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Cheap flights from Winnipeg to Orlando from C$ 286

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 17/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — ORL
13 Jun — 20 Jun1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Orlando are usually found in October or September, booked 14 days in advance, depart on a Saturday or Monday and return on a Tuesday

Cheap flight deals from Winnipeg to Orlando

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Orlando
Explore the most affordable flight options available from Winnipeg to Orlando. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 14 May 2026.

Thu 28/55:41 p.m.
YWG
-
MCO
1 stop5h 39m
Delta
Wed 3/66:05 a.m.
MCO
-
YWG
1 stop5h 49m
Delta
Deal found 11/5C$ 464
Mon 8/68:00 a.m.
YWG
-
MCO
1 stop9h 31m
Air Canada
Mon 15/68:35 p.m.
MCO
-
YWG
1 stop14h 34m
Air Canada
Deal found 11/5C$ 474
Fri 2/1010:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Mon 5/105:05 p.m.
MCO
-
YWG
1 stop8h 50m
WestJet
Deal found 10/5C$ 478
Sun 13/910:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Wed 23/911:30 a.m.
MCO
-
YWG
1 stop9h 50m
WestJet
Deal found 13/5C$ 485
Sun 13/910:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Sat 19/98:35 p.m.
MCO
-
YWG
1 stop29h 20m
WestJet
Deal found 13/5C$ 486
Sat 13/612:56 p.m.
YWG
-
MCO
2 stops11h 05m
United Airlines
Mon 15/64:26 p.m.
MCO
-
YWG
1 stop7h 12m
United Airlines
Deal found 14/5C$ 496
Fri 18/96:05 p.m.
YWG
-
MCO
1 stop24h 40m
WestJet
Sun 27/98:35 p.m.
MCO
-
YWG
1 stop14h 10m
WestJet
Deal found 13/5C$ 514
Mon 14/99:20 a.m.
YWG
-
MCO
2 stops9h 14m
Porter Airlines
Fri 18/911:20 a.m.
MCO
-
YWG
1 stop7h 38m
Porter Airlines
Deal found 9/5C$ 529
Tue 2/63:15 p.m.
YWG
-
MCO
1 stop7h 31m
Air Canada
Wed 3/67:30 p.m.
MCO
-
YWG
1 stop15h 39m
Air Canada
Deal found 13/5C$ 534

Find flight deals from Winnipeg to Orlando

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Orlando (ORL). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 14 May 2026.

Round-trip from

C$ 464

One-way from

C$ 286

Popular in

June

Cheapest in

October

Average price

C$ 610

Good one-way deal

C$ 450 or less
Delta
  • Delta
  • 28/5-3/6
  • 2 total stops
  • 11h 28m total
  • Winnipeg to Orlando
Search Deals
United Airlines
  • United Airlines
  • 17/6
  • 1 total stop
  • 9h 54m total
  • Winnipeg to Orlando
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (C$ 116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a one-way flight from Winnipeg to Orlando (ORL).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Orlando that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 14 May 2026.
Use the filters below to find and compare flights from Winnipeg to Orlando that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 13/6

12:56 p.m.-1:01 a.m.

2 stops11h 05m

Orlando

Mon 15/6

4:26 p.m.-10:38 p.m.

1 stop7h 12m

C$ 496

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 13/6

3:15 p.m.-11:46 p.m.

1 stop7h 31m

Orlando

Mon 15/6

4:26 p.m.-10:38 p.m.

1 stop7h 12m

C$ 634

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Mon 14/9

8:45 p.m.-12:45 p.m.

1 stop15h 00m

Orlando

Fri 18/9

11:20 a.m.-5:58 p.m.

1 stop7h 38m

C$ 744

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sun 12/7

7:45 a.m.-10:40 a.m.

1 stop25h 55m

Orlando

Sat 8/8

5:15 p.m.-12:15 p.m.

1 stop20h 00m

C$ 760

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Mon 17/8

9:20 a.m.-7:34 p.m.

2 stops9h 14m

Orlando

Thu 20/8

9:15 a.m.-12:55 a.m.

3 stops16h 40m

C$ 762
Quickest round-trip

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sun 31/5

5:41 p.m.-12:20 a.m.

1 stop5h 39m

Orlando

Wed 3/6

6:05 a.m.-10:54 a.m.

1 stop5h 49m

C$ 799

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Tue 2/6

7:00 a.m.-6:14 p.m.

2 stops10h 14m

Orlando

Thu 4/6

9:45 a.m.-10:38 p.m.

2 stops13h 53m

C$ 819

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 13/6

1:10 p.m.-10:40 a.m.

2 stops20h 30m

Orlando

Mon 15/6

5:05 p.m.-12:15 p.m.

2 stops20h 10m

C$ 823

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 1/8

6:00 a.m.-4:15 p.m.

1 stop9h 15m

Orlando

Mon 3/8

11:30 a.m.-10:10 p.m.

1 stop11h 40m

C$ 823

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

Sat 15/8

3:58 p.m.-11:58 p.m.

1 stop7h 00m

Orlando

Sat 22/8

7:04 a.m.-3:08 p.m.

1 stop9h 04m

C$ 830

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/5

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

Best time to book a flight from Winnipeg to Orlando

Have a flexible travel schedule? Discover the best time to fly to Orlando from Winnipeg with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Winnipeg to Orlando

How far ahead should I book a flight from Winnipeg to Orlando?

Booking 74 days in advance of your planned departure date is, on average, the best time to get cheap flights from Winnipeg to Orlando. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Winnipeg to Orlando?

Currently, January is the cheapest month in which you can book a flight from Winnipeg to Orlando (average of C$ 111). Flying from Winnipeg to Orlando in May is currently the most expensive (average of C$ 284). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Winnipeg to Orlando?

