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Kissimmee

$61+ 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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Kissimmee are usually found in July or May, 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 julio 30, 2025.

Round-trip from

$102
(Frontier)

One-way from

$61
(FlightHub)

Popular in

March

Cheapest in

July

Average price

$225
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. 7% potential increase in price ($25 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 July 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 julio 30, 2025.

This Frontier deal was found by Cheapflights users on 7/29. 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.
vie. 9/198:49 pmORD - MCO
Nonstop2h 46mFrontier
dom. 9/215:24 pmMCO - ORD
Nonstop3h 20mFrontier
Deal found 7/29$102
This FlightHub deal was found by Cheapflights users on 7/30. 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.
jue. 9/412:05 pmORD - MCO
Nonstop2h 43mSpirit Airlines
dom. 9/77:50 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
Deal found 7/30$103
This FlightHub deal was found by Cheapflights users on 7/30. 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. 8/297:46 pmORD - MCO
Nonstop3h 06mMultiple Airlines
sáb. 9/67:50 pmMCO - ORD
Nonstop3h 08mMultiple Airlines
Deal found 7/30$116

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 julio 30, 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

vie. 9/19

8:49 pm-12:35 am

Nonstop2h 46m

Orlando

dom. 9/21

5:24 pm-7:44 pm

Nonstop3h 20m

$102

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

jue. 9/4

12:05 pm-3:48 pm

Nonstop2h 43m

Orlando

dom. 9/7

7:50 pm-9:58 pm

Nonstop3h 08m

$103

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

vie. 8/29

7:46 pm-11:52 pm

Nonstop3h 06m

Orlando

sáb. 9/6

7:50 pm-9:58 pm

Nonstop3h 08m

$116

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

sáb. 8/9

4:37 pm-8:24 pm

Nonstop2h 47m

$61

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

lun. 8/11

5:00 pm-9:02 pm

Nonstop3h 02m

$62

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

mar. 8/26

5:45 am-10:48 am

1 stop4h 03m

$105

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

mar. 10/28

1:30 pm-9:40 pm

2 stops7h 10m

$110

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

lun. 10/13

6:00 am-9:48 am

Nonstop2h 48m

$115

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 25, 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, 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 $288). 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 julio 30, 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 July 27, 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 julio 30, 2025.

The most flights from ORD to K1S are scheduled on a Monday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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 julio 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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
8,048 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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
5.9
Fair
3,237 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Food

7.0

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.

  • 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 $61 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $62 and United Airlines from $79 one-way.

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

    Consider Sun Country Air (100%), Copa Airlines (95%) or United Airlines (86%) 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 $514, our data shows the cheapest flight currently is $54. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $79 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 $288). 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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$47Average$197FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$173FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$112Average$367FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$158Average$347FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$371FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$407FlexibilityNo cancel feeOn-timeN/A

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