BOS - YWG

£95 Find Cheap Flights from Boston to Winnipeg – Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest return flight
£219
Typical prices: £323-£563
United Airlines, Air Canada
Sat 13/10Tue 23/10
BOS - YWG • 1 stop
Cheapest one-way flight
£95
Typical prices: £132-£273
United Airlines
Sat 22/9
BOS - YWG • 2 stops
Direct 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 stopover airports
Calgary (YYC)
Cheapest • Avg £354 (return)
Montreal Pierre Elliott Trudeau Intl (YUL)
Shortest trip • 6h 03m (one-way)
Insights
Insights
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We hope you enjoy 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 return flight deals from Boston to Winnipeg

Tue, 13 Oct - Fri, 23 Oct
Multiple Airlines Logo
06:00 - 12:37BOS  Boston Logan Intl-YWG Winnipeg
7h 37m1 stop Chicago O'Hare Intl
Multiple Airlines Logo
05:00 - 11:50YWG  Winnipeg-BOS Boston Logan Intl
5h 50m1 stop Toronto Pearson Intl
£219Multiple Airlines
Tue, 13 Oct - Sat, 17 Oct
Multiple Airlines Logo
20:30 - 12:37BOS  Boston Logan Intl-YWG Winnipeg
17h 07m1 stop Chicago O'Hare Intl
Multiple Airlines Logo
05:00 - 14:41YWG  Winnipeg-BOS Boston Logan Intl
8h 41m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
£228Multiple Airlines
Tue, 13 Oct - Fri, 23 Oct
United Airlines Logo
20:25 - 12:37BOS  Boston Logan Intl-YWG Winnipeg
17h 12m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
14:00 - 00:54YWG  Winnipeg-BOS Boston Logan Intl
9h 54m1 stop Chicago O'Hare Intl
£228United Airlines
Fri, 16 Oct - Mon, 19 Oct
Multiple Airlines Logo
07:01 - 22:33BOS  Boston Logan Intl-YWG Winnipeg
16h 32m1 stop Chicago O'Hare Intl
Multiple Airlines Logo
13:30 - 21:26YWG  Winnipeg-BOS Boston Logan Intl
6h 56m2 stops Ottawa Montreal Pierre Elliott Trudeau Intl
£234Multiple Airlines
Tue, 13 Oct - Sat, 17 Oct
United Airlines Logo
06:00 - 22:33BOS  Boston Logan Intl-YWG Winnipeg
17h 33m1 stop Chicago O'Hare Intl
United Airlines Logo
14:00 - 23:25YWG  Winnipeg-BOS Boston Logan Intl
8h 25m1 stop Chicago O'Hare Intl
£235United Airlines
Tue, 27 Oct - Sat, 31 Oct
Multiple Airlines Logo
06:00 - 12:23BOS  Boston Logan Intl-YWG Winnipeg
7h 23m1 stop Chicago O'Hare Intl
Multiple Airlines Logo
11:20 - 21:28YWG  Winnipeg-BOS Boston Logan Intl
9h 08m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
£240Multiple Airlines
Mon, 1 Mar - Tue, 9 Mar
Delta Logo
15:00 - 23:34BOS  Boston Logan Intl-YWG Winnipeg
9h 34m1 stop Minneapolis St Paul
Delta Logo
12:30 - 23:53YWG  Winnipeg-BOS Boston Logan Intl
10h 23m1 stop Minneapolis St Paul
£344Delta
Sat, 26 Sep - Tue, 29 Sep
United Airlines Logo
14:15 - 22:33BOS  Boston Logan Intl-YWG Winnipeg
9h 18m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
United Airlines Logo
05:00 - 11:51YWG  Winnipeg-BOS Boston Logan Intl
5h 51m1 stop Toronto Pearson Intl
£344United Airlines
Mon, 1 Mar - Tue, 9 Mar
Delta Logo
15:00 - 23:34BOS  Boston Logan Intl-YWG Winnipeg
9h 34m1 stop Minneapolis St Paul
Delta Logo
12:30 - 23:53YWG  Winnipeg-BOS Boston Logan Intl
10h 23m1 stop Minneapolis St Paul
£366Delta
Thu, 22 Oct - Thu, 29 Oct
Porter Airlines Logo
10:05 - 15:20BOS  Boston Logan Intl-YWG Winnipeg
6h 15m1 stop Toronto Pearson Intl
Porter Airlines Logo
11:40 - 21:32YWG  Winnipeg-BOS Boston Logan Intl
8h 52m2 stops Ottawa Toronto Island
£385Porter Airlines
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 and 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 £376 return.
  • February (£678) and January (£621) 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.

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Key details for Boston to Winnipeg flights

Low season

March

Cheapest flight

£95
Best time to beat the crowds but there is an average 4% increase in price.
Flights 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 return 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).

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

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

  • 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 £377 return on average, while Sunday is the most expensive at £583, a difference of £206. 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 direct 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, return flight prices on this route showed a wide range, from about £219 to £1,831. That means the highest observed fare was about 8x 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 £95, which is 55% below the typical average for this route.

  • How much time can I save by choosing a different stopover airport from Boston to Winnipeg?

    Flying via Montreal Pierre Elliott Trudeau Intl (YUL) gives the shortest average 1-stop total travel time of 6h 03m, compared to 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.

  • Which car hire options are available at Winnipeg Airport (YWG)?

    Winnipeg Airport (YWG) hosts 5 major car hire companies, with daily rates starting from around £13 for economy cars. Top options include:
    • Thrifty
    • Dollar
    • Hertz
    • Alamo
    • Fox

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

    Return flights from Boston to Winnipeg range from £323 to £563, with an average of £445 over the past 12 months. Anything below £323 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 are flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average £377 – about £206 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 £376 return in that month – typically £302 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
    - The Grand Winnipeg Airport Hotel by Lakeview
    - Holiday Inn Express Winnipeg Airport - Polo Park By IHG

More options for your flight from Boston to Winnipeg

Complete your trip to Winnipeg with a hotel stay or car hire

Car hire in Winnipeg
Hotels in Winnipeg
Holidays in Winnipeg