Cheap flights from Winnipeg to Kissimmee from C$ 164
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 17/1. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — MCO
26 dic. — 2 ene.1
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 October or September, booked 33 days in advance, depart on a Monday or Saturday and return on a Wednesday
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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 26 noviembre 2025.
mar. 16/128:00 a.m.YWG - MCO
Nonstop4h 07mWestJet
vie. 26/1211:10 a.m.MCO - YWG
1 stop14h 25mWestJet
Deal found 25/11C$ 303
mié. 10/127:30 a.m.YWG - MCO
1 stop9h 50mMultiple Airlines
dom. 14/126:34 p.m.MCO - YWG
1 stop24h 29mMultiple Airlines
Deal found 24/11C$ 319
vie. 12/128:40 a.m.YWG - MCO
1 stop9h 55mUnited Airlines
mar. 16/127:13 p.m.MCO - YWG
2 stops17h 44mUnited Airlines
Deal found 26/11C$ 327
mar. 2/129:00 p.m.YWG - MCO
3 stops20h 28mMultiple Airlines
mar. 9/128:25 p.m.MCO - YWG
2 stops22h 41mMultiple Airlines
Deal found 25/11C$ 372
jue. 11/128:05 p.m.YWG - MCO
1 stop26h 20mMultiple Airlines
lun. 15/1211:10 a.m.MCO - YWG
1 stop9h 27mMultiple Airlines
Deal found 25/11C$ 388
mar. 16/128:00 a.m.YWG - MCO
Nonstop4h 07mDelta
vie. 26/128:00 a.m.MCO - YWG
1 stop8h 07mDelta
Deal found 26/11C$ 398
lun. 1/128:00 a.m.YWG - MCO
2 stops36h 59mMultiple Airlines
lun. 8/1211:10 a.m.MCO - YWG
1 stop9h 42mMultiple Airlines
Deal found 24/11C$ 460
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 26 noviembre 2025.
mar. 31/32:15 p.m.YWG - MCO
1 stop6h 40mUnited Airlines
mié. 13/510:30 a.m.MCO - YWG
1 stop11h 18mUnited Airlines
Deal found 25/11C$ 334
vie. 27/24:00 p.m.YWG - MCO
Nonstop3h 59mWestJet
mar. 10/311:10 a.m.MCO - YWG
1 stop8h 59mWestJet
Deal found 26/11C$ 339
jue. 26/22:20 p.m.YWG - MCO
2 stops9h 23mUnited Airlines
dom. 8/38:40 p.m.MCO - YWG
1 stop16h 17mUnited Airlines
Deal found 26/11C$ 334
sáb. 21/22:20 p.m.YWG - MCO
1 stop6h 20mUnited Airlines
jue. 26/28:43 p.m.MCO - YWG
1 stop16h 14mUnited Airlines
Deal found 26/11C$ 339
mié. 14/12:20 p.m.YWG - MCO
1 stop8h 24mUnited Airlines
dom. 18/110:00 a.m.MCO - YWG
2 stops26h 57mUnited Airlines
Deal found 25/11C$ 339
lun. 23/22:20 p.m.YWG - MCO
1 stop6h 20mUnited Airlines
lun. 2/38:43 p.m.MCO - YWG
1 stop16h 14mUnited Airlines
Deal found 25/11C$ 339
lun. 2/32:20 p.m.YWG - MCO
1 stop8h 23mUnited Airlines
sáb. 7/38:40 p.m.MCO - YWG
1 stop15h 17mUnited Airlines
Deal found 26/11C$ 339
sáb. 21/22:20 p.m.YWG - MCO
1 stop6h 20mUnited Airlines
lun. 2/38:43 p.m.MCO - YWG
1 stop16h 14mUnited Airlines
Deal found 25/11C$ 339
sáb. 28/22:20 p.m.YWG - MCO
2 stops9h 23mUnited Airlines
dom. 8/38:40 p.m.MCO - YWG
1 stop16h 17mUnited Airlines
Deal found 26/11C$ 339
mié. 25/22:20 p.m.YWG - MCO
2 stops9h 23mUnited Airlines
vie. 6/38:40 p.m.MCO - YWG
1 stop16h 17mUnited Airlines
Deal found 25/11C$ 339
mar. 3/32:20 p.m.YWG - MCO
1 stop6h 20mUnited Airlines
dom. 8/38:40 p.m.MCO - YWG
1 stop16h 17mUnited Airlines
Deal found 25/11C$ 339
mar. 20/12:20 p.m.YWG - MCO
2 stops20h 34mUnited Airlines
mié. 4/27:15 p.m.MCO - YWG
2 stops17h 42mUnited Airlines
Deal found 23/11C$ 341
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 26 noviembre 2025.
