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Cheap flights from Winnipeg to Boston from C$ 221

YWG — BOS
24 Nov — 1 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Boston

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Boston

Fri 13/117:00 a.m. -
1 stop26h 10m
Sat 14/111:15 p.m. -
1 stop5h 51m
Deal found 22/10C$ 364
Sat 5/123:05 p.m. -
1 stop6h 23m
Sat 12/125:30 a.m. -
1 stop5h 45m
Deal found 21/10C$ 372
Fri 4/1212:40 p.m. -
2 stops8h 59m
Sun 6/121:15 p.m. -
1 stop5h 59m
Deal found 23/10C$ 396
Sat 5/129:40 a.m. -
2 stops12h 13m
Sat 12/1210:01 a.m. -
2 stops11h 54m
Deal found 21/10C$ 422
Fri 27/1112:35 p.m. -
2 stops9h 00m
Mon 30/118:00 a.m. -
2 stops11h 06m
Deal found 22/10C$ 426
Tue 8/1212:40 p.m. -
2 stops8h 59m
Tue 15/128:00 a.m. -
2 stops11h 14m
Deal found 24/10C$ 429
Sat 21/117:55 p.m. -
1 stop14h 27m
Sat 28/115:45 a.m. -
1 stop16h 29m
Deal found 22/10C$ 431
Thu 26/1112:35 p.m. -
2 stops9h 00m
Mon 30/118:00 a.m. -
2 stops11h 06m
Deal found 22/10C$ 436
Mon 23/1112:35 p.m. -
2 stops9h 00m
Sat 28/111:15 p.m. -
1 stop5h 51m
Deal found 24/10C$ 437

Find flight deals from Winnipeg to Boston

Round-trip from

C$ 350

One-way from

C$ 221

Popular in

April

Cheapest in

August

Average price

C$ 675
Air Canada
  • Air Canada
  • 2/2-9/2
  • 2 total stops
  • 13h 01m total
  • Winnipeg to Boston
Search Deals
Air Canada
  • Air Canada
  • 5/12-31/12
  • 1 total stop
  • 6h 23m total
  • Winnipeg to Boston
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 208 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 68 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2026
Search Deals

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 5/12

3:05 p.m.-10:28 p.m.

1 stop6h 23m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 221

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Mon 7/12

6:25 a.m.-6:01 p.m.

1 stop10h 36m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 234

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 27/11

12:35 p.m.-10:35 p.m.

2 stops9h 00m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 246

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 5/12

9:40 a.m.-10:53 p.m.

2 stops12h 13m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 249

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 4/2

7:55 p.m.-11:12 a.m.

1 stop14h 17m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 251

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 4/2

9:40 a.m.-10:53 p.m.

2 stops12h 13m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 260

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Mon 7/12

12:40 p.m.-10:39 p.m.

2 stops8h 59m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 273

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sun 17/1

7:55 p.m.-11:12 a.m.

1 stop14h 17m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 276

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Thu 4/2

7:00 a.m.-10:10 a.m.

3 stops26h 10m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 388

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Fri 27/11

3:10 p.m.-10:10 a.m.

3 stops18h 00m

Boston Logan Intl

Wed 31/12

12:00 a.m.-11:00 p.m.

Nonstop0h 00m

C$ 420

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/10

Showing 1-10 of 21 resultsSorted by cheapest first
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Best time to book a flight from Winnipeg to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Winnipeg with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Boston

What is the cheapest month to book a flight from Winnipeg to Boston?

Currently, August is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 487). Flying from Winnipeg to Boston in April is currently the most expensive (average of C$ 1,281). 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 Boston?

Airfare is below average for this route at the moment.

Winnipeg to Boston flights typically cost between C$ 675 and C$ 1,141 in February.
The cheapest round-trip price found within the last 5 days was C$ 350 on Air Canada (2 Feb-9 Feb).

Reviews of airlines servicing Boston

Read through reviews of airlines operating flights from Winnipeg to Boston, such as Porter Airlines,United Airlines, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
467 reviews
Check prices

Food

7.6

Entertainment

6.9

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Food

7.6

Entertainment

6.9

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
United Airlines
7.3
Good
10,436 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Food

7.6

Entertainment

6.9

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,811 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Food

7.6

Entertainment

6.9

Overall

8.0

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • How long is the flight from Winnipeg to Boston?

    A quick flight from Winnipeg to Boston can take about 6h 23m. Delta provides one of the quickest options available for as low as C$ 422. The distance from Winnipeg to Boston is about 2173 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the cheapest airlines flying from Winnipeg to Boston round-trip?

    Cheapflights users have booked flights from Winnipeg to Boston round-trip from C$ 163. Other airlines that can offer you cheap pricing are Porter Airlines, from C$ 328, and Air Canada, from C$ 399. Users have found that United Airlines is 78% cheaper than the other options available to this destination.

  • Can I find deals for flights from Winnipeg to Boston that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Boston.

  • Can I find deals for business class flights from Winnipeg to Boston?

    Yes. Cheapflights offers flight deals from Winnipeg to Boston 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 Boston?

    Currently, August is the cheapest month in which you can book a flight from Winnipeg to Boston (average of C$ 487). Flying from Winnipeg to Boston in April is currently the most expensive (average of C$ 1,281). 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

Travelling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Old Orchard Beach
Cape Elizabeth
Hampton
Merrimack
Ogunquit
Saugus
Braintree
Milford
Revere
Waltham
Warwick
Lawrence
Pawtucket
Seekonk
Foxborough
Nashua
Kittery

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Winnipeg to Boston

Winnipeg to Albany flights

Top 3 airlines flying from Winnipeg to Boston

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 163AverageC$ 585FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 328AverageC$ 476FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 398AverageC$ 657FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

How does Cheapflights help users find flights from Winnipeg to Boston?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Boston. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Boston?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Boston from Winnipeg.

Can Cheapflights find flights from Winnipeg to Boston with no change fees?

Certainly. Search results for flights to Boston from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Winnipeg to Boston become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Boston from Winnipeg today and book when prices fit your budget.

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