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Cheap flights from Massachusetts to Winnipeg from C$ 145

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 27/11. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
29 Nov — 6 Dec1
1 adult
1 adult, Economy, 0 bags

Find 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 30 October 2025.

Sun 14/125:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Sun 21/127:05 p.m.YWG - BOS
2 stops18h 47mAir Canada
Deal found 30/10C$ 744
Sun 14/123:40 p.m.BOS - YWG
2 stops8h 55mMultiple Airlines
Sun 21/127:05 p.m.YWG - BOS
2 stops18h 47mMultiple Airlines
Deal found 30/10C$ 775
Wed 24/123:40 p.m.BOS - YWG
1 stop20h 33mMultiple Airlines
Tue 30/129:00 p.m.YWG - BOS
2 stops27h 14mMultiple Airlines
Deal found 29/10C$ 776
Wed 24/1211:09 a.m.BOS - YWG
2 stops14h 32mMultiple Airlines
Mon 29/1212:10 p.m.YWG - BOS
1 stop8h 55mMultiple Airlines
Deal found 29/10C$ 811
Wed 24/123:40 p.m.BOS - YWG
1 stop20h 33mPorter Airlines
Tue 30/126:00 a.m.YWG - BOS
1 stop26h 35mPorter Airlines
Deal found 29/10C$ 829
Tue 23/1210:37 a.m.BOS - YWG
1 stop29h 30mMultiple Airlines
Mon 29/1212:10 p.m.YWG - BOS
1 stop8h 55mMultiple Airlines
Deal found 29/10C$ 853
Wed 24/123:40 p.m.BOS - YWG
1 stop20h 33mPorter Airlines
Mon 29/1212:10 p.m.YWG - BOS
1 stop8h 55mPorter Airlines
Deal found 29/10C$ 859
Tue 23/125:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Tue 30/125:30 a.m.YWG - BOS
2 stops8h 22mAir Canada
Deal found 29/10C$ 860
Tue 23/127:50 a.m.BOS - YWG
2 stops16h 45mAmerican Airlines
Tue 30/126:00 a.m.YWG - BOS
2 stops11h 03mAmerican Airlines
Deal found 29/10C$ 894

Cheap flight deals from Massachusetts to Winnipeg

Keep the following information in mind while searching for Massachusetts to Winnipeg flight deals. Data was last updated 30 October 2025.

Round-trip from

C$ 362

One-way from

C$ 145

Popular in

February

Cheapest in

July

Average price

C$ 582
14/1-21/1
  • 14/1-21/1
  • 2 total stops
  • 25h 42m total
  • Massachusetts to Winnipeg
Search Deals
27/11
  • 27/11
  • 1 total stop
  • 18h 13m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 5% potential increase in price (C$ 45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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 30 October 2025.
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

Wed 14/1

6:00 a.m.-3:07 p.m.

1 stop10h 07m

Winnipeg

Wed 21/1

7:30 a.m.-12:05 a.m.

1 stop15h 35m

C$ 362

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 10/3

6:00 a.m.-11:43 a.m.

1 stop6h 43m

Winnipeg

Wed 11/3

5:38 p.m.-11:38 p.m.

1 stop5h 00m

C$ 603

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Tue 10/3

7:47 p.m.-11:39 a.m.

2 stops16h 52m

Winnipeg

Wed 11/3

2:15 p.m.-9:35 p.m.

1 stop6h 20m

C$ 616

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 24/2

5:30 a.m.-10:16 a.m.

1 stop5h 46m

Winnipeg

Thu 26/2

8:15 a.m.-2:52 p.m.

1 stop5h 37m

C$ 634

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Fri 27/3

6:00 a.m.-3:09 p.m.

1 stop10h 09m

Winnipeg

Tue 31/3

12:40 p.m.-11:14 p.m.

2 stops9h 34m

C$ 722

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 14/12

5:30 a.m.-10:16 a.m.

1 stop5h 46m

Winnipeg

Sun 21/12

7:05 p.m.-2:52 p.m.

2 stops18h 47m

C$ 744

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 14/12

3:40 p.m.-11:35 p.m.

2 stops8h 55m

Winnipeg

Sun 21/12

7:05 p.m.-2:52 p.m.

2 stops18h 47m

C$ 775

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 24/12

3:40 p.m.-11:13 a.m.

1 stop20h 33m

Winnipeg

Tue 30/12

9:00 p.m.-1:14 a.m.

2 stops27h 14m

C$ 776

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Fri 27/3

6:15 a.m.-11:39 a.m.

1 stop6h 24m

Winnipeg

Tue 31/3

2:15 p.m.-9:02 p.m.

1 stop5h 47m

C$ 804

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 27/11

9:54 p.m.-3:07 p.m.

1 stop18h 13m

C$ 145

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/10

Showing 1-10 of 16 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, July is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 179). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 603). 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 5h 46m. Fly via Delta, United Airlines, or Air Canada 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, Albany 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, July is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 179). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 603). 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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