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Cheap flights from Boston to Winnipeg from C$ 129

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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
11 Oct — 18 Oct1
1 adult
1 adult, Economy

Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in July or May, booked 63 days in advance, depart on a Tuesday or Monday and return on a Tuesday

Cheap 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 11 September 2025.

Round-trip from

C$ 389

One-way from

C$ 129

Popular in

March

Cheapest in

July

Average price

C$ 683
4/10-11/10
  • 4/10-11/10
  • 2 total stops
  • 38h 06m total
  • Boston to Winnipeg
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3/12
  • 3/12
  • 3 total stops
  • 39h 06m total
  • Boston to Winnipeg
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Highest demand for flights based on searches. 21% potential increase in price (C$ 240 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 35 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Boston to Winnipeg

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 11 September 2025.

Sat 4/106:30 p.m.BOS - YWG
1 stop18h 11mMultiple Airlines
Sat 11/109:15 p.m.YWG - BOS
1 stop19h 55mMultiple Airlines
Deal found 10/9C$ 389
Sat 4/106:30 p.m.BOS - YWG
1 stop18h 11mMultiple Airlines
Mon 6/109:00 a.m.YWG - BOS
1 stop9h 16mMultiple Airlines
Deal found 10/9C$ 400
Fri 12/126:00 a.m.BOS - YWG
1 stop10h 07mMultiple Airlines
Mon 15/128:00 a.m.YWG - BOS
1 stop25h 24mMultiple Airlines
Deal found 11/9C$ 406
Sat 4/106:30 p.m.BOS - YWG
1 stop18h 11mMultiple Airlines
Thu 9/109:00 a.m.YWG - BOS
2 stops13h 59mMultiple Airlines
Deal found 10/9C$ 418
Fri 31/102:15 p.m.BOS - YWG
1 stop12h 11mMultiple Airlines
Wed 5/117:30 a.m.YWG - BOS
2 stops14h 55mMultiple Airlines
Deal found 9/9C$ 421
Sat 27/97:00 p.m.BOS - YWG
1 stop20h 13mWestJet
Sun 19/109:05 p.m.YWG - BOS
1 stop19h 35mWestJet
Deal found 10/9C$ 424
Sun 28/97:00 p.m.BOS - YWG
2 stops29h 40mWestJet
Sun 5/108:15 p.m.YWG - BOS
1 stop20h 55mWestJet
Deal found 10/9C$ 425
Wed 24/93:15 p.m.BOS - YWG
1 stop9h 12mDelta
Sun 28/912:44 p.m.YWG - BOS
1 stop10h 15mDelta
Deal found 10/9C$ 428

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 11 September 2025.
Use the filters below to find and compare flights from Boston to Winnipeg that are best for you.

Fly from

Boston

Fly to

Winnipeg

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 12/12

6:00 a.m.-3:07 p.m.

1 stop10h 07m

Winnipeg

Mon 15/12

8:00 a.m.-10:24 a.m.

1 stop25h 24m

C$ 406

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 24/9

3:15 p.m.-11:27 p.m.

1 stop9h 12m

Winnipeg

Sun 28/9

12:44 p.m.-11:59 p.m.

1 stop10h 15m

C$ 428

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 27/9

7:00 p.m.-11:41 a.m.

2 stops17h 41m

Winnipeg

Sun 19/10

5:30 p.m.-5:40 p.m.

1 stop23h 10m

C$ 446

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 4/10

8:38 a.m.-12:30 a.m.

2 stops16h 52m

Winnipeg

Mon 6/10

9:00 a.m.-7:16 p.m.

1 stop9h 16m

C$ 450

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 16/10

8:24 p.m.-4:22 p.m.

2 stops20h 58m

Winnipeg

Mon 20/10

6:30 a.m.-5:40 p.m.

1 stop10h 10m

C$ 463

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 31/10

6:17 a.m.-12:42 a.m.

3 stops19h 25m

Winnipeg

Wed 5/11

7:30 a.m.-11:25 p.m.

3 stops38h 55m

C$ 482

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 31/10

6:17 a.m.-12:42 a.m.

3 stops19h 25m

Winnipeg

Thu 6/11

8:20 p.m.-9:35 a.m.

1 stop12h 15m

C$ 488

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 28/9

7:00 p.m.-2:13 p.m.

1 stop20h 13m

Winnipeg

Mon 6/10

9:00 a.m.-7:16 p.m.

1 stop9h 16m

C$ 493

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 25/9

6:00 a.m.-10:40 a.m.

1 stop5h 40m

Winnipeg

Thu 2/10

5:00 a.m.-11:29 a.m.

1 stop5h 29m

C$ 521

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 3/12

6:00 a.m.-8:06 p.m.

3 stops39h 06m

C$ 129

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 18 results
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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?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Winnipeg. Price data was last updated on 29 August 2025.

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 63 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, January is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 123). Flying from Boston to Winnipeg in July is currently the most expensive (average of C$ 232). 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 9h 12m. Fly via Delta or WestJet 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, January is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 123). Flying from Boston to Winnipeg in July is currently the most expensive (average of C$ 232). 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

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

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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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