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Cheap flights from Massachusetts to Winnipeg from C$ 182

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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
6 Jun — 13 Jun1
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 7 May 2026.

Thu 17/910:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Tue 29/99:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 3/5C$ 388
Thu 16/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Tue 21/79:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 3/5C$ 408
Wed 9/96:00 a.m.
BOS
-
YWG
1 stop6h 12m
Air Canada
Sat 12/98:10 a.m.
YWG
-
BOS
1 stop5h 31m
Air Canada
Deal found 2/5C$ 425
Sat 5/911:15 a.m.
BOS
-
YWG
1 stop9h 54m
Delta
Sat 12/912:40 p.m.
YWG
-
BOS
1 stop8h 40m
Delta
Deal found 3/5C$ 429
Sun 23/810:40 a.m.
BOS
-
YWG
1 stop5h 34m
Air Canada
Fri 28/83:20 p.m.
YWG
-
BOS
1 stop6h 18m
Air Canada
Deal found 2/5C$ 436
Thu 9/75:55 a.m.
BOS
-
YWG
1 stop10h 12m
Delta
Wed 15/712:46 p.m.
YWG
-
BOS
1 stop10h 09m
Delta
Deal found 3/5C$ 440
Wed 8/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Wed 15/79:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 6/5C$ 441
Sat 5/96:00 a.m.
BOS
-
YWG
1 stop6h 15m
Air Canada
Sun 13/95:10 a.m.
YWG
-
BOS
2 stops8h 31m
Air Canada
Deal found 3/5C$ 442
Thu 9/75:45 a.m.
BOS
-
YWG
2 stops11h 35m
Air Canada
Tue 14/75:00 a.m.
YWG
-
BOS
1 stop5h 52m
Air Canada
Deal found 2/5C$ 455
Tue 13/1010:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Wed 21/109:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 6/5C$ 457
Tue 8/96:00 a.m.
ALB
-
YWG
2 stops19h 55m
WestJet
Sun 20/910:45 a.m.
YWG
-
ALB
2 stops11h 21m
WestJet
Deal found 6/5C$ 679
Sat 20/69:36 a.m.
ALB
-
YWG
2 stops14h 53m
Delta
Sat 27/66:40 a.m.
YWG
-
ALB
2 stops13h 24m
Delta
Deal found 6/5C$ 708

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 7 May 2026.

Round-trip from

C$ 388

One-way from

C$ 182

Popular in

January

Cheapest in

May

Average price

C$ 532
Porter Airlines
  • Porter Airlines
  • 17/9-29/9
  • 2 total stops
  • 13h 29m total
  • Massachusetts to Winnipeg
Search Deals
Delta
  • Delta
  • 9/7
  • 1 total stop
  • 10h 12m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 283 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 7 May 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 9/9

12:30 p.m.-10:33 p.m.

1 stop11h 03m

Winnipeg

Sat 12/9

2:00 p.m.-1:05 a.m.

1 stop10h 05m

C$ 429

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/9

5:50 a.m.-4:17 p.m.

2 stops11h 27m

Winnipeg

Sat 12/9

8:10 a.m.-2:41 p.m.

1 stop5h 31m

C$ 437

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/7

5:55 a.m.-3:07 p.m.

1 stop10h 12m

Winnipeg

Wed 15/7

12:46 p.m.-11:55 p.m.

1 stop10h 09m

C$ 440

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 10/7

2:52 p.m.-11:29 p.m.

1 stop9h 37m

Winnipeg

Wed 15/7

12:46 p.m.-11:55 p.m.

1 stop10h 09m

C$ 440

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 9/7

5:45 a.m.-4:20 p.m.

2 stops11h 35m

Winnipeg

Tue 14/7

5:00 a.m.-11:52 a.m.

1 stop5h 52m

C$ 455

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 16/7

6:00 a.m.-11:15 a.m.

1 stop6h 15m

Winnipeg

Tue 21/7

12:20 p.m.-9:27 p.m.

2 stops8h 07m

C$ 455

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 4/9

11:15 a.m.-8:09 p.m.

1 stop9h 54m

Winnipeg

Sun 13/9

12:40 p.m.-10:20 p.m.

1 stop8h 40m

C$ 470
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 22/10

6:00 a.m.-11:12 a.m.

1 stop6h 12m

Winnipeg

Sat 24/10

5:10 a.m.-11:55 a.m.

1 stop5h 45m

C$ 498

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 14/10

10:05 a.m.-5:58 p.m.

2 stops8h 53m

Winnipeg

Wed 21/10

9:20 a.m.-5:35 p.m.

1 stop7h 15m

C$ 506

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 12/6

6:35 p.m.-12:55 a.m.

1 stop7h 20m

Winnipeg

Tue 16/6

9:20 a.m.-5:35 p.m.

1 stop7h 15m

C$ 521

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/5

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, June is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 150). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 588). 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 10h 12m. Fly via United Airlines, Air Canada, or Delta 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, June is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 150). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 588). 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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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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