Cheap flights from Winnipeg to Kissimmee from C$ 204
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 27/10. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
9 Oct — 16 Oct1
Round-trip
1 adult
Economy
Round-trip
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in April or January, booked 38 days in advance, depart on a Monday or Tuesday and return on a Tuesday
Cheap flight deals from Winnipeg to Kissimmee
Enter your travel dates to find the best prices.
Cheapest
Best
Direct
Last-minute
One-way
Cheapest flights from Winnipeg to Kissimmee
Explore the most affordable flight options available from Winnipeg to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 9 September 2026.
Sun 18/1010:45 a.m. -
1 stop8h 00m
Tue 27/1011:10 a.m. -
2 stops15h 00m
Deal found 6/9C$ 382
Sun 11/1010:45 a.m. -
1 stop22h 55m
Fri 16/105:05 p.m. -
1 stop8h 50m
Deal found 4/9C$ 388
Fri 11/127:35 a.m. -
2 stops11h 45m
Wed 16/1211:10 a.m. -
1 stop9h 40m
Deal found 4/9C$ 389
Tue 27/109:35 p.m. -
2 stops11h 45m
Tue 8/1211:10 a.m. -
2 stops14h 00m
Deal found 4/9C$ 390
Tue 27/109:35 p.m. -
2 stops11h 45m
Tue 3/1111:10 a.m. -
2 stops14h 00m
Deal found 8/9C$ 393
Mon 26/109:35 p.m. -
2 stops13h 14m
Thu 29/1011:10 a.m. -
1 stop9h 40m
Deal found 5/9C$ 403
Fri 11/126:00 a.m. -
2 stops13h 20m
Mon 14/1211:10 a.m. -
2 stops14h 00m
Deal found 4/9C$ 415
Tue 24/119:35 a.m. -
1 stop23h 45m
Fri 27/1111:10 a.m. -
1 stop9h 40m
Deal found 6/9C$ 418
Best flights from Winnipeg to Kissimmee
Discover carefully curated flight deals from Winnipeg to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 9 September 2026.
Tue 27/109:35 p.m. -
2 stops11h 45m
Tue 8/1211:10 a.m. -
2 stops14h 00m
Deal found 4/9C$ 390
Sun 6/122:15 p.m. -
1 stop8h 39m
Fri 11/129:00 a.m. -
2 stops12h 48m
Deal found 6/9C$ 552
Wed 9/122:15 p.m. -
2 stops9h 29m
Sat 12/128:30 a.m. -
2 stops10h 55m
Deal found 6/9C$ 588
Fri 11/129:35 a.m. -
1 stop23h 45m
Mon 14/1211:10 a.m. -
1 stop24h 55m
Deal found 4/9C$ 433
Wed 9/122:15 p.m. -
2 stops9h 29m
Sun 13/128:15 p.m. -
1 stop17h 08m
Deal found 6/9C$ 552
Fri 22/18:05 p.m. -
1 stop13h 15m
Tue 26/111:10 a.m. -
1 stop9h 40m
Deal found 8/9C$ 506
Wed 6/17:00 a.m. -
2 stops11h 25m
Wed 3/39:00 a.m. -
2 stops10h 41m
Deal found 8/9C$ 570
Tue 19/17:00 a.m. -
2 stops13h 47m
Tue 9/24:20 p.m. -
1 stop7h 13m
Deal found 8/9C$ 570
Fri 11/122:15 p.m. -
1 stop6h 22m
Sat 12/128:15 p.m. -
1 stop17h 08m
Deal found 6/9C$ 588
Fri 11/122:15 p.m. -
2 stops9h 29m
Mon 14/128:15 p.m. -
1 stop17h 08m
Deal found 6/9C$ 588
Tue 2/27:00 a.m. -
1 stop9h 05m
Tue 9/24:20 p.m. -
1 stop7h 13m
Deal found 5/9C$ 592
Direct flights from Winnipeg to Kissimmee
Explore direct flight options from Winnipeg to Kissimmee based on user searches, and compare prices and availability for your desired travel dates. Data last updated 9 September 2026.
