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Cheap flights from Winnipeg to Massachusetts from C$ 231

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
13 Dec — 20 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated 13 November 2025.

Round-trip from

C$ 324

One-way from

C$ 231

Popular in

December

Cheapest in

June

Average price

C$ 611
26/11-3/12
  • 26/11-3/12
  • 3 total stops
  • 44h 01m total
  • Winnipeg to Massachusetts
Search Deals
1/12
  • 1/12
  • 3 total stops
  • 22h 49m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 216 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 36 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Find flight deals from Winnipeg to Massachusetts

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Massachusetts
Explore the most affordable flight options available from Winnipeg to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 13 November 2025.

Wed 26/117:30 a.m.YWG - BOS
1 stop16h 14mMultiple Airlines
Wed 3/129:54 p.m.BOS - YWG
2 stops27h 47mMultiple Airlines
Deal found 12/11C$ 324
Wed 3/127:30 a.m.YWG - BOS
1 stop12h 19mMultiple Airlines
Sat 6/125:45 a.m.BOS - YWG
2 stops34h 22mMultiple Airlines
Deal found 11/11C$ 388
Fri 28/117:30 a.m.YWG - BOS
1 stop12h 19mMultiple Airlines
Wed 3/129:54 p.m.BOS - YWG
2 stops27h 47mMultiple Airlines
Deal found 10/11C$ 408
Wed 3/127:30 a.m.YWG - BOS
1 stop12h 19mMultiple Airlines
Wed 10/1210:56 a.m.BOS - YWG
3 stops38h 43mMultiple Airlines
Deal found 11/11C$ 424
Thu 11/122:20 p.m.YWG - ALB
1 stop5h 54mUnited Airlines
Thu 18/126:00 a.m.ALB - YWG
1 stop6h 57mUnited Airlines
Deal found 11/11C$ 489
Thu 11/126:00 a.m.YWG - ALB
2 stops15h 49mAmerican Airlines
Thu 18/126:00 a.m.ALB - YWG
3 stops18h 35mAmerican Airlines
Deal found 11/11C$ 1,024

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 13 November 2025.
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Winnipeg

Fly to

Massachusetts

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 3/12

7:30 a.m.-8:49 p.m.

1 stop12h 19m

Boston Logan Intl

Sat 6/12

5:45 a.m.-3:07 p.m.

2 stops34h 22m

C$ 388

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 28/11

7:30 a.m.-8:49 p.m.

1 stop12h 19m

Boston Logan Intl

Wed 3/12

9:54 p.m.-12:41 a.m.

2 stops27h 47m

C$ 408

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 3/12

7:30 a.m.-8:49 p.m.

1 stop12h 19m

Boston Logan Intl

Wed 10/12

10:56 a.m.-12:39 a.m.

3 stops38h 43m

C$ 424

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Thu 11/12

2:20 p.m.-9:14 p.m.

1 stop5h 54m

Albany Intl

Thu 18/12

6:00 a.m.-11:57 a.m.

1 stop6h 57m

C$ 489

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 24/3

2:15 p.m.-9:06 p.m.

1 stop5h 51m

Albany Intl

Wed 25/3

6:15 a.m.-11:39 a.m.

1 stop6h 24m

C$ 489

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 26/11

7:30 a.m.-11:53 p.m.

2 stops15h 23m

Boston Logan Intl

Wed 3/12

9:54 p.m.-12:39 a.m.

2 stops27h 45m

C$ 496

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 1/12

9:00 p.m.-8:49 p.m.

3 stops22h 49m

C$ 231

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 24/11

9:00 p.m.-12:44 a.m.

2 stops26h 44m

C$ 237

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 24/12

7:30 a.m.-1:14 a.m.

1 stop16h 44m

C$ 315

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 27/12

6:00 a.m.-10:55 p.m.

2 stops15h 55m

C$ 388

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 11 results
1
2

Best time to book a flight from Winnipeg to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Massachusetts

What is the cheapest month to book a flight from Winnipeg to Massachusetts?

Currently, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 230). Flying from Winnipeg to Massachusetts in December is currently the most expensive (average of C$ 490). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YWG to MA?

Find hourly flight availability from Winnipeg to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 13 November 2025.

It’s typically best to fly out from Winnipeg to Massachusetts in the morning. Doing so could potentially save you 65% on the flight price compared to flying in the afternoon, which is usually more expensive.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated 13 November 2025.
Read through reviews of airlines operating flights from Winnipeg to Massachusetts, such as Porter Airlines,United Airlines, andWestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
389 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
United Airlines
7.4
Good
9,015 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
WestJet
7.2
Good
3,159 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Air Canada
7.1
Good
10,444 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Massachusetts?

    Located just 7.3 km from the city centre, Winnipeg (YWG) is the airport most travellers will use when flying to Massachusetts from Winnipeg.

  • How long is the flight from Winnipeg to Massachusetts?

    There are many flights that can get you from Winnipeg to Massachusetts in 5h 54m. Fly via United Airlines to get the fastest option. The distance between Winnipeg and Massachusetts is about 1955 km.

  • What are the most popular routes from Winnipeg to Massachusetts?

    The most popular flight routes from Winnipeg to Massachusetts are Winnipeg - Boston Logan Intl, Winnipeg - Albany Intl and Winnipeg - Provincetown.

  • Can I find deals for flights from Winnipeg to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Massachusetts.

  • Can I find deals for business class flights from Winnipeg to Massachusetts?

    Yes. Cheapflights offers flight deals from Winnipeg to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Massachusetts?

    Currently, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 230). Flying from Winnipeg to Massachusetts in December is currently the most expensive (average of C$ 490). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 4 airlines flying from Winnipeg to Massachusetts

Discover the top 4 airlines that operate flights from Winnipeg to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 13 November 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 242AverageC$ 406FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 348AverageC$ 499FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 418AverageC$ 643FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 480AverageC$ 1,151FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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How does Cheapflights help users find flights from Winnipeg to Massachusetts?

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Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Massachusetts?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Massachusetts for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Winnipeg to Massachusetts with no change fees?

Need flexible booking options for your flight to Massachusetts from Winnipeg? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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