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Cheap flights from Winnipeg to Massachusetts from C$ 220

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 22/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
2 Apr — 9 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap 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 3 March 2026.

Thu 2/46:40 a.m.
YWG
-
BOS
1 stop9h 48m
Delta
Wed 8/45:50 a.m.
BOS
-
YWG
1 stop6h 11m
Delta
Deal found 28/2C$ 368
Fri 24/47:05 p.m.
YWG
-
BOS
1 stop13h 54m
Air Canada
Tue 28/45:30 a.m.
BOS
-
YWG
1 stop5h 39m
Air Canada
Deal found 26/2C$ 426
Tue 17/36:40 a.m.
YWG
-
BOS
1 stop9h 24m
Delta
Tue 24/33:10 p.m.
BOS
-
YWG
1 stop9h 25m
Delta
Deal found 1/3C$ 432
Sun 24/57:00 a.m.
YWG
-
ALB
1 stop7h 26m
United Airlines
Thu 28/512:24 p.m.
ALB
-
YWG
1 stop11h 09m
United Airlines
Deal found 26/2C$ 432
Thu 2/45:30 p.m.
YWG
-
BOS
2 stops20h 22m
Multiple Airlines
Wed 8/46:15 a.m.
BOS
-
YWG
2 stops19h 25m
Multiple Airlines
Deal found 28/2C$ 463
Thu 9/46:40 a.m.
YWG
-
BOS
1 stop9h 48m
Delta
Mon 13/43:10 p.m.
BOS
-
YWG
1 stop9h 20m
Delta
Deal found 28/2C$ 465
Thu 9/45:30 a.m.
YWG
-
BOS
2 stops17h 29m
United Airlines
Mon 13/46:25 p.m.
BOS
-
YWG
2 stops18h 27m
United Airlines
Deal found 28/2C$ 473
Thu 16/46:40 a.m.
YWG
-
BOS
1 stop9h 24m
Delta
Mon 20/48:05 a.m.
BOS
-
YWG
1 stop9h 17m
Delta
Deal found 27/2C$ 493
Wed 21/108:10 a.m.
YWG
-
BOS
1 stop5h 31m
Air Canada
Wed 4/115:30 a.m.
BOS
-
YWG
1 stop5h 46m
Air Canada
Deal found 1/3C$ 515
Sun 18/108:10 a.m.
YWG
-
BOS
1 stop5h 31m
Air Canada
Fri 6/115:30 a.m.
BOS
-
YWG
1 stop5h 46m
Air Canada
Deal found 1/3C$ 518
Fri 23/105:10 a.m.
YWG
-
BOS
1 stop5h 45m
Air Canada
Thu 5/115:30 a.m.
BOS
-
YWG
1 stop5h 46m
Air Canada
Deal found 1/3C$ 523
Thu 25/610:45 a.m.
YWG
-
ALB
2 stops11h 21m
WestJet
Sat 27/66:00 a.m.
ALB
-
YWG
2 stops33h 25m
WestJet
Deal found 1/3C$ 544

Find flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated 3 March 2026.

Round-trip from

C$ 368

One-way from

C$ 220

Popular in

January

Cheapest in

June

Average price

C$ 687
Delta
  • Delta
  • 2/4-8/4
  • 2 total stops
  • 15h 59m total
  • Winnipeg to Massachusetts
Search Deals
Air Canada
  • Air Canada
  • 22/6
  • 1 total stop
  • 6h 18m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 24% potential increase in price (C$ 278 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 56 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 3 March 2026.
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 2/4

6:40 a.m.-5:28 p.m.

1 stop9h 48m

Boston Logan Intl

Wed 8/4

5:50 a.m.-11:01 a.m.

1 stop6h 11m

C$ 368

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 31/3

8:45 a.m.-11:59 p.m.

1 stop14h 14m

Boston Logan Intl

Tue 7/4

5:25 p.m.-11:52 a.m.

2 stops19h 27m

C$ 368

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sun 24/5

8:45 a.m.-11:30 p.m.

1 stop13h 45m

Albany Intl

Thu 28/5

6:00 a.m.-10:33 p.m.

2 stops17h 33m

C$ 432

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 2/4

5:30 p.m.-2:52 p.m.

2 stops20h 22m

Boston Logan Intl

Wed 8/4

6:15 a.m.-12:40 a.m.

2 stops19h 25m

C$ 463

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/4

6:40 a.m.-5:28 p.m.

1 stop9h 48m

Boston Logan Intl

Mon 13/4

3:10 p.m.-11:30 p.m.

1 stop9h 20m

C$ 465

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 9/4

5:30 a.m.-11:59 p.m.

2 stops17h 29m

Boston Logan Intl

Mon 13/4

6:25 p.m.-11:52 a.m.

2 stops18h 27m

C$ 473

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 11/4

6:00 a.m.-2:52 p.m.

2 stops7h 52m

Boston Logan Intl

Sat 18/4

7:00 a.m.-10:07 a.m.

3 stops28h 07m

C$ 537

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 31/3

5:20 p.m.-11:49 p.m.

1 stop5h 29m

Boston Logan Intl

Tue 7/4

5:50 a.m.-11:01 a.m.

1 stop6h 11m

C$ 537

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 16/4

8:45 a.m.-12:59 a.m.

2 stops15h 14m

Boston Logan Intl

Mon 20/4

6:25 p.m.-11:52 a.m.

2 stops18h 27m

C$ 543

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Thu 25/6

10:45 a.m.-11:06 p.m.

2 stops11h 21m

Albany Intl

Sat 27/6

6:00 a.m.-2:25 p.m.

2 stops33h 25m

C$ 544

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/3

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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$ 228). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 1,069). 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.

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 3 March 2026.
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
421 reviews
Check prices

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Porter Airlines
8.0
Very good
421 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
United Airlines
7.4
Good
9,378 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
WestJet
7.2
Good
3,280 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Air Canada
7.1
Good
10,770 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Crew

8.6

Food

7.6

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

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 9h 48m. Fly via Delta or United Airlines to get the fastest option. The distance between Winnipeg and Massachusetts is about 2173 km. This flight may include one or multiple stops.

  • 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$ 228). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 1,069). 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.

See more FAQs

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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 3 March 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 174AverageC$ 395FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 315AverageC$ 518FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 341AverageC$ 579FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 469AverageC$ 1,122FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

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

Cheapflights helps you search for flights from Winnipeg to Massachusetts via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

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.

Can Cheapflights notify me if prices for flights from Winnipeg to Massachusetts become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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