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Kissimmee

$50+ Cheap flights from Midway (MDW) to Kissimmee, FL

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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Kissimmee are usually found in September or January, booked 81 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap flight deals from Midway to Kissimmee

Keep the following information in mind while searching for Midway to Kissimmee flight deals. Data was last updated September 14, 2025.

Round-trip from

$99
(Cheapflightsfares)

One-way from

$50
(Frontier)

Popular in

June

Cheapest in

September

Average price

$237
From Chicago Midway to Kissimmee
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One-way flight from Chicago Midway to Kissimmee
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Highest demand for flights based on searches. 9% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Kissimmee

Cheapest flights from Midway to Kissimmee
Explore the most affordable flight options available from Midway to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 14, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/411:21 amMDW - MCO
Nonstop2h 43mFrontier
Mon 10/65:35 amMCO - MDW
Nonstop2h 48mFrontier
Deal found 9/14$99
This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/298:19 amMDW - MCO
Nonstop2h 41mFrontier
Sun 10/57:25 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 9/13$100
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:48 amMDW - MCO
Nonstop2h 40mFrontier
Sun 9/287:25 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 9/14$102
This Frontier deal was found by Cheapflights users on 9/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/269:48 amMDW - MCO
Nonstop2h 40mFrontier
Mon 9/295:35 amMCO - MDW
Nonstop2h 48mFrontier
Deal found 9/13$104
This Flightnetwork deal was found by Cheapflights users on 9/12. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/275:28 pmMDW - MCO
Nonstop2h 42mFrontier
Mon 11/36:35 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 9/12$107
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 9/199:48 amMDW - MCO
Nonstop2h 40mFrontier
Sun 9/217:25 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 9/12$109
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1912:09 pmMDW - MCO
Nonstop2h 42mFrontier
Thu 10/237:50 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 9/13$110
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 9/228:19 amMDW - MCO
Nonstop2h 41mFrontier
Sat 9/278:00 amMCO - MDW
Nonstop2h 51mFrontier
Deal found 9/12$111
This Priceline deal was found by Cheapflights users on 9/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/31:37 pmMDW - MCO
1 stop6h 29mFrontier
Fri 11/78:24 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 9/12$112
This Booking.com deal was found by Cheapflights users on 9/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2511:31 amMDW - MCO
Nonstop2h 40mFrontier
Mon 10/277:51 pmMCO - MDW
1 stop4h 55mFrontier
Deal found 9/12$113

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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 2,558,603 searches. Data last updated September 14, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Kissimmee that are best for you.

Fly from

Midway

Fly to

Kissimmee

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 11/4

2:25 pm-7:15 pm

1 stop3h 50m

Orlando

Wed 11/12

6:50 pm-8:40 pm

Nonstop2h 50m

$139

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 10/15

8:05 am-2:03 pm

1 stop4h 58m

Orlando

Sat 10/18

8:25 am-10:21 am

Nonstop2h 56m

$142

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 11/12

5:05 am-8:40 am

Nonstop2h 35m

Orlando

Wed 11/19

8:30 am-12:40 pm

1 stop5h 10m

$143

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 10/24

8:45 pm-12:15 am

Nonstop2h 30m

Orlando

Tue 10/28

7:20 am-9:10 am

Nonstop2h 50m

$149

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 10/4

2:50 pm-6:25 pm

Nonstop2h 35m

Orlando

Tue 10/7

9:50 am-11:35 am

Nonstop2h 45m

$156

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 10/22

3:10 pm-6:45 pm

Nonstop2h 35m

Orlando

Sat 10/25

7:10 am-9:00 am

Nonstop2h 50m

$157

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/7

5:25 am-8:55 am

Nonstop2h 30m

Orlando

Sat 10/11

6:10 pm-7:55 pm

Nonstop2h 45m

$168

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/14

8:05 pm-11:35 pm

Nonstop2h 30m

Orlando

Thu 10/16

9:40 pm-11:25 pm

Nonstop2h 45m

$175

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 12/3

5:05 am-8:40 am

Nonstop2h 35m

Orlando

Wed 12/10

4:35 pm-6:25 pm

Nonstop2h 50m

$179

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 10/6

7:05 am-10:35 am

Nonstop2h 30m

Orlando

Mon 10/13

6:35 am-8:20 am

Nonstop2h 45m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 20 results
1
2

Best time to book a flight from Midway to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Midway 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 Chicago Midway Airport to Kissimmee

How far ahead should I book a flight from Chicago Midway Airport to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Kissimmee. Price data was last updated on September 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Kissimmee, you should look to book at least 81 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago Midway Airport to Kissimmee?

Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Kissimmee (average of $206). Flying from Chicago Midway Airport to Kissimmee in November is currently the most expensive (average of $289). 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 MDW to K1S?

Find hourly flight availability from Midway 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 September 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Kissimmee as you normally would.

What is the cheapest day to fly from Chicago Midway Airport to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Midway to Kissimmee. Price data was last updated on September 14, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Kissimmee flight should consider departing on Monday evenings when fares are most often at their lowest. Saturday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago Midway Airport to Kissimmee

Explore weekly flight availability from Midway to Kissimmee. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 14, 2025.

The most flights from MDW to K1S are scheduled on a Sunday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 September 14, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago Midway Airport to Kissimmee have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
8.0
Very good
7,956 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,016 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from Midway to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Kissimmee?

    A quick flight from Chicago Midway Airport to Kissimmee can take about 3h 50m. Southwest provides one of the quickest options available for as low as $139. Airlines will cover a distance of 990 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest flights from Chicago Midway Airport to Kissimmee?

    Looking for the cheapest flight from Chicago Midway Airport to Kissimmee? While on average our users pay $193, our data indicates the cheapest price to be $43. The most popular route (Chicago Midway - Orlando), is priced around $82.

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

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

  • How can I find direct flights from Midway to Kissimmee?

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

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

    Yes. Cheapflights offers flight deals from Midway 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 Chicago Midway Airport to Kissimmee?

    Currently, May is the cheapest month in which you can book a flight from Chicago Midway Airport to Kissimmee (average of $206). Flying from Chicago Midway Airport to Kissimmee in November is currently the most expensive (average of $289). 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

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Alternative routes for Midway to Kissimmee

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Top 5 airlines flying from Midway to Kissimmee

Discover the top 5 airlines that operate flights from Midway 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 2,558,603 searches. Data last updated September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$180FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$235FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$176Average$378FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$349FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$259Average$364FlexibilityNo cancel feeOn-time69%

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