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Kissimmee

$48+ 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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$100
(Kiwi.com)

One-way from

$48
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$267
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
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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 October 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 October 30, 2025.

This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/143:27 pmMDW - MCO
Nonstop2h 42mFrontier
Thu 11/202:34 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 10/30$102
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:30 amMDW - MCO
1 stop14h 39mFrontier
Mon 11/176:35 amMCO - MDW
Nonstop2h 57mFrontier
Deal found 10/30$103
This Trip.com deal was found by Cheapflights users on 10/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/171:37 pmMDW - MCO
1 stop9h 41mFrontier
Mon 11/242:56 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 10/30$104
This Mytrip deal was found by Cheapflights users on 10/29. 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 11/108:00 amMDW - MCO
Nonstop2h 41mFrontier
Sat 11/157:00 amMCO - MDW
1 stop28h 26mFrontier
Deal found 10/29$108
This Frontier deal was found by Cheapflights users on 10/30. 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 11/143:40 pmMDW - MCO
1 stop6h 57mFrontier
Fri 11/219:33 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 10/30$111
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/296:02 pmMDW - MCO
Nonstop2h 47mFrontier
Tue 12/23:57 pmMCO - MDW
1 stop17h 49mFrontier
Deal found 10/28$113
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/53:52 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
Tue 12/98:25 pmMCO - MDW
1 stop13h 21mMultiple Airlines
Deal found 10/30$114
This Frontier deal was found by Cheapflights users on 10/30. 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.
Thu 11/205:30 pmMDW - MCO
Nonstop2h 48mFrontier
Sun 11/232:34 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 10/30$115
This CheapOair deal was found by Cheapflights users on 10/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/43:10 pmMDW - MCO
Nonstop2h 48mFrontier
Thu 12/117:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 10/30$116

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 October 30, 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

Sun 12/7

2:01 pm-11:41 pm

1 stop8h 40m

Orlando

Sat 12/13

4:10 pm-9:22 pm

1 stop6h 12m

$124

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 11/14

3:27 pm-7:09 pm

Nonstop2h 42m

Orlando

Mon 11/17

6:35 am-8:32 am

Nonstop2h 57m

$128

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 11/15

1:37 pm-9:06 pm

1 stop6h 29m

Orlando

Sun 11/16

5:20 am-5:11 pm

1 stop12h 51m

$134

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 2/14

6:50 pm-10:30 pm

Nonstop2h 40m

Orlando

Sat 2/21

7:35 am-9:25 am

Nonstop2h 50m

$137

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 2/8

1:50 pm-8:00 pm

1 stop5h 10m

Orlando

Wed 2/11

7:25 am-9:20 am

Nonstop2h 55m

$143

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 11/19

9:30 am-1:10 pm

Nonstop2h 40m

Orlando

Mon 11/24

9:10 am-2:10 pm

1 stop6h 00m

$193

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/10

11:21 am-6:25 pm

1 stop6h 04m

Orlando

Sat 1/17

10:00 am-4:31 pm

1 stop7h 31m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 12/3

5:29 pm-11:47 pm

1 stop5h 18m

Orlando

Tue 12/9

6:15 am-9:54 am

1 stop4h 39m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 12/9

6:00 am-11:10 am

1 stop4h 10m

Orlando

Wed 12/17

1:15 pm-4:34 pm

1 stop4h 19m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 1/21

12:48 pm-6:43 pm

1 stop4h 55m

Orlando

Sun 1/25

5:30 am-9:58 am

1 stop5h 28m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 21 results
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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 October 24, 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Kissimmee (average of $63). Flying from Chicago Midway Airport to Kissimmee in June is currently the most expensive (average of $167). 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 October 30, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport 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 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 October 26, 2025.

Travelers seeking maximum savings on their Chicago Midway Airport to Kissimmee flight should consider departing on Wednesday afternoons 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.

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 October 30, 2025.
See what other customers who have flown with Southwest, Delta, and Spirit 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
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

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
7.9
Good
7,993 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

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
8,115 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

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
3,123 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

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 2h 40m. Frontier provides one of the quickest options available for as low as $137. 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 $190, our data indicates the cheapest price to be $54. The most popular route (Chicago Midway - Orlando), is priced around $54.

  • 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, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Kissimmee (average of $63). Flying from Chicago Midway Airport to Kissimmee in June is currently the most expensive (average of $167). 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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Top 4 airlines flying from Midway to Kissimmee

Discover the top 4 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$180FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$228FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$177Average$381FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$385FlexibilityNo cancel feeOn-timeN/A

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