YWG - BOS

C$ 189 Find Cheap Flights from Winnipeg to Boston – Compare and Save

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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

Wed, 30 Sep - Mon, 5 Oct
Air Canada Logo
5:00 a.m. - 11:51 a.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 51m1 stop Toronto Pearson Intl
Air Canada Logo
7:05 p.m. - 9:57 a.m.BOS  Boston Logan Intl-YWG Winnipeg
15h 52m1 stop Toronto Pearson Intl
C$ 343Air Canada
Sat, 19 Sep - Sat, 26 Sep
Air Canada Logo
5:00 a.m. - 11:51 a.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 51m1 stop Toronto Pearson Intl
Air Canada Logo
12:30 p.m. - 6:12 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 42m1 stop Toronto Pearson Intl
C$ 349Air Canada
Sat, 3 Oct - Sat, 10 Oct
Air Canada Logo
5:00 a.m. - 11:50 a.m.YWG  Winnipeg-BOS Boston Logan Intl
5h 50m1 stop Toronto Pearson Intl
Air Canada Logo
4:55 p.m. - 11:47 p.m.BOS  Boston Logan Intl-YWG Winnipeg
7h 52m1 stop Toronto Pearson Intl
C$ 349Air Canada
Tue, 22 Sep - Thu, 24 Sep
United Airlines Logo
2:00 p.m. - 1:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 10m1 stop Chicago O'Hare Intl
United Airlines Logo
7:55 a.m. - 10:33 p.m.BOS  Boston Logan Intl-YWG Winnipeg
15h 38m1 stop Chicago O'Hare Intl
C$ 357United Airlines
Tue, 22 Sep - Thu, 24 Sep
United Airlines Logo
2:00 p.m. - 1:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 10m1 stop Chicago O'Hare Intl
United Airlines Logo
10:35 a.m. - 10:33 p.m.BOS  Boston Logan Intl-YWG Winnipeg
12h 58m1 stop Chicago O'Hare Intl
C$ 359United Airlines
Tue, 22 Sep - Thu, 24 Sep
United Airlines Logo
2:00 p.m. - 1:10 a.m.YWG  Winnipeg-BOS Boston Logan Intl
10h 10m1 stop Chicago O'Hare Intl
United Airlines Logo
7:55 a.m. - 10:33 p.m.BOS  Boston Logan Intl-YWG Winnipeg
15h 38m1 stop Chicago O'Hare Intl
C$ 359United Airlines
Sun, 4 Oct - Sun, 11 Oct
Porter Airlines Logo
9:20 a.m. - 6:35 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 15m1 stop Toronto Pearson Intl
Porter Airlines Logo
10:05 a.m. - 3:20 p.m.BOS  Boston Logan Intl-YWG Winnipeg
6h 15m1 stop Toronto Pearson Intl
C$ 364Porter Airlines
Sat, 3 Oct - Sat, 10 Oct
Multiple Airlines Logo
2:00 p.m. - 9:58 p.m.YWG  Winnipeg-BOS Boston Logan Intl
6h 58m1 stop Chicago O'Hare Intl
Multiple Airlines Logo
5:50 a.m. - 2:22 p.m.BOS  Boston Logan Intl-YWG Winnipeg
9h 32m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
C$ 371Multiple Airlines
Sat, 3 Oct - Sat, 10 Oct
Multiple Airlines Logo
2:00 p.m. - 11:59 p.m.YWG  Winnipeg-BOS Boston Logan Intl
8h 59m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
Multiple Airlines Logo
5:50 a.m. - 4:27 p.m.BOS  Boston Logan Intl-YWG Winnipeg
11h 37m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
C$ 385Multiple Airlines
Thu, 26 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$ 388Porter Airlines
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$ 343. Prices are below average for this route right now, with typical round-trip fares ranging from C$ 473 to C$ 776. The lowest price found in the past 5 days was C$ 343 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$ 388 round-trip.
  • April (C$ 1,262) and December (C$ 801) 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$ 189
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 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 cabin classes can I book on flights from Winnipeg to Boston?

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

  • 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$ 492 round-trip on average, while Wednesday is the most expensive at C$ 701, a difference of C$ 208. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • Which popular places can I visit in Boston?

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

  • 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.

  • 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$ 343 to C$ 1,341. 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 C$ 228, which is 37% below the typical average for this route.

  • 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.

  • 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$ 32 for economy cars. Top options include:
    · Dollar
    · Hertz
    · Budget
    · Thrifty
    · Sixt

  • How much should I expect to pay for a Winnipeg to Boston flight?

    Round-trip flights from Winnipeg to Boston range from C$ 473 to C$ 776, with an average of C$ 612 over the past 12 months. Anything below C$ 473 counts as a good deal.

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$ 492 – about C$ 208 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$ 388 round-trip in that month – typically C$ 874 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.
    - Embassy Suites by Hilton Boston at Logan Airport
    - Hilton Garden Inn Boston Logan Airport
    - Hilton 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
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