Tue 8/128:00 a.m. -
Nonstop4h 05m
Fri 11/129:15 p.m. -
Nonstop4h 29m
Deal found 6/9C$ 720
Tue 27/108:00 a.m. -
Nonstop4h 05m
Tue 3/112:00 p.m. -
Nonstop4h 30m
Deal found 8/9C$ 743
Tue 27/108:00 a.m. -
Nonstop4h 05m
Fri 6/119:15 p.m. -
Nonstop4h 29m
Deal found 7/9C$ 816
Tue 8/128:00 a.m. -
Nonstop4h 05m
Tue 29/122:00 p.m. -
Nonstop4h 30m
Deal found 8/9C$ 834
Tue 10/118:00 a.m. -
Nonstop4h 05m
Tue 17/112:00 p.m. -
Nonstop4h 30m
Deal found 8/9C$ 855
Tue 8/128:00 a.m. -
Nonstop4h 05m
Tue 15/122:00 p.m. -
Nonstop4h 30m
Deal found 6/9C$ 957
Tue 27/108:00 a.m. -
Nonstop4h 05m
Tue 8/122:00 p.m. -
Nonstop4h 30m
Deal found 6/9C$ 975
Last-minute flights from Winnipeg to Kissimmee
Discover last-minute flight deals from Winnipeg to Kissimmee. Data last updated 9 September 2026 and is based on user searches.
Sun 11/1010:45 a.m. -
1 stop22h 55m
Fri 16/105:05 p.m. -
1 stop8h 50m
Deal found 4/9C$ 388
Sun 18/1010:45 a.m. -
1 stop8h 00m
Tue 27/1011:10 a.m. -
2 stops15h 00m
Deal found 6/9C$ 382
Sat 24/107:10 p.m. -
2 stops14h 10m
Mon 2/1111:10 a.m. -
2 stops14h 00m
Deal found 4/9C$ 422
Mon 26/109:35 p.m. -
2 stops13h 14m
Thu 29/1011:10 a.m. -
1 stop9h 40m
Deal found 5/9C$ 403
Tue 27/109:35 p.m. -
2 stops11h 45m
Tue 8/1211:10 a.m. -
2 stops14h 00m
Deal found 4/9C$ 390
Tue 27/109:35 p.m. -
2 stops11h 45m
Tue 3/1111:10 a.m. -
2 stops14h 00m
Deal found 8/9C$ 393
One-way flights from Winnipeg to Kissimmee
Search for one-way flight options from Winnipeg to Kissimmee. Find affordable one-way fares based on user searches. Data last updated 9 September 2026.
Tue 27/109:35 p.m. -
2 stops13h 14m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 8/9C$ 204
Fri 30/109:35 p.m. -
2 stops13h 14m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 4/9C$ 206
Sun 1/118:35 p.m. -
2 stops12h 33m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 6/9C$ 214
Tue 27/109:35 p.m. -
2 stops11h 45m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 9/9C$ 223
Thu 1/104:25 p.m. -
1 stop26h 20m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 6/9C$ 265
Sun 29/116:55 p.m. -
1 stop13h 45m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 6/9C$ 274
Sun 1/116:55 p.m. -
1 stop13h 45m
Wed 31/1212:00 a.m. -
Nonstop0h 00m
Deal found 6/9C$ 279
Find flight deals from Winnipeg to Kissimmee
Keep the following information in mind while searching for Winnipeg to Kissimmee flight deals. Data was last updated 9 September 2026.
Customize your flight search to find flights from Winnipeg to Kissimmee 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 7,457,451 searches. Data last updated 9 September 2026.
Use the filters below to find and compare flights from Winnipeg to Kissimmee that are best for you.
Fly from
Fly to
Route
Depart
Return
Price
Cheapest round-trip
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Fri 30/10
9:35 p.m.-11:49 a.m.
2 stops13h 14m
Orlando
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 206
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Tue 10/11
8:35 p.m.-9:38 p.m.
2 stops24h 03m
Orlando
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 206
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Tue 27/10
6:00 a.m.-5:24 p.m.
2 stops34h 24m
Orlando
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 208
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Tue 3/11
8:35 p.m.-11:49 a.m.
2 stops14h 14m
Orlando
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 210
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Tue 3/11
5:00 a.m.-10:20 a.m.
