Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Winnipeg to Massachusetts from C$ 216

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Winnipeg to Massachusetts departing on 28/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Winnipeg to Massachusetts

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
8:00 a.m. - 11:57 p.m.
YWG
-
BOS
14h 57m1 stop
Multiple Airlines Logo
5:34 a.m. - 6:03 p.m.
BOS
-
YWG
13h 29m1 stop
C$ 362Multiple Airlines
Mon, 12 Jan - Mon, 19 Jan
Multiple Airlines Logo
9:00 p.m. - 1:13 a.m.
YWG
-
BOS
27h 13m2 stops
Multiple Airlines Logo
5:34 a.m. - 6:03 p.m.
BOS
-
YWG
13h 29m1 stop
C$ 366Multiple Airlines
Mon, 12 Jan - Mon, 19 Jan
Multiple Airlines Logo
8:00 a.m. - 11:57 p.m.
YWG
-
BOS
14h 57m1 stop
Multiple Airlines Logo
5:23 p.m. - 12:41 a.m.
BOS
-
YWG
32h 18m3 stops
C$ 432Multiple Airlines
Mon, 12 Jan - Mon, 19 Jan
Multiple Airlines Logo
8:05 p.m. - 11:57 p.m.
YWG
-
BOS
26h 52m2 stops
Multiple Airlines Logo
5:27 p.m. - 6:03 p.m.
BOS
-
YWG
25h 36m1 stop
C$ 434Multiple Airlines
Sun, 11 Jan - Sun, 18 Jan
Air Canada Logo
8:15 a.m. - 2:52 p.m.
YWG
-
BOS
5h 37m1 stop
Air Canada Logo
5:30 a.m. - 10:15 a.m.
BOS
-
YWG
5h 45m1 stop
C$ 453Air Canada
Fri, 13 Feb - Sun, 15 Feb
United Airlines Logo
2:20 p.m. - 9:16 p.m.
YWG
-
ALB
5h 56m1 stop
United Airlines Logo
7:30 p.m. - 11:57 a.m.
ALB
-
YWG
17h 27m2 stops
C$ 486United Airlines
Mon, 2 Mar - Wed, 4 Mar
United Airlines Logo
2:20 p.m. - 10:01 a.m.
YWG
-
ALB
18h 41m2 stops
United Airlines Logo
7:30 p.m. - 11:57 a.m.
ALB
-
YWG
17h 27m2 stops
C$ 487United Airlines
Mon, 2 Mar - Wed, 4 Mar
Air Canada Logo
8:15 a.m. - 2:52 p.m.
YWG
-
BOS
5h 37m1 stop
Air Canada Logo
10:15 a.m. - 4:35 p.m.
BOS
-
YWG
7h 20m1 stop
C$ 578Air Canada
Sat, 7 Mar - Mon, 9 Mar
WestJet Logo
7:30 a.m. - 1:24 p.m.
YWG
-
ALB
28h 54m1 stop
WestJet Logo
6:00 a.m. - 3:07 p.m.
ALB
-
YWG
10h 07m1 stop
C$ 642WestJet
Fri, 23 Jan - Sun, 25 Jan
American Airlines Logo
12:10 p.m. - 3:20 p.m.
YWG
-
ALB
26h 10m2 stops
American Airlines Logo
7:23 a.m. - 11:35 p.m.
ALB
-
YWG
17h 12m3 stops
C$ 951American Airlines
Fri, 23 Jan - Sun, 25 Jan

United Airlines flights from Winnipeg to Massachusetts

Our best United Airlines deals on Winnipeg to Massachusetts flight tickets
United Airlines
2 Mar
YWG2:20 p.m.Winnipeg
5h 56m
1 stop
ALB9:16 p.m.Albany Intl
4 Mar
ALB7:30 p.m.Albany Intl
17h 27m
2 stops
YWG11:57 a.m.Winnipeg
C$ 486
Find similar
United Airlines
2 Mar
YWG2:20 p.m.Winnipeg
18h 41m
2 stops
ALB10:01 a.m.Albany Intl
4 Mar
ALB7:30 p.m.Albany Intl
17h 27m
2 stops
YWG11:57 a.m.Winnipeg
C$ 487
Find similar
United Airlines
23 Jan
YWG5:30 a.m.Winnipeg
14h 52m
2 stops
ALB9:22 p.m.Albany Intl
25 Jan
ALB7:25 p.m.Albany Intl
17h 32m
2 stops
YWG11:57 a.m.Winnipeg
C$ 569
Find similar

Air Canada flights from Winnipeg to Massachusetts

Our best Air Canada deals on Winnipeg to Massachusetts flight tickets
Air Canada
13 Feb
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl
15 Feb
BOS5:30 a.m.Boston Logan Intl
5h 45m
1 stop
YWG10:15 a.m.Winnipeg
C$ 453
Find similar
Air Canada
7 Mar
YWG8:15 a.m.Winnipeg
5h 37m
1 stop
BOS2:52 p.m.Boston Logan Intl
9 Mar
BOS10:15 a.m.Boston Logan Intl
7h 20m
1 stop
YWG4:35 p.m.Winnipeg
C$ 578
Find similar
Air Canada
21 Mar
YWG6:00 a.m.Winnipeg
7h 52m
2 stops
BOS2:52 p.m.Boston Logan Intl
23 Mar
BOS5:30 a.m.Boston Logan Intl
5h 45m
1 stop
YWG10:15 a.m.Winnipeg
C$ 582
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Winnipeg to Massachusetts 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, momondo users made 96,600 searches. Data last updated 15 December 2025.
Use the filters below to find and compare flights from Winnipeg to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 12/1

8:00 a.m.-11:57 p.m.

1 stop14h 57m

Boston Logan Intl

Mon 19/1

5:34 a.m.-6:03 p.m.

