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Kissimmee

$52+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Kissimmee are usually found in January or September, booked 22 days in advance, depart on a Thursday or Friday and return on a Friday

Cheap 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 January 29, 2026.

This Super.com deal was found by Cheapflights users on 1/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/29:22 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Mon 3/911:05 am
MCO
-
MDW
Nonstop3h 03m
Frontier
Deal found 1/27$105
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Sun 3/17:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Fri 3/66:48 pm
MCO
-
MDW
Nonstop3h 05m
Frontier
Deal found 1/27$106
This Trip.com deal was found by Cheapflights users on 1/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/97:00 pm
MDW
-
MCO
Nonstop2h 48m
Frontier
Fri 2/1312:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Deal found 1/28$107
This Trip.com deal was found by Cheapflights users on 1/27. 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.
Fri 3/69:51 pm
MDW
-
MCO
Nonstop2h 47m
Frontier
Fri 3/139:51 pm
MCO
-
MDW
Nonstop3h 00m
Frontier
Deal found 1/27$109
This Super.com deal was found by Cheapflights users on 1/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:08 pm
MDW
-
MCO
Nonstop2h 48m
Frontier
Mon 3/96:48 pm
MCO
-
MDW
Nonstop3h 05m
Frontier
Deal found 1/28$112
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/289:15 am
MDW
-
MCO
1 stop10h 32m
Frontier
Thu 3/512:20 pm
MCO
-
MDW
Nonstop3h 06m
Frontier
Deal found 1/28$113
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/57:30 am
MDW
-
MCO
Nonstop2h 50m
Frontier
Mon 3/911:05 am
MCO
-
MDW
Nonstop3h 03m
Frontier
Deal found 1/29$114
This Frontier deal was found by Cheapflights users on 1/27. 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.
Mon 3/26:00 am
MDW
-
MCO
1 stop10h 26m
Frontier
Wed 3/114:05 pm
MCO
-
MDW
Nonstop3h 08m
Frontier
Deal found 1/27$116
This Trip.com deal was found by Cheapflights users on 1/27. 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 4/139:04 pm
MDW
-
MCO
Nonstop2h 50m
Frontier
Fri 4/176:05 am
MCO
-
MDW
Nonstop2h 59m
Frontier
Deal found 1/27$117
This Trip.com deal was found by Cheapflights users on 1/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/289:15 am
MDW
-
MCO
1 stop10h 32m
Frontier
Tue 3/104:05 pm
MCO
-
MDW
Nonstop3h 08m
Frontier
Deal found 1/28$118
This WAYA deal was found by Cheapflights users on 1/27. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/97:00 pm
MDW
-
MCO
Nonstop2h 48m
Multiple Airlines
Thu 2/123:15 pm
MCO
-
MDW
1 stop8h 19m
Multiple Airlines
Deal found 1/27$119

Find flight deals from Midway to Kissimmee

Keep the following information in mind while searching for Midway to Kissimmee flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$105
(Super.com)

One-way from

$52
(Trip.com)

Popular in

June

Cheapest in

January

Average price

$192
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
Search Deals
From Chicago Midway to Kissimmee
Search Deals
One-way flight from Chicago Midway to Kissimmee
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Sat 2/14

8:00 am-11:49 am

Nonstop2h 49m

Orlando

Wed 2/18

10:28 am-7:07 pm

1 stop9h 39m

$163

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 2/25

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Wed 3/4

7:25 am-9:20 am

Nonstop2h 55m

$168

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 3/2

3:15 pm-6:50 pm

Nonstop2h 35m

Orlando

Wed 3/4

7:25 am-9:20 am

Nonstop2h 55m

$168

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/24

11:30 am-3:05 pm

Nonstop2h 35m

Orlando

Wed 3/4

7:25 am-9:20 am

Nonstop2h 55m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 2/27

8:40 pm-12:20 am

Nonstop2h 40m

Orlando

Wed 3/4

7:25 am-9:20 am

Nonstop2h 55m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 3/7

4:55 pm-8:30 pm

Nonstop2h 35m

Orlando

Mon 3/9

10:50 pm-12:45 am

Nonstop2h 55m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 2/22

4:25 pm-8:00 pm

Nonstop2h 35m

Orlando

Wed 2/25

7:25 am-9:20 am

Nonstop2h 55m

$178

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 2/27

8:40 pm-12:20 am

Nonstop2h 40m

Orlando

Tue 3/3

7:05 pm-9:00 pm

Nonstop2h 55m

$188

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 2/21

6:50 pm-10:30 pm

Nonstop2h 40m

Orlando

Tue 2/24

7:05 pm-9:00 pm

Nonstop2h 55m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 3/3

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Fri 3/6

8:15 am-12:40 pm

1 stop5h 25m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 24 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 January 23, 2026.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport to Kissimmee, you should look to book at least 22 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Kissimmee (average of $58). 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 January 29, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Kissimmee in the afternoon. If you’re flexible enough to do this you can expect to save up to 17% on your trip compared to booking a flight in the morning.

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 January 24, 2026.

Travelers seeking maximum savings on their Chicago Midway Airport to Kissimmee flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday at noon 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 January 29, 2026.
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
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
8,127 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
8,394 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

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 45m. Frontier provides one of the quickest options available for as low as $168. Airlines will cover a distance of 990 mi. Most flights are nonstop.

  • What are the most reliable airlines from Chicago Midway Airport to Kissimmee?

    Before booking your flight to Kissimmee from Chicago Midway Airport, check out the most reliable airlines to get you to your destination on time: Volaris (75%), Southwest (73%), Frontier( 66%).

  • 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 $211, our data indicates the cheapest price to be $60. The most popular route (Chicago Midway - Orlando), is priced around $92.

  • 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Kissimmee (average of $58). 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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Alternative routes for Midway to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$131FlexibilityNo cancel feeOn-time65%
FrontierCheapest$68Average$209FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$551FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$178Average$372FlexibilityNo cancel feeOn-time63%

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