Find flights
When to book
FAQs

Cheap flights from Boston to Winnipeg from C$ 185

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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
26 Feb — 5 Mar1
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 27 January 2026.

Tue 24/26:10 p.m.
BOS
-
YWG
2 stops22h 20m
Multiple Airlines
Tue 3/38:20 p.m.
YWG
-
BOS
2 stops24h 41m
Multiple Airlines
Deal found 27/1C$ 492
Fri 13/36:15 a.m.
BOS
-
YWG
1 stop12h 04m
Air Canada
Fri 20/35:30 a.m.
YWG
-
BOS
1 stop9h 27m
Air Canada
Deal found 27/1C$ 548
Fri 13/36:15 a.m.
BOS
-
YWG
2 stops18h 32m
Multiple Airlines
Fri 20/36:00 a.m.
YWG
-
BOS
3 stops12h 12m
Multiple Airlines
Deal found 27/1C$ 646
Tue 24/26:25 p.m.
BOS
-
YWG
2 stops25h 44m
WestJet
Tue 3/35:00 a.m.
YWG
-
BOS
2 stops9h 53m
WestJet
Deal found 27/1C$ 753
Sun 14/65:30 a.m.
BOS
-
YWG
2 stops12h 45m
WestJet
Sat 20/610:45 a.m.
YWG
-
BOS
2 stops11h 47m
WestJet
Deal found 26/1C$ 764
Wed 18/38:05 a.m.
BOS
-
YWG
2 stops12h 04m
WestJet
Sun 22/38:05 p.m.
YWG
-
BOS
2 stops21h 10m
WestJet
Deal found 25/1C$ 796

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 27 January 2026.

Round-trip from

C$ 492

One-way from

C$ 185

Popular in

December

Cheapest in

July

Average price

C$ 786
24/2-3/3
  • 24/2-3/3
  • 4 total stops
  • 47h 01m total
  • Boston to Winnipeg
Search Deals
2/5
  • 2/5
  • 2 total stops
  • 29h 50m total
  • Boston to Winnipeg
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 209 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 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 27 January 2026.
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

Tue 24/2

6:10 p.m.-3:30 p.m.

2 stops22h 20m

Winnipeg

Tue 3/3

8:20 p.m.-11:05 a.m.

1 stop13h 45m

C$ 497

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 13/3

6:15 a.m.-5:19 p.m.

1 stop12h 04m

Winnipeg

Fri 20/3

5:30 a.m.-7:12 p.m.

3 stops12h 42m

C$ 553

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 13/3

6:15 a.m.-11:47 p.m.

2 stops18h 32m

Winnipeg

Fri 20/3

6:00 a.m.-7:12 p.m.

3 stops12h 12m

C$ 646

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 24/2

6:25 p.m.-7:09 p.m.

2 stops25h 44m

Winnipeg

Tue 3/3

5:00 a.m.-3:53 p.m.

2 stops9h 53m

C$ 753

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 14/6

5:30 a.m.-5:15 p.m.

2 stops12h 45m

Winnipeg

Sat 20/6

10:45 a.m.-11:32 p.m.

2 stops11h 47m

C$ 764

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 27/3

9:00 a.m.-7:09 p.m.

2 stops11h 09m

Winnipeg

Mon 30/3

8:05 p.m.-1:15 p.m.

2 stops16h 10m

C$ 796

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 18/3

8:05 a.m.-7:09 p.m.

2 stops12h 04m

Winnipeg

Sun 22/3

8:05 p.m.-6:15 p.m.

2 stops21h 10m

C$ 796

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 2/3

10:15 a.m.-4:35 p.m.

1 stop7h 20m

Winnipeg

Wed 4/3

1:45 p.m.-9:27 p.m.

1 stop6h 42m

C$ 826

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 18/3

5:30 a.m.-10:15 a.m.

1 stop5h 45m

Winnipeg

Sun 22/3

8:15 a.m.-2:52 p.m.

1 stop5h 37m

C$ 826

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 14/6

10:35 a.m.-3:04 p.m.

1 stop5h 29m

Winnipeg

Sat 20/6

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

1 stop5h 46m

C$ 826

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/1

Showing 1-10 of 16 results
1
2

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 23 January 2026.

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 50 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, May is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 162). Flying from Boston to Winnipeg in April is currently the most expensive (average of C$ 615). 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 12h 04m. Fly via Air Canada 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, May is the cheapest month in which you can book a flight from Boston to Winnipeg (average of C$ 162). Flying from Boston to Winnipeg in April is currently the most expensive (average of C$ 615). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Winnipeg from Boston today with Cheapflights!

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.