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YWG - BOS

$163 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
$272
Typical prices: $342-$575
Delta
Fri 11/2Thu 11/8
YWG - BOS • 1 stop
Cheapest one-way
$163
Typical prices: $210-$377
Delta
Fri 12/14
YWG - BOS • 1 stop
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 $231 (round-trip)
Montreal Pierre Elliott Trudeau Intl (YUL)
Shortest trip • 5h 58m (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

Mon, Nov 2 - Sun, Nov 8
Delta Logo
5:40 pm - 11:20 pmYWG  Winnipeg-BOS Boston Logan Intl
5h 40m1 stop Minneapolis St Paul
Delta Logo
5:50 am - 1:48 pmBOS  Boston Logan Intl-YWG Winnipeg
7h 58m1 stop Minneapolis St Paul
$272Delta
Wed, Nov 25 - Mon, Nov 30
Delta Logo
6:35 am - 3:44 pmYWG  Winnipeg-BOS Boston Logan Intl
9h 09m1 stop Minneapolis St Paul
Delta Logo
2:59 pm - 12:33 amBOS  Boston Logan Intl-YWG Winnipeg
9h 34m1 stop Minneapolis St Paul
$312Delta
Thu, Feb 4 - Sun, Feb 7
Porter Airlines Logo
11:40 am - 8:32 pmYWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
Porter Airlines Logo
1:15 pm - 7:10 pmBOS  Boston Logan Intl-YWG Winnipeg
5h 55m1 stop Ottawa
$341Porter Airlines
Tue, Nov 24 - Sun, Nov 29
Porter Airlines Logo
11:40 am - 8:32 pmYWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
Porter Airlines Logo
8:00 am - 7:10 pmBOS  Boston Logan Intl-YWG Winnipeg
11h 10m2 stops Toronto Island Ottawa
$343Porter Airlines
Thu, Feb 4 - Sun, Feb 7
Porter Airlines Logo
11:40 am - 8:32 pmYWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
Porter Airlines Logo
8:00 am - 7:10 pmBOS  Boston Logan Intl-YWG Winnipeg
11h 10m2 stops Toronto Island Ottawa
$343Porter Airlines
Tue, Nov 24 - Sun, Nov 29
Delta Logo
12:45 pm - 10:44 pmYWG  Winnipeg-BOS Boston Logan Intl
9h 59m1 stop Minneapolis St Paul
Delta Logo
7:15 am - 5:42 pmBOS  Boston Logan Intl-YWG Winnipeg
10h 27m1 stop Minneapolis St Paul
$345Delta
Wed, Nov 25 - Thu, Dec 3
Delta Logo
6:35 am - 3:44 pmYWG  Winnipeg-BOS Boston Logan Intl
9h 09m1 stop Minneapolis St Paul
Delta Logo
5:35 am - 2:04 pmBOS  Boston Logan Intl-YWG Winnipeg
8h 29m1 stop Minneapolis St Paul
$351Delta
Wed, Nov 18 - Tue, Nov 24
Air Canada Logo
9:05 am - 1:53 pmYWG  Winnipeg-BOS Boston Logan Intl
4h 48m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
5:45 am - 1:49 pmBOS  Boston Logan Intl-YWG Winnipeg
8h 04m1 stop Toronto Pearson Intl
$528Air Canada
Tue, Nov 17 - Tue, Nov 24
Air Canada Logo
9:05 am - 1:53 pmYWG  Winnipeg-BOS Boston Logan Intl
4h 48m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
5:45 am - 1:49 pmBOS  Boston Logan Intl-YWG Winnipeg
8h 04m1 stop Toronto Pearson Intl
$531Air Canada
Mon, Nov 2 - Sun, Nov 8
Air Canada Logo
3:40 pm - 9:37 pmYWG  Winnipeg-BOS Boston Logan Intl
5h 57m1 stop Toronto Pearson Intl
Air Canada Logo
5:45 am - 3:49 pmBOS  Boston Logan Intl-YWG Winnipeg
10h 04m1 stop Toronto Pearson Intl
$558Air 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 $272, 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

$163
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 $272 to $1,199. 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 lower than usual. Average one-way flight prices are about $226, which is 14% below the typical average for this route.

  • 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) - 52% of one-stop connections
    • Montreal Pierre Elliott Trudeau Intl (YUL) - 24% of one-stop connections
    • Minneapolis St Paul (MSP) - 13% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 4% 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 58m, compared with 6h 20m via Ottawa (YOW) and 6h 25m 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