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Cheap flights from Winnipeg to Massachusetts from C$ 248

YWG — BOS
20 Nov — 27 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 1/1212:40 p.m. -
2 stops8h 59m
Sat 5/121:15 p.m. -
1 stop5h 59m
Deal found 19/10C$ 414
Fri 20/116:35 a.m. -
1 stop10h 09m
Sun 22/115:45 a.m. -
1 stop6h 09m
Deal found 21/10C$ 423
Tue 1/1212:40 p.m. -
2 stops8h 59m
Fri 4/121:15 p.m. -
1 stop5h 59m
Deal found 19/10C$ 429
Sat 21/113:40 p.m. -
1 stop6h 57m
Sat 28/1110:25 a.m. -
1 stop7h 13m
Deal found 19/10C$ 443
Mon 23/119:05 a.m. -
1 stop5h 48m
Sat 28/115:45 a.m. -
1 stop16h 29m
Deal found 21/10C$ 446
Mon 23/1112:35 p.m. -
2 stops9h 00m
Sat 28/111:15 p.m. -
1 stop5h 51m
Deal found 21/10C$ 457
Tue 1/125:24 p.m. -
1 stop6h 23m
Fri 4/123:05 p.m. -
1 stop9h 34m
Deal found 19/10C$ 460
Thu 3/126:25 a.m. -
1 stop10h 36m
Thu 10/123:05 p.m. -
1 stop9h 34m
Deal found 19/10C$ 485
Thu 3/1212:40 p.m. -
2 stops8h 59m
Thu 10/121:15 p.m. -
1 stop5h 59m
Deal found 19/10C$ 498

Find flight deals from Winnipeg to Massachusetts

Round-trip from

C$ 405

One-way from

C$ 248

Popular in

April

Cheapest in

August

Average price

C$ 678
Air Canada
  • Air Canada
  • 27/2-6/3
  • 2 total stops
  • 13h 35m total
  • Winnipeg to Massachusetts
Search Deals
Porter Airlines
  • Porter Airlines
  • 27/11-31/12
  • 2 total stops
  • 9h 00m 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$ 69 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 27/11

12:35 p.m.-10:35 p.m.

2 stops9h 00m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 248

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sun 17/1

11:40 a.m.-10:42 p.m.

2 stops10h 02m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 249
Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 4/2

3:05 p.m.-10:28 p.m.

1 stop6h 23m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 253

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 3/2

7:00 a.m.-10:39 a.m.

2 stops26h 39m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 340

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 3/12

11:40 a.m.-9:39 p.m.

2 stops8h 59m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 349

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 3/12

9:35 p.m.-10:13 a.m.

3 stops35h 38m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 384

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sun 17/1

9:35 p.m.-5:42 p.m.

3 stops19h 07m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 436

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Mon 23/11

12:35 p.m.-10:35 p.m.

2 stops9h 00m

Boston Logan Intl

Sat 28/11

1:15 p.m.-6:06 p.m.

1 stop5h 51m

C$ 457

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Mon 2/11

9:35 p.m.-11:30 a.m.

2 stops12h 55m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 471

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 3/12

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

1 stop10h 36m

Boston Logan Intl

Thu 10/12

3:05 p.m.-11:39 p.m.

1 stop9h 34m

C$ 485

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/10

Showing 1-10 of 20 resultsSorted by cheapest first
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

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$ 489). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,287). 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$ 678 and C$ 1,146 in February.
The cheapest round-trip price found within the last 5 days was C$ 405 on Air Canada (27 Feb-6 Mar).

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
467 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.6

Comfort

8.0

Entertainment

6.9

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
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.6

Comfort

8.0

Entertainment

6.9

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
7.3
Good
10,392 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.6

Comfort

8.0

Entertainment

6.9

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
11,790 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.6

Food

7.6

Comfort

8.0

Entertainment

6.9

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 48m. Fly via Porter Airlines, Delta, or Air Canada 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$ 489). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,287). 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$ 163AverageC$ 587FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 329AverageC$ 478FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 401AverageC$ 649FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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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