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Kissimmee

$79+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — MCO
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago Midway to Kissimmee are usually found in July 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 June 16, 2025.

Round-trip from

$126
(Cheapflightsfares)

One-way from

$79
(Southwest)

Popular in

June

Cheapest in

July

Average price

$428
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. 3% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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 9/128:34 amMDW - MCO
Nonstop2h 41mFrontier
Sun 9/215:45 amMCO - MDW
Nonstop2h 54mFrontier
Deal found 6/16$126
This Southwest deal was found by Cheapflights users on 6/16. 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.
Tue 7/159:00 amMDW - MCO
Nonstop2h 40mSouthwest
Tue 7/2210:30 amMCO - MDW
Nonstop2h 50mSouthwest
Deal found 6/16$159
This Delta deal was found by Cheapflights users on 6/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/296:00 amMDW - MCO
1 stop5h 05mDelta
Tue 8/54:40 pmMCO - MDW
1 stop6h 02mDelta
Deal found 6/14$197
This WAYA deal was found by Cheapflights users on 6/14. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/911:39 amMDW - MCO
1 stop8h 15mMultiple Airlines
Sat 7/126:23 pmMCO - MDW
Nonstop2h 59mMultiple Airlines
Deal found 6/14$211
This Mytrip deal was found by Cheapflights users on 6/15. 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.
Fri 8/11:11 pmMDW - MCO
1 stop24h 08mAllegiant Air
Fri 8/88:27 amMCO - MDW
1 stop6h 29mAllegiant Air
Deal found 6/15$221

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 June 16, 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

Fri 9/12

8:34 am-12:15 pm

Nonstop2h 41m

Orlando

Sun 9/21

5:45 am-7:39 am

Nonstop2h 54m

$126

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 7/15

9:00 am-12:40 pm

Nonstop2h 40m

Orlando

Tue 7/22

10:30 am-12:20 pm

Nonstop2h 50m

$159

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 7/29

12:43 pm-6:39 pm

1 stop4h 56m

Orlando

Tue 8/5

8:50 am-12:29 pm

1 stop4h 39m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 7/9

11:39 am-8:54 pm

1 stop8h 15m

Orlando

Sat 7/12

6:23 pm-8:22 pm

Nonstop2h 59m

$211

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 8/1

1:11 pm-2:19 pm

1 stop24h 08m

Orlando

Fri 8/8

8:27 am-1:56 pm

1 stop6h 29m

$221

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 8/23

3:30 pm-7:10 pm

Nonstop2h 40m

$79

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 7/26

9:12 pm-1:03 am

Nonstop2h 51m

$81

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 8/1

1:11 pm-2:19 pm

1 stop24h 08m

$103

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 7/8

5:05 pm-12:15 am

1 stop6h 10m

$105

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 8/11

1:11 pm-7:15 pm

2 stops29h 04m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/14

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 June 13, 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 June 16, 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 June 15, 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 June 16, 2025.

The most flights from MDW to K1S are scheduled on a Sunday (19 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (9 on average).

Rainfall in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kissimmee ranges from 2.4 - 8.7 inches per month. June is typically the wettest month, when rainfall can reach 8.7 in. November is typically the driest time to visit Kissimmee when rainfall is around 2.4 in.

Temperature in Kissimmee by month

Plan your trip to Kissimmee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kissimmee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 60.8 F).

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 June 16, 2025.
See what other customers who have flown with Southwest, Delta and Allegiant Air from Chicago to Kissimmee have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.6

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
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.6

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
7,963 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.6

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.
Allegiant Air
7.3
Good
722 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.6

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
5.9
Fair
3,296 reviews
Southwest
8.0
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.6

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Kissimmee one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $79. However, be on the lookout for offers from Frontier and Allegiant Air, as they are both options that can get you from Chicago Midway Airport to Kissimmee for a low price.

  • 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 $253, our data indicates the cheapest price to be $49. The most popular route (Chicago Midway - Orlando), is priced around $126.

  • 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.

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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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$70Average$214FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$93Average$179FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$181Average$385FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$294FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$248Average$389FlexibilityNo cancel feeOn-time69%

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