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Cheap flights from Winnipeg to Massachusetts from C$ 208

YWG — BOS
26 Oct — 2 Nov1
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

Tue 24/1111:40 a.m. -
2 stops8h 52m
Sun 29/118:00 a.m. -
2 stops11h 10m
Deal found 21/9C$ 352
Wed 25/1111:40 a.m. -
2 stops8h 52m
Mon 30/118:00 a.m. -
2 stops11h 10m
Deal found 22/9C$ 361
Tue 20/102:00 p.m. -
1 stop8h 24m
Tue 27/106:00 a.m. -
1 stop7h 23m
Deal found 22/9C$ 366
Sat 5/122:05 p.m. -
1 stop6h 23m
Wed 9/125:45 a.m. -
1 stop7h 04m
Deal found 21/9C$ 376
Tue 10/1111:40 a.m. -
2 stops8h 52m
Sat 14/118:00 a.m. -
2 stops11h 10m
Deal found 21/9C$ 378
Wed 21/105:00 a.m. -
1 stop5h 50m
Thu 22/1012:45 p.m. -
1 stop6h 27m
Deal found 22/9C$ 380
Tue 10/1111:40 a.m. -
2 stops8h 52m
Mon 16/111:15 p.m. -
2 stops9h 42m
Deal found 21/9C$ 389
Wed 21/102:00 p.m. -
1 stop9h 54m
Thu 22/106:00 a.m. -
1 stop7h 37m
Deal found 24/9C$ 392
Tue 3/1111:40 a.m. -
2 stops8h 52m
Tue 10/118:00 a.m. -
2 stops11h 10m
Deal found 22/9C$ 393
Sat 24/105:00 a.m. -
1 stop5h 50m
Mon 26/106:35 p.m. -
1 stop16h 30m
Deal found 22/9C$ 396
Wed 18/1111:40 a.m. -
2 stops8h 52m
Tue 24/118:00 a.m. -
2 stops11h 10m
Deal found 20/9C$ 399

Find flight deals from Winnipeg to Massachusetts

Round-trip from

C$ 352

One-way from

C$ 208

Popular in

April

Cheapest in

August

Average price

C$ 505
Porter Airlines
  • Porter Airlines
  • 24/11-29/11
  • 4 total stops
  • 20h 02m total
  • Winnipeg to Massachusetts
Search Deals
Air Canada
  • Air Canada
  • 11/10-31/12
  • 1 total stop
  • 5h 31m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 162 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 63 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals

Cheapflights Fare Finder

 
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 Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sun 11/10

8:10 a.m.-2:41 p.m.

1 stop5h 31m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 208

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 16/10

12:38 p.m.-10:19 p.m.

1 stop8h 41m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 218

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 6/10

8:45 a.m.-12:54 a.m.

2 stops15h 09m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 222

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 10/12

6:25 a.m.-5:01 p.m.

1 stop9h 36m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 263

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sun 22/11

6:35 a.m.-4:44 p.m.

1 stop9h 09m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 264

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Mon 30/11

6:55 p.m.-10:22 a.m.

1 stop14h 27m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 267

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 3/11

2:10 p.m.-9:10 a.m.

2 stops18h 00m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 289

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Mon 30/11

8:35 p.m.-9:10 a.m.

2 stops11h 35m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 290

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 7/10

5:00 a.m.-10:45 p.m.

2 stops16h 45m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 291

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 24/10

2:05 p.m.-7:43 a.m.

2 stops16h 38m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 304

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/9

Showing 1-10 of 21 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

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$ 492). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,294). 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$ 600 and C$ 1,028 in November.
The cheapest round-trip price found within the last 5 days was C$ 352 on Porter Airlines (24 Nov-29 Nov).

Reviews of airlines servicing Massachusetts

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
463 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
463 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
United Airlines
7.4
Good
10,245 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,684 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Crew

8.6

Food

7.6

Entertainment

6.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • 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 40m. Fly via Delta, United Airlines, or Porter 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, August is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 492). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,294). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Winnipeg to Massachusetts

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 164AverageC$ 621FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 331AverageC$ 478FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 403AverageC$ 647FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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How does Cheapflights help users find flights from Winnipeg to Massachusetts?

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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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