What’s the top layover airport for flights from Winnipeg to Orlando?

Share of one-stop round-trip flights from Winnipeg to Orlando chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 47% of one-stop itineraries from Winnipeg to Orlando on Cheapflights.

What’s the cheapest layover airport for flights from Winnipeg to Orlando?

Average round-trip fare for 1-stop flights from Winnipeg to Orlando, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of C$ 343.

What’s the fastest layover option from Winnipeg to Orlando?

Shortest average travel time for 1-stop one-way flights from Winnipeg to Orlando, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Ottawa (YOW) have the shortest average one-way travel time for 1-stop routes: 6h 58m.

Which airport typically offers the quickest layover for flights from Winnipeg to Orlando?

Average layover duration for 1-stop one-way flights from Winnipeg to Orlando, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Chicago (ORD) offer the fastest connection on this route, with an average layover time of 1h 43m.

How often are flights from Winnipeg to Orlando delayed?

About 18% of weekly flights between Winnipeg and Orlando have experienced delays in the past year, with the average delay time being 171 minutes.

What is the most punctual flight time for Winnipeg to Orlando flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the early afternoon tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Thursday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Winnipeg to Orlando flights?

Over the past year, WestJet has had the lowest number of delays on this route, with just 18% of flights being delayed.

Reviews of airlines servicing Orlando

Get insights into the airlines that provide service to Orlando. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Orlando. Reviews last updated 14 May 2026.
Check out reviews from past customers who have flown with Porter Airlines,Delta, andUnited Airlines from Winnipeg to Orlando to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
437 reviews
Check prices

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
437 reviews
Porter Airlines
8.0
Very good
437 reviews
Check prices

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Delta
7.9
Good
8,453 reviews
Porter Airlines
8.0
Very good
437 reviews
Check prices

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,711 reviews
Porter Airlines
8.0
Very good
437 reviews
Check prices

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,335 reviews
Porter Airlines
8.0
Very good
437 reviews
Check prices

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
11,033 reviews
Porter Airlines
8.0
Very good
437 reviews
Check prices

Entertainment

6.9

Crew

8.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

Related info for your journey

Find useful and relevant information for your journey from Winnipeg to Orlando. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Winnipeg to Orlando?

    Winnipeg (YWG) is the airport you will fly out of if you book a flight from Winnipeg to Orlando. You should not have trouble finding flights to Orlando from Winnipeg; the airport handles an average of 0 outbound flights to Orlando per day. You should also have plenty of airline options to choose from since 5 airlines have flights from the Winnipeg airport to Orlando. It is only a 7.3 km journey to Winnipeg (YWG) from Winnipeg’s city centre.

  • How long is the flight from Winnipeg to Orlando?

    There are many flights that can get you from Winnipeg to Orlando in 11h 05m. Fly via United Airlines, Porter Airlines, or WestJet to get the fastest option. There are 2739 km between Winnipeg and Orlando. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Winnipeg to Orlando round-trip?

    Our cheapest airline available from Winnipeg to Orlando is United Airlines. Our recent data shows that you can find tickets from as low as C$ 182 on this airline. Additional options worth looking into are WestJet and Delta, starting at C$ 242 and C$ 282 round-trip. United Airlines is 62% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Winnipeg to Orlando one-way?

    For one-way options, check prices for WestJet. According to our data, you can fly for as low as C$ 154. Users have also found prices from C$ 165 and C$ 215 on Porter Airlines and Delta, respectively.

  • What are the most reliable airlines from Winnipeg to Orlando?

    Before booking your flight to Orlando from Winnipeg, check out the most reliable airlines to get you to your destination on time: LATAM Airlines (100%), Delta (67%), WestJet( 67%).

  • What are the cheapest flights from Winnipeg to Orlando?

    While on average a flight from Winnipeg to Orlando is generally C$ 490, our data shows the cheapest flight currently is C$ 231. When looking at the most popular route, (Winnipeg - Orlando), you can expect to pay C$ 464 for that flight.

  • Can I find deals for flights from Winnipeg to Orlando that include hotel bookings?

    Yes. In addition to deals on Winnipeg to Orlando flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Winnipeg to Orlando?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Orlando.

  • Can I find deals for business class flights from Winnipeg to Orlando?

    Yes. Cheapflights offers flight deals from Winnipeg to Orlando by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Winnipeg to Orlando?

    Currently, January is the cheapest month in which you can book a flight from Winnipeg to Orlando (average of C$ 111). Flying from Winnipeg to Orlando in May is currently the most expensive (average of C$ 284). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Fly from Winnipeg to Orlando on these airlines

Choose from the following airlines for your flight from Winnipeg to Orlando. Flights are based on user searches made on Cheapflights and were last updated on 14 May 2026.
WestJet flights from Winnipeg to Orlando
Air Canada flights from Winnipeg to Orlando

Top 5 airlines flying from Winnipeg to Orlando

Discover the top 5 airlines that operate flights from Winnipeg to Orlando. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 14 May 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 182AverageC$ 353FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
WestJetCheapestC$ 242AverageC$ 438FlexibilityNo cancel feeOn-time60%
Search WestJet flights
DeltaCheapestC$ 282AverageC$ 483FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Air CanadaCheapestC$ 298AverageC$ 664FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 311AverageC$ 466FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Winnipeg to Orlando?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Winnipeg to Orlando. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Orlando?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Winnipeg to Orlando.

Can Cheapflights find flights from Winnipeg to Orlando with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Orlando, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Winnipeg to Orlando become cheaper?

Yes, Cheapflights offers price alerts on Winnipeg to Orlando flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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