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Cheap flights from Massachusetts to Winnipeg from C$ 192

BOS — YWG
1 Nov — 8 Nov1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Massachusetts to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Massachusetts to Winnipeg

Fri 16/1010:05 a.m. -
1 stop6h 15m
Mon 19/109:20 a.m. -
1 stop8h 15m
Deal found 27/9C$ 416
Sat 31/107:27 a.m. -
1 stop10h 23m
Sat 7/115:40 p.m. -
1 stop5h 40m
Deal found 29/9C$ 461
Fri 16/107:01 a.m. -
1 stop6h 36m
Mon 19/108:45 a.m. -
1 stop14h 14m
Deal found 27/9C$ 471
Thu 22/103:15 p.m. -
1 stop9h 04m
Sat 24/105:40 p.m. -
1 stop5h 40m
Deal found 30/9C$ 477
Fri 16/105:50 a.m. -
2 stops11h 37m
Mon 19/105:00 a.m. -
1 stop5h 50m
Deal found 27/9C$ 486
Thu 5/118:00 a.m. -
2 stops11h 10m
Thu 12/1111:40 a.m. -
2 stops8h 52m
Deal found 28/9C$ 494
Thu 22/105:50 a.m. -
2 stops13h 22m
Sat 24/105:00 a.m. -
1 stop5h 50m
Deal found 27/9C$ 520
Tue 8/128:00 a.m. -
2 stops11h 10m
Sun 13/1211:40 a.m. -
2 stops8h 52m
Deal found 30/9C$ 537
Wed 4/111:15 p.m. -
1 stop5h 55m
Sun 8/117:55 p.m. -
1 stop12h 15m
Deal found 27/9C$ 538
Sat 31/101:10 p.m. -
1 stop6h 00m
Sat 7/1111:40 a.m. -
2 stops20h 30m
Deal found 29/9C$ 544

Find flight deals from Massachusetts to Winnipeg

Round-trip from

C$ 416

One-way from

C$ 192

Popular in

February

Cheapest in

September

Average price

C$ 658
Porter Airlines
  • Porter Airlines
  • 16/10-19/10
  • 2 total stops
  • 14h 30m total
  • Massachusetts to Winnipeg
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Delta
  • Delta
  • 23/3-31/12
  • 1 total stop
  • 9h 34m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 348 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 60 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Massachusetts to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 23/3

3:00 p.m.-11:34 p.m.

1 stop9h 34m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 192

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 23/3

8:00 a.m.-6:10 p.m.

2 stops11h 10m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 221
Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 14/11

1:15 p.m.-7:10 p.m.

1 stop5h 55m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 248

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 11/11

5:45 a.m.-12:55 p.m.

1 stop7h 10m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 289

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 26/11

7:15 a.m.-5:42 p.m.

1 stop10h 27m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 289

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 19/11

2:59 p.m.-12:33 a.m.

1 stop9h 34m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 289

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 11/11

1:15 p.m.-11:15 a.m.

2 stops22h 00m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 316

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Wed 25/11

2:59 p.m.-12:33 a.m.

1 stop9h 34m

Winnipeg

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 366

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 4/2

3:00 p.m.-1:34 a.m.

1 stop10h 34m

Winnipeg

Mon 8/2

5:38 p.m.-10:53 p.m.

1 stop5h 15m

C$ 461

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 4/2

3:00 p.m.-12:34 a.m.

1 stop9h 34m

Winnipeg

Sun 7/2

5:38 p.m.-10:53 p.m.

1 stop5h 15m

C$ 461

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/9

Showing 1-10 of 23 resultsSorted by cheapest first
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Best time to book a flight from Massachusetts to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Massachusetts with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Massachusetts to Winnipeg

What is the cheapest month to book a flight from Massachusetts to Winnipeg?

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 518). Flying from Massachusetts to Winnipeg in February is currently the most expensive (average of C$ 1,307). 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 Massachusetts to Winnipeg?

Airfare is below average for this route at the moment.
Massachusetts to Winnipeg flights typically cost between C$ 483 and C$ 739 in October.
The cheapest round-trip price found within the last 5 days was C$ 416 on Porter Airlines (16 Oct-19 Oct).

Related info for your journey

  • What airport do you fly into for flights to Winnipeg from Massachusetts?

    If you book a flight to Winnipeg from Massachusetts, you will be flying to Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.

  • How long is the flight from Massachusetts to Winnipeg?

    There are many flights that can get you from Massachusetts to Winnipeg in 6h 15m. Fly via Porter Airlines to get the fastest option. There are 2173 km between Massachusetts and Winnipeg.

  • What are the most popular routes from Massachusetts to Winnipeg?

    Most travellers choose Boston Logan Intl - Winnipeg, Hartford Bradley Intl - Winnipeg or Albany Intl - Winnipeg when deciding on the best route from Massachusetts to Winnipeg.

  • Can I find deals for flights from Massachusetts to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Winnipeg.

  • Can I find deals for business class flights from Massachusetts to Winnipeg?

    Yes. Cheapflights offers flight deals from Massachusetts to Winnipeg 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 Massachusetts to Winnipeg?

    Currently, September is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 518). Flying from Massachusetts to Winnipeg in February is currently the most expensive (average of C$ 1,307). 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

Travelling to a place near Winnipeg?

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Why should you use Cheapflights to find cheap flight tickets from Massachusetts to Winnipeg?

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Can Cheapflights find flights from Massachusetts to Winnipeg with no change fees?

Need flexible booking options for your flight to Winnipeg from Massachusetts? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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Of course! You can now track prices for flights from Massachusetts to Winnipeg and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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