

Rouge needs to offer seats with better pitch in economy. Many sick people on a full flight.

Overall, I would have to say my experience with Air Canada was mediocre their DC tens. Need to be updated not comfortable at all. Only one out of my four flights was decent. The staffing was very nice. Going through customs in Montreal was quick and easy. Air Canada has room for improvement with their facilities.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

This time my experience was superior! Much better and improved from after the COVID-19. I hope they maintain the same. Earlier, service (specially crew attitude) was awful and sometime rude, but this time, crew was very welcoming, respectful and ready to serve. I will definitely repeat :-)

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

Book cheap flights from Winnipeg to Massachusetts

Recent round-trip flight deals

10/16Wed
2 stopsPorter Airlines
12h 27mYWG-BOS
10/21Mon
2 stopsPorter Airlines
7h 47mBOS-YWG
$356
6/14Fri
1 stopPorter Airlines
5h 15mYWG-BOS
6/17Mon
2 stopsPorter Airlines
10h 52mBOS-YWG
$359
6/25Tue
1 stopAir Canada
7h 54mYWG-BOS
6/30Sun
1 stopAir Canada
6h 01mBOS-YWG
$390
6/3Mon
1 stopDelta
5h 48mYWG-BOS
6/5Wed
1 stopDelta
9h 03mBOS-YWG
$444
6/14Fri
1 stopUnited Airlines
10h 02mYWG-BOS
6/17Mon
1 stopUnited Airlines
17h 31mBOS-YWG
$454
5/30Thu
1 stopDelta
5h 48mYWG-BOS
6/3Mon
1 stopDelta
9h 03mBOS-YWG
$497
6/10Mon
1 stopAir Canada
7h 43mYWG-BOS
6/17Mon
1 stopAir Canada
14h 12mBOS-YWG
$514
5/30Thu
2 stopsUnited Airlines
8h 41mYWG-BOS
6/3Mon
1 stopUnited Airlines
17h 31mBOS-YWG
$536
10/10Thu
1 stop
9h 24mYWG-BOS
10/13Sun
1 stop
6h 00mBOS-YWG
$557
10/10Thu
2 stops
13h 26mYWG-BOS
10/13Sun
2 stops
12h 54mBOS-YWG
$569

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Recent one-way flight deals

9/9Mon
2 stopsPorter Airlines
12h 27mYWG-BOS
$203
5/26Sun
1 stopPorter Airlines
5h 05mYWG-BOS
$206
6/2Sun
1 stopPorter Airlines
5h 40mYWG-BOS
$215
5/26Sun
2 stopsPorter Airlines
7h 52mYWG-BOS
$221
6/1Sat
2 stopsDelta
11h 43mYWG-BOS
$223
9/9Mon
1 stopAir Canada
6h 39mYWG-BOS
$229

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Winnipeg - Massachusetts Flights

Departure:

Winnipeg (YWG)Canada

Return flight deals:

Massachusetts - Winnipeg

Cabin classes: