Cheap Flights from Orlando to Winnipeg

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Flight deals from Orlando to Winnipeg

Looking for a cheap last-minute deal or the best round-trip flight from Orlando to Winnipeg Airport? If you want to travel next month, round-trip fares start from $344. Find the lowest prices on one-way and round-trip tickets right here.

Winnipeg.$344 per passenger.Departing Tue, Oct 20, returning Tue, Oct 27.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Orlando International on Tue, Oct 20, arriving in Winnipeg.Inbound indirect flight with WestJet, departing from Winnipeg on Tue, Oct 27, arriving in Orlando International.Price includes taxes and charges.From $344, select.

Winnipeg.$371 per passenger.Departing Fri, Sep 25, returning Mon, Sep 28.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Orlando International on Fri, Sep 25, arriving in Winnipeg.Inbound indirect flight with WestJet, departing from Winnipeg on Mon, Sep 28, arriving in Orlando International.Price includes taxes and charges.From $371, select.

Winnipeg.$372 per passenger.Departing Tue, Oct 27, returning Tue, Nov 3.Round-trip flight with Porter Airlines and WestJet.Outbound indirect flight with Porter Airlines, departing from Orlando International on Tue, Oct 27, arriving in Winnipeg.Inbound indirect flight with WestJet, departing from Winnipeg on Tue, Nov 3, arriving in Orlando International.Price includes taxes and charges.From $372, select.

Winnipeg.$421 per passenger.Departing Fri, Dec 11, returning Fri, Dec 18.Round-trip flight with WestJet.Outbound indirect flight with WestJet, departing from Orlando International on Fri, Dec 11, arriving in Winnipeg.Inbound indirect flight with WestJet, departing from Winnipeg on Fri, Dec 18, arriving in Orlando International.Price includes taxes and charges.From $421, select.

Winnipeg.$425 per passenger.Departing Fri, Apr 2, returning Fri, Apr 16.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Fri, Apr 2, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Fri, Apr 16, arriving in Orlando International.Price includes taxes and charges.From $425, select.

Winnipeg.$425 per passenger.Departing Mon, Mar 15, returning Fri, Mar 19.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Mon, Mar 15, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Fri, Mar 19, arriving in Orlando International.Price includes taxes and charges.From $425, select.

Winnipeg.$425 per passenger.Departing Sun, Feb 7, returning Sun, Feb 14.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Sun, Feb 7, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Sun, Feb 14, arriving in Orlando International.Price includes taxes and charges.From $425, select.

Winnipeg.$425 per passenger.Departing Mon, Mar 15, returning Fri, Apr 2.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Mon, Mar 15, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Fri, Apr 2, arriving in Orlando International.Price includes taxes and charges.From $425, select.

Winnipeg.$453 per passenger.Departing Fri, Jan 8, returning Sat, Jan 9.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Fri, Jan 8, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Sat, Jan 9, arriving in Orlando International.Price includes taxes and charges.From $453, select.

Winnipeg.$454 per passenger.Departing Mon, Jan 25, returning Sat, Feb 6.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Mon, Jan 25, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Sat, Feb 6, arriving in Orlando International.Price includes taxes and charges.From $454, select.

Winnipeg.$472 per passenger.Departing Tue, Nov 17, returning Sat, Dec 5.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Tue, Nov 17, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Sat, Dec 5, arriving in Orlando International.Price includes taxes and charges.From $472, select.

Winnipeg.$488 per passenger.Departing Fri, Feb 26, returning Fri, Mar 19.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Fri, Feb 26, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Fri, Mar 19, arriving in Orlando International.Price includes taxes and charges.From $488, select.

Winnipeg.$501 per passenger.Departing Tue, Nov 17, returning Sat, Nov 21.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Tue, Nov 17, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Sat, Nov 21, arriving in Orlando International.Price includes taxes and charges.From $501, select.

Winnipeg.$533 per passenger.Departing Fri, Dec 25, returning Sat, Jan 9.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Fri, Dec 25, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Sat, Jan 9, arriving in Orlando International.Price includes taxes and charges.From $533, select.

Winnipeg.$540 per passenger.Departing Tue, Sep 29, returning Mon, Oct 19.Round-trip flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departing from Orlando International on Tue, Sep 29, arriving in Winnipeg.Inbound indirect flight with Porter Airlines, departing from Winnipeg on Mon, Oct 19, arriving in Orlando International.Price includes taxes and charges.From $540, select.

Find the cheapest month to fly from Orlando to Winnipeg

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Orlando to Winnipeg flights are currently cheapest in October.

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Direct flights from Orlando to Winnipeg

Orlando to Winnipeg: Alternative routes

Compare routes from Orlando to Winnipeg below. You may find an airport to fly into that's cheaper, faster, or easier than Winnipeg.

Winnipeg

7km from central Winnipeg

ClosestCheapest

from $344

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Orlando to Winnipeg: Flight information

The things to know before you go.

Cheapest flight found	$344
Cheapest month to fly	October
Average flight time	4 hrs, 30 mins
Most popular airline	Delta
Average flights per week	14

Finding cheap flights from Orlando to Winnipeg: Frequently asked questions

How much are round-trip flights from Orlando to Winnipeg?

The best price we found for a round-trip flight from Orlando to Winnipeg is $344. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Orlando to Winnipeg?

4 hours and 30 minutes is the average flight time from Orlando to Winnipeg.

Which airlines fly direct from Orlando to Winnipeg?

Delta, Aeromexico and WestJet fly direct from Orlando to Winnipeg.

How many flights are there a week from Orlando to Winnipeg?

There are 7 flights per week flying from Orlando to Winnipeg, as of September 2026.

When is the cheapest time to fly from Orlando to Winnipeg?

The cheapest month to fly from Orlando to Winnipeg is usually October.

Which upcoming date is cheapest to fly from Orlando to Winnipeg Airport on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Orlando to Winnipeg Airport on Tuesday, October 20, 2026.

Can I get a direct flight from Orlando to Winnipeg Airport?

Yes – the average flight time is 4 hours and 30 minutes.

How can I find the best flight deal to Winnipeg?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Winnipeg but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Winnipeg?

We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Winnipeg is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly with from Orlando to Winnipeg?

The cheapest airline that flies to Winnipeg is WestJet.

Flying from Orlando to Winnipeg James Armstrong Richardson Intl Airport (YWG): What you need to know

Orlando's main base, Orlando International Airport (MCO), is where great travel stories take off. Explore your departure options from here for your flight from Orlando to Winnipeg James Armstrong Richardson Intl Airport (YWG).
Expect to be traveling for 4 hours 25 minutes. That's the average journey time for a direct Orlando to Winnipeg James Armstrong Richardson Intl Airport flight.
The timezone in Winnipeg is UTC-6, which is one hour behind Orlando. Winnipeg James Armstrong Richardson Intl Airport is located in Winnipeg.
Give yourself plenty of time to make your flight from Orlando to YWG. As a general rule, turn up at least two hours before international departures and an hour ahead for domestic flights.
With more travelers during busy periods like March, get to the terminal earlier than usual. Two hours for domestic flights and as much as four for international journeys will allow extra time for delays. Remember things also get busy during major holidays like Christmas and local events or festivals.

Airports in Orlando

Orlando International Airport (MCO)

Get there in one go from Orlando International Airport (MCO). Nonstop flights from Orlando to Winnipeg James Armstrong Richardson Intl Airport (YWG) can be booked from here.
When jetting out of MCO, you can catch a direct flight from Orlando to Winnipeg James Armstrong Richardson Intl Airport with WestJet.
WestJet is the most frequently chosen airline for flights from MCO to YWG.
The most punctual carrier on this route is WestJet. Its services land as planned 69.7% of the time.
A stopover is the ideal opportunity to break up your journey and possibly even explore another city. When searching for cheap flights from Orlando to YWG leaving from Orlando International Airport (MCO), uncheck the 'Direct flights only' box to get ideas for where to visit along the way. Here's where you could connect through:
- Atlanta Hartsfield-Jackson International Airport (ATL)
- Minneapolis-Saint Paul International Airport (MSP)
- Nashville International Airport (BNA)
Located around 19 kilometers from the center of Orlando, MCO can be reached in about 25 minutes by car (depending on traffic). The journey by public transport takes roughly 1 hour.
Catching an early flight from Orlando to Winnipeg James Armstrong Richardson Intl Airport? Avoid the last-minute rush to the terminal (and get some extra shut-eye) by staying at one of these hotels close to Orlando International Airport:
Of the departures from Orlando International Airport, 77% touch down on time at their destination.
The address for MCO is One Airport Boulevard.

