BOS - YWG

$205 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
$382
Typical prices: $417-$750
Porter Airlines
Wed 11/21Fri 11/30
BOS - YWG • 1 stop
Cheapest one-way
$205
Typical prices: $255-$426
Multiple Airlines
Sat 11/24
BOS - YWG • 1 stop
Nonstop 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 $479 (round-trip)
Montreal Pierre Elliott Trudeau Intl (YUL)
Shortest trip • 6h 03m (one-way)
Insights
Insights
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Flight Deals
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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, Nov 21 - Mon, Nov 30
Multiple Airlines Logo
1:15 pm - 6:06 pmBOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
Multiple Airlines Logo
7:55 pm - 10:10 amYWG  Winnipeg-BOS Boston Logan Intl
13h 15m1 stop Toronto Pearson Intl
$382Multiple Airlines
Sat, Nov 21 - Mon, Nov 30
Multiple Airlines Logo
1:15 pm - 6:06 pmBOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
Multiple Airlines Logo
7:55 pm - 5:46 pmYWG  Winnipeg-BOS Boston Logan Intl
20h 51m2 stops Toronto Pearson Intl Ottawa
$387Multiple Airlines
Mon, Mar 1 - Tue, Mar 9
Porter Airlines Logo
1:15 pm - 6:19 pmBOS  Boston Logan Intl-YWG Winnipeg
6h 04m1 stop Ottawa
Porter Airlines Logo
12:40 pm - 10:34 pmYWG  Winnipeg-BOS Boston Logan Intl
8h 54m2 stops Ottawa Toronto Island
$402Porter Airlines
Tue, Mar 2 - Fri, Mar 5
Porter Airlines Logo
1:15 pm - 6:19 pmBOS  Boston Logan Intl-YWG Winnipeg
6h 04m1 stop Ottawa
Porter Airlines Logo
12:40 pm - 10:34 pmYWG  Winnipeg-BOS Boston Logan Intl
8h 54m2 stops Ottawa Toronto Island
$404Porter Airlines
Wed, Feb 3 - Sat, Feb 6
Air Canada Logo
10:25 am - 4:38 pmBOS  Boston Logan Intl-YWG Winnipeg
7h 13m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
9:05 am - 3:53 pmYWG  Winnipeg-BOS Boston Logan Intl
5h 48m1 stop Montreal Pierre Elliott Trudeau Intl
$689Air Canada
Tue, Dec 8 - Sat, Dec 12
Air Canada Logo
5:30 am - 10:15 amBOS  Boston Logan Intl-YWG Winnipeg
5h 45m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
9:05 am - 3:53 pmYWG  Winnipeg-BOS Boston Logan Intl
5h 48m1 stop Montreal Pierre Elliott Trudeau Intl
$689Air Canada
Mon, Mar 1 - Tue, Mar 9
United Airlines Logo
11:35 am - 8:57 pmBOS  Boston Logan Intl-YWG Winnipeg
10h 22m1 stop Denver Intl
United Airlines Logo
8:00 am - 2:50 pmYWG  Winnipeg-BOS Boston Logan Intl
5h 50m1 stop Chicago O'Hare Intl
$697United Airlines
Thu, Dec 3 - Mon, Dec 7
United Airlines Logo
8:27 am - 8:55 pmBOS  Boston Logan Intl-YWG Winnipeg
13h 28m2 stops Los Angeles Denver Intl
United Airlines Logo
3:15 pm - 10:53 pmYWG  Winnipeg-BOS Boston Logan Intl
6h 38m1 stop Chicago O'Hare Intl
$702United Airlines
Wed, Dec 23 - Wed, Dec 30
Delta Logo
7:05 am - 3:51 pmBOS  Boston Logan Intl-YWG Winnipeg
9h 46m1 stop Minneapolis St Paul
Delta Logo
6:25 am - 5:52 pmYWG  Winnipeg-BOS Boston Logan Intl
10h 27m1 stop Minneapolis St Paul
$843Delta
Wed, Dec 23 - Wed, Dec 30
Delta Logo
5:30 am - 10:31 amBOS  Boston Logan Intl-YWG Winnipeg
6h 01m1 stop Minneapolis St Paul
Delta Logo
6:25 am - 5:52 pmYWG  Winnipeg-BOS Boston Logan Intl
10h 27m1 stop Minneapolis St Paul
$923Delta
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’s the cheapest month to fly from Boston to Winnipeg?

•September is the cheapest month to fly from Boston to Winnipeg at $364 round-trip.
•January ($841) and April ($789) 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.

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Key details for Boston to Winnipeg flights

Low season

March

Cheapest flight

$205
Beat the crowds with an average 52% drop in travelers.
The most popular month to fly with an average 66% increase in travelers.
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.

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

    Two cabin classes are available on flights from Boston to Winnipeg:

    • Economy Class
    • Business Class

  • How long is a flight from Boston to Winnipeg?

    A nonstop flight from Boston to Winnipeg takes 00m, covering 1,350 miles.

  • 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 $417 to $750, with an average of $578 over the past 12 months. Anything below $417 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 $382 to $1,457. 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 higher than usual. Average one-way flight prices are about $361, which is 13% above 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 averaging $43 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 $438 round-trip on average, while Sunday is the most expensive at $805, a difference of $367.

    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 much time can I save by choosing a different layover airport 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).

  • 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 $438, about $367 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 $364 round-trip in that month - typically $477 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