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BOS - YWG

C$ 226 Find Cheap Flights from Boston to Winnipeg – Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 524
Typical prices: C$ 599-C$ 1,050
Air Canada
Mon 22/10Wed 24/10
BOS - YWG • 1 stop
Cheapest one-way flights
C$ 226
Typical prices: C$ 353-C$ 561
Delta
Sun 18/11
BOS - YWG • 1 stop
Direct flights
Not available
There are currently no direct flights between Boston and Winnipeg. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
September
Cheapest • 38% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Calgary (YYC)
Cheapest • Avg C$ 682 (round-trip)
Montreal Pierre Elliott Trudeau Intl (YUL)
Shortest trip • 6h 01m (one-way)
Insights
Insights
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We hope you enjoy your trip to Winnipeg!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Boston to Winnipeg (BOS-YWG)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Winnipeg

Thu, 22 Oct - Sat, 24 Oct
Air Canada Logo
10:50 a.m. - 4:27 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 37m1 stop Toronto Pearson Intl
Air Canada Logo
3:05 p.m. - 9:27 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 22m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 524Air Canada
Wed, 11 Nov - Wed, 18 Nov
Delta Logo
5:45 a.m. - 1:55 p.m.BOS  Boston Logan Intl-YWG Winnipeg
8h 10m1 stop Minneapolis St Paul
Delta Logo
6:35 a.m. - 12:54 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 19m1 stop Minneapolis St Paul
C$ 528Delta
Thu, 3 Dec - Tue, 8 Dec
Delta Logo
7:25 a.m. - 6:34 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 09m1 stop Minneapolis St Paul
Delta Logo
6:25 a.m. - 4:01 p.m.YWG  Winnipeg-BOS Boston Logan Intl
9h 36m1 stop Minneapolis St Paul
C$ 528Delta
Thu, 22 Oct - Sat, 24 Oct
Air Canada Logo
10:50 a.m. - 6:12 p.m.BOS  Boston Logan Intl-YWG Winnipeg
8h 22m1 stop Toronto Pearson Intl
Air Canada Logo
2:05 p.m. - 10:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
7h 35m1 stop Toronto Pearson Intl
C$ 531Air Canada
Thu, 4 Feb - Tue, 9 Feb
Delta Logo
5:40 a.m. - 1:50 p.m.BOS  Boston Logan Intl-YWG Winnipeg
8h 10m1 stop Minneapolis St Paul
Delta Logo
5:38 p.m. - 10:53 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 15m1 stop Minneapolis St Paul
C$ 554Delta
Thu, 4 Feb - Tue, 9 Feb
Delta Logo
5:40 a.m. - 1:50 p.m.BOS  Boston Logan Intl-YWG Winnipeg
8h 10m1 stop Minneapolis St Paul
Delta Logo
5:38 p.m. - 10:53 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 15m1 stop Minneapolis St Paul
C$ 554Delta
Thu, 4 Feb - Tue, 9 Feb
Porter Airlines Logo
1:15 p.m. - 7:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 55m1 stop Ottawa
Porter Airlines Logo
11:40 a.m. - 8:32 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
C$ 570Porter Airlines
Thu, 4 Feb - Mon, 8 Feb
Porter Airlines Logo
1:15 p.m. - 7:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 55m1 stop Ottawa
Porter Airlines Logo
11:40 a.m. - 8:32 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
C$ 582Porter Airlines
Thu, 4 Feb - Tue, 9 Feb
Porter Airlines Logo
1:15 p.m. - 7:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 55m1 stop Ottawa
Porter Airlines Logo
11:40 a.m. - 8:32 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
C$ 582Porter Airlines
Thu, 4 Feb - Tue, 9 Feb
Porter Airlines Logo
8:00 a.m. - 7:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 10m2 stops Toronto Island Ottawa
Porter Airlines Logo
11:40 a.m. - 8:32 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
C$ 582Porter Airlines
Booking Insights

Price, demand, and travel trends for Boston to Winnipeg flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Boston to Winnipeg?

Round-trip flights from Boston to Winnipeg typically range from C$ 599 to C$ 1,050. The lowest price found in the past 5 days was C$ 524, on Air Canada.

