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Kissimmee

$51+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
ago. 23 — ago. 301
sáb. 8/23
sáb. 8/30
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 agosto 18, 2025.

Round-trip from

$97
(Cheapflightsfares)

One-way from

$51
(eDestinos)

Popular in

March

Cheapest in

September

Average price

$233
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 ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
mié. 9/105:17 pmORD - MCO
Nonstop2h 49mSpirit Airlines
sáb. 9/136:31 amMCO - ORD
1 stop5h 21mSpirit Airlines
Deal found 8/17$98
This Frontier deal was found by Cheapflights users on 8/18. 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.
sáb. 10/1811:31 amMDW - MCO
Nonstop2h 40mFrontier
sáb. 10/258:25 amMCO - MDW
Nonstop2h 56mFrontier
Deal found 8/18$98
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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.
jue. 9/48:49 pmORD - MCO
Nonstop2h 46mFrontier
lun. 9/85:24 pmMCO - ORD
Nonstop3h 20mFrontier
Deal found 8/18$99
This Priceline deal was found by Cheapflights users on 8/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/129:48 amMDW - MCO
Nonstop2h 40mFrontier
sáb. 9/138:00 amMCO - MDW
Nonstop2h 51mFrontier
Deal found 8/17$99
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/135:17 pmORD - MCO
Nonstop2h 49mSpirit Airlines
mar. 9/162:07 pmMCO - ORD
Nonstop3h 05mSpirit Airlines
Deal found 8/17$100
This Booking.com deal was found by Cheapflights users on 8/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/510:13 amMDW - MCO
Nonstop2h 42mFrontier
vie. 10/102:26 pmMCO - MDW
Nonstop2h 54mFrontier
Deal found 8/17$100
This CheapOair deal was found by Cheapflights users on 8/16. 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.
sáb. 8/237:46 pmORD - MCO
Nonstop3h 06mFrontier
vie. 9/55:24 pmMCO - ORD
Nonstop3h 20mFrontier
Deal found 8/16$101
This FlightHub deal was found by Cheapflights users on 8/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/58:49 pmORD - MCO
Nonstop2h 46mMultiple Airlines
mar. 9/97:50 pmMCO - ORD
Nonstop3h 08mMultiple Airlines
Deal found 8/17$102
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/129:48 amMDW - MCO
Nonstop2h 40mFrontier
sáb. 9/208:00 amMCO - MDW
Nonstop2h 51mFrontier
Deal found 8/17$102
This Priceline deal was found by Cheapflights users on 8/16. 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.
jue. 9/188:49 pmORD - MCO
Nonstop2h 46mMultiple Airlines
mar. 9/232:07 pmMCO - ORD
Nonstop3h 05mMultiple Airlines
Deal found 8/16$103
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/1410:13 amMDW - MCO
Nonstop2h 42mFrontier
vie. 9/197:00 amMCO - MDW
Nonstop2h 53mFrontier
Deal found 8/17$103
This Cheapflightsfares deal was found by Cheapflights users on 8/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/58:49 pmORD - MCO
Nonstop2h 46mFrontier
lun. 9/85:24 pmMCO - ORD
Nonstop3h 20mFrontier
Deal found 8/17$104

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 agosto 18, 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

vie. 9/12

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

lun. 9/15

5:35 am-7:23 am

Nonstop2h 48m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

lun. 9/22

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

dom. 9/28

7:25 am-9:18 am

Nonstop2h 53m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

lun. 10/13

5:28 pm-9:10 pm

Nonstop2h 42m

Orlando

sáb. 10/18

8:25 am-10:21 am

Nonstop2h 56m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

lun. 9/29

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

vie. 10/3

7:00 am-8:53 am

Nonstop2h 53m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

vie. 10/10

5:28 pm-9:10 pm

Nonstop2h 42m

Orlando

dom. 10/12

9:44 am-11:39 am

Nonstop2h 55m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

vie. 9/12

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

sáb. 9/13

8:00 am-9:51 am

Nonstop2h 51m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

dom. 9/14

10:13 am-1:55 pm

Nonstop2h 42m

Orlando

lun. 9/15

5:35 am-7:23 am

Nonstop2h 48m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

dom. 9/28

10:13 am-1:55 pm

Nonstop2h 42m

Orlando

lun. 9/29

5:35 am-7:23 am

Nonstop2h 48m

$99

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

lun. 9/22

6:30 am-10:13 am

Nonstop2h 43m

Orlando

lun. 9/22

5:24 pm-7:44 pm

Nonstop3h 20m

$103

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

vie. 10/24

8:05 pm-11:56 pm

Nonstop2h 51m

Orlando

lun. 10/27

5:01 am-7:10 am

Nonstop3h 09m

$103

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 42 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 August 8, 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, May is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $206). Flying from Chicago 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 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 agosto 18, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Kissimmee as you normally would.

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 August 17, 2025.

Travelers seeking maximum savings on their Chicago to Kissimmee flight should consider departing on Monday 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.

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 agosto 18, 2025.

The most flights from CHI to K1S are scheduled on a Monday (72 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (14 on average).

How much does it cost to fly round-trip from Chicago to Kissimmee?

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 agosto 18, 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
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
8,925 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
8,038 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
3,212 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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 40m. Frontier provides one of the quickest options available for as low as $98. The distance between Chicago and Kissimmee is about 990 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Consider Copa Airlines (90%), Spirit Airlines (88%) or Southwest (84%) 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 $478 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 $81.

  • 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, May is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $206). Flying from Chicago 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.

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 agosto 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$216FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$119Average$199FlexibilityNo cancel feeOn-time88%
SouthwestCheapest$157Average$368FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$159Average$337FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$160Average$369FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$375FlexibilityNo cancel feeOn-timeN/A

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