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Kissimmee

$50+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
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

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 December 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/3111:23 amORD - MCO
Nonstop2h 55mMultiple Airlines
Wed 1/712:17 pmMCO - ORD
Nonstop3h 04mMultiple Airlines
Deal found 12/13$117
This Cheapflightsfares deal was found by Cheapflights users on 12/12. 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 12/317:20 amORD - MCO
Nonstop2h 52mSpirit Airlines
Wed 1/74:56 pmMCO - ORD
Nonstop3h 06mSpirit Airlines
Deal found 12/12$118
This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - MCO
Nonstop2h 55mFrontier
Wed 1/72:00 pmMCO - ORD
Nonstop3h 19mFrontier
Deal found 12/14$119
This Priceline deal was found by Cheapflights users on 12/13. 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.
Wed 12/312:15 pmORD - MCO
1 stop9h 20mMultiple Airlines
Fri 1/95:28 pmMCO - ORD
Nonstop3h 13mMultiple Airlines
Deal found 12/13$127
This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:23 amORD - MCO
Nonstop2h 55mFrontier
Mon 1/126:00 amMCO - ORD
1 stop9h 22mFrontier
Deal found 12/14$129
This Frontier deal was found by Cheapflights users on 12/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - MCO
1 stop9h 20mFrontier
Tue 1/136:10 amMCO - ORD
1 stop6h 58mFrontier
Deal found 12/14$131
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 12/3111:23 amORD - MCO
Nonstop2h 55mMultiple Airlines
Sun 1/412:17 pmMCO - ORD
Nonstop3h 04mMultiple Airlines
Deal found 12/13$138
This CheapOair deal was found by Cheapflights users on 12/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:09 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Sun 1/412:17 pmMCO - ORD
Nonstop3h 04mSpirit Airlines
Deal found 12/13$141
This Priceline deal was found by Cheapflights users on 12/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - MCO
1 stop9h 20mFrontier
Sun 1/44:30 pmMCO - ORD
Nonstop3h 29mFrontier
Deal found 12/14$142

Find 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 December 15, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$94
(CheapOair)

One-way from

$50
(CheapOair)

Popular in

March

Cheapest in

September

Average price

$304
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. 10% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
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 December 2025
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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 December 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

Mon 2/23

7:59 pm-7:39 am

1 stop10h 40m

Orlando

Fri 2/27

3:03 pm-5:12 pm

Nonstop3h 09m

$125

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 2/8

3:22 pm-11:42 pm

1 stop7h 20m

Orlando

Wed 2/11

3:07 pm-9:03 pm

1 stop6h 56m

$133

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 4/22

3:49 pm-7:39 pm

Nonstop2h 50m

Orlando

Mon 4/27

9:31 am-8:25 pm

1 stop11h 54m

$178

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 4/29

3:49 pm-7:39 pm

Nonstop2h 50m

Orlando

Mon 5/4

9:31 am-8:25 pm

1 stop11h 54m

$178

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 1/24

5:59 pm-12:03 am

1 stop5h 04m

Orlando

Thu 1/29

6:35 pm-11:56 pm

1 stop6h 21m

$198

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 5/13

7:41 am-9:26 pm

1 stop12h 45m

Orlando

Sun 5/17

6:00 am-7:59 am

Nonstop2h 59m

$198

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 12/31

9:41 am-4:54 pm

1 stop6h 13m

Orlando

Wed 1/7

10:00 am-4:45 pm

1 stop7h 45m

$207

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 3/1

12:41 pm-11:09 pm

1 stop9h 28m

Orlando

Sat 3/7

6:00 am-11:58 am

1 stop6h 58m

$217

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 5/25

7:41 am-9:26 pm

1 stop12h 45m

Orlando

Sat 5/30

6:00 am-7:59 am

Nonstop2h 59m

$218

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 1/12

1:45 pm-7:00 pm

1 stop4h 15m

Orlando

Thu 1/15

6:15 am-2:45 pm

2 stops9h 30m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 21 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 December 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, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kissimmee (average of $53). 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 December 15, 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 December 13, 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 December 15, 2025.

The most flights from ORD to K1S are scheduled on a Sunday (59 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (2 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 December 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
7.9
Good
4,250 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
11,052 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
8,185 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

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
3,080 reviews
Southwest
7.9
Good
4,250 reviews

Boarding

8.1

Food

7.0

Overall

7.9

Entertainment

7.5

Crew

8.6

Comfort

8.0

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 $198, Spirit Airlines can have you in Kissimmee from Chicago O'Hare Intl Airport in 5h 04m. 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 cheapest airlines to fly from Chicago O'Hare Intl Airport to Kissimmee one-way?

    One-way options have recently been found by users for as low as $37 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $42 and Southwest from $78 one-way.

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

    Consider Copa Airlines (87%), United Airlines (83%) or Azul (82%) 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 $420, our data shows the cheapest flight currently is $42. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $67 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, March is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kissimmee (average of $53). 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

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Top 7 airlines flying from O'Hare Intl to Kissimmee

Discover the top 7 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 December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$203FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$71Average$173FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$146Average$296FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$333FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$160Average$374FlexibilityNo cancel feeOn-time71%
DeltaCheapest$176Average$420FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$195Average$296FlexibilityNo cancel feeOn-time62%

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