1 stop13h 29m

C$ 362

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 12/1

9:00 p.m.-1:13 a.m.

2 stops27h 13m

Boston Logan Intl

Mon 19/1

5:34 a.m.-6:03 p.m.

1 stop13h 29m

C$ 366

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Mon 12/1

8:00 a.m.-11:57 p.m.

1 stop14h 57m

Boston Logan Intl

Mon 19/1

5:23 p.m.-12:41 a.m.

3 stops32h 18m

C$ 432

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sun 11/1

8:05 p.m.-11:57 p.m.

2 stops26h 52m

Boston Logan Intl

Sun 18/1

5:27 p.m.-6:03 p.m.

1 stop25h 36m

C$ 434

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Fri 13/2

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

1 stop5h 37m

Boston Logan Intl

Sun 15/2

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

1 stop5h 45m

C$ 453

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Mon 2/3

2:20 p.m.-9:16 p.m.

1 stop5h 56m

Albany Intl

Wed 4/3

7:30 p.m.-11:57 a.m.

2 stops17h 27m

C$ 486

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Mon 2/3

2:20 p.m.-10:01 a.m.

2 stops18h 41m

Albany Intl

Wed 4/3

7:30 p.m.-11:57 a.m.

2 stops17h 27m

C$ 487

WinnipegBoston

YWG - BOS

YWGBOS

Winnipeg

Sat 7/3

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

1 stop5h 37m

Boston Logan Intl

Mon 9/3

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

1 stop7h 20m

C$ 578

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Fri 23/1

7:30 a.m.-1:24 p.m.

1 stop28h 54m

Albany Intl

Sun 25/1

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

1 stop10h 07m

C$ 642

WinnipegAlbany

YWG - ALB

YWGALB

Winnipeg

Fri 23/1

12:10 p.m.-3:20 p.m.

2 stops26h 10m

Albany Intl

Sun 25/1

7:23 a.m.-11:35 p.m.

3 stops17h 12m

C$ 951

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Massachusetts from

How to get the cheapest flight ticket from Winnipeg to Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Massachusetts?

The cheapest month to fly to Massachusetts from Winnipeg is in June. Flight prices, which tend to average around C$ 408, are often lower during this time because this is during the off-season. If you are unable to visit Massachusetts during the month of June, then departing from Winnipeg during the month August is also very affordable. Most momondo users find prices during this month for around C$ 441.

What is the cheapest day to depart on your flight to Massachusetts?

On average, the least expensive day to fly to Massachusetts from Winnipeg is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as C$ 424. However, this price may fluctuate depending on the airline, the season, and holidays. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Winnipeg to Massachusetts for around C$ 619.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our most recent data shows that the best time of day to fly to Massachusetts is in the morning. Flights from Winnipeg to Massachusetts during this time can be as low as C$ 535. In contrast, the most expensive time of day to depart to Massachusetts is in the afternoon when prices are around C$ 647.

How far in advance should I book a flight to Massachusetts?

You are more likely to see cheaper flights to Massachusetts from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around C$ 578 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Winnipeg for as low as C$ 333 on momondo.

Can stopping save me money on Winnipeg to Massachusetts flights?

You could potentially save up to 35% on your flight if you consider stops on a Winnipeg to Massachusetts flight.

Cheap Winnipeg to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Winnipeg to Massachusetts

Fastest flight time

5h 42m

Direct flights

None
The fastest flight from Winnipeg to Massachusetts takes 5h 42m
There are no direct flights from Winnipeg to Massachusetts. There are no popular flight routes from Winnipeg to Massachusetts.
Search flight deals

  • When did momondo last update prices for flights from Winnipeg Airport to Massachusetts?

    Prices for flights from Winnipeg Airport to Massachusetts are refreshed on a daily basis.

  • How many operators does momondo search for flights from Winnipeg Airport to Massachusetts?

  • How old do you have to be to fly from Winnipeg Airport to Massachusetts?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Winnipeg Airport to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The travel and health documents you'll need for your trip to Massachusetts may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Massachusetts. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Winnipeg to Massachusetts

Compare and see reviews for airlines that fly from Winnipeg to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom C$ 237Free CancellationRating
7.4
9,094 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 350Free CancellationRating
7.1
10,526 reviews
Search Air Canada flights
Porter AirlinesPriceFrom C$ 421Free CancellationRating
8.0
399 reviews
Search Porter Airlines flights
WestJetPriceFrom C$ 472Free CancellationRating
7.2
3,202 reviews
Search WestJet flights

Why use momondo?

Why should I use momondo to find a flight deal from Winnipeg to Massachusetts?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Winnipeg to Massachusetts for you.

Can I find flights from Winnipeg to Massachusetts with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Winnipeg to Massachusetts flights to just show those with flexible booking policies.

How can momondo help me find flights from Winnipeg to Massachusetts?

Once you have performed a search for Winnipeg to Massachusetts flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Winnipeg to Massachusetts right now. Can momondo alert me if prices change?

Price alerts on flights to Massachusetts from Winnipeg are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Massachusetts trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 14/1
Wed 21/1
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Massachusetts

Popular Cities in Massachusetts

Popular flights according to clicks in the last 7 days on momondo
Flights to Fort Lauderdalefrom C$ 153
Flights to Orlandofrom C$ 158
Flights to New Yorkfrom C$ 256
Flights to Las Vegasfrom C$ 125
Flights to Los Angelesfrom C$ 158
Flights to Miamifrom C$ 317
Flights to San Franciscofrom C$ 125
Flights to Honolulufrom C$ 330
Flights to Phoenixfrom C$ 154
Flights to Tampafrom C$ 212
Flights to Chicagofrom C$ 182
Flights to Houstonfrom C$ 197