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Cheap flights from Boston to Winnipeg from C$ 148

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 5/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 373

One-way from

C$ 148

Popular in

March

Cheapest in

January

Average price

C$ 592
WestJet
  • WestJet
  • 3/10-19/10
  • 2 total stops
  • 28h 21m total
  • Boston to Winnipeg
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WestJet
  • WestJet
  • 5/10
  • 1 total stop
  • 15h 31m total
  • Boston to Winnipeg
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Highest demand for flights based on searches. 18% potential increase in price (C$ 197 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 31 potential savings vs. average RT price).
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Average for round-trip flights in June 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 12 June 2025.

Fri 3/106:30 p.m.BOS - YWG
1 stop18h 11mWestJet
Sun 19/106:30 a.m.YWG - BOS
1 stop10h 10mWestJet
Deal found 11/6C$ 373
Thu 24/75:50 a.m.BOS - YWG
1 stop7h 14mAir Canada
Wed 6/85:00 a.m.YWG - BOS
1 stop5h 28mAir Canada
Deal found 11/6C$ 410
Thu 21/87:45 a.m.BOS - YWG
1 stop15h 48mUnited Airlines
Mon 25/84:25 p.m.YWG - BOS
1 stop12h 34mUnited Airlines
Deal found 10/6C$ 420
Thu 24/77:15 a.m.BOS - YWG
1 stop10h 35mDelta
Wed 6/86:45 a.m.YWG - BOS
2 stops12h 28mDelta
Deal found 11/6C$ 462
Fri 1/89:32 a.m.BOS - YWG
1 stop7h 23mMultiple Airlines
Tue 5/89:05 p.m.YWG - BOS
2 stops20h 05mMultiple Airlines
Deal found 12/6C$ 489
Wed 20/83:30 p.m.BOS - YWG
1 stop8h 16mPorter Airlines
Sun 24/811:45 a.m.YWG - BOS
1 stop5h 13mPorter Airlines
Deal found 12/6C$ 682

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 12 June 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 3/10

6:30 p.m.-11:41 a.m.

1 stop18h 11m

Winnipeg

Sun 19/10

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

1 stop10h 10m

C$ 373

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 24/7

5:50 a.m.-12:04 p.m.

1 stop7h 14m

Winnipeg

Wed 6/8

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

1 stop5h 28m

C$ 410

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 21/8

7:45 a.m.-10:33 p.m.

1 stop15h 48m

Winnipeg

Mon 25/8

4:25 p.m.-5:59 a.m.

1 stop12h 34m

C$ 420

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 4/7

1:10 p.m.-11:29 p.m.

2 stops11h 19m

Winnipeg

Thu 21/8

8:35 a.m.-7:25 p.m.

1 stop9h 50m

C$ 448

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 1/8

9:32 a.m.-3:55 p.m.

1 stop7h 23m

Winnipeg

Tue 5/8

9:05 p.m.-6:10 p.m.

2 stops20h 05m

C$ 489

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Wed 20/8

3:30 p.m.-10:46 p.m.

1 stop8h 16m

Winnipeg

Sun 24/8

11:45 a.m.-5:58 p.m.

1 stop5h 13m

C$ 682

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 5/10

6:30 p.m.-9:01 a.m.

1 stop15h 31m

C$ 148

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 5/10

6:00 a.m.-12:30 a.m.

2 stops19h 30m

C$ 164

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 26/6

6:05 a.m.-10:33 p.m.

1 stop17h 28m

C$ 174

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sat 5/7

5:50 a.m.-5:40 p.m.

2 stops12h 50m

C$ 183

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 12 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 9 June 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$ 123). Flying from Boston to Winnipeg in July is currently the most expensive (average of C$ 229). 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 12 June 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta and United Airlines from Boston to Winnipeg to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,531 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 WestJet. Our recent data shows that you can find tickets from as low as C$ 373 on this airline. Additional options worth looking into are Air Canada and United Airlines, starting at C$ 410 and C$ 420 round-trip. Users have found that WestJet is 41% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Boston to Winnipeg one-way?

    To fly one-way, consider booking your trip with WestJet, which is currently one of the cheapest options available, starting at C$ 148. United Airlines flights start at C$ 174 while deals on Air Canada start at C$ 183 one-way.

  • 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$ 229). 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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