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Cheap flights from Winnipeg to Massachusetts from C$ 343

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
2 Feb — 9 Feb1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Massachusetts

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Massachusetts
Explore the most affordable flight options available from Winnipeg to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 3 January 2026.

Mon 2/28:00 a.m.YWG - BOS
1 stop14h 57mMultiple Airlines
Sun 8/26:00 a.m.BOS - YWG
2 stops19h 40mMultiple Airlines
Deal found 3/1C$ 343
Wed 8/47:30 a.m.YWG - BOS
1 stop16h 34mMultiple Airlines
Wed 22/47:55 p.m.BOS - YWG
2 stops24h 14mMultiple Airlines
Deal found 31/12C$ 387
Tue 28/46:30 a.m.YWG - BOS
1 stop10h 10mWestJet
Fri 8/56:25 p.m.BOS - YWG
1 stop18h 15mWestJet
Deal found 2/1C$ 395
Fri 8/56:30 a.m.YWG - BOS
1 stop10h 10mWestJet
Thu 14/56:25 p.m.BOS - YWG
1 stop26h 50mWestJet
Deal found 2/1C$ 456
Sat 31/18:20 p.m.YWG - BOS
1 stop13h 45mMultiple Airlines
Sat 7/25:23 p.m.BOS - YWG
3 stops32h 17mMultiple Airlines
Deal found 2/1C$ 531
Wed 8/48:15 a.m.YWG - BOS
1 stop5h 37mAir Canada
Wed 22/45:30 a.m.BOS - YWG
1 stop5h 37mAir Canada
Deal found 31/12C$ 557
Mon 2/35:19 p.m.YWG - BOS
1 stop5h 31mDelta
Wed 4/35:50 a.m.BOS - YWG
1 stop6h 11mDelta
Deal found 31/12C$ 560
Mon 2/36:00 a.m.YWG - BOS
2 stops7h 52mAir Canada
Wed 4/310:15 a.m.BOS - YWG
2 stops11h 13mAir Canada
Deal found 31/12C$ 562
Tue 28/46:30 a.m.YWG - BOS
1 stop10h 10mMultiple Airlines
Tue 28/47:55 p.m.BOS - YWG
2 stops24h 30mMultiple Airlines
Deal found 2/1C$ 571
Sat 11/710:45 a.m.YWG - ALB
2 stops11h 21mWestJet
Fri 4/91:15 p.m.ALB - YWG
2 stops12h 15mWestJet
Deal found 2/1C$ 588
Sun 18/12:20 p.m.YWG - ALB
1 stop6h 02mUnited Airlines
Thu 22/16:00 a.m.ALB - YWG
1 stop6h 57mUnited Airlines
Deal found 3/1C$ 703
Sun 18/16:40 a.m.YWG - ALB
2 stops15h 15mDelta
Thu 22/112:29 p.m.ALB - YWG
2 stops13h 13mDelta
Deal found 1/1C$ 740

Find flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated 3 January 2026.

Round-trip from

C$ 343

Popular in

December

Cheapest in

June

Average price

C$ 755
2/2-8/2
  • 2/2-8/2
  • 3 total stops
  • 34h 37m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 210 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Massachusetts 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 3 January 2026.
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Winnipeg

Fly to

Massachusetts

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/2

8:00 a.m.-11:57 p.m.

1 stop14h 57m

Boston Logan Intl

Sun 8/2

6:00 a.m.-12:40 a.m.

2 stops19h 40m

C$ 343

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 28/4

6:30 a.m.-5:40 p.m.

1 stop10h 10m

Boston Logan Intl

Fri 8/5

6:25 p.m.-11:40 a.m.

1 stop18h 15m

C$ 395

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 8/5

6:30 a.m.-5:40 p.m.

1 stop10h 10m

Boston Logan Intl

Thu 14/5

6:25 p.m.-8:15 p.m.

1 stop26h 50m

C$ 456

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 31/1

8:20 p.m.-11:05 a.m.

