YWG - BOS

C$ 206 Find Cheap Flights from Winnipeg to Boston – Compare and Save

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Everything you should know

Cheapest round-trip
C$ 347
Typical prices: C$ 482-C$ 790
Air Canada
Sat 3/11Sat 10/11
YWG - BOS • 2 stops
Cheapest one-way flights
C$ 206
Typical prices: C$ 279-C$ 506
Air Canada
Thu 11/10
YWG - BOS • 1 stop
Direct 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 • 37% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Atlanta Hartsfield-Jackson (ATL)
Cheapest • Avg C$ 324 (round-trip)
Montreal Pierre Elliott Trudeau Intl (YUL)
Shortest trip • 5h 58m (one-way)
Insights
Insights
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We hope you enjoy your trip to Boston!
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

Tue, 3 Nov - Tue, 10 Nov
Air Canada Logo
6:00 a.m. - 2:53 p.m.YWG  Winnipeg-BOS Boston Logan Intl
7h 53m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
10:25 a.m. - 4:38 p.m.BOS  Boston Logan Intl-YWG Winnipeg
7h 13m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 347Air Canada
Tue, 24 Nov - Sun, 29 Nov
Porter Airlines Logo
11:40 a.m. - 9:32 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
Porter Airlines Logo
8:00 a.m. - 6:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 10m2 stops Toronto Island Ottawa
C$ 350Porter Airlines
Wed, 25 Nov - Mon, 30 Nov
Porter Airlines Logo
11:40 a.m. - 9:32 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
Porter Airlines Logo
8:00 a.m. - 6:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 10m2 stops Toronto Island Ottawa
C$ 358Porter Airlines
Tue, 20 Oct - Tue, 27 Oct
United Airlines Logo
2:00 p.m. - 11:24 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 24m1 stop Chicago O'Hare Intl
United Airlines Logo
6:00 a.m. - 12:23 p.m.BOS  Boston Logan Intl-YWG Winnipeg
7h 23m1 stop Chicago O'Hare Intl
C$ 364United Airlines
Tue, 20 Oct - Tue, 27 Oct
United Airlines Logo
2:00 p.m. - 10:32 a.m.YWG  Winnipeg-BOS Boston Logan Intl
19h 32m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
United Airlines Logo
7:41 p.m. - 12:23 p.m.BOS  Boston Logan Intl-YWG Winnipeg
17h 42m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
C$ 364United Airlines
Tue, 3 Nov - Tue, 10 Nov
Delta Logo
5:40 p.m. - 12:20 a.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 40m1 stop Minneapolis St Paul
Delta Logo
6:15 p.m. - 11:33 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 18m1 stop Minneapolis St Paul
C$ 364Delta
Tue, 3 Nov - Tue, 10 Nov
Porter Airlines Logo
11:40 a.m. - 9:32 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
Porter Airlines Logo
1:15 p.m. - 6:10 p.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 55m1 stop Ottawa
C$ 364Porter Airlines
Sat, 5 Dec - Wed, 9 Dec
Air Canada Logo
2:05 p.m. - 9:28 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 23m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
5:45 a.m. - 11:49 a.m.BOS  Boston Logan Intl-YWG Winnipeg
7h 04m1 stop Toronto Pearson Intl
C$ 374Air Canada
Tue, 10 Nov - Sat, 14 Nov
Air Canada Logo
5:15 a.m. - 2:53 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 38m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
5:30 a.m. - 10:05 a.m.BOS  Boston Logan Intl-YWG Winnipeg
5h 35m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 378Air Canada
Wed, 20 Jan - Tue, 26 Jan
Delta Logo
5:38 p.m. - 11:53 p.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 15m1 stop Minneapolis St Paul
Delta Logo
3:00 p.m. - 11:34 p.m.BOS  Boston Logan Intl-YWG Winnipeg
9h 34m1 stop Minneapolis St Paul
C$ 389Delta
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 from Winnipeg to Boston with more confidence.

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

Round-trip flights from Winnipeg to Boston start at C$ 347. Prices are below average for this route right now, with typical round-trip fares ranging from C$ 482 to C$ 790. The lowest price found in the past 5 days was C$ 347 on Air Canada.

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

Tuesday is the cheapest day of the week to fly from Winnipeg to Boston and is 20% cheaper than the average day. Wednesday is the most expensive day with flight prices 14% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

•January is the cheapest month to fly from Winnipeg to Boston at C$ 395 round-trip.
•April (C$ 1,285) and December (C$ 816) 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

April

Cheapest flight

C$ 206
Best time to beat the crowds but there is an average 106% increase in price.
Most popular time to fly and prices are also 22% lower on average.
Flights 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 route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

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

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

    • Economy Class
    • First Class

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

    A direct flight from Winnipeg to Boston takes 0h 00m, covering 3,495 km.

  • 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 C$ 482 to C$ 790, with an average of C$ 623 over the past 12 months. Anything below C$ 482 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 C$ 347 to C$ 1,675. That means the highest observed fare was about 5x 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 C$ 222, which is 40% 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 C$ 33 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

    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 Winnipeg to Boston?

    Yes. Being flexible with your travel dates can save you up to 30% on the Winnipeg to Boston route. Tuesday is the cheapest departure day at C$ 502 round-trip on average, while Wednesday is the most expensive at C$ 714, a difference of C$ 212. 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 when travelling 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.

  • Which popular places can I visit in Boston?

    Some of the most popular sights in Boston are Fenway Park, TD Garden, 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 instead of Wednesday. On this route, Tuesday flights average C$ 502 – about C$ 212 less than Wednesday (30% 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 C$ 395 round-trip in that month – typically C$ 891 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.
    - Hilton Boston Logan Airport
    - Hilton Garden Inn Boston Logan Airport
    - Embassy Suites by Hilton Boston at 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