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Kissimmee

$52+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
jan 18 — jan 251
dom 1/18
dom 1/25
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

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 dezembro 19, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/17. 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.
qua 12/316:05 amORD - MCO
1 stop14h 20mMultiple Airlines
qua 1/74:56 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Deal found 12/17$131
This Cheapflightsfares deal was found by Cheapflights users on 12/18. 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.
qua 12/3112:09 pmORD - MCO
Nonstop2h 52mSpirit Airlines
qua 1/74:56 pmMCO - ORD
Nonstop3h 06mSpirit Airlines
Deal found 12/18$138
This Super.com deal was found by Cheapflights users on 12/17. 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.
qua 12/317:20 amORD - MCO
Nonstop2h 52mSpirit Airlines
sáb 1/102:17 pmMCO - ORD
1 stop9h 25mSpirit Airlines
Deal found 12/17$144
This WAYA deal was found by Cheapflights users on 12/18. 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.
qua 12/313:10 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
qua 1/75:15 pmMCO - MDW
1 stop6h 02mMultiple Airlines
Deal found 12/18$150
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
qua 12/313:10 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
ter 1/68:34 pmMCO - MDW
1 stop26h 43mMultiple Airlines
Deal found 12/18$153
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
qua 12/317:20 amORD - MCO
Nonstop2h 52mMultiple Airlines
ter 1/67:48 pmMCO - ORD
1 stop27h 51mMultiple Airlines
Deal found 12/16$154
This Frontier deal was found by Cheapflights users on 12/17. 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.
qua 12/312:15 pmORD - MCO
1 stop9h 20mFrontier
sex 1/94:48 pmMCO - ORD
Nonstop3h 29mFrontier
Deal found 12/17$157
This Frontier deal was found by Cheapflights users on 12/18. 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.
qua 12/3111:23 amORD - MCO
Nonstop2h 55mFrontier
dom 1/114:48 pmMCO - ORD
Nonstop3h 29mFrontier
Deal found 12/18$158
This Priceline deal was found by Cheapflights users on 12/18. 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.
qua 12/3111:23 amORD - MCO
Nonstop2h 55mMultiple Airlines
sáb 1/102:17 pmMCO - ORD
1 stop9h 25mMultiple Airlines
Deal found 12/18$159
This Frontier deal was found by Cheapflights users on 12/17. 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.
qua 12/312:15 pmORD - MCO
1 stop9h 20mFrontier
sáb 1/104:48 pmMCO - ORD
Nonstop3h 29mFrontier
Deal found 12/17$162
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
qua 12/316:05 amORD - MCO
1 stop24h 32mFrontier
ter 1/65:26 amMCO - ORD
1 stop8h 28mFrontier
Deal found 12/18$164
This Kiwi.com deal was found by Cheapflights users on 12/18. 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.
qua 12/313:10 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
seg 1/58:34 pmMCO - MDW
1 stop26h 43mMultiple Airlines
Deal found 12/18$171

Find flight deals from Chicago to Kissimmee

Keep the following information in mind while searching for Chicago to Kissimmee flight deals. Data was last updated dezembro 19, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$93
(Priceline)

One-way from

$52
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$311
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 (CHI) to Kissimmee
Search Deals
One-way flight from Chicago (CHI) to Kissimmee
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 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 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 dezembro 19, 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

ORD - MCO

ORDMCO

Chicago O'Hare Intl

qua 2/18

10:44 am-2:34 pm

Nonstop2h 50m

Orlando

dom 2/22

6:54 pm-11:47 pm

1 stop5h 53m

$108

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

sáb 1/17

5:59 pm-9:50 pm

Nonstop2h 51m

Orlando

ter 1/20

2:07 pm-4:16 pm

Nonstop3h 09m

$157

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

ter 2/17

5:30 am-9:15 am

Nonstop2h 45m

Orlando

sex 2/27

6:50 am-8:45 am

Nonstop2h 55m

$168

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

dom 1/25

6:00 pm-9:40 pm

Nonstop2h 40m

Orlando

qua 1/28

4:45 pm-6:40 pm

Nonstop2h 55m

$179

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

seg 1/26

1:55 pm-8:00 pm

1 stop5h 05m

Orlando

qua 1/28

11:50 am-1:45 pm

Nonstop2h 55m

$183

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

qua 12/31

11:23 am-3:18 pm

Nonstop2h 55m

Orlando

seg 1/12

5:20 am-11:35 am

1 stop7h 15m

$185

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

dom 1/25

6:00 pm-9:40 pm

Nonstop2h 40m

Orlando

sáb 1/31

2:40 pm-4:35 pm

Nonstop2h 55m

$188

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

dom 2/1

8:40 am-5:11 pm

1 stop7h 31m

Orlando

qua 2/4

1:49 pm-6:27 pm

1 stop5h 38m

$190

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

sáb 1/17

1:28 pm-9:31 pm

1 stop7h 03m

Orlando

sáb 1/24

5:30 am-9:53 am

1 stop5h 23m

$197

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

sáb 1/24

5:30 am-10:55 am

1 stop4h 25m

Orlando

ter 1/27

5:30 am-10:05 am

1 stop5h 35m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

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 December 12, 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, March is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $53). 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 dezembro 19, 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 22% 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 December 13, 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 dezembro 19, 2025.

The most flights from CHI to K1S are scheduled on a Thursday (85 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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 dezembro 19, 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
7.9
Good
4,252 reviews

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Crew

8.6

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
7.9
Good
4,252 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Crew

8.6

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.
United Airlines
7.4
Good
9,093 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Crew

8.6

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.
American Airlines
7.2
Good
11,041 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Crew

8.6

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.
Spirit Airlines
6.3
Okay
8,190 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Crew

8.6

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
5.8
Fair
3,081 reviews
Southwest
7.9
Good
4,252 reviews

Comfort

8.0

Boarding

8.1

Overall

7.9

Entertainment

7.5

Food

7.0

Crew

8.6

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 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 $168. The distance between Chicago and Kissimmee is about 990 mi. Generally, flights for this route are nonstop.

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

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $37. Users have also found prices from $42 and $78 on Spirit Airlines and Southwest, respectively.

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

    Consider Copa Airlines (88%), Volaris (83%) or Azul (81%) 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 $464 for a flight from Chicago to Kissimmee. The cheapest flight overall is $48 while the most popular route, (Chicago O'Hare Intl - Orlando) is currently priced at $62.

  • 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, March is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $53). 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 8 airlines flying from Chicago to Kissimmee

Discover the top 8 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 dezembro 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$210FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$180FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$97Average$197FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$146Average$339FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$156Average$341FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$333FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$415FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$195Average$296FlexibilityNo cancel feeOn-time62%

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