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Cheap flights from Massachusetts to Winnipeg from C$ 164

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 28/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
15 Oct — 22 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Massachusetts to Winnipeg

Keep the following information in mind while searching for Massachusetts to Winnipeg flight deals. Data was last updated 15 September 2025.

Round-trip from

C$ 363

One-way from

C$ 164

Popular in

February

Cheapest in

July

Average price

C$ 727
24/10-31/10
  • 24/10-31/10
  • 2 total stops
  • 44h 29m total
  • Massachusetts to Winnipeg
Search Deals
Air Canada
  • Air Canada
  • 28/9
  • 1 total stop
  • 5h 40m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Massachusetts to Winnipeg

Cheapest flights from Massachusetts to Winnipeg
Explore the most affordable flight options available from Massachusetts to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 15 September 2025.

Fri 24/106:30 p.m.BOS - YWG
1 stop18h 11mMultiple Airlines
Fri 31/107:30 a.m.YWG - BOS
1 stop26h 18mMultiple Airlines
Deal found 13/9C$ 363
Thu 16/108:24 p.m.BOS - YWG
2 stops20h 58mMultiple Airlines
Mon 20/106:30 a.m.YWG - BOS
1 stop10h 10mMultiple Airlines
Deal found 15/9C$ 387
Fri 26/97:00 p.m.BOS - YWG
2 stops29h 40mMultiple Airlines
Thu 2/107:00 p.m.YWG - BOS
1 stop21h 40mMultiple Airlines
Deal found 15/9C$ 457
Thu 23/1012:49 p.m.BOS - YWG
2 stops12h 24mMultiple Airlines
Fri 31/104:00 p.m.YWG - BOS
1 stop15h 28mMultiple Airlines
Deal found 13/9C$ 472
Sat 25/106:00 a.m.BOS - YWG
1 stop6h 35mAir Canada
Tue 28/101:45 p.m.YWG - BOS
1 stop6h 42mAir Canada
Deal found 13/9C$ 475
Sat 25/106:00 a.m.BOS - YWG
2 stops11h 15mAir Canada
Fri 31/101:45 p.m.YWG - BOS
1 stop6h 42mAir Canada
Deal found 13/9C$ 482
Thu 23/1011:02 a.m.BOS - YWG
1 stop12h 31mUnited Airlines
Wed 29/102:20 p.m.YWG - BOS
1 stop6h 29mUnited Airlines
Deal found 13/9C$ 486
Fri 24/106:00 a.m.BOS - YWG
2 stops12h 45mAir Canada
Tue 28/106:00 a.m.YWG - BOS
2 stops7h 52mAir Canada
Deal found 13/9C$ 489
Sat 25/104:45 p.m.BOS - YWG
1 stop7h 09mAir Canada
Mon 3/115:30 a.m.YWG - BOS
2 stops12h 42mAir Canada
Deal found 13/9C$ 492
Fri 24/106:00 a.m.BOS - YWG
2 stops12h 45mAir Canada
Mon 3/115:30 a.m.YWG - BOS
2 stops12h 42mAir Canada
Deal found 13/9C$ 499
Wed 15/106:00 a.m.BDL - YWG
2 stops16h 10mUnited Airlines
Wed 22/102:20 p.m.YWG - BDL
2 stops18h 17mUnited Airlines
Deal found 15/9C$ 707
Fri 10/1011:39 a.m.BDL - YWG
1 stop31h 53mMultiple Airlines
Mon 13/1012:15 p.m.YWG - BDL
2 stops9h 59mMultiple Airlines
Deal found 15/9C$ 941

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Winnipeg 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 15 September 2025.
Use the filters below to find and compare flights from Massachusetts to Winnipeg that are best for you.

Fly from

Massachusetts

Fly to

Winnipeg

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 16/10

8:24 p.m.-4:22 p.m.

2 stops20h 58m

Winnipeg

Mon 20/10

6:30 a.m.-5:40 p.m.

1 stop10h 10m

C$ 387

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 25/10

6:00 a.m.-3:31 p.m.

1 stop10h 31m

Winnipeg

Mon 3/11

8:40 a.m.-11:39 p.m.

1 stop13h 59m

C$ 486

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 23/10

8:00 a.m.-10:33 p.m.

1 stop15h 33m

Winnipeg

Sat 1/11

2:20 p.m.-9:49 p.m.

1 stop6h 29m

C$ 486

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 20/10

7:15 p.m.-9:41 a.m.

1 stop15h 26m

Winnipeg

Tue 28/10

12:20 p.m.-10:05 p.m.

1 stop8h 45m

C$ 486

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 23/10

11:02 a.m.-10:33 p.m.

1 stop12h 31m

Winnipeg

Wed 29/10

2:20 p.m.-9:49 p.m.

1 stop6h 29m

C$ 486

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 24/10

6:00 a.m.-5:45 p.m.

2 stops12h 45m

Winnipeg

Sat 1/11

6:00 a.m.-2:52 p.m.

2 stops7h 52m

C$ 489

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 24/10

6:00 a.m.-5:45 p.m.

2 stops12h 45m

Winnipeg

Tue 28/10

6:00 a.m.-2:52 p.m.

2 stops7h 52m

C$ 489

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 23/10

6:00 a.m.-10:33 p.m.

1 stop17h 33m

Winnipeg

Tue 28/10

8:40 a.m.-10:47 p.m.

2 stops13h 07m

C$ 500

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 23/10

10:40 a.m.-11:25 p.m.

1 stop13h 45m

Winnipeg

Fri 31/10

1:45 p.m.-9:27 p.m.

1 stop6h 42m

C$ 508

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 24/10

6:00 a.m.-5:45 p.m.

1 stop12h 45m

Winnipeg

Sun 2/11

8:15 a.m.-2:52 p.m.

1 stop5h 37m

C$ 508

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

Showing 1-10 of 30 results
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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
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 Massachusetts to Winnipeg

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

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 123). Flying from Massachusetts to Winnipeg in July is currently the most expensive (average of C$ 232). 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.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Winnipeg. 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 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 10h 31m. Fly via United Airlines to get the fastest option. There are 2173 km between Massachusetts and Winnipeg.

  • What are the cheapest airlines to fly from Massachusetts to Winnipeg one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as C$ 164. Users have also found prices from C$ 195 and C$ 461 on WestJet and United Airlines, respectively.

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

    Most travellers choose Boston Logan Intl - Winnipeg, Albany Intl - Winnipeg or Hartford Bradley 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, January is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 123). Flying from Massachusetts to Winnipeg in July is currently the most expensive (average of C$ 232). 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?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

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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 Massachusetts to Winnipeg?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Massachusetts to Winnipeg. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

Cheapflights simply makes it quick and affordable to book flights from Massachusetts to Winnipeg by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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.

Can Cheapflights notify me if prices for flights from Massachusetts to Winnipeg become cheaper?

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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