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$186+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — YWG
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
1 adult, Economy
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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 June 9, 2026.

This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/271:45 pm
MCO
-
YWG
1 stop7h 04m
Porter Airlines
Mon 8/319:20 am
YWG
-
MCO
2 stops9h 14m
Porter Airlines
Deal found 6/8$486
This FlightHub deal was found by Cheapflights users on 6/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:00 pm
MCO
-
YWG
1 stop9h 35m
Porter Airlines
Mon 12/2812:10 pm
YWG
-
MCO
1 stop10h 10m
Porter Airlines
Deal found 6/6$493
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 7/1011:20 am
MCO
-
YWG
2 stops9h 34m
Multiple Airlines
Tue 7/215:10 pm
YWG
-
MCO
1 stop18h 35m
Multiple Airlines
Deal found 6/4$497
This FlightHub deal was found by Cheapflights users on 6/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/153:00 pm
MCO
-
YWG
1 stop9h 35m
Multiple Airlines
Sun 12/278:05 pm
YWG
-
MCO
1 stop13h 19m
Multiple Airlines
Deal found 6/6$503
This Mytrip deal was found by Cheapflights users on 6/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:05 pm
MCO
-
YWG
1 stop16h 35m
Multiple Airlines
Mon 7/68:10 pm
YWG
-
MCO
1 stop13h 30m
Multiple Airlines
Deal found 6/7$511
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 6/191:45 pm
MCO
-
YWG
1 stop7h 04m
Multiple Airlines
Mon 6/228:10 pm
YWG
-
MCO
1 stop15h 35m
Multiple Airlines
Deal found 6/5$521
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Sat 7/1811:20 am
MCO
-
YWG
1 stop7h 38m
Multiple Airlines
Sat 7/255:10 pm
YWG
-
MCO
1 stop18h 35m
Multiple Airlines
Deal found 6/4$522
This FlightHub deal was found by Cheapflights users on 6/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2811:20 am
MCO
-
YWG
2 stops9h 29m
Porter Airlines
Mon 8/319:20 am
YWG
-
MCO
2 stops9h 14m
Porter Airlines
Deal found 6/8$528
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Mon 6/291:45 pm
MCO
-
YWG
1 stop7h 04m
Multiple Airlines
Fri 7/310:45 am
YWG
-
MCO
1 stop8h 00m
Multiple Airlines
Deal found 6/5$539

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 June 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$486
(FlightHub)

One-way from

$186
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$498
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. 19% potential increase in price ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 9, 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 8/27

1:45 pm-7:49 pm

1 stop7h 04m

Winnipeg

Mon 8/31

9:20 am-7:34 pm

2 stops9h 14m

$486

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 7/10

11:20 am-7:54 pm

2 stops9h 34m

Winnipeg

Tue 7/21

5:10 pm-12:45 pm

1 stop18h 35m

$497

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 7/18

11:20 am-5:58 pm

1 stop7h 38m

Winnipeg

Sat 7/25

5:10 pm-12:45 pm

1 stop18h 35m

$522

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Mon 7/6

6:00 am-3:19 pm

2 stops34h 19m

Winnipeg

Mon 7/13

8:10 pm-12:45 pm

1 stop15h 35m

$540

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Tue 6/30

1:45 pm-7:49 pm

1 stop7h 04m

Winnipeg

Mon 7/6

6:05 pm-10:40 am

1 stop15h 35m

$580
Quickest round-trip

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 8/27

7:04 am-3:08 pm

1 stop9h 04m

Winnipeg

Mon 8/31

3:58 pm-11:58 pm

1 stop7h 00m

$585

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 8/28

7:04 am-3:08 pm

1 stop9h 04m

Winnipeg

Mon 8/31

3:58 pm-11:58 pm

1 stop7h 00m

$585

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 6/19

11:15 am-5:58 pm

1 stop7h 43m

Winnipeg

Wed 6/24

4:25 pm-10:40 am

1 stop17h 15m

$612
Cheapest one-way
Quickest one-way

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 7/11

11:20 am-5:58 pm

1 stop7h 38m

$237

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 7/23

1:45 pm-8:40 am

1 stop19h 55m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

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 June.
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 $90). Flying from Orlando to Winnipeg in April is currently the most expensive (average of $411). 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?

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 June 9, 2026.
Read through reviews of airlines operating flights from Orlando to Winnipeg, such as Delta and WestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,394 reviews

Entertainment

7.8

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,394 reviews
Delta
7.9
Good
8,394 reviews

Entertainment

7.8

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
WestJet
7.2
Good
3,356 reviews
Delta
7.9
Good
8,394 reviews

Entertainment

7.8

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.8

Food

7.2

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

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 2 different airlines.

  • How long is the flight from Orlando to Winnipeg?

    For as low as $486, Porter Airlines can have you in Winnipeg from Orlando in 7h 04m. The distance from Orlando to Winnipeg is about 1702 mi.

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

    Flying on WestJet is currently your cheapest option to Winnipeg, with prices starting at $204. Another option worth looking into is Delta, starting at $296 round trip. These flights start at 42% lower than the current average price 3 months from now.

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

    No one likes to see their flight delayed. When booking a flight from Orlando to Winnipeg consider choosing Delta (83%), WestJet (83%) or LATAM Airlines (75%) as they are the most reliable in getting you off to your destination on time.

  • 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 $90). Flying from Orlando to Winnipeg in April is currently the most expensive (average of $411). 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

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Top 2 airlines flying from Orlando to Winnipeg

Discover the top 2 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 June 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
WestJetCheapest$204Average$276FlexibilityNo cancel feeOn-time60%
DeltaCheapest$296Average$642FlexibilityNo cancel feeOn-timeN/A

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