1 stop28h 20m
Orlando
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 250
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Tue 27/10
5:00 a.m.-10:20 a.m.
1 stop28h 20m
Orlando
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 265
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Sun 1/11
6:55 p.m.-9:40 a.m.
1 stop13h 45m
Orlando
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 279
Quickest round-trip
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Fri 22/1
8:35 p.m.-10:20 a.m.
2 stops12h 45m
Orlando
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 280
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Tue 16/2
8:35 p.m.-10:20 a.m.
2 stops12h 45m
Orlando
Wed 31/12
12:00 a.m.-11:00 p.m.
Nonstop0h 00m
C$ 288
WinnipegOrlando
YWG Winnipeg - MCO Orlando
YWGMCO
Winnipeg
Tue 27/10
9:35 p.m.-10:20 a.m.
2 stops11h 45m
Orlando
Tue 8/12
11:10 a.m.-12:10 a.m.
2 stops14h 00m
C$ 390
Flights are sorted by cheapest round-trip flights first.
Deals found on 4/9
Showing 1-10 of 20 resultsSorted by cheapest first
1
2
Best time to book a flight from Winnipeg to Kissimmee
Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Winnipeg with our price prediction graph.
YWG-MCO
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 Kissimmee
YWG-K1S
YWG-MCO
How much does it cost to fly round-trip from Winnipeg to Kissimmee?
Airfare is below average for this route at the moment.
Winnipeg to Kissimmee flights typically cost between C$ 497 and C$ 799 in October.The cheapest round-trip price found within the last 5 days was C$ 382 on WestJet (18 Oct-27 Oct).
Reviews of airlines servicing Kissimmee
Get insights into the airlines that provide service to Kissimmee. 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 Kissimmee. Reviews last updated 9 September 2026.
Check out reviews from past customers who have flown with Porter Airlines,Delta, andUnited Airlines from Winnipeg to Kissimmee to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
My first flight with an all female flight crew who were the best ever.
Related info for your journey
Find useful and relevant information for your journey from Winnipeg to Kissimmee. 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 Kissimmee?
If you book a flight to Kissimmee from Winnipeg, you will be flying from Winnipeg, which is the city’s only airport. Winnipeg (YWG) is located 7.3 km from the centre of Winnipeg. There are 0 flights from Winnipeg to Kissimmee per day from 5 different airlines.
How long is the flight from Winnipeg to Kissimmee?
A quick flight from Winnipeg to Kissimmee can take about 8h 39m. WestJet provides one of the quickest options available for as low as C$ 552. The distance between Winnipeg and Kissimmee is about 2739 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.
What are the cheapest flights from Winnipeg to Kissimmee?
The cheapest flight price from Winnipeg to Kissimmee is C$ 584. On average you can expect to pay C$ 896. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 448.
Can I find deals for business class flights from Winnipeg to Kissimmee?
Yes. Cheapflights offers flight deals from Winnipeg to Kissimmee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on 9 September 2026.
Discover the top 5 airlines that operate flights from Winnipeg to Kissimmee. 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 7,457,451 searches. Data last updated 9 September 2026.
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 Kissimmee?
When you search for this flight from Winnipeg to Kissimmee, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.
Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Kissimmee?
Cheapflights simply makes it quick and affordable to book flights from Winnipeg to Kissimmee by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.
Can Cheapflights find flights from Winnipeg to Kissimmee with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Winnipeg to Kissimmee, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Winnipeg to Kissimmee become cheaper?
Yes! Start tracking prices for Winnipeg to Kissimmee flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.
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.
We value your privacy
Cheapflights and its partners wish to use cookies or similar technologies to store and/or access information on and about your device and process personal data such as your IP address, device identifiers etc., in order to improve your experience on the site, to analyze navigation, to offer and measure personalized advertising, and to facilitate sharing on social networks. We also allow the use of third-party cookies (including those from our advertising partners) on our sites.
By clicking 'Accept', you consent to your data being processed by 0 vendors on this web site for the purposes described in this notice. You can review the vendors and their individual processing purposes on the .
To review individual processing purposes and cookie categories, please click ’Select individual purposes’. You can review and update your choices anytime by clicking the ’Privacy Preferences’ link in the page side navigation.