Find flights
When to book
Airlines
FAQs

Cheap flights from Winnipeg to Massachusetts from C$ 214

YWG — BOS
18 Sep — 25 Sep1
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

Sun 6/95:00 a.m. -
2 stops8h 41m
Mon 14/96:00 a.m. -
1 stop6h 12m
Deal found 14/8C$ 328
Wed 23/99:20 a.m. -
1 stop8h 15m
Wed 30/910:05 a.m. -
1 stop6h 14m
Deal found 14/8C$ 348
Tue 8/93:20 p.m. -
1 stop6h 20m
Tue 29/96:00 a.m. -
1 stop6h 12m
Deal found 16/8C$ 351
Wed 23/99:20 a.m. -
1 stop8h 15m
Thu 1/1010:05 a.m. -
1 stop6h 14m
Deal found 14/8C$ 360
Tue 1/912:46 p.m. -
1 stop10h 12m
Tue 29/95:55 a.m. -
1 stop6h 56m
Deal found 17/8C$ 379
Fri 2/102:00 p.m. -
1 stop9h 54m
Mon 5/108:30 p.m. -
1 stop17h 07m
Deal found 17/8C$ 380
Tue 22/99:20 a.m. -
1 stop8h 15m
Tue 29/910:05 a.m. -
1 stop6h 14m
Deal found 14/8C$ 383
Fri 2/109:20 a.m. -
1 stop8h 15m
Mon 5/107:00 a.m. -
2 stops11h 58m
Deal found 17/8C$ 387
Tue 22/95:44 p.m. -
1 stop5h 15m
Thu 1/107:05 a.m. -
1 stop9h 03m
Deal found 14/8C$ 390
Mon 14/97:00 a.m. -
1 stop7h 04m
Mon 21/99:55 a.m. -
1 stop13h 38m
Deal found 17/8C$ 790
Tue 27/108:40 a.m. -
1 stop13h 50m
Sat 31/108:40 a.m. -
2 stops13h 17m
Deal found 14/8C$ 815
Thu 29/102:15 p.m. -
1 stop6h 18m
Sat 31/107:32 a.m. -
1 stop14h 25m
Deal found 18/8C$ 876

Find flight deals from Winnipeg to Massachusetts

Round-trip from

C$ 328

One-way from

C$ 214

Popular in

April

Cheapest in

August

Average price

C$ 483
Air Canada
  • Air Canada
  • 6/9-14/9
  • 3 total stops
  • 14h 53m total
  • Winnipeg to Massachusetts
Search Deals
Air Canada
  • Air Canada
  • 7/10
  • 1 total stop
  • 5h 31m total
  • Winnipeg to Massachusetts
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 185 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 64 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 12/9

3:20 p.m.-10:40 p.m.

1 stop6h 20m

Boston Logan Intl

Wed 16/9

4:55 p.m.-11:27 p.m.

1 stop7h 32m

C$ 351

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 1/9

12:46 p.m.-11:58 p.m.

1 stop10h 12m

Boston Logan Intl

Tue 29/9

5:55 a.m.-11:51 a.m.

1 stop6h 56m

C$ 379

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 2/10

2:00 p.m.-12:54 a.m.

1 stop9h 54m

Boston Logan Intl

Mon 5/10

8:30 p.m.-12:37 p.m.

1 stop17h 07m

C$ 380

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 17/10

7:00 a.m.-11:24 p.m.

1 stop15h 24m

Boston Logan Intl

Tue 20/10

7:01 a.m.-12:37 p.m.

1 stop6h 36m

C$ 380

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 22/9

5:44 p.m.-11:59 p.m.

1 stop5h 15m

Boston Logan Intl

Fri 2/10

5:55 a.m.-3:08 p.m.

1 stop10h 13m

C$ 390

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 23/9

12:41 p.m.-11:59 p.m.

1 stop10h 18m

Boston Logan Intl

Fri 2/10

5:55 a.m.-3:08 p.m.

1 stop10h 13m

C$ 390

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 2/10

6:00 a.m.-5:40 p.m.

2 stops34h 40m

Boston Logan Intl

Mon 5/10

7:00 a.m.-5:58 p.m.

