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Cheap flights from Massachusetts to Winnipeg from C$ 226

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 31/8. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — YWG
5 Aug — 12 Aug1
1 adult

Cheap flight deals from Massachusetts to Winnipeg

Keep the following information in mind while searching for Massachusetts to Winnipeg flight deals. Data was last updated 31 July 2025.

Round-trip from

C$ 494

One-way from

C$ 226

Popular in

March

Cheapest in

January

Average price

C$ 509
Delta
  • Delta
  • 21/8-26/8
  • 2 total stops
  • 12h 50m total
  • Massachusetts to Winnipeg
Search Deals
Air Canada
  • Air Canada
  • 31/8
  • 1 total stop
  • 5h 29m total
  • Massachusetts to Winnipeg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 207 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Massachusetts to Winnipeg

Cheapest flights from Massachusetts to Winnipeg
Explore the most affordable flight options available from Massachusetts to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 31 July 2025.

Thu 21/85:40 a.m.BOS - YWG
1 stop7h 13mDelta
Tue 26/85:41 p.m.YWG - BOS
1 stop5h 37mDelta
Deal found 30/7C$ 494
Thu 21/87:45 a.m.BOS - YWG
1 stop15h 48mUnited Airlines
Tue 26/87:00 a.m.YWG - BOS
1 stop6h 40mUnited Airlines
Deal found 31/7C$ 533
Thu 21/85:50 a.m.BOS - YWG
2 stops12h 50mAir Canada
Tue 26/88:10 p.m.YWG - BOS
2 stops12h 20mAir Canada
Deal found 30/7C$ 591
Sat 16/86:00 a.m.ALB - YWG
2 stops16h 08mUnited Airlines
Sat 23/82:20 p.m.YWG - ALB
2 stops32h 36mUnited Airlines
Deal found 30/7C$ 1,158
Mon 4/83:30 p.m.BOS - YWG
1 stop8h 16mPorter Airlines
Mon 18/811:45 a.m.YWG - BOS
1 stop5h 43mPorter Airlines
Deal found 31/7C$ 1,243
Fri 1/88:39 p.m.BOS - YWG
3 stops28h 34mMultiple Airlines
Tue 5/86:55 p.m.YWG - BOS
3 stops22h 33mMultiple Airlines
Deal found 30/7C$ 1,305
Sat 16/86:00 a.m.ALB - YWG
1 stop10h 31mMultiple Airlines
Sat 23/82:20 p.m.YWG - ALB
1 stop20h 56mMultiple Airlines
Deal found 30/7C$ 1,414
Mon 20/106:00 a.m.BDL - YWG
1 stop10h 31mUnited Airlines
Sun 26/102:20 p.m.YWG - BDL
1 stop6h 18mUnited Airlines
Deal found 29/7C$ 1,490

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 31 July 2025.
Use the filters below to find and compare flights from Massachusetts to Winnipeg that are best for you.

Fly from

Massachusetts

Fly to

Winnipeg

Route

Depart

Return

Price

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 21/8

5:40 a.m.-11:53 a.m.

1 stop7h 13m

Winnipeg

Tue 26/8

5:41 p.m.-12:18 a.m.

1 stop5h 37m

C$ 494

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 21/8

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

1 stop15h 48m

Winnipeg

Tue 26/8

7:00 a.m.-2:40 p.m.

1 stop6h 40m

C$ 533

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Thu 21/8

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

2 stops12h 50m

Winnipeg

Mon 25/8

6:35 p.m.-9:30 a.m.

2 stops13h 55m

C$ 591

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Sat 16/8

6:00 a.m.-9:08 p.m.

2 stops16h 08m

Winnipeg

Sat 23/8

2:20 p.m.-11:56 p.m.

2 stops32h 36m

C$ 1,158

AlbanyWinnipeg

ALB - YWG

ALBYWG

Albany Intl

Sat 16/8

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

1 stop10h 31m

Winnipeg

Sat 23/8

2:20 p.m.-12:16 p.m.

1 stop20h 56m

C$ 1,414

HartfordWinnipeg

BDL - YWG

BDLYWG

Hartford Bradley Intl

Mon 20/10

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

1 stop10h 31m

Winnipeg

Sun 26/10

2:20 p.m.-9:38 p.m.

1 stop6h 18m

C$ 1,490

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Sun 31/8

5:50 a.m.-10:19 a.m.

1 stop5h 29m

C$ 226

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Tue 12/8

6:15 p.m.-10:46 p.m.

2 stops29h 31m

C$ 245

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Mon 1/9

7:00 p.m.-5:25 p.m.

2 stops23h 25m

C$ 274

BostonWinnipeg

BOS - YWG

BOSYWG

Boston Logan Intl

Fri 15/8

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

1 stop8h 16m

C$ 415

Flights are sorted by cheapest round-trip flights first.

Deals found on 31/7

Showing 1-10 of 11 results
1
2

Best time to book a flight from Massachusetts to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Massachusetts 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 Massachusetts to Winnipeg

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

Currently, January is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 123). Flying from Massachusetts 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.

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 31 July 2025.
Read reviews from past customers who have flown Porter Airlines,Delta, andUnited Airlines from Massachusetts to Winnipeg. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,981 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,900 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,978 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,851 reviews
Porter Airlines
8.0
Very good
318 reviews
Check prices

Comfort

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Winnipeg from Massachusetts?

    If you book a flight to Winnipeg from Massachusetts, you will be flying to Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg.

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

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as C$ 226. Users have also found prices from C$ 274 and C$ 415 on WestJet and Porter Airlines, respectively.

  • What are the most popular routes from Massachusetts to Winnipeg?

    Most travellers choose Boston Logan Intl - Winnipeg, Albany Intl - Winnipeg or Hartford Bradley Intl - Winnipeg when deciding on the best route from Massachusetts to Winnipeg.

  • Can I find deals for flights from Massachusetts to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Winnipeg.

  • Can I find deals for business class flights from Massachusetts to Winnipeg?

    Yes. Cheapflights offers flight deals from Massachusetts 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 Massachusetts to Winnipeg?

    Currently, January is the cheapest month in which you can book a flight from Massachusetts to Winnipeg (average of C$ 123). Flying from Massachusetts 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

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Why should you use Cheapflights to find cheap flight tickets from Massachusetts to Winnipeg?

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