What are the cheapest airlines to fly from Winnipeg to Kissimmee one-way?

C$ 174 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on United Airlines and Air Canada, with prices starting from C$ 206 and C$ 301, respectively.

What are the cheapest flights from Winnipeg to Kissimmee?

The cheapest flight price from Winnipeg to Kissimmee is C$ 265. On average you can expect to pay C$ 337. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 330.

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 Aeromexico (100%), Delta (85%) or WestJet (76%) as they are the most reliable in getting you off to your destination on time.

What are the most popular airlines that fly from Winnipeg to Kissimmee?

When booking a flight from Winnipeg to Kissimmee, you may want to consider flying on Air Canada, Delta or Porter Airlines as they are the most popular for this route.

How far in advance should I book a flight from Winnipeg to Kissimmee?

To save on the cost of your flight from Winnipeg to Kissimmee, book at least 48 days before your planned departure. Booking around this time can save you about 42% on the cost of this flight compared to booking a flight leaving this week. We have found prices from C$ 365 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as C$ 950.

What is the cheapest month to fly from Winnipeg to Kissimmee?

Flights from Winnipeg to Kissimmee lean towards being more expensive in December. Prices are generally better when you fly from Winnipeg to Kissimmee in November, with the cheapest ticket starting at C$ 273.

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.

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

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

How can I find direct flights from Winnipeg to Kissimmee?

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

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.

C$ 174+ Flights from Winnipeg to Kissimmee

Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in October or May, booked 69 days in advance, depart on a Wednesday or Saturday and return on a Tuesday

Cheap flight deals from Winnipeg to Kissimmee

Round-trip from	C$ 288
One-way from	C$ 174
Popular in	December
Cheapest in	October
Average price	C$ 371

WestJet
5/7-26/7
Nonstop
8h 24m total
Winnipeg to Kissimmee

Search Deals

WestJet
12/7
Nonstop
4h 00m total
Winnipeg to Kissimmee

Search Deals

Highest demand for flights based on searches. 5% potential increase in price (C$ 34 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in June 2025

Search Deals

Find flight deals from Winnipeg to Kissimmee

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 12 junio 2025.

sáb. 5/79:10 a.m.YWG - MCO

Nonstop4h 00mWestJet

sáb. 26/73:15 p.m.MCO - YWG

Nonstop4h 24mWestJet

Deal found 11/6C$ 288

mar. 21/103:45 p.m.YWG - MCO

1 stop7h 07mAir Canada

mar. 28/108:25 a.m.MCO - YWG

2 stops12h 33mAir Canada

Deal found 10/6C$ 325

mar. 15/711:45 a.m.YWG - MCO

1 stop6h 59mMultiple Airlines

vie. 1/811:00 a.m.MCO - YWG

1 stop6h 58mMultiple Airlines

Deal found 11/6C$ 330

jue. 23/104:25 p.m.YWG - MCO

1 stop12h 08mUnited Airlines

vie. 31/108:00 a.m.MCO - YWG

1 stop13h 48mUnited Airlines

Deal found 10/6C$ 338

mar. 8/76:45 a.m.YWG - MCO

1 stop9h 27mDelta

mar. 15/73:00 p.m.MCO - YWG

1 stop9h 25mDelta

Deal found 10/6C$ 371

vie. 12/125:00 a.m.YWG - MCO

1 stop9h 50mPorter Airlines

dom. 21/128:45 a.m.MCO - YWG

2 stops10h 19mPorter Airlines

Deal found 9/6C$ 604

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 12 junio 2025.

sáb. 5/79:10 a.m.YWG - MCO

Nonstop4h 00mWestJet

sáb. 26/73:15 p.m.MCO - YWG

Nonstop4h 24mWestJet

Deal found 11/6C$ 288

mar. 15/711:45 a.m.YWG - MCO

1 stop6h 59mMultiple Airlines

vie. 1/811:00 a.m.MCO - YWG

1 stop6h 58mMultiple Airlines

Deal found 11/6C$ 330

vie. 25/72:20 p.m.YWG - MCO

1 stop6h 26mUnited Airlines

vie. 1/810:53 a.m.MCO - YWG

1 stop12h 40mUnited Airlines

Deal found 10/6C$ 338

mar. 8/76:45 a.m.YWG - MCO

1 stop9h 27mDelta

mar. 15/73:00 p.m.MCO - YWG

1 stop9h 25mDelta

Deal found 10/6C$ 371

lun. 23/611:45 a.m.YWG - MCO

1 stop6h 56mPorter Airlines

vie. 27/61:45 p.m.MCO - YWG

1 stop10h 01mPorter Airlines

Deal found 11/6C$ 606

Last-minute flights from Winnipeg to Kissimmee
Discover last-minute flight deals from Winnipeg to Kissimmee. Data last updated 12 junio 2025 and is based on user searches.

