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Cheap flights from Massachusetts to Winnipeg from C$ 183

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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
28 Feb — 7 Mar1
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
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 29 January 2026.

Sun 22/25:30 a.m.
BOS
-
YWG
1 stop5h 45m
Air Canada
Sat 28/26:00 a.m.
YWG
-
BOS
2 stops7h 52m
Air Canada
Deal found 28/1C$ 467
Tue 24/26:10 p.m.
BOS
-
YWG
2 stops22h 20m
Multiple Airlines
Tue 3/38:20 p.m.
YWG
-
BOS
2 stops24h 41m
Multiple Airlines
Deal found 27/1C$ 487
Fri 13/36:15 a.m.
BOS
-
YWG
1 stop12h 04m
Air Canada
Fri 20/35:30 a.m.
YWG
-
BOS
1 stop9h 27m
Air Canada
Deal found 27/1C$ 543
Wed 25/34:23 p.m.
BOS
-
YWG
2 stops20h 09m
Multiple Airlines
Mon 30/38:00 a.m.
YWG
-
BOS
1 stop14h 59m
Multiple Airlines
Deal found 27/1C$ 554
Thu 26/26:00 a.m.
ALB
-
YWG
1 stop6h 57m
United Airlines
Mon 2/32:20 p.m.
YWG
-
ALB
1 stop5h 44m
United Airlines
Deal found 26/1C$ 578
Sun 15/33:30 p.m.
BOS
-
YWG
2 stops21h 02m
Multiple Airlines
Sun 22/37:30 a.m.
YWG
-
BOS
1 stop27h 11m
Multiple Airlines
Deal found 28/1C$ 582
Fri 27/33:30 p.m.
BOS
-
YWG
2 stops10h 09m
Multiple Airlines
Mon 30/38:00 a.m.
YWG
-
BOS
1 stop14h 59m
Multiple Airlines
Deal found 27/1C$ 593
Thu 13/86:00 a.m.
ALB
-
YWG
2 stops11h 58m
WestJet
Tue 25/810:45 a.m.
YWG
-
ALB
2 stops11h 21m
WestJet
Deal found 28/1C$ 619
Wed 12/84:30 p.m.
ALB
-
YWG
1 stop6h 54m
United Airlines
Tue 25/88:30 a.m.
YWG
-
ALB
1 stop14h 00m
United Airlines
Deal found 28/1C$ 661
Fri 14/86:00 a.m.
ALB
-
YWG
2 stops11h 58m
WestJet
Tue 25/810:45 a.m.
YWG
-
ALB
2 stops11h 21m
WestJet
Deal found 28/1C$ 664
Wed 12/86:00 a.m.
ALB
-
YWG
2 stops19h 30m
WestJet
Mon 24/86:30 a.m.
YWG
-
ALB
2 stops15h 36m
WestJet
Deal found 28/1C$ 682
Thu 26/26:05 a.m.
BDL
-
YWG
2 stops14h 04m
WestJet
Mon 2/311:53 a.m.
YWG
-
BDL
1 stop10h 28m
WestJet
Deal found 26/1C$ 684

Find flight deals from Massachusetts to Winnipeg

Keep the following information in mind while searching for Massachusetts to Winnipeg flight deals. Data was last updated 29 January 2026.

Round-trip from

C$ 467

One-way from

C$ 183

Popular in

December

Cheapest in

July

Average price

C$ 779
Air Canada
  • Air Canada
  • 22/2-28/2
  • 3 total stops
  • 13h 37m total
  • Massachusetts to Winnipeg
Search Deals
2/5
  • 2/5
  • 2 total stops
  • 29h 50m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 206 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 29 January 2026.
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

Tue 24/2

6:10 p.m.-3:30 p.m.

2 stops22h 20m

Winnipeg

Tue 3/3

8:20 p.m.-11:05 a.m.

1 stop13h 45m

C$ 493

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 13/3

6:15 a.m.-5:19 p.m.

1 stop12h 04m

Winnipeg

Fri 20/3

5:30 a.m.-7:12 p.m.

3 stops12h 42m

C$ 548

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 26/3

3:30 p.m.-12:39 a.m.

2 stops10h 09m

Winnipeg

Mon 30/3

8:00 a.m.-11:59 p.m.

1 stop14h 59m

C$ 577

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Fri 20/3

6:00 a.m.-11:57 a.m.

1 stop6h 57m

Winnipeg

Mon 23/3

2:20 p.m.-12:30 a.m.

1 stop9h 10m

C$ 578

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 26/2

6:00 a.m.-11:57 a.m.

1 stop6h 57m

Winnipeg

Mon 2/3

2:20 p.m.-9:04 p.m.

1 stop5h 44m

C$ 578

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 26/2

6:00 a.m.-11:57 a.m.

1 stop6h 57m

Winnipeg

Thu 5/3

2:20 p.m.-12:30 a.m.

1 stop9h 10m

C$ 578

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 15/3

3:30 p.m.-11:32 a.m.

2 stops21h 02m

Winnipeg

Sun 22/3

7:30 a.m.-11:41 a.m.

1 stop27h 11m

C$ 582

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 13/3

6:15 a.m.-11:47 p.m.

2 stops18h 32m

Winnipeg

Fri 20/3

6:00 a.m.-7:12 p.m.

3 stops12h 12m

C$ 641

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Thu 26/2

6:05 a.m.-7:09 p.m.

2 stops14h 04m

Winnipeg

Mon 2/3

11:53 a.m.-11:21 p.m.

1 stop10h 28m

C$ 684

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Thu 26/2

6:00 a.m.-11:57 a.m.

1 stop6h 57m

Winnipeg

Mon 2/3

5:30 a.m.-9:04 p.m.

2 stops14h 34m

C$ 699

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

Showing 1-10 of 26 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, May is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 160). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 610). 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 6h 57m. Fly via Air Canada, United Airlines, or WestJet to get the fastest option. There are 1955 km between Massachusetts and Winnipeg. This flight may include one or multiple stops.

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

    Most travellers choose Albany Intl - Winnipeg, Boston Logan 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, May is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 160). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 610). 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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