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Cheap flights from Winnipeg to Massachusetts from C$ 219

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 25/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 362

One-way from

C$ 219

Popular in

December

Cheapest in

October

Average price

C$ 461
United Airlines
  • United Airlines
  • 10/7-14/7
  • 2 total stops
  • 29h 57m total
  • Winnipeg to Massachusetts
United Airlines
  • United Airlines
  • 25/6
  • 2 total stops
  • 14h 46m total
  • Winnipeg to Massachusetts
Highest demand for flights based on searches. 22% potential increase in price (C$ 216 potential increase over avg. RT price).
Cheapest flight prices on average. 5% potential price decrease (C$ 40 potential savings vs. average RT price).
Average for round-trip flights in June 2025

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 12 June 2025.

Thu 10/74:25 p.m.YWG - BOS
2 stops16h 01mUnited Airlines
Mon 14/78:48 p.m.BOS - YWG
1 stop17h 21mUnited Airlines
Deal found 11/6C$ 362
Thu 10/710:45 a.m.YWG - BOS
2 stops12h 08mDelta
Wed 6/85:30 a.m.BOS - YWG
1 stop7h 01mDelta
Deal found 11/6C$ 479
Thu 10/79:00 a.m.YWG - BOS
2 stops25h 31mMultiple Airlines
Sun 13/712:26 p.m.BOS - YWG
3 stops37h 05mMultiple Airlines
Deal found 10/6C$ 491
Thu 10/75:00 a.m.YWG - BOS
1 stop5h 28mAir Canada
Wed 6/810:40 a.m.BOS - YWG
1 stop6h 38mAir Canada
Deal found 11/6C$ 499
Thu 10/711:45 a.m.YWG - BOS
2 stops25h 56mPorter Airlines
Wed 6/812:15 p.m.BOS - YWG
2 stops11h 31mPorter Airlines
Deal found 10/6C$ 733
Sat 26/79:10 a.m.YWG - ALB
2 stops27h 02mMultiple Airlines
Sat 2/86:30 p.m.ALB - YWG
3 stops29h 16mMultiple Airlines
Deal found 10/6C$ 926
Sat 26/75:00 a.m.YWG - ALB
2 stops17h 58mUnited Airlines
Sat 2/86:00 a.m.ALB - YWG
2 stops18h 28mUnited Airlines
Deal found 11/6C$ 1,129
Wed 30/77:00 a.m.YWG - ALB
1 stop7h 09mAir Canada
Sat 2/86:00 a.m.ALB - YWG
1 stop10h 31mAir Canada
Deal found 10/6C$ 1,822

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 12 June 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 10/7

4:25 p.m.-6:01 a.m.

1 stop12h 36m

Boston Logan Intl

Mon 14/7

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

1 stop17h 21m

C$ 362

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 10/7

10:45 a.m.-11:53 p.m.

2 stops12h 08m

Boston Logan Intl

Wed 6/8

5:30 a.m.-11:31 a.m.

1 stop7h 01m

C$ 479

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 10/7

9:00 a.m.-11:31 a.m.

2 stops25h 31m

Boston Logan Intl

Sun 13/7

12:26 p.m.-12:31 a.m.

3 stops37h 05m

C$ 491

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 10/7

5:00 a.m.-11:28 a.m.

1 stop5h 28m

Boston Logan Intl

Wed 6/8

10:40 a.m.-4:18 p.m.

1 stop6h 38m

C$ 499

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Thu 10/7

11:45 a.m.-2:41 p.m.

2 stops25h 56m

Boston Logan Intl

Wed 6/8

12:15 p.m.-10:46 p.m.

2 stops11h 31m

C$ 733

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 26/7

9:10 a.m.-1:12 p.m.

2 stops27h 02m

Albany Intl

Sat 2/8

6:30 p.m.-10:46 p.m.

3 stops29h 16m

C$ 926

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Sat 26/7

5:00 a.m.-11:58 p.m.

2 stops17h 58m

Albany Intl

Sat 2/8

6:00 a.m.-11:28 p.m.

2 stops18h 28m

C$ 1,129

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Wed 30/7

7:00 a.m.-3:09 p.m.

1 stop7h 09m

Albany Intl

Sat 2/8

6:00 a.m.-3:31 p.m.

1 stop10h 31m

C$ 1,822

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Wed 25/6

4:25 p.m.-8:11 a.m.

2 stops14h 46m

C$ 219

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 13/10

8:50 a.m.-10:24 p.m.

2 stops12h 34m

C$ 230

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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$ 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 12 June 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.

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 78.0 - 101.0 mm per month. March is typically the wettest month, when rainfall can reach 101.0 mm. July is typically the driest time to visit Massachusetts when rainfall is around 78.0 mm.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -1.0 C).

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 12 June 2025.
See what other customers who have flown with Porter Airlines, Delta and United Airlines from Winnipeg to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

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!!!

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

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!!!
8.0
Very good

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

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!!!

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

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!!!

Food

7.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

Comfort

8.1

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$ 219 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and Air Canada, with prices starting from C$ 230 and C$ 245, respectively.

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

  • 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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Alternative routes for Winnipeg to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.

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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 236AverageC$ 393FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 324AverageC$ 514FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 333AverageC$ 495FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 363AverageC$ 474FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 824AverageC$ 1,123FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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How does Cheapflights help users find flights from Winnipeg to Massachusetts?

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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.

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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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