mar. 17/64:25 p.m.YWG - MCO

1 stop12h 11mUnited Airlines

mié. 18/69:32 a.m.MCO - YWG

1 stop6h 59mUnited Airlines

Deal found 10/6C$ 498

mar. 17/68:15 p.m.YWG - MCO

2 stops20h 48mMultiple Airlines

mar. 24/66:05 p.m.MCO - YWG

1 stop27h 05mMultiple Airlines

Deal found 9/6C$ 649

mar. 17/66:45 a.m.YWG - MCO

1 stop5h 54mDelta

mar. 24/63:02 p.m.MCO - YWG

1 stop9h 27mDelta

Deal found 9/6C$ 695

mar. 17/66:15 p.m.YWG - MCO

2 stops14h 54mWestJet

mar. 24/611:00 a.m.MCO - YWG

2 stops28h 11mWestJet

Deal found 9/6C$ 710

lun. 23/611:45 a.m.YWG - MCO

1 stop6h 56mPorter Airlines

vie. 27/61:45 p.m.MCO - YWG

1 stop10h 01mPorter Airlines

Deal found 11/6C$ 606

sáb. 5/79:10 a.m.YWG - MCO

Nonstop4h 00mWestJet

sáb. 26/73:15 p.m.MCO - YWG

Nonstop4h 24mWestJet

Deal found 11/6C$ 288

mar. 8/76:45 a.m.YWG - MCO

1 stop9h 27mDelta

mar. 15/73:00 p.m.MCO - YWG

1 stop9h 25mDelta

Deal found 10/6C$ 371

mar. 15/711:45 a.m.YWG - MCO

1 stop6h 59mMultiple Airlines

vie. 1/811:00 a.m.MCO - YWG

1 stop6h 58mMultiple Airlines

Deal found 11/6C$ 330

vie. 25/72:20 p.m.YWG - MCO

1 stop6h 26mUnited Airlines

vie. 1/810:53 a.m.MCO - YWG

1 stop12h 40mUnited Airlines

Deal found 10/6C$ 338

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 12 junio 2025.

sáb. 12/79:10 a.m.YWG - MCO

Nonstop4h 00mWestJet

Deal found 11/6C$ 174

dom. 13/79:05 p.m.YWG - MCO

2 stops22h 49mMultiple Airlines

Deal found 11/6C$ 205

mié. 9/77:00 a.m.YWG - MCO

1 stop10h 00mUnited Airlines

Deal found 11/6C$ 206

mié. 25/64:25 p.m.YWG - MCO

1 stop18h 20mAir Canada

Deal found 10/6C$ 301

sáb. 28/611:45 a.m.YWG - MCO

1 stop6h 56mPorter Airlines

Deal found 11/6C$ 399

Cheapflights Fare Finder

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

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

sáb. 5/7

9:10 a.m.-2:10 p.m.

Nonstop4h 00m

Orlando

sáb. 26/7

3:15 p.m.-6:39 p.m.

Nonstop4h 24m

C$ 288

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

mar. 15/7

11:45 a.m.-7:44 p.m.

1 stop6h 59m

Orlando

vie. 1/8

11:00 a.m.-4:58 p.m.

1 stop6h 58m

C$ 330

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

jue. 23/10

4:25 p.m.-5:33 a.m.

1 stop12h 08m

Orlando

dom. 2/11

4:20 p.m.-10:30 p.m.

1 stop7h 10m

C$ 338

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

mié. 22/10

3:45 p.m.-11:52 p.m.

1 stop7h 07m

Orlando

lun. 27/10

8:25 a.m.-7:58 p.m.

2 stops12h 33m

C$ 364

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

mar. 8/7

6:45 a.m.-5:12 p.m.

1 stop9h 27m

Orlando

mar. 15/7

3:00 p.m.-11:25 p.m.

1 stop9h 25m

C$ 371

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

mié. 15/10

11:45 a.m.-7:41 p.m.

1 stop6h 56m

Orlando

dom. 19/10

1:45 p.m.-8:46 p.m.

1 stop8h 01m

C$ 574

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

sáb. 12/7

9:10 a.m.-2:10 p.m.

Nonstop4h 00m

C$ 174

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

dom. 13/7

9:05 p.m.-8:54 p.m.

2 stops22h 49m

C$ 205

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

mié. 9/7

7:00 a.m.-6:00 p.m.

1 stop10h 00m

C$ 206

WinnipegOrlando

YWG - MCO

YWGMCO

Winnipeg

jue. 30/10

5:15 a.m.-5:08 p.m.

