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Cheap flights from Boston to Winnipeg from C$ 172

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 15/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
28 May — 4 Jun1
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 28 April 2026.

Sat 3/1010:40 a.m.
BOS
-
YWG
1 stop5h 29m
Air Canada
Tue 6/108:10 a.m.
YWG
-
BOS
1 stop5h 31m
Air Canada
Deal found 27/4C$ 418
Sat 9/510:45 a.m.
BOS
-
YWG
1 stop6h 33m
Air Canada
Mon 18/58:00 a.m.
YWG
-
BOS
1 stop5h 47m
Air Canada
Deal found 24/4C$ 421
Tue 15/95:00 p.m.
BOS
-
YWG
1 stop7h 07m
Air Canada
Sat 19/98:10 a.m.
YWG
-
BOS
1 stop5h 31m
Air Canada
Deal found 26/4C$ 425
Sat 3/103:13 p.m.
BOS
-
YWG
1 stop8h 11m
United Airlines
Tue 6/107:00 a.m.
YWG
-
BOS
1 stop6h 02m
United Airlines
Deal found 24/4C$ 429
Fri 21/87:10 a.m.
BOS
-
YWG
1 stop10h 44m
Delta
Tue 25/812:40 p.m.
YWG
-
BOS
1 stop8h 40m
Delta
Deal found 24/4C$ 440
Tue 15/96:00 a.m.
BOS
-
YWG
1 stop6h 52m
United Airlines
Sat 19/98:30 a.m.
YWG
-
BOS
2 stops15h 35m
United Airlines
Deal found 26/4C$ 442
Sat 4/76:00 a.m.
BOS
-
YWG
1 stop6h 15m
Air Canada
Sat 11/75:10 a.m.
YWG
-
BOS
1 stop5h 42m
Air Canada
Deal found 25/4C$ 443
Sat 4/710:40 a.m.
BOS
-
YWG
2 stops8h 55m
Air Canada
Fri 10/77:55 a.m.
YWG
-
BOS
1 stop5h 46m
Air Canada
Deal found 25/4C$ 448

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 28 April 2026.

Round-trip from

C$ 418

One-way from

C$ 172

Popular in

January

Cheapest in

May

Average price

C$ 815
Air Canada
  • Air Canada
  • 3/10-6/10
  • 2 total stops
  • 11h 00m total
  • Boston to Winnipeg
Search Deals
Porter Airlines
  • Porter Airlines
  • 15/7
  • 1 total stop
  • 6h 14m total
  • Boston to Winnipeg
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 279 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 42 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 28 April 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

Sat 3/10

10:40 a.m.-3:09 p.m.

1 stop5h 29m

Winnipeg

Tue 6/10

8:10 a.m.-2:41 p.m.

1 stop5h 31m

C$ 418

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 9/5

10:45 a.m.-4:18 p.m.

1 stop6h 33m

Winnipeg

Mon 18/5

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

1 stop5h 47m

C$ 421

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 3/10

3:13 p.m.-10:24 p.m.

1 stop8h 11m

Winnipeg

Tue 6/10

7:00 a.m.-2:02 p.m.

1 stop6h 02m

C$ 429

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 21/8

7:10 a.m.-4:54 p.m.

1 stop10h 44m

Winnipeg

Tue 25/8

6:40 a.m.-5:19 p.m.

1 stop9h 39m

C$ 440

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 30/7

6:00 a.m.-11:52 a.m.

1 stop6h 52m

Winnipeg

Fri 7/8

7:00 a.m.-11:18 p.m.

1 stop15h 18m

C$ 440

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/7

5:00 p.m.-10:33 p.m.

1 stop6h 33m

Winnipeg

Wed 8/7

7:00 a.m.-11:18 p.m.

1 stop15h 18m

C$ 440

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 4/9

6:50 p.m.-10:05 a.m.

1 stop16h 15m

Winnipeg

Mon 7/9

7:40 p.m.-9:55 a.m.

1 stop13h 15m

C$ 500
Cheapest one-way

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 4/9

7:10 a.m.-10:33 p.m.

1 stop16h 23m

C$ 177

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 21/8

7:10 a.m.-4:54 p.m.

1 stop10h 44m

C$ 183

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 25/8

6:00 a.m.-11:52 a.m.

1 stop6h 52m

C$ 183

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/4

Showing 1-10 of 18 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$ 558). Flying from Boston to Winnipeg in January is currently the most expensive (average of C$ 1,055). 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 Boston to Winnipeg?

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 29m. Fly via Air Canada or United 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$ 558). Flying from Boston to Winnipeg in January is currently the most expensive (average of C$ 1,055). 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

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

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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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