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Cheap flights from Winnipeg to Massachusetts from C$ 243

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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
7 Jul — 14 Jul1
1 adult

Cheap flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated 2 July 2025.

Round-trip from

C$ 406

One-way from

C$ 243

Popular in

December

Cheapest in

October

Average price

C$ 492
United Airlines
  • United Airlines
  • 17/7-23/7
  • 2 total stops
  • 27h 00m total
  • Winnipeg to Massachusetts
Search Deals
Porter Airlines
  • Porter Airlines
  • 4/9
  • 1 total stop
  • 6h 03m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 212 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 39 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Winnipeg to Massachusetts

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 2 July 2025.

Thu 17/72:20 p.m.YWG - BOS
1 stop9h 39mUnited Airlines
Wed 23/78:48 p.m.BOS - YWG
1 stop17h 21mUnited Airlines
Deal found 1/7C$ 406
Sat 16/812:00 p.m.YWG - BOS
1 stop8h 56mAir Canada
Sat 23/86:00 a.m.BOS - YWG
1 stop12h 40mAir Canada
Deal found 2/7C$ 476
Wed 16/76:45 a.m.YWG - BOS
2 stops14h 23mDelta
Tue 22/75:15 a.m.BOS - YWG
2 stops12h 43mDelta
Deal found 1/7C$ 493
Wed 16/711:45 a.m.YWG - BOS
2 stops20h 13mMultiple Airlines
Tue 22/76:10 a.m.BOS - YWG
3 stops19h 21mMultiple Airlines
Deal found 1/7C$ 548
Thu 10/711:45 a.m.YWG - BOS
1 stop5h 43mPorter Airlines
Wed 6/812:15 p.m.BOS - YWG
2 stops11h 31mPorter Airlines
Deal found 1/7C$ 789
Thu 10/712:30 p.m.YWG - BOS
2 stops10h 27mWestJet
Wed 6/85:30 a.m.BOS - YWG
2 stops12h 28mWestJet
Deal found 1/7C$ 1,014

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 2 July 2025.
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

Thu 17/7

2:20 p.m.-12:59 a.m.

1 stop9h 39m

Boston Logan Intl

Wed 23/7

8:48 p.m.-1:09 p.m.

1 stop17h 21m

C$ 406

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 16/8

12:00 p.m.-9:56 p.m.

1 stop8h 56m

Boston Logan Intl

Sat 23/8

6:00 a.m.-5:40 p.m.

1 stop12h 40m

C$ 476

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 16/7

6:45 a.m.-10:08 p.m.

2 stops14h 23m

Boston Logan Intl

Tue 22/7

5:15 a.m.-4:58 p.m.

2 stops12h 43m

C$ 493

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 16/7

11:45 a.m.-8:58 a.m.

2 stops20h 13m

Boston Logan Intl

Tue 22/7

6:10 a.m.-12:31 a.m.

3 stops19h 21m

C$ 548

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 4/9

11:25 a.m.-6:28 p.m.

1 stop6h 03m

C$ 243

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 15/8

8:35 a.m.-7:19 p.m.

1 stop9h 44m

C$ 244

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 4/9

7:00 a.m.-5:34 p.m.

2 stops9h 34m

C$ 251

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 16/8

12:00 p.m.-9:56 p.m.

1 stop8h 56m

C$ 298

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 16/8

3:00 p.m.-11:18 a.m.

3 stops19h 18m

C$ 376

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

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$ 291). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 350). 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.

What is the cheapest time of day to fly from YWG to MA?

Find hourly flight availability from Winnipeg to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 2 July 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Winnipeg to Massachusetts as you normally would.

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 2 July 2025.
Read through reviews of airlines operating flights from Winnipeg to Massachusetts, such as Porter Airlines,Delta, andUnited Airlines. 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
298 reviews
Check prices

Food

7.7

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
298 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Food

7.7

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,983 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Food

7.7

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,861 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Food

7.7

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,912 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Food

7.7

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,669 reviews
Porter Airlines
8.0
Very good
298 reviews
Check prices

Food

7.7

Boarding

8.2

Comfort

8.1

Entertainment

7.0

Overall

8.0

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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.

  • What are the cheapest airlines to fly from Winnipeg to Massachusetts one-way?

    C$ 243 is the cheapest one-way deal found within the past few days, from Porter Airlines. You may also be able to find cheap deals on Air Canada and United Airlines, with prices starting from C$ 244 and C$ 251, respectively.

  • 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$ 291). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 350). 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 5 airlines flying from Winnipeg to Massachusetts

Discover the top 5 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 2 July 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 235AverageC$ 392FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 315AverageC$ 509FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 331AverageC$ 487FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 362AverageC$ 473FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 821AverageC$ 1,119FlexibilityNo 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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