1 stop13h 45m

Boston Logan Intl

Sat 7/2

5:23 p.m.-12:40 a.m.

3 stops32h 17m

C$ 531

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 8/4

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

1 stop5h 37m

Boston Logan Intl

Wed 22/4

5:30 a.m.-10:07 a.m.

1 stop5h 37m

C$ 557

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/3

5:19 p.m.-11:50 p.m.

1 stop5h 31m

Boston Logan Intl

Wed 4/3

5:50 a.m.-11:01 a.m.

1 stop6h 11m

C$ 560

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 2/3

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

2 stops7h 52m

Boston Logan Intl

Wed 4/3

10:15 a.m.-8:28 p.m.

2 stops11h 13m

C$ 562

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Tue 28/4

6:30 a.m.-5:40 p.m.

1 stop10h 10m

Boston Logan Intl

Tue 28/4

7:55 p.m.-7:25 p.m.

2 stops24h 30m

C$ 571

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sun 18/1

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

1 stop6h 02m

Albany Intl

Thu 22/1

6:00 a.m.-11:57 a.m.

1 stop6h 57m

C$ 703

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sun 18/1

6:40 a.m.-10:55 p.m.

2 stops15h 15m

Albany Intl

Thu 22/1

12:29 p.m.-12:42 a.m.

2 stops13h 13m

C$ 740

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

Showing 1-10 of 12 results
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Best time to book a flight from Winnipeg to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Winnipeg 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 Winnipeg to Massachusetts

What is the cheapest month to book a flight from Winnipeg to Massachusetts?

Currently, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 221). Flying from Winnipeg to Massachusetts in March is currently the most expensive (average of C$ 450). 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.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated 3 January 2026.
Read through reviews of airlines operating flights from Winnipeg to Massachusetts, such as Porter Airlines,United Airlines, andWestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
403 reviews
Check prices

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
403 reviews
Porter Airlines
8.0
Very good
403 reviews
Check prices

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,137 reviews
Porter Airlines
8.0
Very good
403 reviews
Check prices

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,231 reviews
Porter Airlines
8.0
Very good
403 reviews
Check prices

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,587 reviews
Porter Airlines
8.0
Very good
403 reviews
Check prices

Crew

8.6

Food

7.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Massachusetts. 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 from for flights from Winnipeg to Massachusetts?

    Located just 7.3 km from the city centre, Winnipeg (YWG) is the airport most travellers will use when flying to Massachusetts from Winnipeg.

  • How long is the flight from Winnipeg to Massachusetts?

    There are many flights that can get you from Winnipeg to Massachusetts in 6h 02m. Fly via WestJet, United Airlines, or Delta to get the fastest option. The distance between Winnipeg and Massachusetts is about 1955 km. This flight may include one or multiple stops.

  • What are the most popular routes from Winnipeg to Massachusetts?

    The most popular flight routes from Winnipeg to Massachusetts are Winnipeg - Boston Logan Intl, Winnipeg - Albany Intl and Winnipeg - Provincetown.

  • Can I find deals for flights from Winnipeg to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Massachusetts.

  • Can I find deals for business class flights from Winnipeg to Massachusetts?

    Yes. Cheapflights offers flight deals from Winnipeg to Massachusetts 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 Winnipeg to Massachusetts?

    Currently, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 221). Flying from Winnipeg to Massachusetts in March is currently the most expensive (average of C$ 450). 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

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Top 4 airlines flying from Winnipeg to Massachusetts

Discover the top 4 airlines that operate flights from Winnipeg to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 3 January 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 237AverageC$ 398FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 349AverageC$ 499FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 420AverageC$ 630FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 471AverageC$ 1,128FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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 Winnipeg to Massachusetts?

Cheapflights helps you search for flights from Winnipeg to Massachusetts via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Massachusetts?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Massachusetts for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Winnipeg to Massachusetts with no change fees?

Need flexible booking options for your flight to Massachusetts from Winnipeg? 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 Winnipeg to Massachusetts become cheaper?

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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