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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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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 December 15, 2025.

This Frontier deal was found by Cheapflights users on 12/13. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Thu 1/85:20 amMCO - MDW
1 stop7h 11mFrontier
Deal found 12/13$108
This Frontier deal was found by Cheapflights users on 12/13. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Sun 1/119:03 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 12/13$135
This Kiwi.com deal was found by Cheapflights users on 12/12. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
Wed 1/75:15 pmMCO - MDW
1 stop6h 02mMultiple Airlines
Deal found 12/12$154
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:15 amMDW - MCO
1 stop15h 10mFrontier
Fri 1/99:13 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 12/14$160
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/248:15 amMDW - MCO
1 stop15h 10mFrontier
Thu 1/85:20 amMCO - MDW
1 stop7h 11mFrontier
Deal found 12/14$171
This Kiwi.com deal was found by Cheapflights users on 12/12. 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.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Wed 1/75:20 amMCO - MDW
2 stops9h 46mFrontier
Deal found 12/12$190
This Expedia deal was found by Cheapflights users on 12/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:10 pmMDW - MCO
Nonstop2h 48mFrontier
Mon 1/512:15 pmMCO - MDW
1 stop10h 57mFrontier
Deal found 12/13$191
This Frontier deal was found by Cheapflights users on 12/13. 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.
Mon 12/153:10 pmMDW - MCO
Nonstop2h 48mFrontier
Thu 12/257:58 pmMCO - MDW
Nonstop3h 00mFrontier
Deal found 12/13$194
This Frontier deal was found by Cheapflights users on 12/13. 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.
Tue 12/306:14 amMDW - MCO
1 stop9h 22mFrontier
Fri 1/99:13 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 12/13$195
This Southwest deal was found by Cheapflights users on 12/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:25 pmMDW - MCO
1 stop4h 25mSouthwest
Wed 1/710:45 amMCO - MDW
1 stop4h 45mSouthwest
Deal found 12/12$198

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 December 15, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$94
(CheapOair)

One-way from

$50
(CheapOair)

Popular in

June

Cheapest in

January

Average price

$330
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. 10% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 15, 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 1/18

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Wed 1/21

2:35 pm-4:30 pm

Nonstop2h 55m

$167

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 2/7

2:45 pm-6:20 pm

Nonstop2h 35m

Orlando

Wed 2/11

7:25 am-9:20 am

Nonstop2h 55m

$177

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 1/12

5:30 pm-9:05 pm

Nonstop2h 35m

Orlando

Tue 1/13

2:35 pm-4:30 pm

Nonstop2h 55m

$178

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 1/27

2:20 pm-8:45 pm

1 stop5h 25m

Orlando

Tue 2/10

7:05 pm-9:00 pm

Nonstop2h 55m

$183

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/3

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Tue 2/10

10:45 am-2:30 pm

1 stop4h 45m

$183

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/31

5:40 pm-9:15 pm

Nonstop2h 35m

Orlando

Sat 2/7

6:00 pm-7:55 pm

Nonstop2h 55m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 2/23

8:15 am-11:55 am

Nonstop2h 40m

Orlando

Fri 2/27

6:50 am-8:45 am

Nonstop2h 55m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/24

5:40 pm-9:15 pm

Nonstop2h 35m

Orlando

Fri 1/30

7:25 am-9:20 am

Nonstop2h 55m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/17

5:40 pm-9:15 pm

Nonstop2h 35m

Orlando

Tue 1/20

8:15 am-12:25 pm

1 stop5h 10m

$202

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 1/10

9:45 am-2:50 pm

1 stop4h 05m

Orlando

Sat 1/17

7:00 am-8:55 am

Nonstop2h 55m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 22 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 December 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 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 $59). 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 December 15, 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 22% 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 December 13, 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 December 15, 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
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

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
7.9
Good
4,249 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

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
8,008 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

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
8,188 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

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
3,079 reviews
Southwest
7.9
Good
4,249 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

7.9

Boarding

8.1

Comfort

8.0

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. Southwest provides one of the quickest options available for as low as $167. Airlines will cover a distance of 990 mi. Most flights are nonstop.

  • 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 $208, our data indicates the cheapest price to be $33. The most popular route (Chicago Midway - Orlando), is priced around $58.

  • 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 $59). 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$193FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$221FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$180Average$382FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$408FlexibilityNo cancel feeOn-timeN/A

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