BOS - YWG

C$ 292 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$ 559
Typical prices: C$ 588-C$ 1,059
Porter Airlines
Wed 5/12Wed 12/12
BOS - YWG • 1 stop
Cheapest one-way flights
C$ 292
Typical prices: C$ 360-C$ 601
Multiple Airlines
Wed 12/12
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 • 37% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Calgary (YYC)
Cheapest • Avg C$ 676 (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

Sat, 5 Dec - Sat, 12 Dec
Multiple Airlines Logo
1:15 p.m. - 7:14 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 59m1 stop Ottawa
Multiple Airlines Logo
11:00 a.m. - 7:10 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 10m1 stop Toronto Pearson Intl
C$ 559Multiple Airlines
Mon, 30 Nov - Sun, 6 Dec
Multiple Airlines Logo
1:15 p.m. - 7:06 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
Multiple Airlines Logo
7:55 p.m. - 9:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
13h 15m1 stop Toronto Pearson Intl
C$ 569Multiple Airlines
Tue, 8 Dec - Sat, 12 Dec
Multiple Airlines Logo
4:35 p.m. - 10:15 a.m.BOS  Boston Logan Intl-YWG Winnipeg
17h 40m1 stop Toronto Island
Multiple Airlines Logo
11:00 a.m. - 7:10 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 10m1 stop Toronto Pearson Intl
C$ 583Multiple Airlines
Mon, 30 Nov - Fri, 4 Dec
Multiple Airlines Logo
1:15 p.m. - 7:06 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
Multiple Airlines Logo
7:55 p.m. - 9:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
13h 15m1 stop Toronto Pearson Intl
C$ 595Multiple Airlines
Tue, 8 Dec - Sat, 12 Dec
Multiple Airlines Logo
1:15 p.m. - 10:15 a.m.BOS  Boston Logan Intl-YWG Winnipeg
21h 00m2 stops Ottawa Toronto Pearson Intl
Multiple Airlines Logo
11:00 a.m. - 7:10 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 10m1 stop Toronto Pearson Intl
C$ 610Multiple Airlines
Thu, 1 Apr - Mon, 5 Apr
Multiple Airlines Logo
1:15 p.m. - 6:11 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 56m1 stop Ottawa
Multiple Airlines Logo
10:00 a.m. - 7:10 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 10m1 stop Toronto Pearson Intl
C$ 618Multiple Airlines
Mon, 30 Nov - Thu, 3 Dec
Multiple Airlines Logo
1:15 p.m. - 7:06 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
Multiple Airlines Logo
9:05 p.m. - 9:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
12h 05m1 stop Toronto Pearson Intl
C$ 622Multiple Airlines
Thu, 3 Dec - Mon, 7 Dec
Multiple Airlines Logo
5:30 p.m. - 10:15 a.m.BOS  Boston Logan Intl-YWG Winnipeg
16h 45m1 stop Toronto Pearson Intl
Multiple Airlines Logo
7:55 p.m. - 9:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
13h 15m1 stop Toronto Pearson Intl
C$ 628Multiple Airlines
Thu, 1 Apr - Sat, 3 Apr
Multiple Airlines Logo
1:15 p.m. - 6:11 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 56m1 stop Ottawa
Multiple Airlines Logo
10:00 a.m. - 7:10 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 10m1 stop Toronto Pearson Intl
C$ 642Multiple Airlines
Mon, 30 Nov - Sat, 5 Dec
Multiple Airlines Logo
1:15 p.m. - 7:06 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
Multiple Airlines Logo
9:35 p.m. - 9:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
11h 35m2 stops Calgary Toronto Pearson Intl
C$ 643Multiple 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.

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 25% cheaper than the average day, while Sunday is the most expensive, with prices 39% 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$ 514 round-trip.
•January (C$ 1,187) and April (C$ 1,113) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 131% 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$ 292
Beat the crowds with an average 52% drop in traveller numbers.
The most popular month to fly with an average 66% 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$ 588 to C$ 1,059, with an average of C$ 815 over the past 12 months. Anything below C$ 588 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$ 559 to C$ 1,997. 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 in line with typical prices for this route. Average one-way fares are about C$ 449.

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

    Winnipeg Airport (YWG) hosts 5 major car rental companies, with daily rates averaging C$ 61 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) – 65% of one-stop connections
    • Minneapolis St Paul (MSP) – 17% of one-stop connections
    • Montreal Pierre Elliott Trudeau Intl (YUL) – 10% 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 46% on flights from Boston to Winnipeg. Wednesday is the cheapest departure day at C$ 618 round-trip on average, while Sunday is the most expensive at C$ 1,136, a difference of C$ 518.

    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 03m, compared with 6h 33m via Toronto Pearson Intl (YYZ) and 7h 16m via Minneapolis St Paul (MSP).

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$ 618, about C$ 518 less than Sunday fares (46% 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$ 514 round-trip in that month – typically C$ 673 less than the most expensive month, which is January (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