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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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 12 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 October 29, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$100
(Kiwi.com)

One-way from

$49
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$254
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 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 ($30 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 October 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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/106:48 amORD - MCO
Nonstop2h 42mSpirit Airlines
Tue 11/186:29 amMCO - ORD
1 stop9h 02mSpirit Airlines
Deal found 10/28$100
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/135:25 amORD - MCO
Nonstop2h 42mMultiple Airlines
Tue 11/186:29 amMCO - ORD
1 stop9h 02mMultiple Airlines
Deal found 10/28$101
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 12/62:26 pmORD - MCO
Nonstop3h 05mFrontier
Mon 12/85:25 amMCO - ORD
1 stop12h 29mFrontier
Deal found 10/28$102
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/131:36 pmORD - MCO
1 stop8h 34mMultiple Airlines
Sat 11/229:00 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Deal found 10/28$103
This Frontier deal was found by Cheapflights users on 10/27. 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.
Sun 11/95:25 amORD - MCO
Nonstop2h 42mFrontier
Fri 11/1410:17 amMCO - ORD
Nonstop3h 09mFrontier
Deal found 10/27$104
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 11/135:25 amORD - MCO
Nonstop2h 42mFrontier
Mon 11/177:42 pmMCO - ORD
1 stop5h 29mFrontier
Deal found 10/28$105
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Thu 11/206:48 amORD - MCO
Nonstop2h 42mMultiple Airlines
Sun 11/233:46 pmMCO - ORD
Nonstop3h 13mMultiple Airlines
Deal found 10/28$106
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/106:48 amORD - MCO
Nonstop2h 42mMultiple Airlines
Mon 11/177:42 pmMCO - ORD
1 stop5h 29mMultiple Airlines
Deal found 10/28$107
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 12/115:15 amORD - MCO
1 stop18h 13mFrontier
Tue 12/236:45 amMCO - ORD
Nonstop3h 17mFrontier
Deal found 10/28$108
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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.
Tue 12/26:48 amORD - MCO
Nonstop2h 42mSpirit Airlines
Sat 12/65:27 pmMCO - ORD
1 stop5h 44mSpirit Airlines
Deal found 10/28$109
This CheapOair deal was found by Cheapflights users on 10/28. 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.
Thu 12/115:15 amORD - MCO
1 stop18h 13mFrontier
Sat 12/132:51 pmMCO - ORD
1 stop21h 37mFrontier
Deal found 10/28$110
This Priceline deal was found by Cheapflights users on 10/28. 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 12/1212:09 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Mon 12/226:30 amMCO - ORD
Nonstop3h 17mMultiple Airlines
Deal found 10/28$111

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 October 29, 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

Tue 12/16

7:20 am-5:28 pm

1 stop9h 08m

Orlando

Sat 1/10

6:00 am-3:55 pm

1 stop10h 55m

$136

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 2/8

3:45 pm-7:30 pm

Nonstop2h 45m

Orlando

Sun 2/15

7:55 am-12:15 pm

1 stop5h 20m

$147

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 2/14

4:25 pm-8:10 pm

Nonstop2h 45m

Orlando

Sat 2/21

6:30 am-1:00 pm

1 stop7h 30m

$147

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 2/17

3:45 pm-7:30 pm

Nonstop2h 45m

Orlando

Tue 2/24

7:30 am-12:15 pm

1 stop5h 45m

$147

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 1/6

1:45 pm-9:25 pm

1 stop6h 40m

Orlando

Mon 1/12

7:30 am-12:15 pm

1 stop5h 45m

$157

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 1/29

2:15 pm-10:00 pm

1 stop6h 45m

Orlando

Sun 2/1

6:40 am-12:15 pm

1 stop6h 35m

$157

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 2/18

1:45 pm-7:00 pm

1 stop4h 15m

Orlando

Mon 2/23

6:40 am-12:15 pm

1 stop6h 35m

$157

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 1/19

1:45 pm-8:50 pm

1 stop6h 05m

Orlando

Sat 1/24

6:10 am-1:00 pm

1 stop7h 50m

$157

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 1/18

1:45 pm-7:00 pm

1 stop4h 15m

Orlando

Wed 1/21

7:30 am-12:15 pm

1 stop5h 45m

$157

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 2/27

2:30 pm-6:22 pm

Nonstop2h 52m

Orlando

Tue 3/3

2:00 pm-4:17 pm

Nonstop3h 17m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 22 results
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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 October 24, 2025.

Booking 12 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kissimmee (average of $42). Flying from Chicago O'Hare Intl Airport 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 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 October 29, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Kissimmee in the evening. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight at noon.

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 October 26, 2025.

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

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 29, 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
4,241 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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
8,999 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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
8,114 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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
3,124 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

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 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 $147, Spirit Airlines can have you in Kissimmee from Chicago O'Hare Intl Airport in 2h 45m. 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 ITA Airways (91%), Spirit Airlines (90%) or Southwest (88%) 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 $464, our data shows the cheapest flight currently is $40. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $61 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, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kissimmee (average of $42). Flying from Chicago O'Hare Intl Airport 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.

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Alternative routes for O'Hare Intl to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$51Average$204FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$75Average$174FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$157Average$299FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$334FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$358FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$420FlexibilityNo cancel feeOn-timeN/A

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