How to get from Winnipeg to Orlando: connecting flights, about 8h 29m total

Flights from Winnipeg to Orlando

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.

Best fares from Winnipeg to Orlando

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $225 24 February 2027, with a connection Cheapest month February 2027 tickets from $225

Where to connect

Options with one connection, fastest first

fastest, via Toronto: 8h 29m
two tickets, via Toronto: $218
connection options: 2
straight-line distance: 1,692 mi (2,723 km)

fastest

Via Toronto

8h 29m

with the connection

Winnipeg to Toronto flight 2h 26m

Connection of about 3h Arrival: Pearson International. Departure to Orlando: Hamilton, Pearson International.

Toronto to Orlando flight 3h 3m

two ticketsfrom $218

Via Cancun

Mexico

9h 55m

with the connection

Winnipeg to Cancun flight 4h 50m

Connection of about 3h

Cancun to Orlando flight 2h 5m

two ticketsfrom $517

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 Orlando

Winnipeg to Cancun Cancun: 614 mi (988 km) from Orlando, flight 4h 50m from $213 Winnipeg to Montego Bay Montego Bay: 729 mi (1,173 km) from Orlando, flight 4h 35m Winnipeg to Toronto Toronto: 1,051 mi (1,691 km) from Orlando, flight 2h 26m from $62 Winnipeg to Ottawa Ottawa: 1,207 mi (1,942 km) from Orlando, flight 2h 34m from $231 Winnipeg to Montreal Montreal: 1,248 mi (2,009 km) from Orlando, flight 2h 45m from $168 Winnipeg to Regina Regina: 1,939 mi (3,121 km) from Orlando, flight 40m from $222

To Orlando from cities closest to Winnipeg

Sioux Falls to Orlando Sioux Falls: 439 mi (706 km) from Winnipeg, flight 3h 6m Appleton to Orlando Appleton: 565 mi (909 km) from Winnipeg, flight 2h 53m Omaha to Orlando Omaha: 599 mi (964 km) from Winnipeg, flight 2h 55m from $208 Chicago to Orlando Chicago: 717 mi (1,154 km) from Winnipeg, flight 2h 46m from $81 Grand Rapids to Orlando Grand Rapids: 725 mi (1,167 km) from Winnipeg, flight 2h 41m from $92 Denver to Orlando Denver: 798 mi (1,285 km) from Winnipeg, flight 3h 38m from $175

Frequently asked questions

Is there a nonstop flight from Winnipeg to Orlando?

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 Orlando?

Via Toronto: 2h 26m to the connection, 3h 3m after it, about 8h 29m in total with 3h for the connection.

How much does a flight from Winnipeg to Orlando with a connection cost?

Two nonstop tickets via Toronto from $218. 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 Orlando?

Toronto (8h 29m total) and Cancun (9h 55m total).

How far is Orlando from Winnipeg?

1,692 mi (2,723 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.