Cheap flights from Winnipeg to Orlando from $156

The month of October is, on average, the cheapest month to fly to Orlando from Winnipeg, with most prices found around $244. If you’re not able to fly to Orlando in October, then September is your next best option. Flight prices from Winnipeg to Orlando during September average around $269.

Our data shows that Saturday is the least expensive day to fly to Orlando. Tickets to fly out on this day can be as low as $238. On the other hand, Thursday is the most expensive day to depart from Winnipeg because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $630.

The cheapest time of day to fly to Orlando is in the morning when flights can be purchased for as low as $342. In contrast, the most expensive time of day to depart to Orlando is in the afternoon when prices are around $583.

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 $330 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 $222 on momondo.

There is only 1 cabin class available to choose from on Winnipeg to Orlando flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 29% on your flight if you consider stops on a Winnipeg to Orlando flight.

As of March 2026, prices for Winnipeg to Orlando flights are approximately 44% more expensive when compared to flights at the same time last year.

Delta is the most popular carrier operating from Winnipeg to Orlando

WestJet, Delta and United Airlines 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 53% of people opting to fly with this airline when traveling to Orlando. Keep in mind that there are 4 different airlines that fly to Orlando on a routine basis, so you have a few additional options to choose from.

Historically, on average around 20% 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 163 minutes.

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

Saturday is statistically the day of the week which experiences the fewest number of 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 have had the least number of delays on this route over the last 12 months; with about 20% of their flights experiencing any sort of delay.

Ottawa (YOW) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Toronto (YYZ) offer the lowest average round-trip price of $277.

Flights connecting via Ottawa (YOW) have the shortest average one-way travel time: 6h 59m.

Toronto (YYZ) has the shortest average layover time for this route: 2h 19m.