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Kissimmee

$57+ 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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kissimmee are usually found in July or September, 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 June 18, 2025.

Round-trip from

$120
(Expedia)

One-way from

$57
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$321
From Chicago (CHI) to Kissimmee
Search Deals
One-way flight from Chicago (CHI) to Kissimmee
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 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 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 June 18, 2025.

This Expedia deal was found by Cheapflights users on 6/18. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/147:39 pmORD - MCO
Nonstop2h 53mSpirit Airlines
Fri 9/194:33 pmMCO - ORD
Nonstop3h 10mSpirit Airlines
Deal found 6/18$120
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.
Sat 9/1312:51 pmMDW - MCO
Nonstop2h 38mFrontier
Sun 9/215:45 amMCO - MDW
Nonstop2h 54mFrontier
Deal found 6/16$126
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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.
Fri 8/227:46 pmORD - MCO
Nonstop3h 06mFrontier
Sun 8/244:18 pmMCO - ORD
Nonstop3h 23mFrontier
Deal found 6/17$127
This Cheapflightsfares deal was found by Cheapflights users on 6/18. 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.
Mon 7/144:26 pmORD - MCO
Nonstop3h 02mMultiple Airlines
Sat 7/192:49 pmMCO - ORD
Nonstop3h 08mMultiple Airlines
Deal found 6/18$132
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/27:40 amMDW - MCO
Nonstop2h 30mSouthwest
Fri 9/58:40 pmMCO - MDW
Nonstop2h 45mSouthwest
Deal found 6/17$158
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/76:00 amORD - MCO
1 stop5h 57mDelta
Tue 10/146:20 amMCO - ORD
1 stop7h 19mDelta
Deal found 6/15$197
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/306:00 amMDW - MCO
1 stop7h 25mDelta
Sat 9/64:50 pmMCO - MDW
1 stop5h 22mDelta
Deal found 6/16$207
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/94:53 pmORD - MCO
Nonstop2h 47mAmerican Airlines
Tue 10/146:00 amMCO - ORD
Nonstop3h 01mAmerican Airlines
Deal found 6/18$212
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/64:05 pmORD - MCO
1 stop6h 25mJetBlue
Sat 12/136:00 amMCO - ORD
1 stop10h 08mJetBlue
Deal found 6/16$217
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1110:31 amMDW - MCO
1 stop9h 12mAllegiant Air
Mon 7/148:27 amMCO - MDW
1 stop6h 37mAllegiant Air
Deal found 6/16$220
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 10/77:30 amORD - MCO
2 stops11h 25mSouthwest
Sat 10/118:40 amMCO - ORD
Nonstop3h 05mSouthwest
Deal found 6/16$233

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 June 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

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 9/14

7:39 pm-11:32 pm

Nonstop2h 53m

Orlando

Fri 9/19

4:33 pm-6:43 pm

Nonstop3h 10m

$120

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 9/13

12:51 pm-4:29 pm

Nonstop2h 38m

Orlando

Sun 9/21

5:45 am-7:39 am

Nonstop2h 54m

$126

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 8/22

7:46 pm-11:52 pm

Nonstop3h 06m

Orlando

Sun 8/24

4:18 pm-6:41 pm

Nonstop3h 23m

$127

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 7/14

4:26 pm-8:28 pm

Nonstop3h 02m

Orlando

Sat 7/19

2:49 pm-4:57 pm

Nonstop3h 08m

$132

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 9/2

8:05 pm-11:40 pm

Nonstop2h 35m

Orlando

Fri 9/5

6:20 am-8:05 am

Nonstop2h 45m

$158

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 8/9

4:04 pm-10:16 pm

1 stop5h 12m

Orlando

Wed 8/13

11:00 am-4:28 pm

1 stop6h 28m

$207

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 8/30

6:00 am-2:25 pm

1 stop7h 25m

Orlando

Sat 9/6

4:50 pm-9:12 pm

1 stop5h 22m

$207

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

$219

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 7/10

6:00 am-9:40 am

Nonstop2h 40m

Orlando

Mon 7/14

9:45 am-11:50 am

Nonstop3h 05m

$257

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 7/5

7:56 am-11:40 am

Nonstop2h 44m

$57

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 23 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 June 13, 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 June 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 June 15, 2025.

Travelers seeking maximum savings on their Chicago to Kissimmee flight should consider departing on Tuesday afternoons 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 June 18, 2025.

The most flights from CHI to K1S are scheduled on a Monday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 18, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Chicago to Kissimmee by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

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
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

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
8,810 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

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.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,280 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

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
4,280 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

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.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $57. Users have also found prices from $73 and $79 on Frontier and Southwest, respectively.

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

    Consider Copa Airlines (93%), Azul (89%) or United Airlines (87%) 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 $508 for a flight from Chicago to Kissimmee. The cheapest flight overall is $53 while the most popular route, (Chicago O'Hare Intl - Orlando) is currently priced at $101.

  • 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$44Average$195FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$177FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$122Average$207FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$156Average$361FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$362FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$181Average$382FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$360FlexibilityNo cancel feeOn-timeN/A

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