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Cheap flights from Winnipeg to Boston from C$ 189

YWG — BOS
10 Oct — 17 Oct1
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

Mon 5/105:00 a.m. -
1 stop5h 50m
Wed 14/1010:40 a.m. -
1 stop5h 29m
Deal found 9/9C$ 303
Wed 9/125:15 a.m. -
1 stop8h 02m
Thu 10/1210:25 a.m. -
1 stop7h 13m
Deal found 9/9C$ 318
Wed 30/95:00 a.m. -
1 stop5h 51m
Mon 5/107:05 p.m. -
1 stop15h 52m
Deal found 8/9C$ 343
Sat 3/105:00 a.m. -
1 stop5h 50m
Sat 10/104:55 p.m. -
1 stop7h 52m
Deal found 5/9C$ 349
Tue 22/92:00 p.m. -
1 stop10h 10m
Thu 24/97:55 a.m. -
1 stop15h 38m
Deal found 6/9C$ 357
Sun 6/1211:40 a.m. -
2 stops8h 52m
Wed 9/121:15 p.m. -
1 stop5h 55m
Deal found 9/9C$ 361
Sun 4/109:20 a.m. -
1 stop8h 15m
Sun 11/1010:05 a.m. -
1 stop6h 15m
Deal found 6/9C$ 364
Sat 24/102:00 p.m. -
2 stops8h 59m
Sat 31/107:41 p.m. -
2 stops18h 42m
Deal found 8/9C$ 367
Fri 2/107:00 a.m. -
1 stop11h 22m
Mon 5/109:23 a.m. -
1 stop14h 10m
Deal found 5/9C$ 368

Find flight deals from Winnipeg to Boston

Round-trip from

C$ 303

One-way from

C$ 189

Popular in

April

Cheapest in

August

Average price

C$ 505
Air Canada
  • Air Canada
  • 5/10-14/10
  • 2 total stops
  • 11h 19m total
  • Winnipeg to Boston
Search Deals
Air Canada
  • Air Canada
  • 7/10-31/12
  • 1 total stop
  • 5h 50m 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$ 65 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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

Wed 7/10

5:00 a.m.-11:50 a.m.

1 stop5h 50m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 189

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Tue 3/11

8:05 a.m.-2:53 p.m.

1 stop5h 48m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 214

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 30/9

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

1 stop9h 54m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 216
Quickest round-trip

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 4/11

5:40 p.m.-12:20 a.m.

1 stop5h 40m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 227

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 7/11

5:40 p.m.-12:20 a.m.

1 stop5h 40m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 227

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 24/10

5:40 p.m.-12:20 a.m.

1 stop5h 40m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 262

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Sat 7/11

11:40 a.m.-9:10 a.m.

2 stops20h 30m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 270

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Mon 12/10

7:10 p.m.-11:50 a.m.

1 stop15h 40m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 270

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 7/10

5:00 a.m.-5:52 p.m.

2 stops11h 52m

Boston Logan Intl

Wed 31/12

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

Nonstop0h 00m

C$ 306

WinnipegBoston

YWG Winnipeg - BOS Boston Logan Intl

YWGBOS

Winnipeg

Wed 9/12

5:15 a.m.-2:17 p.m.

1 stop8h 02m

Boston Logan Intl

Thu 10/12

10:25 a.m.-4:38 p.m.

1 stop7h 13m

C$ 318

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

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$ 480). Flying from Winnipeg to Boston in April is currently the most expensive (average of C$ 1,262). 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$ 426 and C$ 662 in October.
The cheapest round-trip price found within the last 5 days was C$ 303 on Air Canada (5 Oct-14 Oct).

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
460 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Boarding

8.2

Crew

8.6

Food

7.6

Overall

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
460 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Boarding

8.2

Crew

8.6

Food

7.6

Overall

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
7.4
Good
10,194 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Boarding

8.2

Crew

8.6

Food

7.6

Overall

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
11,608 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Boarding

8.2

Crew

8.6

Food

7.6

Overall

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 8h 02m. Air Canada provides one of the quickest options available for as low as C$ 318. 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$ 160. Other airlines that can offer you cheap pricing are Porter Airlines, from C$ 323, and Air Canada, from C$ 391. 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$ 480). Flying from Winnipeg to Boston in April is currently the most expensive (average of C$ 1,262). 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
Revere
Braintree
Milford
Waltham
Watertown
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$ 160AverageC$ 606FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Porter AirlinesCheapestC$ 323AverageC$ 468FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 391AverageC$ 620FlexibilityNo 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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