Cheap flights from Winnipeg to Orlando from C$ 286

The month of January is, on average, the cheapest month to fly to Orlando from Winnipeg, with most prices found around C$ 111. If you’re not able to fly to Orlando in January, then November is your next best option. Flight prices from Winnipeg to Orlando during November average around C$ 118.

According to our data, Saturday is the cheapest day to fly to Orlando from Winnipeg. The lowest ticket price found for a Saturday departure recently was C$ 326. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 684.

Flying to Orlando from Winnipeg in the morning is the least expensive time of day to depart. momondo users have found prices as low as C$ 473 when looking at flights departing in the morning. In contrast, the most expensive time of day to depart to Orlando is in the afternoon when prices are around C$ 636.

Fly from Winnipeg to Orlando for the best Winnipeg - Orlando flight prices

You are more likely to see cheaper flights to Orlando from Winnipeg when booking weeks ahead of your departure date. In general, you can expect to find flights to Orlando for around C$ 502 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Orlando from Winnipeg for as low as C$ 329 on momondo.

No. A direct flight is the cheapest option for a flight between Winnipeg to Orlando.

As of May 2026, prices for Winnipeg to Orlando flights are approximately 18% cheaper when compared to flights at the same time last year.

United Airlines, Air Canada, and WestJet are the most popular carriers operating from Winnipeg to Orlando

WestJet, Porter Airlines and Air Canada are the top three most popular airlines that fly to Orlando from Winnipeg according to our data. WestJet is the first choice among our users, with 50% of people opting to fly with this airline when travelling to Orlando. Keep in mind that there are 5 different airlines that fly to Orlando on a routine basis, so you have a few additional options to choose from.

Historically, on average around 18% of flights between Winnipeg and Orlando have experienced a delay on any given week. The average delay length over the past 12 months has been 171 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights departing in the early afternoon have, in the past, seen delays more frequently in comparison.

Thursday is statistically the day of the week that experiences the fewest delays on this flight route. Friday has historically seen more delays on average compared to the rest of the week.

According to our data, WestJet has had the least delays on this route over the last 12 months, with about 18% of their flights experiencing any sort of delay.

Ottawa (YOW) was the most common stop: 46% of momondo users choosing one-stop flights on this route connected there.

Flights via Ottawa (YOW) offer the lowest average round-trip price of C$ 341.

Flights connecting via Minneapolis (MSP) have the shortest average one-way travel time: 5h 46m.

Minneapolis (MSP) has the shortest average layover time for this route: 0h 49m.