Cheap flights from Winnipeg to Kissimmee from C$ 344
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 15/7. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
8 Jul — 15 Jul1
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 September or October, booked 37 days in advance, depart on a Saturday or Wednesday 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 8 June 2026.
Sun 18/109:05 p.m.
YWG
-
MCO
2 stops12h 35m
WestJet
Fri 30/102:00 p.m.
MCO
-
YWG
Nonstop4h 26m
WestJet
Deal found 6/6C$ 481
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 5/6C$ 564
Fri 2/1010:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Mon 5/105:05 p.m.
MCO
-
YWG
1 stop17h 40m
WestJet
Deal found 7/6C$ 587
Fri 2/1010:45 a.m.
YWG
-
MCO
1 stop8h 00m
WestJet
Wed 7/1011:30 a.m.
MCO
-
YWG
1 stop23h 15m
WestJet
Deal found 4/6C$ 597
Thu 26/118:15 a.m.
YWG
-
MCO
1 stop7h 52m
Air Canada
Sat 5/128:25 a.m.
MCO
-
YWG
1 stop9h 11m
Air Canada
Deal found 8/6C$ 598
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 8 June 2026.
Tue 21/75:41 p.m.
YWG
-
MCO
1 stop5h 17m
Delta
Sun 9/87:04 a.m.
MCO
-
YWG
1 stop9h 04m
Delta
Deal found 7/6C$ 638
Sun 5/73:54 p.m.
YWG
-
MCO
1 stop7h 03m
Delta
Sun 12/76:24 p.m.
MCO
-
YWG
1 stop6h 05m
Delta
Deal found 7/6C$ 638
Tue 21/75:41 p.m.
YWG
-
MCO
1 stop5h 17m
Delta
Wed 12/87:04 a.m.
MCO
-
YWG
1 stop9h 04m
Delta
Deal found 7/6C$ 638
Fri 21/85:42 p.m.
YWG
-
MCO
1 stop5h 16m
Delta
Mon 31/87:04 a.m.
MCO
-
YWG
1 stop5h 50m
Delta
Deal found 6/6C$ 640
Fri 28/812:46 p.m.
YWG
-
MCO
1 stop10h 12m
Delta
Wed 2/97:04 a.m.
MCO
-
YWG
1 stop9h 04m
Delta
Deal found 4/6C$ 640
Tue 29/93:58 p.m.
YWG
-
MCO
1 stop5h 58m
Delta
Sat 3/1012:16 p.m.
MCO
-
YWG
1 stop5h 38m
Delta
Deal found 7/6C$ 700
Sat 18/76:40 a.m.
YWG
-
MCO
1 stop9h 24m
Delta
Wed 12/87:04 a.m.
MCO
-
YWG
1 stop9h 04m
Delta
Deal found 7/6C$ 700
Fri 10/75:41 p.m.
YWG
-
MCO
1 stop5h 17m
Delta
Sun 19/73:00 p.m.
MCO
-
YWG
1 stop9h 29m
Delta
Deal found 5/6C$ 701
Sun 12/712:46 p.m.
YWG
-
MCO
1 stop10h 12m
Delta
Sun 19/73:00 p.m.
MCO
-
YWG
1 stop9h 29m
Delta
Deal found 5/6C$ 701
Wed 1/75:41 p.m.
YWG
-
MCO
1 stop5h 16m
Delta
Wed 8/73:00 p.m.
MCO
-
YWG
1 stop9h 29m
Delta
Deal found 3/6C$ 704
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 8 June 2026.
Fri 6/118:00 a.m.
YWG
-
MCO
Nonstop4h 03m
WestJet
Fri 13/112:00 p.m.
MCO
-
YWG
Nonstop4h 26m
WestJet
Deal found 4/6C$ 2,974
Last-minute flights from Winnipeg to Kissimmee
Discover last-minute flight deals from Winnipeg to Kissimmee. Data last updated 8 June 2026 and is based on user searches.
Wed 1/75:41 p.m.
YWG
-
MCO
1 stop5h 16m
Delta
Wed 8/73:00 p.m.
MCO
-
YWG
1 stop9h 29m
Delta
Deal found 3/6C$ 704
Thu 2/75:41 p.m.
YWG
-
MCO
1 stop5h 16m
Delta
Thu 9/711:17 a.m.
MCO
-
YWG
1 stop6h 34m
Delta
Deal found 3/6C$ 702
Thu 9/76:40 a.m.
YWG
-
MCO
1 stop9h 24m
Delta
Sun 12/76:24 p.m.
MCO
-
YWG
1 stop6h 05m
Delta
Deal found 4/6C$ 641
Sun 12/76:15 a.m.
YWG
-
MCO
1 stop27h 25m
Multiple Airlines
Fri 17/711:20 a.m.
MCO
-
YWG
1 stop7h 38m
Multiple Airlines
Deal found 7/6C$ 689
Wed 15/78:10 p.m.
YWG
-
MCO
1 stop15h 35m
Multiple Airlines
Tue 11/85:05 p.m.
MCO
-
YWG
1 stop16h 35m
Multiple Airlines
Deal found 7/6C$ 698
Thu 16/75:41 p.m.
YWG
-
MCO
1 stop5h 17m
Delta
Mon 10/87:04 a.m.
MCO
-
YWG
1 stop9h 04m
Delta
Deal found 7/6C$ 700
Sat 18/76:40 a.m.
YWG
-
MCO
1 stop9h 24m
Delta
Sun 23/87:04 a.m.
MCO
-
YWG
1 stop9h 04m
Delta
Deal found 5/6C$ 701
Mon 20/78:50 p.m.
