Flights from Winnipeg to Boston
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 7m
- two tickets, via Toronto
- $230
- connection options
- 2
- straight-line distance
- 1,345 mi (2,164 km)
fastest
Via Toronto
7h 7m
with the connection
Winnipeg to Toronto
flight 2h 26m
Connection of about 3h
Arrival: Pearson International. Departure to Boston: Pearson International, Toronto City Centre.
Toronto to Boston
flight 1h 41m
two ticketsfrom $230
Via Montreal
7h 13m
with the connection
Winnipeg to Montreal
flight 2h 45m
Connection of about 3h
Arrival: Montreal-Pierre Elliott Trudeau International, St. Hubert. Departure to Boston: Montreal-Pierre Elliott Trudeau International.
Montreal to Boston
flight 1h 28m
two ticketsfrom $397
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 Winnipeg to cities closest to Boston
Winnipeg to Montreal
Montreal: 250 mi (403 km) from Boston, flight 2h 45m
from $168
Winnipeg to Ottawa
Ottawa: 313 mi (503 km) from Boston, flight 2h 34m
from $203
Winnipeg to Toronto
Toronto: 430 mi (692 km) from Boston, flight 2h 26m
from $62
Winnipeg to Regina
Regina: 1,677 mi (2,699 km) from Boston, flight 40m
from $222
Winnipeg to Montego Bay
Montego Bay: 1,698 mi (2,733 km) from Boston, flight 4h 35m
Winnipeg to Cancun
Cancun: 1,727 mi (2,779 km) from Boston, flight 4h 50m
from $215
To Boston from cities closest to Winnipeg
Minneapolis to Boston
Minneapolis: 385 mi (619 km) from Winnipeg, flight 2h 52m
from $156
Des Moines to Boston
Des Moines: 598 mi (962 km) from Winnipeg, flight 2h 45m
from $490
Chicago to Boston
Chicago: 717 mi (1,154 km) from Winnipeg, flight 2h 26m
from $143
Grand Rapids to Boston
Grand Rapids: 725 mi (1,167 km) from Winnipeg, flight 2h 3m
from $85
Kansas City to Boston
Kansas City: 756 mi (1,216 km) from Winnipeg, flight 2h 59m
Denver to Boston
Denver: 798 mi (1,285 km) from Winnipeg, flight 3h 54m
from $117
Frequently asked questions
Is there a nonstop flight from Winnipeg to Boston?
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 Winnipeg to Boston?
Via Toronto: 2h 26m to the connection, 1h 41m after it, about 7h 7m in total with 3h for the connection.
How much does a flight from Winnipeg to Boston with a connection cost?
Two nonstop tickets via Toronto from $230. 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 Winnipeg and Boston?
Toronto (7h 7m total) and Montreal (7h 13m total).
How far is Boston from Winnipeg?
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.