2 stops11h 58m

C$ 487

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 1/10

9:20 a.m.-6:35 p.m.

1 stop8h 15m

Boston Logan Intl

Thu 8/10

11:10 a.m.-12:15 p.m.

3 stops26h 05m

C$ 509

WinnipegAlbany

YWG Winnipeg - ALB Albany Intl

YWGALB

Winnipeg

Mon 14/9

7:00 a.m.-11:58 p.m.

2 stops15h 58m

Albany Intl

Mon 21/9

7:35 p.m.-11:52 a.m.

2 stops17h 17m

C$ 815

WinnipegAlbany

YWG Winnipeg - ALB Albany Intl

YWGALB

Winnipeg

Tue 27/10

8:40 a.m.-11:30 p.m.

1 stop13h 50m

Albany Intl

Sat 31/10

8:40 a.m.-8:57 p.m.

2 stops13h 17m

C$ 815

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/8

Showing 1-10 of 27 resultsSorted by cheapest first
1
2
3

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

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, August is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 483). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,270). 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.

How much does it cost to fly round-trip from Winnipeg to Massachusetts?

Airfare is below average for this route at the moment.
Winnipeg to Massachusetts flights typically cost between C$ 447 and C$ 615 in September.
The cheapest round-trip price found within the last 5 days was C$ 328 on Air Canada (6 Sep-14 Sep).

Reviews of airlines servicing Massachusetts

Read through reviews of airlines operating flights from Winnipeg to Massachusetts, such as Porter Airlines,United Airlines, andAir Canada. 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
457 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
457 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,104 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,501 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Entertainment

6.9

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

Related info for your journey

  • 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 6h 20m. Fly via Air Canada, Delta, or United Airlines to get the fastest option. The distance between Winnipeg and Massachusetts is about 2173 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, August is the cheapest month in which you can book a flight from Winnipeg to Massachusetts (average of C$ 483). Flying from Winnipeg to Massachusetts in April is currently the most expensive (average of C$ 1,270). 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

Alternative routes for Winnipeg to Massachusetts

Winnipeg to Los Angeles flights
Winnipeg to Minneapolis flights
Winnipeg to Las Vegas flights
Winnipeg to Newark flights
Winnipeg to Orlando flights
Winnipeg to LaGuardia flights
Winnipeg to O'Hare Intl flights
Winnipeg to Santa Ana flights
Winnipeg to John F Kennedy Intl flights
Winnipeg to Sky Harbor Intl flights
Winnipeg to Fort Lauderdale flights
Winnipeg to Ontario flights
Winnipeg to Burbank flights
Winnipeg to Denver flights
Winnipeg to Dallas/Fort Worth flights
Winnipeg to Miami flights
Winnipeg to Honolulu flights
Winnipeg to Tampa flights
Winnipeg to Dulles Intl flights
Winnipeg to Reagan-National flights
Winnipeg to San Francisco flights
Winnipeg to Baltimore flights
Winnipeg to Philadelphia flights
Winnipeg to Hobby flights
Winnipeg to Nashville flights
Winnipeg to Palm Springs flights
Winnipeg to Fort Myers flights
Winnipeg to Kahului flights
Winnipeg to San Diego flights
Winnipeg to Detroit flights
Winnipeg to Indianapolis flights
Winnipeg to Portland flights
Winnipeg to George Bush Intcntl flights
Winnipeg to Austin flights
Winnipeg to Kailua-Kona flights
Winnipeg to Seattle flights
Winnipeg to Boston flights
Winnipeg to Love Field flights
Winnipeg to Columbus flights
Winnipeg to Buffalo flights
Winnipeg to Atlanta flights
Winnipeg to Salt Lake City flights
Winnipeg to San Jose flights
Winnipeg to Memphis flights
Winnipeg to Tulsa flights
Winnipeg to Sacramento flights
Winnipeg to Jacksonville flights
Winnipeg to Myrtle Beach flights
Winnipeg to New Orleans flights

Top 3 airlines flying from Winnipeg to Massachusetts

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 161AverageC$ 621FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 325AverageC$ 471FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 394AverageC$ 622FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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.