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Cheap flights from Massachusetts to Winnipeg from C$ 227

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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
25 Jul — 1 Aug1
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 25 June 2026.

Wed 16/910:05 a.m.
BOS
-
YWG
1 stop8h 10m
Multiple Airlines
Thu 17/98:45 p.m.
YWG
-
BOS
1 stop11h 20m
Multiple Airlines
Deal found 22/6C$ 502
Mon 13/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Mon 27/712:15 p.m.
YWG
-
BOS
1 stop5h 20m
Porter Airlines
Deal found 25/6C$ 505
Wed 19/85:30 p.m.
BOS
-
YWG
1 stop17h 15m
Multiple Airlines
Tue 25/811:15 a.m.
YWG
-
BOS
2 stops22h 15m
Multiple Airlines
Deal found 21/6C$ 508
Fri 14/811:10 a.m.
BOS
-
YWG
1 stop10h 20m
Multiple Airlines
Tue 25/86:15 a.m.
YWG
-
BOS
1 stop9h 31m
Multiple Airlines
Deal found 21/6C$ 512
Sat 15/85:30 p.m.
BOS
-
YWG
1 stop18h 49m
Porter Airlines
Tue 25/811:15 a.m.
YWG
-
BOS
2 stops22h 15m
Porter Airlines
Deal found 21/6C$ 519
Mon 13/78:25 p.m.
BOS
-
YWG
1 stop13h 15m
Multiple Airlines
Mon 27/711:15 a.m.
YWG
-
BOS
2 stops22h 14m
Multiple Airlines
Deal found 25/6C$ 520
Thu 9/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Wed 15/712:15 p.m.
YWG
-
BOS
1 stop5h 20m
Porter Airlines
Deal found 21/6C$ 522
Thu 20/811:10 a.m.
BOS
-
YWG
1 stop23h 35m
Multiple Airlines
Tue 25/86:15 a.m.
YWG
-
BOS
1 stop9h 31m
Multiple Airlines
Deal found 21/6C$ 525
Wed 12/86:00 a.m.
ALB
-
YWG
1 stop6h 52m
United Airlines
Wed 12/82:00 p.m.
YWG
-
ALB
1 stop6h 36m
United Airlines
Deal found 21/6C$ 876
Wed 12/84:00 p.m.
ALB
-
YWG
1 stop7h 33m
United Airlines
Fri 14/87:00 a.m.
YWG
-
ALB
1 stop13h 36m
United Airlines
Deal found 21/6C$ 893
Fri 7/84:23 p.m.
ALB
-
YWG
1 stop7h 15m
United Airlines
Fri 14/87:00 a.m.
YWG
-
ALB
1 stop13h 36m
United Airlines
Deal found 21/6C$ 965
Wed 2/96:50 a.m.
BDL
-
YWG
1 stop9h 18m
WestJet
Mon 7/910:45 a.m.
YWG
-
BDL
2 stops12h 06m
WestJet
Deal found 23/6C$ 1,000

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 25 June 2026.

Round-trip from

C$ 502

One-way from

C$ 227

Popular in

February

Cheapest in

August

Average price

C$ 779
Porter Airlines
  • Porter Airlines
  • 16/9-17/9
  • 2 total stops
  • 19h 30m total
  • Massachusetts to Winnipeg
Search Deals
Air Canada
  • Air Canada
  • 15/9
  • 1 total stop
  • 6h 39m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 23% potential increase in price (C$ 361 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 61 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 25 June 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

Wed 16/9

10:05 a.m.-5:15 p.m.

1 stop8h 10m

Winnipeg

Thu 17/9

6:00 a.m.-6:35 p.m.

2 stops11h 35m

C$ 508

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 28/8

7:30 p.m.-9:45 a.m.

1 stop15h 15m

Winnipeg

Sat 5/9

11:15 a.m.-10:30 a.m.

2 stops22h 15m

C$ 509

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 13/7

8:25 p.m.-8:40 a.m.

1 stop13h 15m

Winnipeg

Mon 27/7

11:15 a.m.-10:29 a.m.

2 stops22h 14m

C$ 520

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 13/8

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

1 stop6h 14m

Winnipeg

Thu 27/8

12:15 p.m.-6:35 p.m.

1 stop5h 20m

C$ 527

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 14/10

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

1 stop6h 14m

Winnipeg

Fri 16/10

9:20 a.m.-6:35 p.m.

1 stop8h 15m

C$ 530

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 19/8

4:45 p.m.-9:45 a.m.

2 stops18h 00m

Winnipeg

Tue 25/8

4:15 p.m.-10:30 a.m.

2 stops17h 15m

C$ 556

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 27/9

10:05 a.m.-4:25 p.m.

1 stop7h 20m

Winnipeg

Sat 3/10

11:15 a.m.-10:30 a.m.

2 stops22h 15m

C$ 559

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 9/8

10:05 a.m.-8:20 p.m.

1 stop11h 15m

Winnipeg

Sun 16/8

11:15 a.m.-9:05 a.m.

2 stops20h 50m

C$ 563

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 25/8

10:40 a.m.-3:14 p.m.

1 stop5h 34m

Winnipeg

Wed 26/8

2:05 p.m.-10:38 p.m.

1 stop7h 33m

C$ 584

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Wed 12/8

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

1 stop15h 23m

Winnipeg

Sat 15/8

7:00 a.m.-11:58 p.m.

2 stops15h 58m

C$ 965

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/6

Showing 1-10 of 31 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$ 158). Flying from Massachusetts to Winnipeg in September is currently the most expensive (average of C$ 471). 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 6h 14m. Fly via Porter Airlines, United 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$ 158). Flying from Massachusetts to Winnipeg in September is currently the most expensive (average of C$ 471). 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

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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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