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Kissimmee

$47+ Cheap flights from Chicago (CHI) 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kissimmee are usually found in September or July, booked 85 days in advance, depart on a Tuesday or Thursday and return on a Friday

Cheap flight deals from Chicago to Kissimmee

Keep the following information in mind while searching for Chicago to Kissimmee flight deals. Data was last updated October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$99
(Cheapflightsfares)

One-way from

$47
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$250
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 (CHI) to Kissimmee
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One-way flight from Chicago (CHI) to Kissimmee
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 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 Chicago to Kissimmee

Cheapest flights from Chicago to Kissimmee
Explore the most affordable flight options available from Chicago to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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.
Mon 11/106:48 amORD - MCO
Nonstop2h 42mSpirit Airlines
Sat 11/156:00 amMCO - ORD
1 stop7h 50mSpirit Airlines
Deal found 10/14$99
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:30 amMDW - MCO
1 stop15h 14mFrontier
Sat 11/88:30 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 10/16$100
This Cheapflightsfares deal was found by Cheapflights users on 10/14. 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 10/317:51 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Tue 11/46:40 pmMCO - ORD
1 stop6h 47mSpirit Airlines
Deal found 10/14$100
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:58 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Wed 10/2212:58 pmMCO - ORD
Nonstop3h 10mMultiple Airlines
Deal found 10/15$101
This Priceline deal was found by Cheapflights users on 10/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/39:32 amMDW - MCO
Nonstop2h 42mFrontier
Thu 11/61:10 pmMCO - MDW
1 stop6h 29mFrontier
Deal found 10/16$102
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/35:15 amORD - MCO
Nonstop2h 42mMultiple Airlines
Sat 11/86:30 amMCO - ORD
1 stop5h 42mMultiple Airlines
Deal found 10/13$102
This CheapOair deal was found by Cheapflights users on 10/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1610:12 amMDW - MCO
Nonstop2h 38mFrontier
Thu 11/202:34 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 10/16$103
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/105:15 amORD - MCO
Nonstop2h 42mMultiple Airlines
Mon 11/176:29 amMCO - ORD
1 stop9h 02mMultiple Airlines
Deal found 10/16$103
This Priceline deal was found by Cheapflights users on 10/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/228:00 amORD - MCO
Nonstop2h 48mFrontier
Fri 10/245:25 amMCO - ORD
Nonstop3h 09mFrontier
Deal found 10/14$104
This Kiwi.com deal was found by Cheapflights users on 10/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1511:36 amMDW - MCO
Nonstop2h 40mFrontier
Mon 11/1710:16 pmMCO - MDW
1 stop14h 22mFrontier
Deal found 10/15$105
This Cheapflightsfares deal was found by Cheapflights users on 10/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/25:25 amORD - MCO
Nonstop2h 42mFrontier
Fri 11/74:47 pmMCO - ORD
1 stop7h 41mFrontier
Deal found 10/15$105
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1811:31 amMDW - MCO
Nonstop2h 40mFrontier
Fri 10/242:26 pmMCO - MDW
Nonstop2h 54mFrontier
Deal found 10/16$106

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 16, 2025.
Use the filters below to find and compare flights from Chicago to Kissimmee that are best for you.

Fly from

Chicago

Fly to

Kissimmee

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 11/3

9:32 am-1:14 pm

Nonstop2h 42m

Orlando

Thu 11/6

2:40 pm-6:39 pm

1 stop4h 59m

$108

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 12/7

12:09 pm-4:01 pm

Nonstop2h 52m

Orlando

Thu 12/11

2:16 pm-7:47 pm

1 stop6h 31m

$109

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 1/1

11:28 am-3:23 pm

Nonstop2h 55m

Orlando

Sun 1/11

7:15 pm-9:23 pm

Nonstop3h 08m

$122

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 12/23

3:10 pm-6:58 pm

Nonstop2h 48m

Orlando

Wed 12/31

7:58 pm-9:58 pm

Nonstop3h 00m

$132

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 12/23

12:32 pm-7:37 am

1 stop18h 05m

Orlando

Wed 12/31

7:46 am-10:18 am

Nonstop3h 32m

$136

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 12/1

6:15 pm-10:19 pm

Nonstop3h 04m

Orlando

Mon 12/8

5:25 am-4:54 pm

1 stop12h 29m

$142

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 1/6

5:00 am-8:45 am

Nonstop2h 45m

Orlando

Fri 1/16

4:10 pm-7:45 pm

1 stop4h 35m

$143

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 10/30

1:55 pm-11:29 pm

1 stop8h 34m

Orlando

Sun 11/2

12:49 pm-12:49 am

1 stop13h 00m

$156

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 11/7

6:00 am-5:44 am

1 stop22h 44m

Orlando

Sun 11/9

6:50 am-11:28 pm

1 stop17h 38m

$156

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 1/8

1:45 pm-7:00 pm

1 stop4h 15m

Orlando

Tue 1/13

7:30 am-12:15 pm

1 stop5h 45m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 45 results
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Best time to book a flight from Chicago to Kissimmee

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

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Kissimmee. Price data was last updated on October 10, 2025.

The price you pay for your flight from Chicago to Kissimmee may vary depending on when you book. For the best chance of a lower fare, look to book 85 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $42). Flying from Chicago to Kissimmee in June is currently the most expensive (average of $108). 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 CHI to K1S?

Find hourly flight availability from Chicago 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 16, 2025.

When flying from Chicago to Kissimmee, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 21% versus a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Chicago to Kissimmee. Price data was last updated on October 12, 2025.

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

Weekly flight availability from Chicago to Kissimmee

Explore weekly flight availability from Chicago 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 October 16, 2025.

The most flights from CHI to K1S are scheduled on a Thursday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 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 October 16, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Chicago to Kissimmee. 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
4,241 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
8,982 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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.
American Airlines
7.2
Good
11,043 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
8,097 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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
3,137 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

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 Chicago 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 to Kissimmee?

    A quick flight from Chicago to Kissimmee can take about 2h 45m. Spirit Airlines provides one of the quickest options available for as low as $143. The distance between Chicago and Kissimmee is about 990 mi. Generally, flights for this route are nonstop.

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

    Consider ITA Airways (91%), Spirit Airlines (90%) or Southwest (88%) when booking your flight. These represent the most reliable airlines when flying from Chicago to Kissimmee.

  • What are the cheapest flights from Chicago to Kissimmee?

    On average you can expect to pay $452 for a flight from Chicago to Kissimmee. The cheapest flight overall is $40 while the most popular route, (Chicago O'Hare Intl - Orlando) is currently priced at $54.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago 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 to Kissimmee?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $42). Flying from Chicago to Kissimmee in June is currently the most expensive (average of $108). 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 7 airlines flying from Chicago to Kissimmee

Discover the top 7 airlines that operate flights from Chicago 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$49Average$217FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$178FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$96Average$184FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$157Average$345FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$353FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$160Average$359FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$392FlexibilityNo cancel feeOn-timeN/A

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