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Cheap flights from Winnipeg to Massachusetts

YWG — BOS
19 Aug — 26 Aug1
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 14 August 2025.

Round-trip from

C$ 378

One-way from

C$ 201

Popular in

December

Cheapest in

October

Average price

C$ 458
Air Canada
  • Air Canada
  • 15/9-23/9
  • 2 total stops
  • 11h 09m total
  • Winnipeg to Massachusetts
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WestJet
  • WestJet
  • 27/9
  • 1 total stop
  • 10h 10m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 24% potential increase in price (C$ 244 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 43 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 14 August 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
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,980 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,916 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
3,015 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,949 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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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 14 August 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 238AverageC$ 397FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 318AverageC$ 513FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 338AverageC$ 472FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
DeltaCheapestC$ 366AverageC$ 454FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
WestJetCheapestC$ 473AverageC$ 1,132FlexibilityNo cancel feeOn-time60%
Search WestJet flights

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