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Cheap flights from Winnipeg to Massachusetts from C$ 300

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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
6 Mar — 13 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 4 February 2026.

Sun 24/58:30 a.m.
YWG
-
ALB
1 stop14h 00m
United Airlines
Thu 28/54:43 p.m.
ALB
-
YWG
1 stop6h 41m
United Airlines
Deal found 2/2C$ 479
Wed 25/28:15 a.m.
YWG
-
BOS
1 stop5h 37m
Air Canada
Thu 5/310:15 a.m.
BOS
-
YWG
1 stop7h 20m
Air Canada
Deal found 3/2C$ 520
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 3/2C$ 531
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 2/2C$ 542
Tue 24/28:15 a.m.
YWG
-
BOS
1 stop5h 37m
Air Canada
Tue 3/35:30 a.m.
BOS
-
YWG
1 stop5h 45m
Air Canada
Deal found 2/2C$ 550
Sun 24/55:10 a.m.
YWG
-
ALB
2 stops9h 15m
Air Canada
Thu 28/56:15 a.m.
ALB
-
YWG
1 stop6h 24m
Air Canada
Deal found 2/2C$ 564
Fri 26/69:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Mon 29/610:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 3/2C$ 570
Sat 21/32:20 p.m.
YWG
-
BOS
1 stop6h 23m
United Airlines
Thu 26/36:00 a.m.
BOS
-
YWG
1 stop6h 57m
United Airlines
Deal found 3/2C$ 576
Sun 14/68:00 a.m.
YWG
-
BOS
1 stop5h 47m
Air Canada
Mon 22/65:10 a.m.
BOS
-
YWG
1 stop5h 50m
Air Canada
Deal found 3/2C$ 580
Wed 25/27:30 a.m.
YWG
-
BOS
1 stop16h 43m
Multiple Airlines
Thu 5/311:45 a.m.
BOS
-
YWG
2 stops24h 47m
Multiple Airlines
Deal found 3/2C$ 594
Mon 2/36:00 a.m.
YWG
-
BOS
2 stops7h 52m
Air Canada
Wed 4/35:30 a.m.
BOS
-
YWG
1 stop5h 45m
Air Canada
Deal found 2/2C$ 606
Mon 2/35:19 p.m.
YWG
-
BOS
1 stop5h 31m
Delta
Wed 4/35:50 a.m.
BOS
-
YWG
1 stop6h 11m
Delta
Deal found 3/2C$ 634

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 4 February 2026.

Round-trip from

C$ 479

One-way from

C$ 305

Popular in

January

Cheapest in

June

Average price

C$ 627
United Airlines
  • United Airlines
  • 24/5-28/5
  • 2 total stops
  • 20h 41m total
  • Winnipeg to Massachusetts
Search Deals
Air Canada
  • Air Canada
  • 23/4
  • 1 total stop
  • 5h 37m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 161 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 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 4 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

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

1 stop14h 00m

Albany Intl

Thu 28/5

4:43 p.m.-10:24 p.m.

1 stop6h 41m

C$ 479

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 11/7

7:00 a.m.-11:38 p.m.

2 stops15h 38m

Albany Intl

Fri 4/9

1:15 p.m.-11:00 p.m.

2 stops10h 45m

C$ 531

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sun 24/5

5:10 a.m.-3:25 p.m.

2 stops9h 15m

Albany Intl

Thu 28/5

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

1 stop6h 24m

C$ 564

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 26/6

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

1 stop7h 15m

Boston Logan Intl

Mon 29/6

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

1 stop6h 14m

C$ 570

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 21/3

2:20 p.m.-9:43 p.m.

1 stop6h 23m

Boston Logan Intl

Thu 26/3

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

1 stop6h 57m

C$ 576

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 14/6

8:00 a.m.-2:47 p.m.

1 stop5h 47m

Boston Logan Intl

Mon 22/6

5:10 a.m.-10:00 a.m.

1 stop5h 50m

C$ 580

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 25/2

7:30 a.m.-1:13 a.m.

1 stop16h 43m

Boston Logan Intl

Thu 5/3

11:45 a.m.-11:32 a.m.

2 stops24h 47m

C$ 594

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/3

1:45 p.m.-9:27 p.m.

1 stop6h 42m

Boston Logan Intl

Wed 4/3

5:30 a.m.-10:15 a.m.

1 stop5h 45m

C$ 606

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/3

5:19 p.m.-11:50 p.m.

1 stop5h 31m

Boston Logan Intl

Wed 4/3

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

1 stop6h 11m

C$ 634

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 24/2

9:00 p.m.-11:59 p.m.

3 stops25h 59m

Boston Logan Intl

Tue 3/3

12:43 p.m.-11:32 a.m.

2 stops23h 49m

C$ 639

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 23 results
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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$ 231). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 582). 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 4 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
7.9
Good
412 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Food

7.5

Comfort

7.9

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

Boarding

8.2

Entertainment

6.9

Food

7.5

Comfort

7.9

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
9,236 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Food

7.5

Comfort

7.9

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
3,255 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Food

7.5

Comfort

7.9

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
10,688 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Boarding

8.2

Entertainment

6.9

Food

7.5

Comfort

7.9

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 5h 37m. Fly via United Airlines, Air Canada, or WestJet 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$ 231). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 582). 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 4 February 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 174AverageC$ 394FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 314AverageC$ 500FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 418AverageC$ 627FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 468AverageC$ 1,122FlexibilityNo cancel feeOn-time60%
Search WestJet flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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