YWG
-
MCO
2 stops20h 54m
American Airlines
Thu 13/89:17 a.m.
MCO
-
YWG
2 stops11h 32m
American Airlines
Deal found 7/6C$ 705
Tue 21/75:41 p.m.
YWG
-
MCO
1 stop5h 17m
Delta
Mon 10/87:04 a.m.
MCO
-
YWG
1 stop9h 04m
Delta
Deal found 7/6C$ 638
Tue 21/75:41 p.m.
YWG
-
MCO
1 stop5h 17m
Delta
Tue 18/812:14 p.m.
MCO
-
YWG
1 stop5h 38m
Delta
Deal found 5/6C$ 640
Tue 21/75:10 p.m.
YWG
-
MCO
1 stop18h 35m
Multiple Airlines
Mon 27/71:45 p.m.
MCO
-
YWG
1 stop7h 09m
Multiple Airlines
Deal found 6/6C$ 714
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 8 June 2026.
Wed 15/78:10 p.m.
YWG
-
MCO
1 stop15h 35m
Multiple Airlines
Deal found 7/6C$ 344
Wed 17/68:10 p.m.
YWG
-
MCO
1 stop15h 35m
Multiple Airlines
Deal found 3/6C$ 350
Sat 18/75:10 p.m.
YWG
-
MCO
1 stop16h 30m
Multiple Airlines
Deal found 7/6C$ 353
Tue 16/69:25 a.m.
YWG
-
MCO
1 stop26h 20m
Multiple Airlines
Deal found 3/6C$ 355
Tue 21/75:41 p.m.
YWG
-
MCO
1 stop5h 17m
Delta
Deal found 7/6C$ 357
Mon 27/78:10 p.m.
YWG
-
MCO
1 stop15h 35m
Multiple Airlines
Deal found 4/6C$ 365
Mon 15/68:10 p.m.
YWG
-
MCO
1 stop15h 35m
Multiple Airlines
Deal found 3/6C$ 367
Mon 20/78:10 p.m.
YWG
-
MCO
1 stop15h 35m
Multiple Airlines
Deal found 7/6C$ 368
Sun 14/69:25 a.m.
YWG
-
MCO
1 stop26h 20m
Multiple Airlines
Deal found 3/6C$ 371
Thu 18/612:46 p.m.
YWG
-
MCO
1 stop10h 11m
Delta
Deal found 4/6C$ 385
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 8 June 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 629,999 searches. Data last updated 8 June 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 - MCO
YWGMCO
Winnipeg
Tue 21/7
5:41 p.m.-11:58 p.m.
1 stop5h 17m
Orlando
Sun 9/8
7:04 a.m.-3:08 p.m.
1 stop9h 04m
C$ 638
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
Sun 5/7
3:54 p.m.-11:57 p.m.
1 stop7h 03m
Orlando
Sun 12/7
6:24 p.m.-11:29 p.m.
1 stop6h 05m
C$ 638
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
Tue 21/7
5:41 p.m.-11:58 p.m.
1 stop5h 17m
Orlando
Wed 12/8
7:04 a.m.-3:08 p.m.
1 stop9h 04m
C$ 638
Quickest round-trip
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
Fri 21/8
5:42 p.m.-11:58 p.m.
1 stop5h 16m
Orlando
Mon 31/8
7:04 a.m.-11:54 a.m.
1 stop5h 50m
C$ 640
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
Fri 28/8
12:46 p.m.-11:58 p.m.
1 stop10h 12m
Orlando
Wed 2/9
7:04 a.m.-3:08 p.m.
1 stop9h 04m
C$ 640
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
Tue 29/9
3:58 p.m.-10:56 p.m.
1 stop5h 58m
Orlando
Sat 3/10
12:16 p.m.-4:54 p.m.
1 stop5h 38m
C$ 700
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
Sat 18/7
6:40 a.m.-5:04 p.m.
1 stop9h 24m
Orlando
Wed 12/8
7:04 a.m.-3:08 p.m.
1 stop9h 04m
C$ 700
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
Fri 10/7
5:41 p.m.-11:58 p.m.
1 stop5h 17m
Orlando
Sun 19/7
3:00 p.m.-11:29 p.m.
1 stop9h 29m
C$ 701
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
Sun 12/7
12:46 p.m.-11:58 p.m.
1 stop10h 12m
Orlando
Sun 19/7
3:00 p.m.-11:29 p.m.
1 stop9h 29m
C$ 701
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
Wed 1/7
5:41 p.m.-11:57 p.m.
1 stop5h 16m
Orlando
Wed 8/7
3:00 p.m.-11:29 p.m.
1 stop9h 29m
C$ 704
Flights are sorted by cheapest round-trip flights first.
Deals found on 3/6
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?
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 8 June 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.
Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
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 5h 17m. Delta provides one of the quickest options available for as low as C$ 638. The distance between Winnipeg and Kissimmee is about 2739 km.
What are the cheapest airlines to fly from Winnipeg to Kissimmee one-way?
C$ 157 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on Porter Airlines and Delta, with prices starting from C$ 168 and C$ 219, respectively.
What are the most reliable airlines from Winnipeg to Kissimmee?
No one likes to see their flight delayed. When booking a flight from Winnipeg to Kissimmee consider choosing Delta (50%), WestJet (50%) or Aeromexico (50%) as they are the most reliable in getting you off to your destination on time.
What are the cheapest flights from Winnipeg to Kissimmee?
The cheapest flight price from Winnipeg to Kissimmee is C$ 235. On average you can expect to pay C$ 594. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 553.
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.
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 629,999 searches. Data last updated 8 June 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.
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