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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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
29 Aug — 5 Sep1
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 30 July 2026.

Tue 18/812:15 p.m.
YWG
-
BOS
1 stop5h 35m
Porter Airlines
Sat 22/810:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 27/7C$ 448
Sun 6/97:55 a.m.
YWG
-
BOS
1 stop5h 46m
Air Canada
Sat 12/93:35 p.m.
BOS
-
YWG
1 stop6h 39m
Air Canada
Deal found 26/7C$ 449
Wed 9/98:15 a.m.
YWG
-
BOS
1 stop6h 50m
Air Canada
Wed 16/94:55 p.m.
BOS
-
YWG
1 stop7h 32m
Air Canada
Deal found 26/7C$ 462
Fri 18/97:00 a.m.
YWG
-
BOS
1 stop15h 30m
United Airlines
Tue 22/96:00 a.m.
BOS
-
YWG
1 stop6h 52m
United Airlines
Deal found 27/7C$ 463
Thu 10/97:45 a.m.
YWG
-
BOS
1 stop9h 50m
Multiple Airlines
Mon 14/910:05 a.m.
BOS
-
YWG
1 stop8h 10m
Multiple Airlines
Deal found 30/7C$ 464
Fri 2/109:05 p.m.
YWG
-
BOS
1 stop19h 35m
WestJet
Mon 5/106:30 p.m.
BOS
-
YWG
1 stop17h 40m
WestJet
Deal found 26/7C$ 481
Sat 5/96:15 a.m.
YWG
-
BOS
1 stop12h 00m
Multiple Airlines
Tue 8/910:05 a.m.
BOS
-
YWG
1 stop15h 50m
Multiple Airlines
Deal found 28/7C$ 484
Mon 17/87:45 p.m.
YWG
-
BOS
1 stop15h 07m
Air Canada
Fri 21/86:00 a.m.
BOS
-
YWG
1 stop6h 15m
Air Canada
Deal found 27/7C$ 487
Tue 8/97:00 a.m.
YWG
-
ALB
1 stop7h 04m
United Airlines
Sat 12/94:53 p.m.
ALB
-
YWG
1 stop6h 40m
United Airlines
Deal found 26/7C$ 791
Mon 26/1012:20 p.m.
YWG
-
ALB
2 stops10h 07m
Delta
Fri 30/101:03 p.m.
ALB
-
YWG
2 stops7h 50m
Delta
Deal found 29/7C$ 880
Mon 26/105:00 a.m.
YWG
-
ALB
2 stops29h 15m
WestJet
Fri 30/1012:21 p.m.
ALB
-
YWG
2 stops24h 14m
WestJet
Deal found 27/7C$ 895
Fri 9/106:15 a.m.
YWG
-
ALB
2 stops16h 35m
WestJet
Mon 12/1012:21 p.m.
ALB
-
YWG
2 stops27h 04m
WestJet
Deal found 28/7C$ 964

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 30 July 2026.

Round-trip from

C$ 448

One-way from

C$ 248

Popular in

April

Cheapest in

August

Average price

C$ 654
Porter Airlines
  • Porter Airlines
  • 18/8-22/8
  • 2 total stops
  • 11h 49m total
  • Winnipeg to Massachusetts
Search Deals
Porter Airlines
  • Porter Airlines
  • 9/9
  • 2 total stops
  • 21h 50m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 210 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 67 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 30 July 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

Cheapest round-trip
Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 18/8

12:15 p.m.-6:50 p.m.

1 stop5h 35m

Boston Logan Intl

Sat 22/8

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

1 stop6h 14m

C$ 448

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 18/9

7:00 a.m.-11:30 p.m.

1 stop15h 30m

Boston Logan Intl

Tue 22/9

6:00 a.m.-11:52 a.m.

1 stop6h 52m

C$ 463

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 9/9

12:41 p.m.-11:59 p.m.

1 stop10h 18m

Boston Logan Intl

Wed 16/9

7:05 a.m.-11:51 a.m.

1 stop5h 46m

C$ 463

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 18/9

3:58 p.m.-11:59 p.m.

1 stop7h 01m

Boston Logan Intl

Tue 22/9

5:55 a.m.-11:51 a.m.

1 stop6h 56m

C$ 463

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 2/10

7:10 p.m.-11:55 a.m.

1 stop15h 45m

Boston Logan Intl

Mon 5/10

6:00 a.m.-11:12 a.m.

1 stop6h 12m

C$ 491

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 6/9

10:45 a.m.-6:35 p.m.

1 stop6h 50m

Boston Logan Intl

Sat 12/9

7:00 a.m.-5:58 p.m.

2 stops11h 58m

C$ 497

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 9/9

12:20 p.m.-9:26 p.m.

2 stops8h 06m

Boston Logan Intl

Wed 16/9

5:50 a.m.-2:22 p.m.

2 stops9h 32m

C$ 516

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 18/9

3:20 p.m.-10:40 p.m.

1 stop6h 20m

Boston Logan Intl

Tue 22/9

10:40 a.m.-8:00 p.m.

2 stops10h 20m

C$ 532

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 19/8

12:46 p.m.-11:58 p.m.

1 stop10h 12m

Boston Logan Intl

Sun 23/8

5:51 a.m.-3:08 p.m.

1 stop10h 17m

C$ 536

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 29/8

2:00 p.m.-10:18 a.m.

2 stops19h 18m

Boston Logan Intl

Sun 6/9

8:31 p.m.-11:52 a.m.

1 stop16h 21m

C$ 549

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/7

Showing 1-10 of 33 resultsSorted by cheapest first
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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, August is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 488). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,284). 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.

How much does it cost to fly round-trip from Winnipeg to Massachusetts?

Airfare is below average for this route at the moment.
Winnipeg to Massachusetts flights typically cost between C$ 464 and C$ 616 in August.
The cheapest round-trip price found within the last 5 days was C$ 448 on Porter Airlines (18 Aug-22 Aug).

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 30 July 2026.
Read through reviews of airlines operating flights from Winnipeg to Massachusetts, such as Porter Airlines,United Airlines, andAir Canada. 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
449 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.5

Crew

8.6

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Porter Airlines
8.0
Very good
449 reviews
Porter Airlines
8.0
Very good
449 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.5

Crew

8.6

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
United Airlines
7.4
Good
10,053 reviews
Porter Airlines
8.0
Very good
449 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.5

Crew

8.6

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats
Air Canada
7.1
Good
11,413 reviews
Porter Airlines
8.0
Very good
449 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.5

Crew

8.6

Entertainment

6.9

Reviews

1 / 20
6.0
Good

Shannon,Jul 2026

YQT - YOW

Seats need to be a bit bigger & I'm not impressed that you have to pay to change seats

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 35m. Fly via Porter Airlines, United Airlines, or Delta 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, August is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 488). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,284). 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 3 airlines flying from Winnipeg to Massachusetts

Discover the top 3 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 30 July 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 163AverageC$ 628FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 329AverageC$ 488FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 398AverageC$ 629FlexibilityNo cancel feeOn-time67%
Search Air Canada 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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