mar. 16/128:00 a.m.YWG - MCO
Nonstop4h 07mWestJet
vie. 26/1210:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 24/11C$ 435
mar. 24/28:00 a.m.YWG - MCO
Nonstop4h 03mWestJet
mar. 3/32:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 25/11C$ 528
vie. 16/14:00 p.m.YWG - MCO
Nonstop4h 03mWestJet
mar. 20/12:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 25/11C$ 540
mar. 24/28:00 a.m.YWG - MCO
Nonstop4h 03mWestJet
vie. 27/210:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 24/11C$ 645
mar. 23/128:00 a.m.YWG - MCO
Nonstop4h 07mWestJet
mar. 30/122:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 26/11C$ 653
mar. 27/18:00 a.m.YWG - MCO
Nonstop4h 07mWestJet
mar. 3/22:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 26/11C$ 677
mar. 23/128:00 a.m.YWG - MCO
Nonstop4h 07mWestJet
vie. 2/110:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 23/11C$ 687
mar. 16/128:00 a.m.YWG - MCO
Nonstop4h 07mWestJet
mar. 30/122:00 p.m.MCO - YWG
Nonstop4h 26mWestJet
Deal found 24/11C$ 728
Last-minute flights from Winnipeg to Kissimmee
Discover last-minute flight deals from Winnipeg to Kissimmee. Data last updated 26 noviembre 2025 and is based on user searches.
lun. 1/128:00 a.m.YWG - MCO
2 stops36h 59mMultiple Airlines
lun. 8/1211:10 a.m.MCO - YWG
1 stop9h 42mMultiple Airlines
Deal found 24/11C$ 460
mar. 2/129:00 p.m.YWG - MCO
3 stops20h 28mMultiple Airlines
mar. 9/128:25 p.m.MCO - YWG
2 stops22h 41mMultiple Airlines
Deal found 25/11C$ 372
mié. 10/127:30 a.m.YWG - MCO
1 stop9h 50mMultiple Airlines
dom. 14/126:34 p.m.MCO - YWG
1 stop24h 29mMultiple Airlines
Deal found 24/11C$ 319
jue. 11/128:05 p.m.YWG - MCO
1 stop26h 20mMultiple Airlines
lun. 15/1211:10 a.m.MCO - YWG
1 stop9h 27mMultiple Airlines
Deal found 25/11C$ 388
vie. 12/128:40 a.m.YWG - MCO
2 stops25h 29mUnited Airlines
mar. 16/124:28 p.m.MCO - YWG
2 stops20h 29mUnited Airlines
Deal found 26/11C$ 327
mar. 16/128:00 a.m.YWG - MCO
Nonstop4h 07mWestJet
vie. 26/1211:10 a.m.MCO - YWG
1 stop14h 25mWestJet
Deal found 25/11C$ 303
mar. 16/128:00 a.m.YWG - MCO
Nonstop4h 07mDelta
vie. 26/128:00 a.m.MCO - YWG
1 stop8h 07mDelta
Deal found 26/11C$ 398
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 26 noviembre 2025.
sáb. 17/112:20 p.m.YWG - MCO
1 stop7h 02mWestJet
Deal found 25/11C$ 164
sáb. 24/112:20 p.m.YWG - MCO
1 stop7h 02mWestJet
Deal found 25/11C$ 168
mié. 21/112:20 p.m.YWG - MCO
1 stop7h 02mWestJet
Deal found 25/11C$ 169
mar. 20/19:00 p.m.YWG - MCO
2 stops26h 01mMultiple Airlines
Deal found 25/11C$ 179
lun. 19/14:10 p.m.YWG - MCO
3 stops21h 32mMultiple Airlines
Deal found 25/11C$ 182
sáb. 24/16:55 p.m.YWG - MCO
3 stops23h 59mMultiple Airlines
Deal found 25/11C$ 183
sáb. 10/16:55 p.m.YWG - MCO
3 stops22h 05mMultiple Airlines
Deal found 25/11C$ 195
jue. 15/112:20 p.m.YWG - MCO
1 stop21h 04mWestJet
Deal found 25/11C$ 198
dom. 18/15:00 a.m.YWG - MCO
1 stop17h 07mWestJet
Deal found 25/11C$ 200
vie. 23/16:55 p.m.YWG - MCO
3 stops22h 05mMultiple Airlines
Deal found 25/11C$ 202
Cheap flight deals from Winnipeg to Kissimmee
Keep the following information in mind while searching for Winnipeg to Kissimmee flight deals. Data was last updated 26 noviembre 2025.
