HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$142+ Cheap flights from Orlando (ORL) to Winnipeg (YWG)

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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — YWG
Aug 23 — Aug 301
Sun 8/23
Sun 8/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Orlando to Winnipeg with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Orlando to Winnipeg

Cheapest flights from Orlando to Winnipeg
Explore the most affordable flight options available from Orlando to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 24, 2026.

This Trip.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am
MCO
-
YWG
1 stop14h 25m
WestJet
Mon 10/126:15 am
YWG
-
MCO
1 stop27h 25m
WestJet
Deal found 7/23$348
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am
MCO
-
YWG
1 stop10h 15m
Multiple Airlines
Mon 10/129:05 pm
YWG
-
MCO
2 stops11h 59m
Multiple Airlines
Deal found 7/23$354
This Trip.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:35 pm
MCO
-
YWG
1 stop14h 10m
WestJet
Mon 10/126:15 am
YWG
-
MCO
1 stop27h 25m
WestJet
Deal found 7/23$355
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am
MCO
-
YWG
1 stop10h 15m
Multiple Airlines
Tue 10/139:05 pm
YWG
-
MCO
2 stops11h 59m
Multiple Airlines
Deal found 7/22$375
This oojo deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am
MCO
-
YWG
1 stop14h 25m
WestJet
Tue 10/136:05 pm
YWG
-
MCO
1 stop15h 35m
WestJet
Deal found 7/22$380
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2010:03 am
MCO
-
YWG
2 stops13h 07m
Multiple Airlines
Thu 8/276:05 pm
YWG
-
MCO
1 stop15h 35m
Multiple Airlines
Deal found 7/23$385
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:05 pm
MCO
-
YWG
1 stop8h 50m
Multiple Airlines
Wed 8/267:00 am
YWG
-
MCO
2 stops14h 14m
Multiple Airlines
Deal found 7/23$386
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:35 pm
MCO
-
YWG
1 stop14h 10m
WestJet
Sun 9/2010:45 am
YWG
-
MCO
1 stop8h 00m
WestJet
Deal found 7/22$395

Find flight deals from Orlando to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (ORL) to Winnipeg (YWG). 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 July 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$348
(Trip.com)

One-way from

$142
(Kiwi.com)

Popular in

June

Cheapest in

November

Average price

$428
Provider with most accurate pricing for Orlando (ORL)-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Orlando (ORL)-Winnipeg flights.
Search Deals
From Orlando (ORL) to Winnipeg
Search Deals
One-way flight from Orlando (ORL) to Winnipeg
Search Deals
Highest demand for flights based on searches. 35% potential increase in price ($207 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando to Winnipeg 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 2,558,603 searches. Data last updated July 24, 2026.
Use the filters below to find and compare flights from Orlando to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 8/20

10:03 am-10:10 pm

2 stops13h 07m

Winnipeg

Thu 8/27

6:05 pm-10:40 am

1 stop15h 35m

$385

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Tue 8/18

5:05 pm-12:55 am

1 stop8h 50m

Winnipeg

Wed 8/26

7:00 am-10:14 pm

2 stops14h 14m

$386

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 10/8

11:30 am-8:45 pm

1 stop10h 15m

Winnipeg

Mon 10/12

9:05 pm-10:04 am

2 stops11h 59m

$398

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 10/9

8:35 pm-9:45 am

1 stop14h 10m

Winnipeg

Mon 10/12

9:20 am-7:34 pm

2 stops9h 14m

$400
Quickest round-trip

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 10/9

11:20 am-5:58 pm

1 stop7h 38m

Winnipeg

Mon 10/12

11:40 am-7:34 pm

1 stop6h 54m

$415

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 10/8

11:30 am-9:45 am

1 stop23h 15m

Winnipeg

Mon 10/12

6:15 am-10:40 am

1 stop27h 25m

$423

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 9/5

5:15 pm-11:10 am

1 stop18h 55m

Winnipeg

Sat 9/12

10:45 am-7:45 pm

1 stop8h 00m

$472

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 10/2

2:24 pm-10:33 pm

1 stop9h 09m

Winnipeg

Sat 10/3

2:00 pm-11:53 pm

1 stop8h 53m

$513

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 9/17

7:00 am-4:54 pm

1 stop10h 54m

Winnipeg

Wed 10/7

8:00 am-5:02 pm

1 stop8h 02m

$514

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 9/10

7:00 am-3:08 pm

1 stop9h 08m

Winnipeg

Thu 9/17

3:58 pm-11:06 pm

1 stop6h 08m

$518

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Orlando to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Orlando to Winnipeg in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Orlando-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Orlando-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Orlando to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Orlando 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 Orlando to Winnipeg

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

Currently, November is the cheapest month in which you can book a flight from Orlando to Winnipeg (average of $253). Flying from Orlando to Winnipeg in May is currently the most expensive (average of $642). 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 Orlando to Winnipeg?

Airfare is typical for this route at the moment.
Orlando to Winnipeg flights typically cost between $319 and $488 in October.
The cheapest round-trip price found within the last 5 days was $348 on WestJet (Oct 8-Oct 12).

Reviews of airlines servicing Winnipeg

Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated July 24, 2026.
Read through reviews of airlines operating flights from Orlando to Winnipeg, such as Delta,WestJet, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.8
Good
8,481 reviews

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

7.8

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Delta
7.8
Good
8,481 reviews
Delta
7.8
Good
8,481 reviews

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

7.8

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
WestJet
7.2
Good
3,416 reviews
Delta
7.8
Good
8,481 reviews

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

7.8

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Air Canada
7.1
Good
11,378 reviews
Delta
7.8
Good
8,481 reviews

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

7.8

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Related info for your journey

Find useful and relevant information for your journey from Orlando to Winnipeg. 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 into for flights to Winnipeg from Orlando?

    Located just 4.6 mi from the city center, Winnipeg is the airport most travelers will use when flying to Winnipeg from Orlando. Booking flights from Orlando to Winnipeg (YWG) should be relatively easy as there are 0 daily inbound flights from Orlando from 3 different airlines.

  • How long is the flight from Orlando to Winnipeg?

    For as low as $415, Porter Airlines can have you in Winnipeg from Orlando in 7h 38m. The distance from Orlando to Winnipeg is about 1702 mi.

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

    Flying on Air Canada is currently your cheapest option to Winnipeg, with prices starting at $97. Additional round-trip tickets that might be worth considering are offered by WestJet and Delta, with the lowest prices starting at $204 and $296, respectively. These flights start at 74% lower than the current average price 3 months from now.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Orlando to Winnipeg 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 Orlando to Winnipeg?

    Currently, November is the cheapest month in which you can book a flight from Orlando to Winnipeg (average of $253). Flying from Orlando to Winnipeg in May is currently the most expensive (average of $642). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 3 airlines flying from Orlando to Winnipeg

Discover the top 3 airlines that operate flights from Orlando to Winnipeg. 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 2,558,603 searches. Data last updated July 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$97Average$428FlexibilityNo cancel feeOn-time67%
WestJetCheapest$204Average$284FlexibilityNo cancel feeOn-time60%
DeltaCheapest$296Average$642FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.