Find flights
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Massachusetts from C$ 234

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 22/4. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — BOS
26 feb. — 5 mar.1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Massachusetts

Enter your travel dates to find the best prices.

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 27 enero 2026.

lun. 16/28:00 a.m.
YWG
-
BOS
1 stop25h 26m
Multiple Airlines
lun. 23/26:00 a.m.
BOS
-
YWG
2 stops37h 05m
Multiple Airlines
Deal found 26/1C$ 393
mié. 11/37:30 a.m.
YWG
-
BOS
1 stop27h 11m
Multiple Airlines
mar. 24/312:36 p.m.
BOS
-
YWG
1 stop27h 33m
Multiple Airlines
Deal found 27/1C$ 437
sáb. 25/46:55 p.m.
YWG
-
BOS
1 stop19h 55m
WestJet
dom. 3/54:45 p.m.
BOS
-
YWG
1 stop9h 10m
WestJet
Deal found 26/1C$ 445
lun. 16/28:00 a.m.
YWG
-
BOS
1 stop25h 26m
Multiple Airlines
mar. 24/26:55 p.m.
BOS
-
YWG
1 stop17h 37m
Multiple Airlines
Deal found 26/1C$ 477
mié. 11/37:30 a.m.
YWG
-
BOS
1 stop27h 11m
Multiple Airlines
mié. 25/35:49 p.m.
BOS
-
YWG
2 stops26h 20m
Multiple Airlines
Deal found 25/1C$ 479
dom. 15/28:05 p.m.
YWG
-
BOS
1 stop12h 30m
Multiple Airlines
mar. 24/26:00 a.m.
BOS
-
YWG
2 stops19h 40m
Multiple Airlines
Deal found 26/1C$ 492
mar. 17/28:05 p.m.
YWG
-
BOS
1 stop17h 40m
Multiple Airlines
mar. 24/26:00 a.m.
BOS
-
YWG
2 stops19h 40m
Multiple Airlines
Deal found 26/1C$ 496
mar. 17/212:10 p.m.
YWG
-
BOS
2 stops21h 16m
Multiple Airlines
lun. 23/26:55 p.m.
BOS
-
YWG
1 stop17h 37m
Multiple Airlines
Deal found 26/1C$ 523
lun. 16/28:00 a.m.
YWG
-
BOS
1 stop25h 26m
Multiple Airlines
dom. 22/26:55 p.m.
BOS
-
YWG
1 stop17h 37m
Multiple Airlines
Deal found 26/1C$ 526
sáb. 11/710:45 a.m.
YWG
-
ALB
2 stops11h 21m
WestJet
vie. 4/91:15 p.m.
ALB
-
YWG
2 stops10h 45m
WestJet
Deal found 27/1C$ 531
mar. 3/22:20 p.m.
YWG
-
ALB
2 stops8h 21m
United Airlines
jue. 5/27:25 p.m.
ALB
-
YWG
2 stops17h 32m
United Airlines
Deal found 25/1C$ 639
mar. 3/211:53 a.m.
YWG
-
ALB
2 stops10h 02m
Delta
jue. 5/212:29 p.m.
ALB
-
YWG
2 stops12h 09m
Delta
Deal found 26/1C$ 757

Find flight deals from Winnipeg to Massachusetts

Keep the following information in mind while searching for Winnipeg to Massachusetts flight deals. Data was last updated 27 enero 2026.

Round-trip from

C$ 393

One-way from

C$ 234

Popular in

January

Cheapest in

June

Average price

C$ 753
16/2-24/2
  • 16/2-24/2
  • 3 total stops
  • 45h 06m total
  • Winnipeg to Massachusetts
Search Deals
22/4
  • 22/4
  • 1 total stop
  • 16h 21m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 17% potential increase in price (C$ 168 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 27 enero 2026.
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

lun. 16/2

8:00 a.m.-10:26 a.m.

1 stop25h 26m

Boston Logan Intl

lun. 23/2

6:00 a.m.-6:05 p.m.

2 stops37h 05m

C$ 393

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mié. 11/3

7:30 a.m.-11:41 a.m.

1 stop27h 11m

Boston Logan Intl

mar. 24/3

12:36 p.m.-3:09 p.m.

1 stop27h 33m

C$ 437

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

lun. 16/2

8:00 a.m.-10:26 a.m.

1 stop25h 26m

Boston Logan Intl

mar. 24/2

6:55 p.m.-11:32 a.m.

1 stop17h 37m

C$ 477

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

sáb. 25/4

6:45 a.m.-3:50 p.m.

2 stops32h 05m

Boston Logan Intl

dom. 3/5

4:45 p.m.-12:55 a.m.

