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Cheap flights from Winnipeg to Massachusetts from C$ 229

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 16/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
25 Apr — 2 May1
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 26 March 2026.

Tue 2/69:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Wed 10/610:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 24/3C$ 324
Tue 2/69:20 a.m.
YWG
-
BOS
2 stops10h 35m
Porter Airlines
Tue 9/610:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Deal found 24/3C$ 334
Fri 29/57:00 a.m.
YWG
-
BOS
1 stop16h 59m
United Airlines
Tue 2/68:15 a.m.
BOS
-
YWG
1 stop15h 18m
United Airlines
Deal found 24/3C$ 348
Mon 1/65:41 p.m.
YWG
-
BOS
1 stop5h 13m
Delta
Tue 9/65:55 a.m.
BOS
-
YWG
1 stop10h 09m
Delta
Deal found 24/3C$ 349
Mon 1/69:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Wed 10/67:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Deal found 25/3C$ 361
Tue 2/65:10 a.m.
YWG
-
BOS
1 stop5h 36m
Air Canada
Tue 9/65:10 a.m.
BOS
-
YWG
1 stop6h 58m
Air Canada
Deal found 24/3C$ 363
Mon 1/69:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Tue 9/610:05 a.m.
BOS
-
YWG
2 stops8h 53m
Porter Airlines
Deal found 24/3C$ 378
Wed 22/75:42 p.m.
YWG
-
BOS
1 stop5h 15m
Delta
Sun 26/75:55 a.m.
BOS
-
YWG
1 stop10h 13m
Delta
Deal found 22/3C$ 381
Tue 5/52:00 p.m.
YWG
-
ALB
1 stop6h 12m
United Airlines
Wed 6/57:30 p.m.
ALB
-
YWG
2 stops17h 22m
United Airlines
Deal found 25/3C$ 433
Tue 5/511:55 a.m.
YWG
-
ALB
2 stops10h 26m
Delta
Thu 7/55:55 a.m.
ALB
-
YWG
2 stops10h 00m
Delta
Deal found 22/3C$ 436
Tue 5/55:10 a.m.
YWG
-
ALB
2 stops11h 41m
United Airlines
Thu 7/56:00 a.m.
ALB
-
YWG
1 stop6h 52m
United Airlines
Deal found 22/3C$ 520
Thu 25/610:45 a.m.
YWG
-
ALB
2 stops11h 24m
WestJet
Sat 27/66:00 a.m.
ALB
-
YWG
2 stops33h 25m
WestJet
Deal found 24/3C$ 590

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 26 March 2026.

Round-trip from

C$ 324

One-way from

C$ 244

Popular in

January

Cheapest in

June

Average price

C$ 764
Porter Airlines
  • Porter Airlines
  • 2/6-10/6
  • 2 total stops
  • 13h 29m total
  • Winnipeg to Massachusetts
Search Deals
United Airlines
  • United Airlines
  • 7/5
  • 1 total stop
  • 9h 59m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 264 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 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 26 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

Cheapest round-trip
Quickest round-trip

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 2/6

5:10 a.m.-11:46 a.m.

1 stop5h 36m

Boston Logan Intl

Tue 9/6

5:10 a.m.-11:08 a.m.

1 stop6h 58m

C$ 363

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 4/5

5:20 p.m.-11:35 p.m.

1 stop5h 15m

Boston Logan Intl

Thu 7/5

8:10 a.m.-2:55 p.m.

1 stop7h 45m

C$ 412

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 7/9

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

1 stop8h 40m

Boston Logan Intl

Tue 15/9

3:05 p.m.-11:27 p.m.

1 stop9h 22m

C$ 412

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 29/5

7:20 p.m.-9:54 a.m.

1 stop13h 34m

Boston Logan Intl

Tue 2/6

5:10 a.m.-11:08 a.m.

1 stop6h 58m

C$ 412

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 5/5

2:00 p.m.-9:12 p.m.

1 stop6h 12m

Albany Intl

Wed 6/5

7:30 p.m.-11:52 a.m.

2 stops17h 22m

C$ 433

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 5/5

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

1 stop13h 45m

Albany Intl

Thu 7/5

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

1 stop6h 52m

C$ 434

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Tue 5/5

11:55 a.m.-11:21 p.m.

2 stops10h 26m

Albany Intl

Thu 7/5

5:55 a.m.-2:55 p.m.

2 stops10h 00m

C$ 436

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 1/6

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

1 stop7h 15m

Boston Logan Intl

Wed 10/6

7:10 a.m.-5:58 p.m.

2 stops11h 48m

C$ 445

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 1/6

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

2 stops15h 59m

Boston Logan Intl

Tue 9/6

5:45 a.m.-10:33 p.m.

2 stops17h 48m

C$ 462

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 10/5

5:41 p.m.-11:54 p.m.

1 stop5h 13m

Boston Logan Intl

Sat 23/5

3:15 p.m.-11:26 p.m.

1 stop9h 11m

C$ 485

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/3

Showing 1-10 of 25 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$ 214). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 1,078). 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?

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 26 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
428 reviews
Check prices

Food

7.6

Crew

8.6

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
428 reviews
Porter Airlines
8.0
Very good
428 reviews
Check prices

Food

7.6

Crew

8.6

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,488 reviews
Porter Airlines
8.0
Very good
428 reviews
Check prices

Food

7.6

Crew

8.6

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,303 reviews
Porter Airlines
8.0
Very good
428 reviews
Check prices

Food

7.6

Crew

8.6

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,843 reviews
Porter Airlines
8.0
Very good
428 reviews
Check prices

Food

7.6

Crew

8.6

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 7h 15m. Fly via Porter Airlines 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$ 214). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 1,078). 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 26 March 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 176AverageC$ 398FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 303AverageC$ 574FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 344AverageC$ 593FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 473AverageC$ 1,133FlexibilityNo 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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