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YWG - BOS

$220 Find Cheap Flights from Winnipeg to Boston - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$304
Typical prices: $342-$575
Delta
Tue 11/13Thu 11/22
YWG - BOS • 1 stop
Cheapest one-way
$220
Typical prices: $210-$377
Porter Airlines
Fri 2/9
YWG - BOS • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Winnipeg and Boston. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
January
Cheapest • 38% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Atlanta Hartsfield-Jackson (ATL)
Cheapest • Avg $215 (round-trip)
Montreal Pierre Elliott Trudeau Intl (YUL)
Shortest trip • 5h 59m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Winnipeg to Boston (YWG-BOS)

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

Recent round-trip flight deals from Winnipeg to Boston

Fri, Nov 13 - Sun, Nov 22
Delta Logo
6:35 am - 4:44 pmYWG  Winnipeg-BOS Boston Logan Intl
9h 09m1 stop Minneapolis St Paul
Delta Logo
5:45 am - 12:55 pmBOS  Boston Logan Intl-YWG Winnipeg
8h 10m1 stop Minneapolis St Paul
$304Delta
Tue, Nov 24 - Sun, Nov 29
Porter Airlines Logo
11:35 am - 9:35 pmYWG  Winnipeg-BOS Boston Logan Intl
9h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
8:00 am - 6:06 pmBOS  Boston Logan Intl-YWG Winnipeg
11h 06m2 stops Toronto Island Ottawa
$362Porter Airlines
Mon, Nov 23 - Sat, Nov 28
Porter Airlines Logo
11:35 am - 9:35 pmYWG  Winnipeg-BOS Boston Logan Intl
9h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
8:00 am - 6:06 pmBOS  Boston Logan Intl-YWG Winnipeg
11h 06m2 stops Toronto Island Ottawa
$362Porter Airlines
Wed, Nov 18 - Tue, Nov 24
Porter Airlines Logo
11:35 am - 9:35 pmYWG  Winnipeg-BOS Boston Logan Intl
9h 00m2 stops Ottawa Toronto Island
Porter Airlines Logo
8:00 am - 6:06 pmBOS  Boston Logan Intl-YWG Winnipeg
11h 06m2 stops Toronto Island Ottawa
$374Porter Airlines
Mon, Nov 30 - Fri, Dec 4
Multiple Airlines Logo
7:55 pm - 9:10 amYWG  Winnipeg-BOS Boston Logan Intl
12h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
1:15 pm - 6:14 pmBOS  Boston Logan Intl-YWG Winnipeg
5h 59m1 stop Ottawa
$392Multiple Airlines
Fri, Nov 13 - Sun, Nov 22
Multiple Airlines Logo
7:55 pm - 9:10 amYWG  Winnipeg-BOS Boston Logan Intl
12h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
1:15 pm - 6:06 pmBOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
$402Multiple Airlines
Mon, Nov 23 - Mon, Nov 30
Multiple Airlines Logo
7:55 pm - 9:10 amYWG  Winnipeg-BOS Boston Logan Intl
12h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
1:15 pm - 6:06 pmBOS  Boston Logan Intl-YWG Winnipeg
5h 51m1 stop Ottawa
$403Multiple Airlines
Thu, Dec 24 - Sun, Jan 3
Air Canada Logo
9:05 am - 2:53 pmYWG  Winnipeg-BOS Boston Logan Intl
4h 48m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
5:45 am - 2:49 pmBOS  Boston Logan Intl-YWG Winnipeg
10h 04m1 stop Toronto Pearson Intl
$693Air Canada
Thu, Dec 24 - Sun, Jan 3
Air Canada Logo
9:05 am - 2:53 pmYWG  Winnipeg-BOS Boston Logan Intl
4h 48m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
5:45 am - 2:49 pmBOS  Boston Logan Intl-YWG Winnipeg
10h 04m1 stop Toronto Pearson Intl
$694Air Canada
Mon, Mar 29 - Sun, Apr 4
Air Canada Logo
8:05 am - 2:52 pmYWG  Winnipeg-BOS Boston Logan Intl
5h 47m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
5:45 am - 1:48 pmBOS  Boston Logan Intl-YWG Winnipeg
9h 03m1 stop Toronto Pearson Intl
$720Air Canada
Booking Insights

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

Round-trip flights from Winnipeg to Boston typically range from $342 to $575. The lowest price found in the past 5 days was $304, on Delta.

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

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Winnipeg to Boston. It’s 33% cheaper than the average day, while Sunday is the most expensive, with prices 17% higher.

What’s the cheapest month to fly from Winnipeg to Boston?

•January is the cheapest month to fly from Winnipeg to Boston at $281 round-trip.
•April ($915) and November ($586) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 225% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Winnipeg to Boston flights

Low season

December

Cheapest flight

$220
Beat the crowds with an average 5% drop in travelers.
The most popular month to fly with an average 148% increase in travelers.
One-way flight from Winnipeg to Boston

When to book flights from Winnipeg to Boston

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

Your Winnipeg to Boston 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 Winnipeg to Boston?

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

  • How long is a flight from Winnipeg to Boston?

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

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

    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 Winnipeg to Boston flight?

    Round-trip flights from Winnipeg to Boston range from $342 to $575, with an average of $457 over the past 12 months. Anything below $342 counts as a good deal.

  • Have flight prices from Winnipeg to Boston 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 $304 to $1,143. That means the highest observed fare was about 4x higher than the lowest one.

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

    One-way fares from Winnipeg to Boston are currently in line with typical prices for this route. Average one-way fares are about $266.

  • What car rental options are available at Boston Logan Intl Airport (BOS)?

    Boston Logan Intl Airport (BOS) hosts 5 major car rental companies, with daily rates starting from around $23 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Budget
    • Thrifty
    • Sixt

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

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

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

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

    • Toronto Pearson Intl (YYZ) - 54% of one-stop connections
    • Montreal Pierre Elliott Trudeau Intl (YUL) - 24% of one-stop connections
    • Minneapolis St Paul (MSP) - 12% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 7% of one-stop connections

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

    Yes. Flexible dates can save you up to 43% on flights from Winnipeg to Boston. Tuesday is the cheapest departure day at $308 round-trip on average, while Sunday is the most expensive at $539, a difference of $231.

    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 Winnipeg to Boston?

    Flying via Montreal Pierre Elliott Trudeau Intl (YUL) gives the shortest average 1-stop total travel time at 5h 59m, compared with 6h 11m via Ottawa (YOW) and 6h 27m via Toronto Pearson Intl (YYZ).

  • What is the time difference between Winnipeg and Boston?

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

  • What popular places can I visit in Boston?

    Some of the most popular sights in Boston are TD Garden, Fenway Park and Boston Common. These are among the most viewed places in Boston on KAYAK.

Your guide to booking Winnipeg to Boston 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 Tuesday departure and avoid flying on Sunday. On this route, Tuesday flights average $308, about $231 less than Sunday fares (43% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Winnipeg to Boston trip for January. Fares historically average $281 round-trip in that month - typically $634 less than the most expensive month, which is April (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Boston Logan Intl Airport.

    • Hyatt Regency Boston Harbor
    • Hilton Boston Logan Airport
    • Hilton Garden Inn Boston Logan Airport

More options for your flight from Winnipeg to Boston

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

Car rentals in Boston
Hotels in Boston
Vacations in Boston