1 stop9h 10m

C$ 505

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

lun. 16/2

8:00 a.m.-10:26 a.m.

1 stop25h 26m

Boston Logan Intl

dom. 22/2

6:55 p.m.-11:32 a.m.

1 stop17h 37m

C$ 526

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

sáb. 11/7

10:45 a.m.-11:06 p.m.

2 stops11h 21m

Albany Intl

vie. 4/9

1:15 p.m.-11:00 p.m.

2 stops10h 45m

C$ 531

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mié. 11/3

7:30 a.m.-11:44 p.m.

2 stops15h 14m

Boston Logan Intl

mié. 25/3

5:40 a.m.-11:32 a.m.

2 stops30h 52m

C$ 572

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

dom. 15/2

8:05 p.m.-9:35 a.m.

1 stop12h 30m

Boston Logan Intl

lun. 23/2

6:55 p.m.-11:32 a.m.

1 stop17h 37m

C$ 575

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

mar. 17/2

8:05 p.m.-2:45 p.m.

1 stop17h 40m

Boston Logan Intl

lun. 23/2

6:55 p.m.-11:32 a.m.

1 stop17h 37m

C$ 579

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

sáb. 11/7

5:10 a.m.-9:02 p.m.

2 stops14h 52m

Albany Intl

vie. 4/9

11:24 a.m.-10:24 p.m.

1 stop12h 00m

C$ 979

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/1

Showing 1-10 of 17 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, May is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 231). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 583). 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 27 enero 2026.
Read through reviews of airlines operating flights from Winnipeg to Massachusetts, such as Porter Airlines,United Airlines, andWestJet. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

6.9

Overall

7.9

Boarding

8.2

Food

7.5

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

6.9

Overall

7.9

Boarding

8.2

Food

7.5

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,205 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

6.9

Overall

7.9

Boarding

8.2

Food

7.5

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
WestJet
7.2
Good
3,251 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

6.9

Overall

7.9

Boarding

8.2

Food

7.5

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,660 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Crew

8.6

Comfort

7.9

Entertainment

6.9

Overall

7.9

Boarding

8.2

Food

7.5

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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.

  • How long is the flight from Winnipeg to Massachusetts?

    There are many flights that can get you from Winnipeg to Massachusetts in 14h 52m. Fly via WestJet, United Airlines, or Air Canada to get the fastest option. The distance between Winnipeg and Massachusetts is about 1955 km. This flight may include one or multiple stops.

  • 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$ 231). Flying from Winnipeg to Massachusetts in January is currently the most expensive (average of C$ 583). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
Winnipeg to Las Vegas flights
Winnipeg to Sky Harbor Intl flights
Winnipeg to Orlando flights
Winnipeg to Los Angeles flights
Winnipeg to Fort Lauderdale flights
Winnipeg to Atlanta flights
Winnipeg to Miami flights
Winnipeg to O'Hare Intl flights
Winnipeg to Honolulu flights
Winnipeg to Minneapolis flights
Winnipeg to Newark flights
Winnipeg to LaGuardia flights
Winnipeg to Sacramento flights
Winnipeg to Seattle flights
Winnipeg to John F Kennedy Intl flights
Winnipeg to Dallas/Fort Worth flights
Winnipeg to Hobby flights
Winnipeg to George Bush Intcntl flights
Winnipeg to San Francisco flights
Winnipeg to Palm Springs flights
Winnipeg to New Orleans flights
Winnipeg to Ontario flights
Winnipeg to Tampa flights
Winnipeg to Phoenix-Mesa Gateway flights
Winnipeg to Austin flights
Winnipeg to Nashville flights
Winnipeg to Fort Myers flights
Winnipeg to Boston flights
Winnipeg to Love Field flights
Winnipeg to Dulles Intl flights
Winnipeg to Kahului flights
Winnipeg to Santa Ana flights
Winnipeg to Kailua-Kona flights
Winnipeg to Columbus flights
Winnipeg to Denver flights
Winnipeg to San Diego flights
Winnipeg to San Antonio flights
Winnipeg to Baltimore flights
Winnipeg to Detroit flights
Winnipeg to Reagan-National flights
Winnipeg to Jacksonville flights
Winnipeg to Louisville flights
Winnipeg to Albany flights
Winnipeg to Pensacola flights
Winnipeg to Kansas City flights
Winnipeg to Philadelphia flights
Winnipeg to Tucson flights
Winnipeg to Harrisburg flights
Winnipeg to Lihue flights

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 629,999 searches. Data last updated 27 enero 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 174AverageC$ 395FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 315AverageC$ 491FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 419AverageC$ 629FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
WestJetCheapestC$ 469AverageC$ 1,125FlexibilityNo 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!

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.