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Cheap flights from Massachusetts to Winnipeg from C$ 191

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 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
15 Jan — 22 Jan1
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 16 December 2025.

Mon 22/123:15 p.m.BOS - YWG
1 stop26h 40mWestJet
Mon 5/18:05 p.m.YWG - BOS
2 stops17h 12mWestJet
Deal found 15/12C$ 1,157
Tue 16/128:11 p.m.BOS - YWG
2 stops24h 24mMultiple Airlines
Tue 23/128:00 a.m.YWG - BOS
1 stop25h 01mMultiple Airlines
Deal found 15/12C$ 1,207
Tue 30/1212:10 p.m.ALB - YWG
1 stop27h 57mWestJet
Fri 2/15:00 a.m.YWG - ALB
2 stops12h 02mWestJet
Deal found 15/12C$ 1,219
Tue 23/125:45 a.m.BOS - YWG
1 stop7h 00mWestJet
Tue 30/128:05 p.m.YWG - BOS
2 stops20h 00mWestJet
Deal found 16/12C$ 1,284
Mon 22/126:01 a.m.BOS - YWG
1 stop6h 56mUnited Airlines
Mon 5/12:20 p.m.YWG - BOS
1 stop9h 25mUnited Airlines
Deal found 15/12C$ 1,289
Tue 23/127:15 a.m.BOS - YWG
1 stop14h 36mUnited Airlines
Tue 30/122:20 p.m.YWG - BOS
1 stop9h 25mUnited Airlines
Deal found 15/12C$ 1,335
Tue 16/1212:10 p.m.BOS - YWG
2 stops12h 34mDelta
Tue 23/126:40 a.m.YWG - BOS
2 stops12h 34mDelta
Deal found 15/12C$ 1,439
Tue 16/1212:47 p.m.ALB - YWG
1 stop27h 20mWestJet
Mon 22/1212:20 p.m.YWG - ALB
2 stops21h 55mWestJet
Deal found 15/12C$ 1,460
Fri 19/126:24 p.m.BOS - YWG
1 stop23h 31mWestJet
Wed 31/128:05 p.m.YWG - BOS
2 stops22h 42mWestJet
Deal found 16/12C$ 1,463
Tue 16/125:40 a.m.ALB - YWG
2 stops12h 15mDelta
Mon 22/126:40 a.m.YWG - ALB
2 stops14h 52mDelta
Deal found 15/12C$ 1,536
Tue 16/126:00 a.m.ALB - YWG
1 stop6h 57mAir Canada
Mon 22/122:20 p.m.YWG - ALB
1 stop5h 45mAir Canada
Deal found 15/12C$ 1,629
Tue 30/126:00 a.m.ALB - YWG
3 stops18h 35mAmerican Airlines
Fri 2/16:00 a.m.YWG - ALB
2 stops15h 53mAmerican Airlines
Deal found 15/12C$ 1,738

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 16 December 2025.

Round-trip from

C$ 315

One-way from

C$ 191

Popular in

December

Cheapest in

July

Average price

C$ 883
14/1-20/1
  • 14/1-20/1
  • 3 total stops
  • 37h 10m total
  • Massachusetts to Winnipeg
Search Deals
8/3
  • 8/3
  • 3 total stops
  • 35h 05m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 168 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 16 December 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

Tue 20/1

9:00 p.m.-1:03 a.m.

2 stops27h 03m

C$ 315

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 5/1

5:30 a.m.-9:44 p.m.

2 stops17h 14m

Winnipeg

Tue 13/1

6:00 a.m.-2:52 p.m.

2 stops7h 52m

C$ 501

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 16/1

3:43 p.m.-1:26 a.m.

1 stop10h 43m

Winnipeg

Sun 18/1

7:30 a.m.-11:19 p.m.

2 stops14h 49m

C$ 526

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Tue 28/4

6:00 a.m.-11:39 a.m.

1 stop6h 39m

Winnipeg

Wed 13/5

2:15 p.m.-9:10 p.m.

1 stop5h 55m

C$ 594

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Mon 2/2

3:02 p.m.-11:57 a.m.

2 stops21h 55m

Winnipeg

Thu 5/2

2:20 p.m.-9:29 p.m.

1 stop6h 09m

C$ 608

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Mon 2/2

7:25 p.m.-11:57 a.m.

2 stops17h 32m

Winnipeg

Thu 5/2

2:20 p.m.-9:22 p.m.

1 stop6h 02m

C$ 608

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Tue 28/4

1:15 p.m.-12:30 a.m.

2 stops12h 15m

Winnipeg

Wed 13/5

7:00 a.m.-11:38 p.m.

2 stops15h 38m

C$ 647

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 20/1

6:00 a.m.-12:41 a.m.

2 stops19h 41m

Winnipeg

Sat 24/1

4:25 p.m.-6:10 p.m.

1 stop24h 45m

C$ 688

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Mon 2/2

6:03 a.m.-11:03 a.m.

1 stop6h 00m

Winnipeg

Thu 5/2

5:21 p.m.-11:50 p.m.

1 stop5h 29m

C$ 747

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 5/1

6:15 a.m.-10:08 a.m.

2 stops28h 53m

Winnipeg

Tue 13/1

4:10 p.m.-10:02 a.m.

3 stops16h 52m

C$ 760

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/12

Showing 1-10 of 17 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$ 176). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 618). 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 6h 39m. Fly via Air Canada, United Airlines, or WestJet to get the fastest option. There are 1955 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$ 176). Flying from Massachusetts to Winnipeg in April is currently the most expensive (average of C$ 618). 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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