Orlando Sanford International Airport (SFB)

Using public transport, you can travel from central Orlando to SFB in around 1 hour. The airport is roughly 40 kilometers away, and getting there by car will take approximately 35 minutes.
Want to enjoy an extra night away before catching your Orlando to YWG flight? Check in to a hotel near Orlando Sanford International Airport before your vacation officially begins. These stays are calling your name:
69% of flights departing Orlando Sanford International Airport arrive within the expected time frame.

About Winnipeg James Armstrong Richardson Intl Airport (YWG)

Have a late flight from Orlando to Winnipeg James Armstrong Richardson Intl Airport? Don't let it hijack your sleep schedule. Stay at one of these hotels near YWG and turn in quicker:
Get the best deal by booking your ride around one week before your Orlando to Winnipeg James Armstrong Richardson Intl Airport flight.
YWG is located at 2000 Wellington Avenue.

Getting from Winnipeg James Armstrong Richardson Intl Airport (YWG) to central Winnipeg

Central Winnipeg is around 13 kilometers from Winnipeg James Armstrong Richardson Intl Airport and takes about 20 minutes to reach by car. Work out your options for getting into the city, whether that's with a car rental, cab or ride-share.
Traveling on public transport typically takes 40 minutes.

How to find the cheapest flights from Orlando to Winnipeg James Armstrong Richardson Intl Airport (YWG)

The lowest price we've found for a one-way ticket from Orlando to Winnipeg James Armstrong Richardson Intl Airport is $125. For a return flight on this route, the best price is $344. Depending on the availability when you book, these fares could change.
Book six months before traveling. Research into pricing trends suggests this is the ideal window for finding cheap flights from Orlando to YWG.
The best month for picking up cheap Orlando to Winnipeg James Armstrong Richardson Intl Airport tickets is November. Use the 'Whole month' tool to compare prices, then choose the dates with the lowest fares.
Be the first to know about deals for plane tickets from Orlando to YWG by setting up a Price Alert. We'll send you an email or notification through the app when a new discounted fare appears.
Tailor your trip using filters. Select your preferred arrival and departure times, airlines and total journey duration. You can also sort your results by 'Cheapest,' 'Fastest' or 'Best' flights from Orlando to Winnipeg James Armstrong Richardson Intl Airport.

The best time to fly from Orlando to Winnipeg James Armstrong Richardson Intl Airport (YWG)

It's time to work out your travel dates for your flight from Orlando to Winnipeg James Armstrong Richardson Intl Airport (YWG). July is the busiest month to visit Winnipeg. If a slower pace sounds more appealing, go in January.
When booking your Orlando to YWG plane ticket, consider the type of weather you enjoy. July is the warmest month in Winnipeg, with temperatures ranging from 12ºC (54ºF) to 29ºC (84ºF).
For cooler conditions, search for a cheap ticket from Orlando to Winnipeg James Armstrong Richardson Intl Airport in January when temperatures are between -25ºC (-13ºF) and -6ºC (21ºF).

More about Winnipeg

Once you've booked your flight from Orlando to Winnipeg James Armstrong Richardson Intl Airport, find a hotel that keeps you close to what you want to see. Make one of these accommodation options your base for exploring Winnipeg:
Every great adventure has to include some sightseeing. Canadian Museum for Human Rights, Vimy Ridge Memorial Park and Saint Mary's Cathedral are must-do's during your Winnipeg adventure.

Explore more of Canada

Winnipeg will leave a lasting impression, but there are so many other corners of Canada just waiting to be explored. Around 193 kilometers west of Winnipeg, a trip to Brandon will keep your itinerary busy. Don't miss top attractions like The Daly House Museum, Commonwealth Air Training Plan Museum and Patricia Beach Provincial Park.
Around 209 kilometers east of Winnipeg, Kenora is another essential stop in Canada. Experience this destination's highlights firsthand at Morgan Falls, Husky The Muskie and Cecilia Jeffery Indian Residential School Memorial.