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Cheap flights from Massachusetts to Winnipeg from C$ 209

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
13 Sep — 20 Sep1
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 14 August 2026.

Sat 29/810:05 a.m. -
1 stop6h 14m
Sat 5/912:15 p.m. -
1 stop6h 00m
Deal found 13/8C$ 413
Sat 26/910:05 a.m. -
1 stop6h 14m
Wed 30/99:20 a.m. -
1 stop8h 15m
Deal found 9/8C$ 461
Thu 17/910:05 a.m. -
1 stop8h 10m
Mon 21/911:15 a.m. -
2 stops22h 15m
Deal found 9/8C$ 468
Sat 3/106:30 p.m. -
1 stop18h 45m
Tue 13/106:00 a.m. -
1 stop10h 40m
Deal found 10/8C$ 485
Thu 3/97:00 a.m. -
1 stop10h 25m
Wed 9/911:15 a.m. -
2 stops22h 15m
Deal found 11/8C$ 492
Thu 10/94:30 p.m. -
1 stop9h 25m
Sun 20/911:15 a.m. -
2 stops22h 15m
Deal found 10/8C$ 495
Sat 19/910:05 a.m. -
1 stop11h 15m
Mon 21/97:45 a.m. -
1 stop9h 50m
Deal found 12/8C$ 498
Mon 7/126:15 a.m. -
1 stop6h 24m
Tue 8/128:30 a.m. -
1 stop14h 00m
Deal found 12/8C$ 884
Wed 21/108:10 a.m. -
2 stops12h 43m
Sat 24/105:40 p.m. -
1 stop4h 57m
Deal found 9/8C$ 944
Tue 1/910:33 a.m. -
2 stops10h 28m
Sat 5/91:30 p.m. -
2 stops9h 29m
Deal found 11/8C$ 945
Tue 1/96:50 a.m. -
2 stops16h 20m
Sat 5/93:58 p.m. -
1 stop6h 27m
Deal found 11/8C$ 970
Wed 21/1011:55 a.m. -
1 stop8h 58m
Wed 28/106:40 a.m. -
1 stop15h 57m
Deal found 10/8C$ 980

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 14 August 2026.

Round-trip from

C$ 413

One-way from

C$ 209

Popular in

February

Cheapest in

May

Average price

C$ 818
Porter Airlines
  • Porter Airlines
  • 29/8-5/9
  • 2 total stops
  • 12h 14m total
  • Massachusetts to Winnipeg
Search Deals
WestJet
  • WestJet
  • 15/9
  • 1 total stop
  • 17h 40m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 283 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 53 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 14 August 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 Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 17/9

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

1 stop8h 10m

Winnipeg

Mon 21/9

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

1 stop11h 20m

C$ 482
Quickest round-trip

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 1/10

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

1 stop6h 14m

Winnipeg

Mon 5/10

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

1 stop8h 15m

C$ 482

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Thu 3/9

7:00 a.m.-4:25 p.m.

1 stop10h 25m

Winnipeg

Wed 9/9

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

2 stops22h 15m

C$ 513

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 1/9

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

1 stop6h 14m

Winnipeg

Thu 10/9

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

1 stop8h 15m

C$ 533

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 1/9

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

1 stop17h 40m

Winnipeg

Fri 4/9

7:45 a.m.-7:40 p.m.

1 stop10h 55m

C$ 534

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Tue 1/9

6:30 p.m.-9:20 a.m.

2 stops15h 50m

Winnipeg

Sat 5/9

7:00 a.m.-10:20 p.m.

2 stops14h 20m

C$ 566

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Mon 31/8

7:25 a.m.-9:20 a.m.

2 stops26h 55m

Winnipeg

Fri 4/9

10:30 p.m.-5:40 p.m.

2 stops18h 10m

C$ 569

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 28/8

7:10 a.m.-4:52 p.m.

1 stop10h 42m

Winnipeg

Sun 30/8

12:46 p.m.-11:58 p.m.

1 stop10h 12m

C$ 633

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Fri 9/10

6:50 p.m.-9:59 a.m.

1 stop16h 09m

Winnipeg

Sun 11/10

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

1 stop5h 31m

C$ 651

BostonWinnipeg

BOS Boston Logan Intl - YWG Winnipeg

BOSYWG

Boston Logan Intl

Sat 19/9

2:20 p.m.-8:40 a.m.

2 stops19h 20m

Winnipeg

Mon 21/9

9:05 p.m.-3:50 p.m.

2 stops17h 45m

C$ 661

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Showing 1-10 of 35 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$ 721). Flying from Massachusetts to Winnipeg in February is currently the most expensive (average of C$ 1,280). 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?

Airfare is below average for this route at the moment.
Massachusetts to Winnipeg flights typically cost between C$ 573 and C$ 954 in August.
The cheapest round-trip price found within the last 5 days was C$ 413 on Porter Airlines (29 Aug-5 Sep).

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, WestJet, or United Airlines 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$ 721). Flying from Massachusetts to Winnipeg in February is currently the most expensive (average of C$ 1,280). 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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