2 stops10h 53m

C$ 249

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

Showing 1-10 of 11 results

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?

The best time to book flights from Winnipeg to Kissimmee is 69 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, June is the cheapest month in which you can book a flight from Winnipeg to Kissimmee (average of C$ 196). Flying from Winnipeg to Kissimmee in February is currently the most expensive (average of C$ 313). 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?

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

What is the cheapest day to fly from Winnipeg to Kissimmee?

Travelers seeking maximum savings on their Winnipeg to Kissimmee flight should consider departing on Sunday mornings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Kissimmee by month

In terms of precipitation, rainfall in Kissimmee ranges from 61.0 - 221.0 mm per month. June is typically the wettest month, when rainfall can reach 221.0 mm. November is typically the driest time to visit Kissimmee when rainfall is around 61.0 mm.

Temperature in Kissimmee by month

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 29.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 16.0 C).

Reviews of airlines servicing Kissimmee

See what other customers who have flown with Porter Airlines, Delta and United Airlines from Winnipeg to Kissimmee have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Porter Airlines

8.0

Very good

288 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Delta

8.0

Very good

7,946 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

United Airlines

7.4

Good

8,790 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

WestJet

7.2

Good

2,868 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Air Canada

7.1

Good

9,537 reviews

Porter Airlines

8.0

Very good

288 reviews

Check prices

Reviews

1 / 20

4.0

Okay

Mary,Jun 2025

FLL - YYZ

Related info for your journey

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.
What are the cheapest airlines to fly from Winnipeg to Kissimmee one-way?
C$ 174 is the cheapest one-way deal found within the past few days, from WestJet. You may also be able to find cheap deals on United Airlines and Air Canada, with prices starting from C$ 206 and C$ 301, 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 Aeromexico (100%), Delta (85%) or WestJet (76%) 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$ 265. On average you can expect to pay C$ 337. The most popular route, (Winnipeg - Orlando), can usually be booked for C$ 330.
Can I find deals for flights from Winnipeg to Kissimmee that include hotel bookings?
Yes. In addition to deals on Winnipeg to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Winnipeg to Kissimmee?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Winnipeg to Kissimmee.
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, June is the cheapest month in which you can book a flight from Winnipeg to Kissimmee (average of C$ 196). Flying from Winnipeg to Kissimmee in February is currently the most expensive (average of C$ 313). 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

Browse thousands of different options on Cheapflights for your next trip

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Top 5 airlines flying from Winnipeg to Kissimmee

Airline	Cheapest	Average	Flexibility	On-time
United Airlines	CheapestC$ 217	AverageC$ 405	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
Porter Airlines	CheapestC$ 250	AverageC$ 462	FlexibilityNo cancel fee	On-time52%	Search Porter Airlines flights
WestJet	CheapestC$ 281	AverageC$ 589	FlexibilityNo cancel fee	On-time60%	Search WestJet flights
Air Canada	CheapestC$ 307	AverageC$ 561	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights
Delta	CheapestC$ 341	AverageC$ 564	FlexibilityNo cancel fee	On-timeN/A	Search Delta flights

Fly with Cheapflights

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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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.

Cheap flights from Winnipeg to Kissimmee from C$ 174

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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.

Cheapflights Tip: The best prices from Winnipeg to Kissimmee are usually found in October or May, booked 69 days in advance, depart on a Wednesday or Saturday and return on a Tuesday

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 12 junio 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Winnipeg to Kissimmee

Cheapest flights from Winnipeg to KissimmeeExplore 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 12 junio 2025.

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 12 junio 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Winnipeg to Kissimmee that are best for you.

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.

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 9 June 2025.

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

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 12 junio 2025.

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 8 June 2025.

Rainfall in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average rainfall totals by month.

Temperature in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average temperature totals by month.

Reviews of airlines servicing Kissimmee

See what other customers who have flown with Porter Airlines, Delta and United Airlines from Winnipeg to Kissimmee have to say. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

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?

What are the cheapest airlines to fly from Winnipeg to Kissimmee one-way?

What are the most reliable airlines from Winnipeg to Kissimmee?

What are the cheapest flights from Winnipeg to Kissimmee?

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

How can I find direct flights from Winnipeg to Kissimmee?

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Winnipeg to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from Winnipeg to Kissimmee

Fly with Cheapflights

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?

Why should you use Cheapflights to find cheap flight tickets from Winnipeg to Kissimmee?

Can Cheapflights find flights from Winnipeg to Kissimmee with no change fees?

Can Cheapflights notify me if prices for flights from Winnipeg to Kissimmee become cheaper?

100% Free

Book with Flexibility

Travel Smart

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 12 junio 2025.