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Cheap flights from Boston to Winnipeg from C$ 219

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 19/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
8 Jul — 15 Jul1
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 8 June 2026.

Fri 3/73:35 p.m.
BOS
-
YWG
1 stop6h 44m
Air Canada
Thu 9/72:05 p.m.
YWG
-
BOS
1 stop7h 33m
Air Canada
Deal found 7/6C$ 517
Sun 5/77:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Tue 21/712:15 p.m.
YWG
-
BOS
1 stop6h 00m
Porter Airlines
Deal found 5/6C$ 521
Fri 3/77:10 a.m.
BOS
-
YWG
2 stops11h 48m
Multiple Airlines
Thu 9/75:00 a.m.
YWG
-
BOS
1 stop5h 52m
Multiple Airlines
Deal found 5/6C$ 532
Fri 3/77:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Thu 9/712:15 p.m.
YWG
-
BOS
1 stop5h 20m
Porter Airlines
Deal found 7/6C$ 534
Tue 28/77:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Wed 29/712:15 p.m.
YWG
-
BOS
1 stop6h 00m
Porter Airlines
Deal found 3/6C$ 542
Fri 3/710:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Mon 6/712:15 p.m.
YWG
-
BOS
1 stop6h 00m
Porter Airlines
Deal found 4/6C$ 551
Fri 17/77:10 a.m.
BOS
-
YWG
2 stops11h 48m
Porter Airlines
Sat 25/712:15 p.m.
YWG
-
BOS
1 stop6h 00m
Porter Airlines
Deal found 7/6C$ 564
Wed 9/910:05 a.m.
BOS
-
YWG
1 stop6h 14m
Porter Airlines
Tue 29/99:20 a.m.
YWG
-
BOS
1 stop8h 55m
Porter Airlines
Deal found 3/6C$ 567

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 8 June 2026.

Round-trip from

C$ 517

One-way from

C$ 219

Popular in

January

Cheapest in

August

Average price

C$ 746
Air Canada
  • Air Canada
  • 3/7-9/7
  • 2 total stops
  • 14h 17m total
  • Boston to Winnipeg
Search Deals
Air Canada
  • Air Canada
  • 19/7
  • 1 total stop
  • 5h 34m total
  • Boston to Winnipeg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 242 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 8 June 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

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 3/7

3:35 p.m.-9:19 p.m.

1 stop6h 44m

Winnipeg

Thu 9/7

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

1 stop7h 33m

C$ 517
Quickest round-trip

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 28/9

6:00 a.m.-11:12 a.m.

1 stop6h 12m

Winnipeg

Thu 22/10

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

1 stop5h 31m

C$ 535

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/9

10:05 a.m.-3:19 p.m.

1 stop6h 14m

Winnipeg

Tue 29/9

9:20 a.m.-7:15 p.m.

1 stop8h 55m

C$ 564

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 27/6

3:25 p.m.-8:40 a.m.

2 stops18h 15m

Winnipeg

Fri 3/7

12:15 p.m.-6:35 p.m.

1 stop5h 20m

C$ 573

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 4/9

10:05 a.m.-3:19 p.m.

1 stop6h 14m

Winnipeg

Mon 7/9

12:15 p.m.-7:15 p.m.

1 stop6h 00m

C$ 590

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 2/7

10:05 a.m.-3:19 p.m.

1 stop6h 14m

Winnipeg

Mon 6/7

8:10 p.m.-10:29 a.m.

1 stop13h 19m

C$ 592

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 14/8

6:00 a.m.-11:15 a.m.

1 stop6h 15m

Winnipeg

Sat 15/8

7:55 a.m.-2:41 p.m.

1 stop5h 46m

C$ 623

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 4/9

10:05 a.m.-3:19 p.m.

1 stop6h 14m

Winnipeg

Tue 8/9

9:20 a.m.-7:15 p.m.

1 stop8h 55m

C$ 626

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 5/7

5:55 a.m.-3:04 p.m.

1 stop10h 09m

Winnipeg

Tue 21/7

5:41 p.m.-11:55 p.m.

1 stop5h 14m

C$ 627

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 21/7

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

2 stops11h 48m

Winnipeg

Thu 23/7

9:20 a.m.-8:55 p.m.

2 stops10h 35m

C$ 652

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/6

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

How far ahead should I book a flight from Boston to Winnipeg?

The price you pay for your flight from Boston to Winnipeg may vary depending on when you book. For the best chance of a lower fare, look to book 42 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 595). Flying from Boston to Winnipeg in January is currently the most expensive (average of C$ 1,079). 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 6h 14m. Fly via Air Canada 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, August is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 595). Flying from Boston to Winnipeg in January is currently the most expensive (average of C$ 1,079). 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

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Alternative routes for Boston to Winnipeg

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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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