BOS - YWG

$132 Find Cheap Flights from Boston to Winnipeg - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$267
Typical prices: $437-$762
Porter Airlines, WestJet
Tue 10/16Fri 10/19
BOS - YWG • 1 stop
Cheapest one-way
$132
Typical prices: $178-$369
Air Canada
Sat 10/6
BOS - YWG • 2 stops
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
August
Cheapest • 15% price drop
June
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
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Winnipeg!
Flight Deals
Booking Insights
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

Fri, Oct 16 - Mon, Oct 19
Multiple Airlines Logo
10:05 am - 3:20 pmBOS  Boston Logan Intl-YWG Winnipeg
6h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
7:00 am - 5:40 pmYWG  Winnipeg-BOS Boston Logan Intl
9h 40m1 stop Calgary
$267Multiple Airlines
Fri, Oct 16 - Mon, Oct 19
Multiple Airlines Logo
7:01 am - 10:33 pmBOS  Boston Logan Intl-YWG Winnipeg
16h 32m1 stop Chicago O'Hare Intl
Multiple Airlines Logo
1:30 pm - 9:26 pmYWG  Winnipeg-BOS Boston Logan Intl
6h 56m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
$298Multiple Airlines
Thu, Oct 22 - Sat, Oct 24
United Airlines Logo
6:00 am - 12:37 pmBOS  Boston Logan Intl-YWG Winnipeg
7h 37m1 stop Chicago O'Hare Intl
United Airlines Logo
2:00 pm - 9:59 pmYWG  Winnipeg-BOS Boston Logan Intl
6h 59m1 stop Chicago O'Hare Intl
$299United Airlines
Thu, Oct 22 - Sat, Oct 24
Air Canada Logo
5:50 am - 4:27 pmBOS  Boston Logan Intl-YWG Winnipeg
11h 37m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
Air Canada Logo
5:00 am - 11:50 amYWG  Winnipeg-BOS Boston Logan Intl
5h 50m1 stop Toronto Pearson Intl
$309Air Canada
Thu, Oct 15 - Thu, Oct 15
Air Canada Logo
6:00 am - 11:12 amBOS  Boston Logan Intl-YWG Winnipeg
6h 12m1 stop Toronto Pearson Intl
Air Canada Logo
1:30 pm - 9:26 pmYWG  Winnipeg-BOS Boston Logan Intl
6h 56m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
$311Air Canada
Wed, Nov 11 - Wed, Nov 18
Porter Airlines Logo
1:15 pm - 6:10 pmBOS  Boston Logan Intl-YWG Winnipeg
5h 55m1 stop Ottawa
Porter Airlines Logo
11:40 am - 9:32 pmYWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
$314Porter Airlines
Wed, Nov 11 - Wed, Nov 18
Porter Airlines Logo
8:00 am - 6:10 pmBOS  Boston Logan Intl-YWG Winnipeg
11h 10m2 stops Toronto Island Ottawa
Porter Airlines Logo
11:40 am - 9:32 pmYWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
$322Porter Airlines
Wed, Nov 11 - Wed, Nov 18
United Airlines Logo
6:00 am - 12:23 pmBOS  Boston Logan Intl-YWG Winnipeg
7h 23m1 stop Chicago O'Hare Intl
United Airlines Logo
2:15 pm - 11:35 pmYWG  Winnipeg-BOS Boston Logan Intl
8h 20m1 stop Chicago O'Hare Intl
$337United Airlines
Mon, Mar 1 - Tue, Mar 9
Delta Logo
3:00 pm - 11:34 pmBOS  Boston Logan Intl-YWG Winnipeg
9h 34m1 stop Minneapolis St Paul
Delta Logo
12:30 pm - 11:53 pmYWG  Winnipeg-BOS Boston Logan Intl
10h 23m1 stop Minneapolis St Paul
$338Delta
Mon, Mar 1 - Tue, Mar 9
Delta Logo
3:00 pm - 11:34 pmBOS  Boston Logan Intl-YWG Winnipeg
9h 34m1 stop Minneapolis St Paul
Delta Logo
12:30 pm - 11:53 pmYWG  Winnipeg-BOS Boston Logan Intl
10h 23m1 stop Minneapolis St Paul
$355Delta
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 from Boston to Winnipeg with more confidence.

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

Wednesday is the cheapest day of the week to fly from Boston to Winnipeg, it is 16% cheaper than the average day. Sunday is the most expensive day with flight prices 31% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

•August is the cheapest month to fly from Boston to Winnipeg at $509 round-trip.
•February ($918) and January ($841) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 80% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Boston to Winnipeg flights

Low season

March

Cheapest flight

$132
Best time to beat the crowds but there is an average 4% increase in price.
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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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).

  • 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

  • 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) - 55% of one-stop connections
    • Minneapolis St Paul (MSP) - 17% of one-stop connections
    • Montreal Pierre Elliott Trudeau Intl (YUL) - 17% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 9% 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 Boston to Winnipeg?

    Yes. Being flexible with your travel dates can save you up to 36% on the Boston to Winnipeg route. Wednesday is the cheapest departure day at $510 round-trip on average, while Sunday is the most expensive at $789, a difference of $279. 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 long is a flight from Boston to Winnipeg?

    A nonstop flight from Boston to Winnipeg takes 0h 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.

  • 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 $267 to $1,154. 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 lower than usual. Average one-way flight prices are about $155, which is 46% below the typical average for this route.

  • 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 24m via Toronto Pearson Intl (YYZ) and 7h 27m 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.

  • What car rental options are available at Winnipeg Airport (YWG)?

    Winnipeg Airport (YWG) hosts 5 major car rental companies, with daily rates starting from around $18 for economy cars. Top options include:
    • Thrifty
    • Dollar
    • Hertz
    • Alamo
    • Fox

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

    Round-trip flights from Boston to Winnipeg range from $437 to $762, with an average of $602 over the past 12 months. Anything below $437 counts as a good deal.

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 can be flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average $510 - about $279 less than Sunday (35% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Boston to Winnipeg trip for August. Fares historically average $509 round-trip in that month - typically $409 less than the most expensive month, which is February (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
    - The Grand Winnipeg Airport Hotel by Lakeview

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