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$186+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — YWG
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
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 June 9, 2026.

This FlightHub deal was found by Cheapflights users on 6/8. 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.
Thu 8/271:45 pm
MCO
-
YWG
1 stop7h 04m
Porter Airlines
Mon 8/319:20 am
YWG
-
MCO
2 stops9h 14m
Porter Airlines
Deal found 6/8$486
This FlightHub deal was found by Cheapflights users on 6/6. 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.
Tue 12/153:00 pm
MCO
-
YWG
1 stop9h 35m
Porter Airlines
Mon 12/2812:10 pm
YWG
-
MCO
1 stop10h 10m
Porter Airlines
Deal found 6/6$493
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Fri 7/1011:20 am
MCO
-
YWG
2 stops9h 34m
Multiple Airlines
Tue 7/215:10 pm
YWG
-
MCO
1 stop18h 35m
Multiple Airlines
Deal found 6/4$497
This FlightHub deal was found by Cheapflights users on 6/6. 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.
Tue 12/153:00 pm
MCO
-
YWG
1 stop9h 35m
Multiple Airlines
Sun 12/278:05 pm
YWG
-
MCO
1 stop13h 19m
Multiple Airlines
Deal found 6/6$503
This Mytrip deal was found by Cheapflights users on 6/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:05 pm
MCO
-
YWG
1 stop16h 35m
Multiple Airlines
Mon 7/68:10 pm
YWG
-
MCO
1 stop13h 30m
Multiple Airlines
Deal found 6/7$511
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Fri 6/191:45 pm
MCO
-
YWG
1 stop7h 04m
Multiple Airlines
Mon 6/228:10 pm
YWG
-
MCO
1 stop15h 35m
Multiple Airlines
Deal found 6/5$521
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Sat 7/1811:20 am
MCO
-
YWG
1 stop7h 38m
Multiple Airlines
Sat 7/255:10 pm
YWG
-
MCO
1 stop18h 35m
Multiple Airlines
Deal found 6/4$522
This FlightHub deal was found by Cheapflights users on 6/8. 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.
Fri 8/2811:20 am
MCO
-
YWG
2 stops9h 29m
Porter Airlines
Mon 8/319:20 am
YWG
-
MCO
2 stops9h 14m
Porter Airlines
Deal found 6/8$528
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Mon 6/291:45 pm
MCO
-
YWG
1 stop7h 04m
Multiple Airlines
Fri 7/310:45 am
YWG
-
MCO
1 stop8h 00m
Multiple Airlines
Deal found 6/5$539

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 June 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$486
(FlightHub)

One-way from

$186
(Kiwi.com)

Popular in

January

Cheapest in

June

Average price

$178
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. 27% potential increase in price ($178 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($50 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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 June 9, 2026.
Use the filters below to find and compare flights from Kissimmee to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 8/27

1:45 pm-7:49 pm

1 stop7h 04m

Winnipeg

Mon 8/31

9:20 am-7:34 pm

2 stops9h 14m

$486

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 7/10

11:20 am-7:54 pm

2 stops9h 34m

Winnipeg

Tue 7/21

5:10 pm-12:45 pm

1 stop18h 35m

$497

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 7/18

11:20 am-5:58 pm

1 stop7h 38m

Winnipeg

Sat 7/25

5:10 pm-12:45 pm

1 stop18h 35m

$522

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Mon 7/6

6:00 am-3:19 pm

2 stops34h 19m

Winnipeg

Mon 7/13

8:10 pm-12:45 pm

1 stop15h 35m

$540

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Tue 6/30

1:45 pm-7:49 pm

1 stop7h 04m

Winnipeg

Mon 7/6

6:05 pm-10:40 am

1 stop15h 35m

$580
Quickest round-trip

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 8/27

7:04 am-3:08 pm

1 stop9h 04m

Winnipeg

Mon 8/31

3:58 pm-11:58 pm

1 stop7h 00m

$585

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 8/28

7:04 am-3:08 pm

1 stop9h 04m

Winnipeg

Mon 8/31

3:58 pm-11:58 pm

1 stop7h 00m

$585

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Fri 6/19

11:15 am-5:58 pm

1 stop7h 43m

Winnipeg

Wed 6/24

4:25 pm-10:40 am

1 stop17h 15m

$612
Cheapest one-way
Quickest one-way

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Sat 7/11

11:20 am-5:58 pm

1 stop7h 38m

$237

OrlandoWinnipeg

MCO - YWG

MCOYWG

Orlando

Thu 7/23

1:45 pm-8:40 am

1 stop19h 55m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 18 resultsSorted by cheapest first
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

How much does it cost to fly round-trip from Kissimmee to Winnipeg?

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 June 9, 2026.
See what other customers who have flown with Delta 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
8,393 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

7.9

Entertainment

7.8

Food

7.2

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
8,393 reviews
Delta
7.9
Good
8,393 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

7.9

Entertainment

7.8

Food

7.2

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
3,356 reviews
Delta
7.9
Good
8,393 reviews

Boarding

8.1

Crew

8.5

Comfort

7.8

Overall

7.9

Entertainment

7.8

Food

7.2

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 3 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 7h 04m. Porter Airlines provides one of the quickest options available for as low as $486. 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 (83%), WestJet (83%), LATAM Airlines( 75%).

  • 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.

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 3 airlines flying from Kissimmee to Winnipeg

Discover the top 3 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 June 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$169Average$588FlexibilityNo cancel feeOn-time69%
DeltaCheapest$201Average$577FlexibilityNo cancel feeOn-timeN/A
WestJetCheapest$204Average$276FlexibilityNo cancel feeOn-time60%

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