Flights from Boston to Winnipeg
Pick a departure date to see flights and seller prices
We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.
Where to connect
Options with one connection, fastest first
- fastest, via Toronto
- 7h 46m
- two tickets, via Toronto
- $178
- connection options
- 2
- straight-line distance
- 1,345 mi (2,164 km)
fastest
Via Toronto
Canada
7h 46m
with the connection
Boston to Toronto
flight 2h 1m
Connection of about 3h
Arrival: Pearson International, Toronto City Centre. Departure to Winnipeg: Pearson International.
Toronto to Winnipeg
flight 2h 45m
two ticketsfrom $178
Via Montreal
Canada
8h 2m
with the connection
Boston to Montreal
flight 1h 25m
Connection of about 3h
Arrival: Montreal-Pierre Elliott Trudeau International. Departure to Winnipeg: Montreal-Pierre Elliott Trudeau International, St. Hubert.
Montreal to Winnipeg
flight 3h 37m
two ticketsfrom $322
One ticket or two
How the options are calculated and what to keep in mind at the connection
Flight times come from the nonstop schedule (estimated from the distance where there is no schedule), with 3h allowed for the connection. The price of an option is the sum of the lowest known fares for each leg; their dates may not match, so treat it as a guide. The search shows tickets for your dates, including connections on a single ticket.
Nearest nonstop flights
The closest you can get without a connection
From Boston to cities closest to Winnipeg
Boston to Minneapolis
Minneapolis: 385 mi (619 km) from Winnipeg, flight 3h 21m
from $153
Boston to Des Moines
Des Moines: 598 mi (962 km) from Winnipeg, flight 3h 25m
from $88
Boston to Chicago
Chicago: 717 mi (1,154 km) from Winnipeg, flight 3h 3m
from $119
Boston to Grand Rapids
Grand Rapids: 725 mi (1,167 km) from Winnipeg, flight 2h 24m
Boston to Calgary
Calgary: 747 mi (1,202 km) from Winnipeg, flight 5h 25m
from $340
Boston to Kansas City
Kansas City: 756 mi (1,216 km) from Winnipeg, flight 3h 43m
To Winnipeg from cities closest to Boston
Montreal to Winnipeg
Montreal: 250 mi (403 km) from Boston, flight 3h 37m
from $170
Ottawa to Winnipeg
Ottawa: 313 mi (503 km) from Boston, flight 2h 56m
from $141
Toronto to Winnipeg
Toronto: 430 mi (692 km) from Boston, flight 2h 45m
from $63
Regina to Winnipeg
Regina: 1,677 mi (2,699 km) from Boston, flight 3h 30m
Cancun to Winnipeg
Cancun: 1,727 mi (2,779 km) from Boston, flight 6h 10m
Saskatoon to Winnipeg
Saskatoon: 1,780 mi (2,864 km) from Boston, flight 1h 35m
from $242
Frequently asked questions
Is there a nonstop flight from Boston to Winnipeg?
There are no nonstop flights in the schedule. You will need a connection, the fastest is via Toronto.
What is the fastest way to fly from Boston to Winnipeg?
Via Toronto: 2h 1m to the connection, 2h 45m after it, about 7h 46m in total with 3h for the connection.
How much does a flight from Boston to Winnipeg with a connection cost?
Two nonstop tickets via Toronto from $178. This is the sum of the lowest known prices for each leg, and their dates may not match.
Which cities can you connect in between Boston and Winnipeg?
Toronto (7h 46m total) and Montreal (8h 2m total).
How far is Winnipeg from Boston?
1,345 mi (2,164 km) in a straight line between the cities.
How much time should I allow for the connection?
The options allow 3h. On a single ticket the carrier is responsible for the connection; on separate tickets you set the margin yourself, allowing time to collect and re-check your bags.