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Cheap flights from Winnipeg to Massachusetts from C$ 248

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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
28 Feb — 7 Mar1
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 29 January 2026.

Wed 11/37:30 a.m.
YWG
-
BOS
1 stop27h 11m
Multiple Airlines
Tue 24/312:36 p.m.
BOS
-
YWG
1 stop27h 33m
Multiple Airlines
Deal found 27/1C$ 433
Sun 5/47:30 a.m.
YWG
-
BOS
1 stop16h 56m
Multiple Airlines
Thu 9/45:40 a.m.
BOS
-
YWG
2 stops14h 29m
Multiple Airlines
Deal found 27/1C$ 479
Wed 1/47:30 a.m.
YWG
-
BOS
1 stop16h 56m
Multiple Airlines
Thu 9/45:40 a.m.
BOS
-
YWG
2 stops14h 29m
Multiple Airlines
Deal found 27/1C$ 498
Sun 5/47:30 a.m.
YWG
-
BOS
1 stop16h 56m
Multiple Airlines
Wed 8/43:30 p.m.
BOS
-
YWG
2 stops10h 09m
Multiple Airlines
Deal found 27/1C$ 500
Wed 1/47:30 a.m.
YWG
-
BOS
1 stop16h 56m
Multiple Airlines
Wed 8/43:30 p.m.
BOS
-
YWG
2 stops10h 09m
Multiple Airlines
Deal found 27/1C$ 519
Tue 31/35:00 a.m.
YWG
-
BOS
2 stops17h 59m
Multiple Airlines
Wed 8/410:20 a.m.
BOS
-
YWG
1 stop9h 49m
Multiple Airlines
Deal found 27/1C$ 521
Mon 6/48:20 p.m.
YWG
-
BOS
1 stop12h 15m
Multiple Airlines
Thu 9/45:40 a.m.
BOS
-
YWG
2 stops14h 29m
Multiple Airlines
Deal found 27/1C$ 524
Sat 11/710:45 a.m.
YWG
-
ALB
2 stops11h 21m
WestJet
Fri 4/91:15 p.m.
ALB
-
YWG
2 stops10h 45m
WestJet
Deal found 27/1C$ 527
Tue 3/26:40 a.m.
YWG
-
ALB
2 stops15h 15m
Delta
Thu 5/212:29 p.m.
ALB
-
YWG
2 stops12h 09m
Delta
Deal found 27/1C$ 698
Tue 3/22:20 p.m.
YWG
-
ALB
1 stop6h 03m
United Airlines
Thu 5/27:25 p.m.
ALB
-
YWG
2 stops17h 32m
United Airlines
Deal found 27/1C$ 760
Sat 11/78:15 a.m.
YWG
-
ALB
2 stops11h 47m
United Airlines
Fri 4/98:00 a.m.
ALB
-
YWG
1 stop13h 48m
United Airlines
Deal found 28/1C$ 982
Tue 3/22:20 p.m.
YWG
-
ALB
1 stop6h 03m
Air Canada
Thu 5/26:00 a.m.
ALB
-
YWG
1 stop6h 57m
Air Canada
Deal found 26/1C$ 984

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 29 January 2026.

Round-trip from

C$ 433

One-way from

C$ 248

Popular in

January

Cheapest in

June

Average price

C$ 747
11/3-24/3
  • 11/3-24/3
  • 2 total stops
  • 54h 44m total
  • Winnipeg to Massachusetts
Search Deals
12/4
  • 12/4
  • 1 total stop
  • 27h 15m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 166 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 29 January 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

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 11/3

7:30 a.m.-11:41 a.m.

1 stop27h 11m

Boston Logan Intl

Tue 24/3

12:36 p.m.-3:09 p.m.

1 stop27h 33m

C$ 433

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 5/4

7:30 a.m.-1:26 a.m.

1 stop16h 56m

Boston Logan Intl

Thu 9/4

5:40 a.m.-7:09 p.m.

2 stops14h 29m

C$ 479

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 4/4

8:20 p.m.-9:35 a.m.

1 stop12h 15m

Boston Logan Intl

Wed 8/4

1:25 p.m.-12:39 a.m.

1 stop12h 14m

C$ 544

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 3/4

12:20 p.m.-10:05 p.m.

1 stop8h 45m

Boston Logan Intl

Thu 9/4

5:40 a.m.-7:09 p.m.

2 stops14h 29m

C$ 555

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 6/3

5:00 a.m.-6:02 p.m.

1 stop12h 02m

Boston Logan Intl

Mon 9/3

6:10 p.m.-12:40 a.m.

3 stops31h 30m

C$ 559

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 2/4

5:00 a.m.-2:45 p.m.

1 stop8h 45m

Boston Logan Intl

Wed 8/4

3:30 p.m.-12:39 a.m.

2 stops10h 09m

C$ 570

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 20/3

5:00 a.m.-2:45 p.m.

1 stop8h 45m

Boston Logan Intl

Mon 23/3

3:30 p.m.-11:32 a.m.

2 stops21h 02m

C$ 589

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 3/2

11:53 a.m.-10:55 p.m.

2 stops10h 02m

Albany Intl

Thu 5/2

12:29 p.m.-11:38 p.m.

2 stops12h 09m

C$ 751

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 3/2

2:20 p.m.-9:23 p.m.

1 stop6h 03m

Albany Intl

Thu 5/2

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

1 stop6h 57m

C$ 760

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 3/2

2:20 p.m.-9:23 p.m.

1 stop6h 03m

Albany Intl

Thu 5/2

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

1 stop6h 57m

C$ 984

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

Showing 1-10 of 16 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$ 229). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 578). 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 29 January 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
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,215 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,253 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,667 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Comfort

7.9

Entertainment

6.9

Food

7.5

Boarding

8.2

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 6h 03m. Fly via Delta, United Airlines, or Air Canada to get the fastest option. The distance between Winnipeg and Massachusetts is about 1955 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$ 229). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 578). 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 29 January 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 173AverageC$ 392FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 313AverageC$ 487FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 415AverageC$ 623FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 465AverageC$ 1,115FlexibilityNo 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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