What's the cheapest day of the week to fly from Boston to Winnipeg?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Boston to Winnipeg. It’s 13% cheaper than the average day, while Sunday is the most expensive, with prices 38% higher.

What is the cheapest month to fly from Boston to Winnipeg?

•September is the cheapest month to fly from Boston to Winnipeg at C$ 518 round-trip.
•February (C$ 1,307) and January (C$ 1,198) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 152% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Boston to Winnipeg flights

Low season

March

Cheapest flight

C$ 226
Beat the crowds with an average 27% drop in traveller numbers.
The most popular month to fly with an average 112% increase in traveller numbers.
One-way flight from Boston to Winnipeg

When to book flights from Boston to Winnipeg

Are your dates flexible? Find out the best times to travel from Boston to Winnipeg based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Boston to Winnipeg flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines, and booking tips.

  • Which cabin classes can I book on flights from Boston to Winnipeg?

    Only Economy Class is available on flights from Boston to Winnipeg.

  • How long does a flight from Boston to Winnipeg take?

    A direct flight from Boston to Winnipeg takes 00m, covering 3,495 km.

  • Do I need a passport to fly from Boston to Winnipeg?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Boston to Winnipeg flight?

    Round-trip flights from Boston to Winnipeg range from C$ 599 to C$ 1,050, with an average of C$ 830 over the past 12 months. Anything below C$ 599 counts as a good deal.

  • Have flight prices from Boston to Winnipeg changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about C$ 524 to C$ 1,874. That means the highest observed fare was about 4x higher than the lowest one.

  • How are flight prices from Boston to Winnipeg looking right now?

    One-way fares from Boston to Winnipeg are currently lower than usual. Average one-way flight prices are about C$ 281, which is 38% below the typical average for this route.

  • What car rental options are available at Winnipeg Airport (YWG)?

    Winnipeg Airport (YWG) hosts 5 major car rental companies, with daily rates starting from around C$ 25 for economy cars. Top options include:

    • Thrifty
    • Dollar
    • Hertz
    • Alamo
    • Fox

  • Which airports can I use when flying from Boston to Winnipeg?

    Flights from Boston to Winnipeg usually depart from Boston Logan Intl (BOS) and arrive at Winnipeg (YWG).

  • Which airports do connecting flights from Boston to Winnipeg pass through?

    One-stop flights from Boston to Winnipeg most commonly connect through:

    • Toronto Pearson Intl (YYZ) – 66% of one-stop connections
    • Minneapolis St Paul (MSP) – 16% of one-stop connections
    • Montreal Pierre Elliott Trudeau Intl (YUL) – 12% of one-stop connections
    • Chicago O'Hare Intl (ORD) – 6% of one-stop connections

  • Can I save money by using flexible dates for flights from Boston to Winnipeg?

    Yes. Flexible dates can save you up to 37% on flights from Boston to Winnipeg. Wednesday is the cheapest departure day at C$ 726 round-trip on average, while Sunday is the most expensive at C$ 1,146, a difference of C$ 420.

    KAYAK's flexible dates feature shows options up to three days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport when travelling from Boston to Winnipeg?

    Flying via Montreal Pierre Elliott Trudeau Intl (YUL) gives the shortest average 1-stop total travel time at 6h 01m, compared with 6h 25m via Toronto Pearson Intl (YYZ) and 7h 14m via Minneapolis St Paul (MSP).

  • What is the time difference between Boston and Winnipeg?

    Winnipeg is 1 hour behind Boston (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Your guide to booking Boston to Winnipeg flights

Get tips on when to book, when to fly, and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average C$ 726, about C$ 420 less than Sunday fares (37% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Boston to Winnipeg trip for September. Fares historically average C$ 518 round-trip in that month – typically C$ 789 less than the most expensive month, which is February (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Winnipeg Airport.

    • Victoria Inn Hotel & Convention Centre
    • Lakeview Signature, Trademark Collection by Wyndham
    • Days Inn and Suites Winnipeg Airport, Manitoba

More options for your flight from Boston to Winnipeg

Complete your trip to Winnipeg with a hotel stay or car rental

Car rentals in Winnipeg
Hotels in Winnipeg
Vacations in Winnipeg