BOS - YWG

C$ 148 Find Cheap Flights from Boston to Winnipeg – Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 354
Typical prices: C$ 603-C$ 1,051
Air Canada
Mon 22/10Wed 24/10
BOS - YWG • 1 stop
Cheapest one-way flights
C$ 148
Typical prices: C$ 246-C$ 509
Air Canada
Sat 22/9
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
August
Cheapest • 15% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Calgary (YYC)
Cheapest • Avg C$ 661 (round-trip)
Montreal Pierre Elliott Trudeau Intl (YUL)
Shortest trip • 6h 03m (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
12:45 p.m. - 6:12 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 27m1 stop Toronto Pearson Intl
Air Canada Logo
1:30 p.m. - 9:27 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 57m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 354Air Canada
Sat, 24 Oct - Sat, 31 Oct
Air Canada Logo
5:50 a.m. - 12:29 p.m.BOS  Boston Logan Intl-YWG Winnipeg
7h 39m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:05 a.m. - 2:53 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 48m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 358Air Canada
Sat, 10 Oct - Sat, 17 Oct
Air Canada Logo
12:45 p.m. - 6:12 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 27m1 stop Toronto Pearson Intl
Air Canada Logo
3:20 p.m. - 10:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 20m1 stop Toronto Pearson Intl
C$ 361Air Canada
Fri, 16 Oct - Mon, 19 Oct
Multiple Airlines Logo
7:00 a.m. - 5:58 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 58m2 stops Toronto Island Ottawa
Multiple Airlines Logo
6:00 a.m. - 5:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 40m1 stop Calgary
C$ 376Multiple Airlines
Sat, 10 Oct - Fri, 16 Oct
Porter Airlines Logo
10:05 a.m. - 3:20 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 15m1 stop Toronto Pearson Intl
Porter Airlines Logo
9:20 a.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 15m1 stop Toronto Pearson Intl
C$ 407Porter Airlines
Thu, 22 Oct - Sat, 24 Oct
Air Canada Logo
12:45 p.m. - 6:12 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 27m1 stop Toronto Pearson Intl
Air Canada Logo
1:30 p.m. - 9:27 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 57m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 408Air Canada
Sat, 26 Sep - Tue, 29 Sep
Air Canada Logo
4:55 p.m. - 11:27 p.m.BOS  Boston Logan Intl-YWG Winnipeg
7h 32m1 stop Toronto Pearson Intl
Air Canada Logo
3:20 p.m. - 10:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 20m1 stop Toronto Pearson Intl
C$ 412Air Canada
Sat, 10 Oct - Mon, 12 Oct
Multiple Airlines Logo
10:05 a.m. - 3:20 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
9:05 p.m. - 5:40 p.m.YWG  Winnipeg-BOS Boston Logan Intl
19h 35m1 stop Calgary
C$ 416Multiple Airlines
Thu, 22 Oct - Sat, 24 Oct
Air Canada Logo
5:50 a.m. - 4:27 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 37m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
1:30 p.m. - 9:27 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 57m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 421Air Canada
Tue, 13 Oct - Sat, 17 Oct
Multiple Airlines Logo
8:30 p.m. - 12:37 p.m.BOS  Boston Logan Intl-YWG Winnipeg
17h 07m1 stop Chicago O'Hare Intl
Multiple Airlines Logo
5:00 a.m. - 2:41 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 41m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
C$ 425Multiple 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 from Boston to Winnipeg with more confidence.

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

Round-trip flights from Boston to Winnipeg start at C$ 354. Prices are below average for this route right now, with typical round-trip fares ranging from C$ 603 to C$ 1,051. The lowest price found in the past 5 days was C$ 354 on Air Canada.

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

Wednesday is the cheapest day of the week to fly from Boston to Winnipeg and is 16% cheaper than the average day. Sunday is the most expensive day with flight prices 31% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • August is the cheapest month to fly from Boston to Winnipeg at C$ 702 round-trip.
  • February (C$ 1,266) and January (C$ 1,159) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 80% 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$ 148
Best time to beat the crowds but there is an average 4% increase in price.
Flights 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 route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

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

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

  • 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) – 55% of one-stop connections
    • Minneapolis St Paul (MSP) – 17% of one-stop connections
    • Montreal Pierre Elliott Trudeau Intl (YUL) – 17% of one-stop connections
    • Chicago O'Hare Intl (ORD) – 9% of one-stop connections

    Toronto Pearson Intl (YYZ) handles the largest share of one-stop connections on this route.

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

    Yes. Being flexible with your travel dates can save you up to 36% on the Boston to Winnipeg route. Wednesday is the cheapest departure day at C$ 703 round-trip on average, while Sunday is the most expensive at C$ 1,088, a difference of C$ 385. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

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

    A direct flight from Boston to Winnipeg takes 0h 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.

  • 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$ 354 to C$ 2,921. That means the highest observed fare was about 8x 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$ 225, which is 44% below the typical average for this route.

  • 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 03m, compared with 6h 24m via Toronto Pearson Intl (YYZ) and 7h 27m 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.

  • 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

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

    Round-trip flights from Boston to Winnipeg range from C$ 603 to C$ 1,051, with an average of C$ 829 over the past 12 months. Anything below C$ 603 counts as a good deal.

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 instead of Sunday. On this route, Wednesday flights average C$ 703 – about C$ 385 less than Sunday (35% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Boston to Winnipeg trip for August. Fares historically average C$ 702 round-trip in that month – typically C$ 564 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
    - The Grand Winnipeg Airport Hotel by Lakeview

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