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Cheap flights from Winnipeg to Massachusetts from C$ 200
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 25/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
15 Oct — 22 Oct1
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 15 September 2025.
Find flight deals from Winnipeg to Massachusetts
Cheapest flights from Winnipeg to MassachusettsExplore 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 15 September 2025.
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 15 September 2025.
Tue 7/105:40 p.m.YWG - BOS
1 stop5h 19mDelta
Wed 15/105:45 a.m.BOS - YWG
1 stop6h 45mDelta
Deal found 14/9C$ 345
Tue 25/118:15 a.m.YWG - BOS
1 stop5h 37mAir Canada
Sun 30/115:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 13/9C$ 452
Fri 14/112:20 p.m.YWG - BOS
1 stop9h 25mUnited Airlines
Sun 16/118:30 p.m.BOS - YWG
1 stop16h 27mUnited Airlines
Deal found 13/9C$ 470
Tue 7/105:00 a.m.YWG - BOS
1 stop5h 29mAir Canada
Wed 15/106:00 a.m.BOS - YWG
2 stops11h 15mAir Canada
Deal found 14/9C$ 501
Fri 14/117:05 p.m.YWG - BOS
2 stops13h 27mAir Canada
Sun 16/115:30 a.m.BOS - YWG
1 stop5h 46mAir Canada
Deal found 13/9C$ 511
Tue 25/116:40 a.m.YWG - BOS
2 stops12h 30mDelta
Sun 30/118:00 a.m.BOS - YWG
1 stop9h 59mDelta
Deal found 13/9C$ 555
Sun 12/109:15 p.m.YWG - BOS
1 stop19h 55mMultiple Airlines
Sun 19/106:16 a.m.BOS - YWG
3 stops32h 57mMultiple Airlines
Deal found 12/9C$ 590
Sun 12/105:00 a.m.YWG - BOS
1 stop5h 29mUnited Airlines
Sun 19/106:00 a.m.BOS - YWG
1 stop17h 33mUnited Airlines
Deal found 12/9C$ 638
Fri 14/116:40 a.m.YWG - BOS
2 stops11h 50mDelta
Sun 16/115:29 a.m.BOS - YWG
2 stops12h 30mDelta
Deal found 13/9C$ 691
Thu 30/102:20 p.m.YWG - ALB
1 stop6h 13mUnited Airlines
Thu 6/116:00 a.m.ALB - YWG
1 stop6h 57mUnited Airlines
Deal found 15/9C$ 880
Wed 26/118:40 a.m.YWG - ALB
2 stops14h 03mUnited Airlines
Sat 29/116:00 a.m.ALB - YWG
1 stop6h 57mUnited Airlines
Deal found 15/9C$ 932
Wed 26/117:30 a.m.YWG - ALB
2 stops15h 05mDelta
Sat 29/115:45 a.m.ALB - YWG
2 stops12h 14mDelta
Deal found 15/9C$ 946
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 15 September 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
Tue 7/10
12:20 p.m.-10:43 p.m.
2 stops9h 23m
Boston Logan Intl
Wed 15/10
5:45 a.m.-11:30 a.m.
1 stop6h 45m
C$ 345
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Tue 25/11
8:15 a.m.-2:52 p.m.
1 stop5h 37m
Boston Logan Intl
Sun 30/11
5:30 a.m.-10:16 a.m.
1 stop5h 46m
C$ 452
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Fri 14/11
2:20 p.m.-12:45 a.m.
1 stop9h 25m
Boston Logan Intl
Sun 16/11
8:30 p.m.-11:57 a.m.
1 stop16h 27m
C$ 470
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Tue 7/10
5:00 a.m.-11:29 a.m.
1 stop5h 29m
Boston Logan Intl
Wed 15/10
6:00 a.m.-4:15 p.m.
2 stops11h 15m
C$ 501
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Fri 14/11
7:05 p.m.-9:32 a.m.
2 stops13h 27m
Boston Logan Intl
Sun 16/11
5:30 a.m.-10:16 a.m.
1 stop5h 46m
C$ 511
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Sun 12/10
9:15 p.m.-6:10 p.m.
1 stop19h 55m
Boston Logan Intl
Sun 19/10
6:16 a.m.-2:13 p.m.
3 stops32h 57m
C$ 590
WinnipegBoston
YWG - BOS
YWGBOS
Winnipeg
Sun 12/10
5:00 a.m.-11:29 a.m.
1 stop5h 29m
Boston Logan Intl
Sun 19/10
6:00 a.m.-10:33 p.m.
1 stop17h 33m
C$ 638
WinnipegAlbany
YWG - ALB
YWGALB
Winnipeg
Thu 30/10
2:20 p.m.-9:33 p.m.
1 stop6h 13m
Albany Intl
Thu 6/11
6:29 p.m.-8:56 p.m.
2 stops27h 27m
C$ 880
WinnipegAlbany
YWG - ALB
YWGALB
Winnipeg
Wed 26/11
8:40 a.m.-11:43 p.m.
2 stops14h 03m
Albany Intl
Sat 29/11
6:00 a.m.-11:57 a.m.
1 stop6h 57m
C$ 932
WinnipegAlbany
YWG - ALB
YWGALB
Winnipeg
Wed 26/11
7:30 a.m.-11:35 p.m.
2 stops15h 05m
Albany Intl
Sat 29/11
5:45 a.m.-4:59 p.m.
2 stops12h 14m
C$ 946
Showing 1-10 of 20 results
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$ 292). 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 15 September 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 15 September 2025.
Read through reviews of airlines operating flights from Winnipeg to Massachusetts, such as Delta,Porter Airlines, andUnited Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Food
7.3
Comfort
7.9
Entertainment
7.9
Overall
8.0
Boarding
8.2
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
Crew
8.5
Food
7.3
Comfort
7.9
Entertainment
7.9
Overall
8.0
Boarding
8.2
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
Crew
8.5
Food
7.3
Comfort
7.9
Entertainment
7.9
Overall
8.0
Boarding
8.2
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
Crew
8.5
Food
7.3
Comfort
7.9
Entertainment
7.9
Overall
8.0
Boarding
8.2
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
Crew
8.5
Food
7.3
Comfort
7.9
Entertainment
7.9
Overall
8.0
Boarding
8.2
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
Crew
8.5
Food
7.3
Comfort
7.9
Entertainment
7.9
Overall
8.0
Boarding
8.2
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
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.
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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 15 September 2025.
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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?
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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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