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Cheap flights from Massachusetts to Winnipeg from C$ 234

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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
17 Apr — 24 Apr1
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 18 March 2026.

Fri 8/55:10 a.m.
BOS
-
YWG
1 stop5h 53m
Air Canada
Sun 17/58:00 a.m.
YWG
-
BOS
1 stop5h 47m
Air Canada
Deal found 14/3C$ 445
Sat 2/510:35 a.m.
BOS
-
YWG
1 stop5h 39m
Air Canada
Sat 9/55:10 a.m.
YWG
-
BOS
1 stop5h 36m
Air Canada
Deal found 18/3C$ 467
Sat 23/55:10 a.m.
BOS
-
YWG
1 stop6h 58m
Air Canada
Sat 30/58:00 a.m.
YWG
-
BOS
1 stop5h 47m
Air Canada
Deal found 13/3C$ 509
Thu 14/57:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Tue 19/59:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 14/3C$ 527
Mon 27/46:30 p.m.
BOS
-
YWG
1 stop17h 40m
WestJet
Mon 4/57:00 a.m.
YWG
-
BOS
1 stop9h 40m
WestJet
Deal found 13/3C$ 538
Wed 13/55:10 a.m.
BOS
-
YWG
1 stop5h 53m
Air Canada
Sun 17/58:00 a.m.
YWG
-
BOS
1 stop5h 47m
Air Canada
Deal found 15/3C$ 540
Fri 1/58:25 p.m.
BOS
-
YWG
1 stop16h 27m
United Airlines
Fri 8/52:00 p.m.
YWG
-
BOS
1 stop9h 59m
United Airlines
Deal found 17/3C$ 542
Sun 31/55:10 a.m.
BOS
-
YWG
1 stop5h 53m
Air Canada
Thu 4/68:10 a.m.
YWG
-
BOS
1 stop6h 58m
Air Canada
Deal found 17/3C$ 545
Wed 29/46:05 a.m.
ALB
-
YWG
1 stop6h 47m
United Airlines
Sun 3/52:00 p.m.
YWG
-
ALB
1 stop9h 48m
United Airlines
Deal found 15/3C$ 546
Wed 2/96:00 a.m.
BDL
-
YWG
2 stops17h 10m
WestJet
Sat 12/912:40 p.m.
YWG
-
BDL
1 stop9h 52m
WestJet
Deal found 16/3C$ 597
Mon 27/46:00 a.m.
BDL
-
YWG
1 stop5h 56m
WestJet
Mon 4/55:20 p.m.
YWG
-
BDL
1 stop5h 36m
WestJet
Deal found 13/3C$ 612
Wed 19/86:30 p.m.
BDL
-
YWG
1 stop5h 57m
WestJet
Thu 27/810:45 a.m.
YWG
-
BDL
2 stops11h 51m
WestJet
Deal found 14/3C$ 613

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 18 March 2026.

Round-trip from

C$ 445

One-way from

C$ 234

Popular in

January

Cheapest in

May

Average price

C$ 809
Air Canada
  • Air Canada
  • 8/5-17/5
  • 2 total stops
  • 11h 40m total
  • Massachusetts to Winnipeg
Search Deals
United Airlines
  • United Airlines
  • 1/5
  • 1 total stop
  • 16h 27m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 25% potential increase in price (C$ 320 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 18 March 2026.
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 - YWG

BOSYWG

Boston Logan Intl

Fri 8/5

5:10 a.m.-10:03 a.m.

1 stop5h 53m

Winnipeg

Sun 17/5

8:00 a.m.-2:47 p.m.

1 stop5h 47m

C$ 445
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 2/5

10:35 a.m.-3:14 p.m.

1 stop5h 39m

Winnipeg

Sat 9/5

5:10 a.m.-11:46 a.m.

1 stop5h 36m

C$ 467

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 23/5

10:05 a.m.-3:19 p.m.

1 stop6h 14m

Winnipeg

Sat 30/5

9:20 a.m.-8:55 p.m.

2 stops10h 35m

C$ 522

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 27/4

6:30 p.m.-11:10 a.m.

1 stop17h 40m

Winnipeg

Mon 4/5

7:00 a.m.-5:40 p.m.

1 stop9h 40m

C$ 538

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 30/4

5:30 a.m.-10:09 a.m.

1 stop5h 39m

Winnipeg

Thu 7/5

5:10 a.m.-11:46 a.m.

1 stop5h 36m

C$ 540

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 13/5

5:10 a.m.-10:03 a.m.

1 stop5h 53m

Winnipeg

Sun 17/5

8:00 a.m.-2:47 p.m.

1 stop5h 47m

C$ 540

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/5

8:25 p.m.-11:52 a.m.

1 stop16h 27m

Winnipeg

Fri 8/5

2:00 p.m.-12:59 a.m.

1 stop9h 59m

C$ 542

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Wed 29/4

6:05 a.m.-11:52 a.m.

1 stop6h 47m

Winnipeg

Sun 3/5

2:00 p.m.-12:48 a.m.

1 stop9h 48m

C$ 546

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Sat 23/5

5:30 a.m.-12:55 a.m.

2 stops20h 25m

Winnipeg

Sat 30/5

7:00 a.m.-11:35 p.m.

2 stops15h 35m

C$ 649

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Thu 14/5

6:00 a.m.-11:52 a.m.

1 stop6h 52m

Winnipeg

Mon 18/5

2:00 p.m.-9:37 a.m.

2 stops18h 37m

C$ 659

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/3

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
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$ 162). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 600). 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?

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 5h 39m. Fly via Air Canada, Porter Airlines, or WestJet to get the fastest option. There are 2173 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 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, May is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 162). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 600). 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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