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Cheap flights from Boston to Winnipeg from C$ 140

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 25/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
20 Apr — 27 Apr1
1 adult

Cheapflights Tip: The best prices from Boston Logan Intl to Winnipeg are usually found in January or October, booked 22 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 15 April 2025.

Round-trip from

C$ 334

One-way from

C$ 140

Popular in

April

Cheapest in

January

Average price

C$ 1,068
United Airlines
  • United Airlines
  • 9/7-14/7
  • 2 total stops
  • 15h 49m total
  • Boston to Winnipeg
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United Airlines
  • United Airlines
  • 25/5
  • 1 total stop
  • 10h 31m total
  • Boston to Winnipeg
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Highest demand for flights based on searches. 22% potential increase in price (C$ 286 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 48 potential savings vs. average RT price).
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Average for round-trip flights in April 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 15 April 2025.

Wed 9/76:10 a.m.BOS - YWG
1 stop10h 21mUnited Airlines
Mon 14/75:00 a.m.YWG - BOS
1 stop5h 28mUnited Airlines
Deal found 15/4C$ 334
Wed 9/710:20 a.m.BOS - YWG
2 stops8h 30mAir Canada
Tue 15/78:00 a.m.YWG - BOS
1 stop5h 35mAir Canada
Deal found 13/4C$ 362
Wed 11/63:20 p.m.BOS - YWG
1 stop9h 09mDelta
Sat 14/612:26 p.m.YWG - BOS
1 stop5h 46mDelta
Deal found 14/4C$ 380
Mon 11/86:00 a.m.BOS - YWG
1 stop11h 23mMultiple Airlines
Fri 15/89:00 a.m.YWG - BOS
1 stop7h 34mMultiple Airlines
Deal found 13/4C$ 438
Mon 16/612:15 p.m.BOS - YWG
2 stops11h 31mPorter Airlines
Fri 20/611:45 a.m.YWG - BOS
2 stops9h 16mPorter Airlines
Deal found 13/4C$ 552

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 15 April 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

Wed 9/7

6:10 a.m.-3:31 p.m.

1 stop10h 21m

Winnipeg

Mon 14/7

5:00 a.m.-11:28 a.m.

1 stop5h 28m

C$ 334

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 16/6

8:59 p.m.-1:09 p.m.

1 stop17h 10m

Winnipeg

Fri 20/6

5:00 a.m.-11:28 a.m.

1 stop5h 28m

C$ 348

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 9/7

10:20 a.m.-5:50 p.m.

2 stops8h 30m

Winnipeg

Tue 15/7

8:00 a.m.-2:35 p.m.

1 stop5h 35m

C$ 362

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 11/6

3:20 p.m.-11:29 p.m.

1 stop9h 09m

Winnipeg

Sat 14/6

12:26 p.m.-7:12 p.m.

1 stop5h 46m

C$ 380

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 16/6

12:15 p.m.-10:46 p.m.

2 stops11h 31m

Winnipeg

Fri 20/6

11:45 a.m.-10:01 p.m.

2 stops9h 16m

C$ 552

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 25/5

6:00 a.m.-3:31 p.m.

1 stop10h 31m

C$ 140

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/4

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 11 April 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 20 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$ 124). 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.

Rainfall in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Winnipeg ranges from 20.0 - 80.0 mm per month. June is typically the wettest month, when rainfall can reach 80.0 mm. January is typically the driest time to visit Winnipeg when rainfall is around 20.0 mm.

Temperature in Winnipeg by month

Plan your trip to Winnipeg by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Winnipeg, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 20.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -16.0 C).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Winnipeg. Reviews last updated 15 April 2025.
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Overall

8.0

Entertainment

6.9

Boarding

8.2

Food

7.6

Comfort

8.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
8.0
Very good
280 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Overall

8.0

Entertainment

6.9

Boarding

8.2

Food

7.6

Comfort

8.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Delta
8.0
Very good
7,916 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Overall

8.0

Entertainment

6.9

Boarding

8.2

Food

7.6

Comfort

8.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
United Airlines
7.4
Good
8,656 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Overall

8.0

Entertainment

6.9

Boarding

8.2

Food

7.6

Comfort

8.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Air Canada
7.0
Good
9,118 reviews
Porter Airlines
8.0
Very good
280 reviews
Check prices

Crew

8.7

Overall

8.0

Entertainment

6.9

Boarding

8.2

Food

7.6

Comfort

8.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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.

  • What are the cheapest airlines flying from Boston to Winnipeg round-trip?

    Our cheapest airline available from Boston to Winnipeg is United Airlines. Our recent data shows that you can find tickets from as low as C$ 334 on this airline. Additional options worth looking into are Air Canada and Delta, starting at C$ 362 and C$ 380 round-trip. Users have found that United Airlines is 51% cheaper than the other options available to this destination.

  • 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$ 124). 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 Boston?

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

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Alternative routes for Boston to Winnipeg

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Hartford to Winnipeg flights

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

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