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$104+ Cheap flights from Kissimmee, FL 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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — YWG
fev 28 — mar 71
sáb 2/28
sáb 3/7
1 adult, Economy
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Cheap flight deals from Kissimmee to Winnipeg

Cheapest flights from Kissimmee to Winnipeg
Explore the most affordable flight options available from Kissimmee to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on janeiro 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
ter 2/249:15 pm
MCO
-
YWG
1 stop15h 17m
WestJet
ter 3/312:20 pm
YWG
-
MCO
1 stop6h 56m
WestJet
Deal found 1/27$239
This Air Canada deal was found by Cheapflights users on 1/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 7/318:00 am
MCO
-
YWG
1 stop8h 04m
Air Canada
qua 8/57:55 am
YWG
-
MCO
1 stop9h 32m
Air Canada
Deal found 1/29$251
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
sex 4/249:00 am
MCO
-
YWG
1 stop7h 09m
Multiple Airlines
seg 4/279:05 pm
YWG
-
MCO
2 stops12h 22m
Multiple Airlines
Deal found 1/28$264
This FlightHub deal was found by Cheapflights users on 1/27. 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.
qui 3/129:15 pm
MCO
-
YWG
1 stop22h 54m
Multiple Airlines
qui 3/1912:10 pm
YWG
-
MCO
1 stop10h 13m
Multiple Airlines
Deal found 1/27$271
This FlightHub deal was found by Cheapflights users on 1/28. 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.
sex 5/85:05 pm
MCO
-
YWG
1 stop8h 50m
WestJet
dom 5/1010:45 am
YWG
-
MCO
1 stop8h 00m
WestJet
Deal found 1/28$289
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
ter 2/2410:28 am
MCO
-
YWG
2 stops15h 12m
Multiple Airlines
ter 3/312:20 pm
YWG
-
MCO
1 stop6h 56m
Multiple Airlines
Deal found 1/27$290
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
sex 3/1311:20 am
MCO
-
YWG
1 stop8h 49m
Multiple Airlines
sex 3/2012:10 pm
YWG
-
MCO
1 stop10h 13m
Multiple Airlines
Deal found 1/27$293
This FlightHub deal was found by Cheapflights users on 1/28. 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.
sex 4/249:15 pm
MCO
-
YWG
1 stop28h 24m
WestJet
seg 4/276:05 pm
YWG
-
MCO
1 stop15h 35m
WestJet
Deal found 1/28$296
This Trip.com deal was found by Cheapflights users on 1/27. 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.
sex 2/2711:20 am
MCO
-
YWG
1 stop14h 15m
Multiple Airlines
sex 3/69:05 am
YWG
-
MCO
2 stops13h 22m
Multiple Airlines
Deal found 1/27$297

Find flight deals from Kissimmee to Winnipeg

Keep the following information in mind while searching for Kissimmee to Winnipeg flight deals. Data was last updated janeiro 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$239
(Kiwi.com)

One-way from

$104
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$604
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 Kissimmee to Winnipeg
Search Deals
One-way flight from Kissimmee to Winnipeg
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($97 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 January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kissimmee 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 janeiro 29, 2026.
Use the filters below to find and compare flights from Kissimmee to Winnipeg that are best for you.

Fly from

Kissimmee

Fly to

Winnipeg

Route

Depart

Return

Price

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

sex 4/24

9:00 am-3:09 pm

1 stop7h 09m

Winnipeg

seg 4/27

9:05 pm-10:27 am

2 stops12h 22m

$264

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

sex 5/8

5:05 pm-12:55 am

1 stop8h 50m

Winnipeg

dom 5/10

10:45 am-7:45 pm

1 stop8h 00m

$289

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

sex 3/13

11:20 am-7:09 pm

1 stop8h 49m

Winnipeg

sex 3/20

12:10 pm-11:23 pm

1 stop10h 13m

$293

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

sex 2/27

11:20 am-12:35 am

1 stop14h 15m

Winnipeg

sex 3/6

9:05 am-11:27 pm

2 stops13h 22m

$297

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

sáb 5/30

12:20 pm-9:40 pm

1 stop10h 20m

Winnipeg

sáb 6/6

4:25 pm-10:40 am

1 stop17h 15m

$306

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

sex 4/17

2:00 pm-11:35 pm

2 stops10h 35m

Winnipeg

sáb 4/18

6:45 am-4:29 pm

1 stop8h 44m

$317

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

sex 4/17

9:42 am-8:57 pm

1 stop12h 15m

Winnipeg

sáb 4/18

8:45 am-7:33 pm

1 stop9h 48m

$323

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

ter 2/24

9:15 pm-3:20 pm

2 stops19h 05m

Winnipeg

ter 3/3

6:15 am-8:16 pm

2 stops13h 01m

$328

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

qua 3/11

11:20 am-12:35 am

1 stop14h 15m

$104

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

dom 3/29

5:15 am-3:09 pm

1 stop10h 54m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 16 results
1
2

Best time to book a flight from Kissimmee to Winnipeg

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

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

Currently, May is the cheapest month in which you can book a flight from Kissimmee to Winnipeg (average of $109). Flying from Kissimmee to Winnipeg in February is currently the most expensive (average of $299). 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.

What is the cheapest time of day to fly from K1S to YWG?

Find hourly flight availability from Kissimmee to Winnipeg. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated janeiro 29, 2026.

When flying from Kissimmee to Winnipeg, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 janeiro 29, 2026.
See what other customers who have flown with Delta, United Airlines, and WestJet from Kissimmee to Winnipeg have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,127 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

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
8,127 reviews
Delta
7.9
Good
8,127 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

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.
United Airlines
7.4
Good
9,214 reviews
Delta
7.9
Good
8,127 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

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
3,252 reviews
Delta
7.9
Good
8,127 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

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.
Air Canada
7.1
Good
10,667 reviews
Delta
7.9
Good
8,127 reviews

Entertainment

7.8

Overall

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

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 Kissimmee 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 Kissimmee?

    Winnipeg (YWG) is the airport you will fly into if you book a flight from Kissimmee to Winnipeg. You should not have trouble finding flights to Winnipeg from Kissimmee; the airport handles an average of 0 inbound flights from Kissimmee per day. You should also have plenty of airline options to choose from since 4 airlines have flights to the Winnipeg airport from Kissimmee. It is only a 4.6 mi journey from Winnipeg (YWG) to Winnipeg’s city center.

  • How long is the flight from Kissimmee to Winnipeg?

    A quick flight from Kissimmee to Winnipeg can take about 15h 17m. WestJet provides one of the quickest options available for as low as $239. The distance from Kissimmee to Winnipeg is about 1702 mi.

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

    Before booking your flight to Winnipeg from Kissimmee, check out the most reliable airlines to get you to your destination on time: Delta (71%), WestJet (71%), Aeromexico( 71%).

  • What are the cheapest flights from Kissimmee to Winnipeg?

    Looking at all options, your cheapest flight can be booked for $81. While the most popular route (Orlando - Winnipeg) can be booked for $264 on average, our data indicates $414 when flying from Kissimmee to Winnipeg.

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Kissimmee to Winnipeg (average of $109). Flying from Kissimmee to Winnipeg in February is currently the most expensive (average of $299). 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

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Top 4 airlines flying from Kissimmee to Winnipeg

Discover the top 4 airlines that operate flights from Kissimmee 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 janeiro 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$97Average$342FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$127Average$479FlexibilityNo cancel feeOn-time69%
DeltaCheapest$138Average$404FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$204Average$276FlexibilityNo cancel feeOn-time60%

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