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Kissimmee

$49+ Cheap flights from O'Hare Intl (ORD) 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Kissimmee are usually found in September or July, booked 42 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap flight deals from O'Hare Intl to Kissimmee

Keep the following information in mind while searching for O'Hare Intl to Kissimmee flight deals. Data was last updated September 15, 2025.

Round-trip from

$94
(Kiwi.com)

One-way from

$49
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$215
From Chicago O'Hare Intl to Kissimmee
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One-way flight from Chicago O'Hare Intl to Kissimmee
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Highest demand for flights based on searches. 9% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from O'Hare Intl to Kissimmee

Cheapest flights from O'Hare Intl to Kissimmee
Explore the most affordable flight options available from O'Hare Intl to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Expedia deal was found by Cheapflights users on 9/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:17 pmORD - MCO
Nonstop2h 49mSpirit Airlines
Fri 10/37:50 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
Deal found 9/13$94
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Sat 10/258:30 amORD - MCO
Nonstop2h 48mMultiple Airlines
Tue 12/27:15 pmMCO - ORD
Nonstop3h 08mMultiple Airlines
Deal found 9/13$95
This Priceline deal was found by Cheapflights users on 9/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:51 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Sun 10/265:05 amMCO - ORD
Nonstop3h 09mMultiple Airlines
Deal found 9/13$96
This Trip.com deal was found by Cheapflights users on 9/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:51 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Sat 10/184:23 pmMCO - ORD
Nonstop3h 10mMultiple Airlines
Deal found 9/13$98
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:58 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Sat 11/17:30 pmMCO - ORD
Nonstop3h 03mSpirit Airlines
Deal found 9/13$99
This Cheapflightsfares deal was found by Cheapflights users on 9/14. 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.
Thu 10/25:17 pmORD - MCO
Nonstop2h 49mSpirit Airlines
Thu 10/97:30 pmMCO - ORD
Nonstop3h 03mSpirit Airlines
Deal found 9/14$100
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
Wed 10/226:00 amORD - MCO
Nonstop2h 44mMultiple Airlines
Sun 10/265:05 amMCO - ORD
Nonstop3h 09mMultiple Airlines
Deal found 9/13$101
This Flightnetwork deal was found by Cheapflights users on 9/14. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/46:30 amORD - MCO
Nonstop2h 43mMultiple Airlines
Sat 10/114:23 pmMCO - ORD
Nonstop3h 10mMultiple Airlines
Deal found 9/14$102
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:49 pmORD - MCO
Nonstop2h 46mFrontier
Sat 9/271:02 pmMCO - ORD
Nonstop3h 15mFrontier
Deal found 9/13$103
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:51 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Sat 10/254:23 pmMCO - ORD
Nonstop3h 10mMultiple Airlines
Deal found 9/13$104
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:49 pmORD - MCO
Nonstop2h 46mMultiple Airlines
Tue 9/307:50 pmMCO - ORD
Nonstop3h 08mMultiple Airlines
Deal found 9/13$105
This Booking.com deal was found by Cheapflights users on 9/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/268:49 pmORD - MCO
Nonstop2h 46mFrontier
Mon 9/295:24 pmMCO - ORD
Nonstop3h 20mFrontier
Deal found 9/13$106

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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 September 15, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Kissimmee that are best for you.

Fly from

O'Hare Intl

Fly to

Kissimmee

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 10/23

6:58 pm-10:50 pm

Nonstop2h 52m

Orlando

Tue 10/28

2:26 pm-4:23 pm

Nonstop2h 57m

$120

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 11/15

5:45 pm-12:12 am

1 stop5h 27m

Orlando

Tue 11/18

2:59 pm-5:04 pm

Nonstop3h 05m

$123

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 11/15

5:45 pm-12:12 am

1 stop5h 27m

Orlando

Thu 11/20

3:00 pm-5:13 pm

Nonstop3h 13m

$126

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 10/23

6:58 pm-10:50 pm

Nonstop2h 52m

Orlando

Mon 10/27

8:41 am-3:49 pm

1 stop8h 08m

$137

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 9/26

4:03 pm-8:13 pm

1 stop27h 10m

Orlando

Mon 9/29

6:00 am-3:50 pm

1 stop10h 50m

$142

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 10/15

6:58 pm-10:50 pm

Nonstop2h 52m

Orlando

Mon 10/20

4:46 pm-6:46 pm

Nonstop3h 00m

$149

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 12/11

2:47 pm-11:30 pm

1 stop7h 43m

Orlando

Mon 12/15

10:19 pm-9:44 am

1 stop12h 25m

$174

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 12/6

7:55 pm-11:53 pm

Nonstop2h 58m

Orlando

Mon 12/8

6:39 pm-8:50 pm

Nonstop3h 11m

$177

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 11/15

2:30 pm-8:39 pm

1 stop5h 09m

Orlando

Tue 11/18

6:15 am-10:19 am

1 stop5h 04m

$197

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 10/28

11:23 am-4:25 pm

1 stop4h 02m

Orlando

Wed 12/3

6:00 am-9:55 am

1 stop4h 55m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 23 results
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2
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Best time to book a flight from O'Hare Intl to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from O'Hare Intl 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 O'Hare Intl Airport to Kissimmee

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Kissimmee. Price data was last updated on September 12, 2025.

Booking 42 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport to Kissimmee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Kissimmee?

Currently, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kissimmee (average of $206). Flying from Chicago O'Hare Intl 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 ORD to K1S?

Find hourly flight availability from O'Hare Intl 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 September 15, 2025.

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

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Kissimmee. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Kissimmee flight should consider departing on Wednesday 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 O'Hare Intl Airport to Kissimmee

Explore weekly flight availability from O'Hare Intl 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 September 15, 2025.

The most flights from ORD to K1S are scheduled on a Sunday (53 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 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 September 15, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to Kissimmee by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
8,931 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
4,245 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
8,016 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

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
3,173 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

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 O'Hare Intl 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 O'Hare Intl Airport to Kissimmee?

    For as low as $120, Spirit Airlines can have you in Kissimmee from Chicago O'Hare Intl Airport in 2h 52m. Airlines will cover a distance of 1006 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Kissimmee?

    Consider Copa Airlines (86%), Spirit Airlines (79%) or Southwest (79%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Kissimmee.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Kissimmee?

    While on average a flight from Chicago O'Hare Intl Airport to Kissimmee is generally $439, our data shows the cheapest flight currently is $47. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $82 for that flight.

  • Can I find deals for flights from O'Hare Intl to Kissimmee that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Kissimmee?

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

  • Can I find deals for business class flights from O'Hare Intl to Kissimmee?

    Yes. Cheapflights offers flight deals from O'Hare Intl 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 O'Hare Intl Airport to Kissimmee?

    Currently, May is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kissimmee (average of $206). Flying from Chicago O'Hare Intl 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 6 airlines flying from O'Hare Intl to Kissimmee

Discover the top 6 airlines that operate flights from O'Hare Intl 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$201FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$68Average$175FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$157Average$326FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$160Average$363FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$164Average$344FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$407FlexibilityNo cancel feeOn-timeN/A

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