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Cheap flights from Winnipeg to Massachusetts from C$ 227

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 28/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
26 Mar — 2 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 24 February 2026.

Sun 24/52:00 p.m.
YWG
-
ALB
2 stops8h 47m
United Airlines
Thu 28/512:24 p.m.
ALB
-
YWG
1 stop11h 09m
United Airlines
Deal found 19/2C$ 461
Sun 24/59:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Fri 12/610:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 22/2C$ 462
Mon 15/69:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Tue 23/610:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 23/2C$ 472
Sun 24/57:00 a.m.
YWG
-
BOS
2 stops15h 59m
United Airlines
Fri 12/67:19 a.m.
BOS
-
YWG
1 stop16h 14m
United Airlines
Deal found 22/2C$ 517
Thu 16/45:10 p.m.
YWG
-
BOS
1 stop15h 25m
Multiple Airlines
Tue 21/47:43 p.m.
BOS
-
YWG
2 stops24h 42m
Multiple Airlines
Deal found 21/2C$ 520
Mon 6/48:00 a.m.
YWG
-
BOS
1 stop30h 28m
Multiple Airlines
Sun 12/44:23 p.m.
BOS
-
YWG
2 stops28h 12m
Multiple Airlines
Deal found 21/2C$ 524
Sun 24/57:20 a.m.
YWG
-
ALB
2 stops13h 23m
Air Canada
Thu 28/512:24 p.m.
ALB
-
YWG
1 stop11h 09m
Air Canada
Deal found 22/2C$ 536
Sun 24/57:00 a.m.
YWG
-
ALB
2 stops15h 28m
WestJet
Thu 28/56:00 a.m.
ALB
-
YWG
2 stops19h 55m
WestJet
Deal found 19/2C$ 543
Mon 6/45:00 a.m.
YWG
-
BOS
1 stop16h 05m
Multiple Airlines
Mon 13/43:30 p.m.
BOS
-
YWG
2 stops10h 09m
Multiple Airlines
Deal found 20/2C$ 559
Sat 11/710:45 a.m.
YWG
-
ALB
2 stops11h 21m
WestJet
Fri 4/96:00 a.m.
ALB
-
YWG
2 stops19h 55m
WestJet
Deal found 20/2C$ 564
Mon 6/45:30 a.m.
YWG
-
BOS
2 stops8h 22m
Air Canada
Mon 13/43:35 p.m.
BOS
-
YWG
2 stops9h 13m
Air Canada
Deal found 20/2C$ 577
Thu 2/48:20 p.m.
YWG
-
BOS
2 stops37h 41m
Multiple Airlines
Wed 22/46:00 a.m.
BOS
-
YWG
1 stop10h 09m
Multiple Airlines
Deal found 20/2C$ 580

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 24 February 2026.

Round-trip from

C$ 461

One-way from

C$ 227

Popular in

January

Cheapest in

June

Average price

C$ 687
United Airlines
  • United Airlines
  • 24/5-28/5
  • 3 total stops
  • 19h 56m total
  • Winnipeg to Massachusetts
Search Deals
Air Canada
  • Air Canada
  • 28/4
  • 1 total stop
  • 5h 41m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 269 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 55 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 24 February 2026.
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

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sun 24/5

2:00 p.m.-11:47 p.m.

2 stops8h 47m

Albany Intl

Thu 28/5

12:24 p.m.-10:33 p.m.

1 stop11h 09m

C$ 461

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 15/6

9:20 a.m.-5:35 p.m.

1 stop7h 15m

Boston Logan Intl

Tue 23/6

10:05 a.m.-3:19 p.m.

1 stop6h 14m

C$ 472

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 24/5

7:00 a.m.-11:59 p.m.

2 stops15h 59m

Boston Logan Intl

Fri 12/6

7:19 a.m.-10:33 p.m.

1 stop16h 14m

C$ 517

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 16/4

5:10 p.m.-9:35 a.m.

1 stop15h 25m

Boston Logan Intl

Tue 21/4

7:43 p.m.-7:25 p.m.

2 stops24h 42m

C$ 520

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sun 24/5

7:20 a.m.-9:43 p.m.

2 stops13h 23m

Albany Intl

Thu 28/5

12:24 p.m.-10:33 p.m.

1 stop11h 09m

C$ 536

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 11/7

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

2 stops11h 21m

Albany Intl

Fri 4/9

6:00 a.m.-12:55 a.m.

2 stops19h 55m

C$ 564

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 6/4

8:15 a.m.-2:52 p.m.

1 stop5h 37m

Boston Logan Intl

Sun 12/4

5:30 a.m.-10:09 a.m.

1 stop5h 39m

C$ 584

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 22/6

12:40 p.m.-10:20 p.m.

1 stop8h 40m

Boston Logan Intl

Mon 6/7

7:10 a.m.-3:23 p.m.

1 stop9h 13m

C$ 587

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 10/6

9:20 a.m.-5:35 p.m.

1 stop7h 15m

Boston Logan Intl

Sun 14/6

7:15 a.m.-5:58 p.m.

2 stops11h 43m

C$ 596

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 2/4

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

1 stop9h 48m

Boston Logan Intl

Wed 22/4

5:50 a.m.-10:56 a.m.

1 stop6h 06m

C$ 616

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/2

Showing 1-10 of 24 results
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$ 1,070). 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 24 February 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
419 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Food

7.6

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
419 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Food

7.6

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
9,344 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Food

7.6

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
3,273 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Food

7.6

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
10,742 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Food

7.6

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 5h 37m. Fly via United Airlines, Porter Airlines, or Air Canada 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$ 1,070). 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 24 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 174AverageC$ 395FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 315AverageC$ 507FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 342AverageC$ 579FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 469AverageC$ 1,123FlexibilityNo 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.

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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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