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Cheap flights from Winnipeg to Massachusetts from C$ 300

YWG — BOS
30 Nov — 7 Dec1
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

Wed 25/117:00 a.m. -
2 stops7h 53m
Wed 2/125:30 a.m. -
1 stop5h 45m
Deal found 26/10C$ 412
Fri 27/116:15 a.m. -
1 stop8h 03m
Sat 28/1110:25 a.m. -
2 stops9h 00m
Deal found 26/10C$ 419
Wed 25/117:00 a.m. -
2 stops7h 53m
Sat 28/1110:25 a.m. -
2 stops9h 00m
Deal found 26/10C$ 420
Thu 26/116:15 a.m. -
2 stops8h 38m
Fri 27/1110:25 a.m. -
1 stop7h 13m
Deal found 26/10C$ 423
Thu 26/116:15 a.m. -
2 stops8h 38m
Mon 30/115:45 a.m. -
1 stop7h 04m
Deal found 26/10C$ 430
Wed 25/117:00 a.m. -
2 stops7h 53m
Tue 1/125:30 a.m. -
2 stops9h 39m
Deal found 26/10C$ 432
Wed 25/117:00 a.m. -
2 stops7h 53m
Sun 29/115:45 a.m. -
1 stop9h 04m
Deal found 26/10C$ 452
Fri 27/116:15 a.m. -
2 stops8h 38m
Fri 27/117:40 p.m. -
1 stop15h 44m
Deal found 26/10C$ 464
Tue 24/119:05 a.m. -
1 stop5h 48m
Thu 3/125:30 a.m. -
1 stop5h 45m
Deal found 26/10C$ 465
Mon 23/119:05 a.m. -
1 stop5h 48m
Thu 26/115:45 a.m. -
1 stop7h 04m
Deal found 26/10C$ 471

Find flight deals from Winnipeg to Massachusetts

Round-trip from

C$ 412

One-way from

C$ 300

Popular in

April

Cheapest in

August

Average price

C$ 673
Air Canada
  • Air Canada
  • 25/11-2/12
  • 3 total stops
  • 13h 38m total
  • Winnipeg to Massachusetts
Search Deals
25/11-31/12
  • 25/11-31/12
  • 1 total stop
  • 22h 10m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 201 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 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

Wed 25/11

11:00 a.m.-9:10 a.m.

1 stop22h 10m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 300

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sun 22/11

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

1 stop10h 09m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 304

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sun 22/11

12:35 p.m.-9:35 p.m.

2 stops9h 00m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 306
Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 10/12

11:00 a.m.-7:10 p.m.

1 stop8h 10m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 324

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 26/11

11:00 a.m.-9:10 a.m.

1 stop22h 10m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 327

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sun 22/11

11:00 a.m.-9:10 a.m.

1 stop22h 10m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 335

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 20/1

10:35 a.m.-9:39 a.m.

2 stops23h 04m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 339

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 18/11

12:35 p.m.-9:35 p.m.

2 stops9h 00m

Boston Logan Intl

Tue 24/11

8:00 a.m.-7:06 p.m.

2 stops11h 06m

C$ 478

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 21/11

5:45 p.m.-11:44 p.m.

1 stop5h 59m

Boston Logan Intl

Sat 28/11

5:45 a.m.-11:54 a.m.

1 stop6h 09m

C$ 478

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 24/11

12:35 p.m.-9:35 p.m.

2 stops9h 00m

Boston Logan Intl

Thu 3/12

1:15 p.m.-10:57 p.m.

2 stops9h 42m

C$ 517

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

Showing 1-10 of 15 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$ 486). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,278). 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$ 768 and C$ 1,214 in November.
The cheapest round-trip price found within the last 5 days was C$ 412 on Air Canada (25 Nov-2 Dec).

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

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Food

7.6

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

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Food

7.6

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
10,453 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Food

7.6

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
11,833 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Food

7.6

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 59m. Fly via Porter 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$ 486). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,278). 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$ 162AverageC$ 583FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 327AverageC$ 474FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 396AverageC$ 655FlexibilityNo 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.

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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