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$170+ Cheap flights from Winnipeg (YWG) to Massachusetts

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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
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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 julio 30, 2025.

Round-trip from

$294
(Air Canada)

One-way from

$170
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$353
From Winnipeg to Massachusetts
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One-way flight from Winnipeg to Massachusetts
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Highest demand for flights based on searches. 22% potential increase in price ($119 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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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 julio 30, 2025.

This Air Canada deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/115:00 amYWG - BOS
1 stop5h 29mAir Canada
mié. 10/1510:40 amBOS - YWG
1 stop8h 05mAir Canada
Deal found 7/29$294
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/126:30 amYWG - BOS
1 stop10h 10mWestJet
lun. 10/137:00 pmBOS - YWG
2 stops17h 41mWestJet
Deal found 7/29$324
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/116:40 amYWG - BOS
1 stop9h 32mDelta
mar. 10/145:45 amBOS - YWG
1 stop6h 45mDelta
Deal found 7/29$328
This United Airlines deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/204:25 pmYWG - BOS
2 stops14h 44mUnited Airlines
sáb. 9/275:30 amBOS - YWG
2 stops18h 03mUnited Airlines
Deal found 7/30$355
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/156:30 amYWG - BOS
1 stop9h 21mMultiple Airlines
dom. 10/1912:18 pmBOS - YWG
2 stops12h 55mMultiple Airlines
Deal found 7/30$364
This Trip.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/2211:45 amYWG - BOS
1 stop5h 43mPorter Airlines
jue. 8/283:30 pmBOS - YWG
1 stop8h 16mPorter Airlines
Deal found 7/30$458

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 2,558,603 searches. Data last updated julio 30, 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

sáb. 10/11

5:00 am-11:29 am

1 stop5h 29m

Boston Logan Intl

mié. 10/15

10:40 am-5:45 pm

1 stop8h 05m

$294

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dom. 10/12

6:30 am-5:40 pm

1 stop10h 10m

Boston Logan Intl

lun. 10/13

7:00 pm-11:41 am

2 stops17h 41m

$324

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 10/11

6:40 am-5:12 pm

1 stop9h 32m

Boston Logan Intl

mar. 10/14

5:45 am-11:30 am

1 stop6h 45m

$328

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 9/20

4:25 pm-8:09 am

2 stops14h 44m

Boston Logan Intl

sáb. 9/27

5:30 am-10:33 pm

2 stops18h 03m

$355

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mié. 10/15

6:30 am-4:51 pm

1 stop9h 21m

Boston Logan Intl

dom. 10/19

12:18 pm-12:13 am

2 stops12h 55m

$364

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

vie. 8/22

11:45 am-6:28 pm

1 stop5h 43m

Boston Logan Intl

jue. 8/28

3:30 pm-10:46 pm

1 stop8h 16m

$458

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

jue. 9/11

8:15 pm-6:10 pm

1 stop20h 55m

$170

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dom. 9/14

12:44 pm-11:59 pm

1 stop10h 15m

$206

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dom. 9/14

11:20 am-10:01 pm

2 stops9h 41m

$222

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

lun. 8/18

9:05 pm-10:34 pm

3 stops24h 29m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 13 results
1
2

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, January is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $218). Flying from Winnipeg to Massachusetts in July is currently the most expensive (average of $311). 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 julio 30, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta, and United Airlines from Winnipeg to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Food

7.6

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
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Food

7.6

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
318 reviews

Crew

8.7

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Food

7.6

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
8,896 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Food

7.6

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
2,975 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Food

7.6

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
9,837 reviews
Porter Airlines
8.0
Very good
318 reviews

Crew

8.7

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Food

7.6

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

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?

    For a flight from Winnipeg to Massachusetts, you will be flying from Winnipeg. Winnipeg (YWG) is just 4.6 mi from the center of the city.

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

    $170 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Delta and Porter Airlines, with prices starting from $206 and $222, respectively.

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

    The most popular route from Winnipeg to Massachusetts is Winnipeg - Boston Logan Intl. You may also consider Winnipeg - Albany Intl or 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, January is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of $218). Flying from Winnipeg to Massachusetts in July is currently the most expensive (average of $311). 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 2,558,603 searches. Data last updated julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$100Average$369FlexibilityNo cancel feeOn-time69%
DeltaCheapest$241Average$364FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$254Average$356FlexibilityNo cancel feeOn-time67%
Porter AirlinesCheapest$267Average$398FlexibilityNo cancel feeOn-time52%

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