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Cheap flights from Boston to Winnipeg from C$ 171

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 26/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
9 Apr — 16 Apr1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Boston to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Boston to Winnipeg
Explore the most affordable flight options available from Boston to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 10 March 2026.

Sun 26/45:30 a.m.
BOS
-
YWG
1 stop5h 39m
Air Canada
Sat 2/53:15 p.m.
YWG
-
BOS
1 stop6h 24m
Air Canada
Deal found 7/3C$ 403
Wed 27/510:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Tue 2/69:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 8/3C$ 411
Sun 24/55:10 a.m.
BOS
-
YWG
1 stop5h 53m
Air Canada
Sat 30/55:10 a.m.
YWG
-
BOS
1 stop5h 36m
Air Canada
Deal found 5/3C$ 438
Fri 12/610:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Sat 20/69:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 7/3C$ 472
Wed 13/55:10 a.m.
BOS
-
YWG
1 stop6h 58m
Air Canada
Sun 17/58:00 a.m.
YWG
-
BOS
1 stop5h 47m
Air Canada
Deal found 8/3C$ 475
Sun 24/59:50 a.m.
BOS
-
YWG
1 stop13h 43m
United Airlines
Sat 30/57:00 a.m.
YWG
-
BOS
1 stop8h 29m
United Airlines
Deal found 8/3C$ 479
Mon 15/67:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Mon 22/69:20 a.m.
YWG
-
BOS
1 stop7h 15m
Porter Airlines
Deal found 10/3C$ 480
Sun 31/55:10 a.m.
BOS
-
YWG
1 stop6h 58m
Air Canada
Thu 4/62:00 p.m.
YWG
-
BOS
1 stop7h 39m
Air Canada
Deal found 6/3C$ 482

Find flight deals from Boston to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Winnipeg (YWG). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 10 March 2026.

Round-trip from

C$ 403

One-way from

C$ 171

Popular in

January

Cheapest in

May

Average price

C$ 802
Air Canada
  • Air Canada
  • 26/4-2/5
  • 2 total stops
  • 12h 03m total
  • Boston to Winnipeg
Search Deals
26/4
  • 26/4
  • 3 total stops
  • 39h 15m total
  • Boston to Winnipeg
Search Deals
Highest demand for flights based on searches. 25% potential increase in price (C$ 313 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Winnipeg 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 10 March 2026.
Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 24/5

5:10 a.m.-10:03 a.m.

1 stop5h 53m

Winnipeg

Sat 30/5

5:10 a.m.-11:46 a.m.

1 stop5h 36m

C$ 438

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 24/5

9:50 a.m.-10:33 p.m.

1 stop13h 43m

Winnipeg

Sat 30/5

7:00 a.m.-4:29 p.m.

1 stop8h 29m

C$ 479

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 15/6

7:10 a.m.-5:58 p.m.

2 stops11h 48m

Winnipeg

Mon 22/6

9:20 a.m.-5:35 p.m.

1 stop7h 15m

C$ 480

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 13/5

5:50 a.m.-2:18 p.m.

2 stops9h 28m

Winnipeg

Sun 17/5

8:00 a.m.-2:47 p.m.

1 stop5h 47m

C$ 487

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 12/6

5:00 p.m.-11:18 p.m.

1 stop7h 18m

Winnipeg

Fri 19/6

2:05 p.m.-10:38 p.m.

1 stop7h 33m

C$ 512

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 15/6

5:00 p.m.-11:18 p.m.

1 stop7h 18m

Winnipeg

Mon 22/6

8:00 a.m.-2:41 p.m.

1 stop5h 41m

C$ 520

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 26/4

3:30 p.m.-11:35 p.m.

2 stops9h 05m

Winnipeg

Sat 2/5

5:10 a.m.-2:47 p.m.

2 stops8h 37m

C$ 583
Cheapest one-way

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 26/4

6:00 a.m.-8:15 p.m.

3 stops39h 15m

C$ 171
Quickest one-way

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 26/4

5:30 a.m.-10:09 a.m.

1 stop5h 39m

C$ 201

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 15/6

7:10 a.m.-5:58 p.m.

2 stops11h 48m

C$ 224

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/3

Showing 1-10 of 16 resultsSorted by cheapest first
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Best time to book a flight from Boston to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Boston 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 Boston to Winnipeg

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

Currently, May is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 159). Flying from Boston to Winnipeg in April is currently the most expensive (average of C$ 594). 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.

Related info for your journey

Find useful and relevant information for your journey from Boston to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Boston to Winnipeg?

    There are many flights that can get you from Boston to Winnipeg in 5h 53m. Fly via Air Canada, United Airlines, or Porter Airlines to get the fastest option. Boston and Winnipeg are separated by a distance of 2173 km. Both multi-stop and direct flights can be found to your destination and back.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 159). Flying from Boston to Winnipeg in April is currently the most expensive (average of C$ 594). 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 Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Boston to Winnipeg

See prices for flight routes from nearby airports that may be better suited for you.
Hartford to Winnipeg flights

Fly with Cheapflights

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

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

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 Winnipeg from Boston.

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

Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to Winnipeg flexibly with Cheapflights today.

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

Yes! Start tracking prices for Boston to Winnipeg flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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