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 26 noviembre 2025.
Use the filters below to find and compare flights from Winnipeg to Kissimmee that are best for you.
Fly from
Winnipeg
Fly to
Kissimmee
Route
Depart
Return
Price
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
mar. 31/3
2:15 p.m.-9:55 p.m.
1 stop6h 40m
Orlando
mié. 13/5
10:30 a.m.-8:48 p.m.
1 stop11h 18m
C$ 334
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
jue. 26/2
2:20 p.m.-12:43 a.m.
2 stops9h 23m
Orlando
dom. 8/3
8:40 p.m.-11:57 a.m.
1 stop16h 17m
C$ 334
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
vie. 27/2
4:00 p.m.-8:59 p.m.
Nonstop3h 59m
Orlando
mar. 10/3
11:10 a.m.-7:09 p.m.
1 stop8h 59m
C$ 339
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
sáb. 21/2
2:20 p.m.-9:40 p.m.
1 stop6h 20m
Orlando
jue. 26/2
8:43 p.m.-11:57 a.m.
1 stop16h 14m
C$ 339
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
mié. 14/1
2:20 p.m.-11:44 p.m.
1 stop8h 24m
Orlando
dom. 18/1
10:00 a.m.-11:57 a.m.
2 stops26h 57m
C$ 339
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
lun. 23/2
2:20 p.m.-9:40 p.m.
1 stop6h 20m
Orlando
lun. 2/3
8:43 p.m.-11:57 a.m.
1 stop16h 14m
C$ 339
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
lun. 2/3
2:20 p.m.-11:43 p.m.
1 stop8h 23m
Orlando
sáb. 7/3
8:40 p.m.-10:57 a.m.
1 stop15h 17m
C$ 339
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
sáb. 21/2
2:20 p.m.-9:40 p.m.
1 stop6h 20m
Orlando
lun. 2/3
8:43 p.m.-11:57 a.m.
1 stop16h 14m
C$ 339
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
sáb. 28/2
2:20 p.m.-12:43 a.m.
2 stops9h 23m
Orlando
dom. 8/3
8:40 p.m.-11:57 a.m.
1 stop16h 17m
C$ 339
WinnipegOrlando
YWG - MCO
YWGMCO
Winnipeg
mié. 25/2
2:20 p.m.-12:43 a.m.
2 stops9h 23m
Orlando
vie. 6/3
8:40 p.m.-11:57 a.m.
1 stop16h 17m
C$ 339
Flights are sorted by cheapest round-trip flights first.
Deals found on 25/11
Showing 1-10 of 23 results
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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.
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
How far ahead should I book a flight from Winnipeg to Kissimmee?
Use this chart to determine the optimal time to book a round-trip flight from Winnipeg to Kissimmee. Price data was last updated on 21 November 2025.
The best time to book flights from Winnipeg to Kissimmee is 33 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Winnipeg to Kissimmee?
Currently, May is the cheapest month in which you can book a flight from Winnipeg to Kissimmee (average of C$ 224). Flying from Winnipeg to Kissimmee in January is currently the most expensive (average of C$ 316). 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 YWG to K1S?
Find hourly flight availability from Winnipeg to Kissimmee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 26 noviembre 2025.
A simple way to save on the total cost of your ticket is to fly from Winnipeg to Kissimmee in the evening. If you’re flexible enough to do this you can expect to save up to 21% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Winnipeg to Kissimmee?
Use this chart to determine the cheapest time to fly round-trip from Winnipeg to Kissimmee. Price data was last updated on 25 November 2025.
Travelers seeking maximum savings on their Winnipeg to Kissimmee flight should consider departing on Sunday afternoons when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
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 26 noviembre 2025.
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.
It's good. Planes are new and fresh. WiFi is best and stands out
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 6h 40m. United Airlines provides one of the quickest options available for as low as C$ 334. The distance between Winnipeg and Kissimmee is about 2739 km.
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 LATAM Airlines (100%), Delta (100%) or WestJet (100%) 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$ 201. On average you can expect to pay C$ 439. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 279.
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.
What is the cheapest month to book a flight from Winnipeg to Kissimmee?
Currently, May is the cheapest month in which you can book a flight from Winnipeg to Kissimmee (average of C$ 224). Flying from Winnipeg to Kissimmee in January is currently the most expensive (average of C$ 316). 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.
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on 26 noviembre 2025.
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 26 noviembre 2025.
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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