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Kissimmee

$48+ 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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Kissimmee are usually found in May or July, booked 70 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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$104
(Cheapflightsfares)

One-way from

$48
(Cheapflightsfares)

Popular in

March

Cheapest in

May

Average price

$256
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. 4% potential increase in price ($15 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 April 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 April 15, 2025.

This eDestinos deal was found by Cheapflights users on 4/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/104:35 pmORD - MCO
Nonstop2h 45mSpirit Airlines
Wed 5/149:42 pmMCO - ORD
1 stop12h 08mSpirit Airlines
Deal found 4/14$108
This Frontier deal was found by Cheapflights users on 4/14. 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.
Mon 4/284:30 pmORD - MCO
Nonstop3h 00mFrontier
Thu 5/19:23 pmMCO - ORD
Nonstop3h 09mFrontier
Deal found 4/14$110
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/94:15 pmORD - MCO
Nonstop3h 03mMultiple Airlines
Wed 5/149:42 pmMCO - ORD
1 stop12h 08mMultiple Airlines
Deal found 4/14$115
This American Airlines deal was found by Cheapflights users on 4/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/52:33 pmORD - MCO
Nonstop2h 55mAmerican Airlines
Sat 7/121:57 pmMCO - ORD
Nonstop3h 15mAmerican Airlines
Deal found 4/15$188
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/147:15 pmORD - MCO
Nonstop3h 00mSouthwest
Tue 6/1711:05 amMCO - ORD
Nonstop3h 00mSouthwest
Deal found 4/14$197
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1411:20 amORD - MCO
1 stop6h 17mDelta
Tue 6/171:05 pmMCO - ORD
1 stop4h 54mDelta
Deal found 4/14$217
This United Airlines deal was found by Cheapflights users on 4/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/246:00 amORD - MCO
Nonstop2h 47mUnited Airlines
Mon 7/2811:00 amMCO - ORD
Nonstop3h 07mUnited Airlines
Deal found 4/13$237

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 April 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

Sat 5/10

4:35 pm-8:20 pm

Nonstop2h 45m

Orlando

Wed 5/14

9:42 pm-8:50 am

1 stop12h 08m

$108

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 4/28

4:30 pm-8:30 pm

Nonstop3h 00m

Orlando

Thu 5/1

9:23 pm-11:32 pm

Nonstop3h 09m

$110

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 5/9

4:15 pm-8:18 pm

Nonstop3h 03m

Orlando

Tue 5/13

9:42 pm-8:50 am

1 stop12h 08m

$111

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 7/5

2:33 pm-6:28 pm

Nonstop2h 55m

Orlando

Sat 7/12

1:57 pm-4:12 pm

Nonstop3h 15m

$188

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 6/14

7:15 pm-11:15 pm

Nonstop3h 00m

Orlando

Tue 6/17

11:05 am-1:05 pm

Nonstop3h 00m

$197

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 6/14

11:20 am-6:37 pm

1 stop6h 17m

Orlando

Tue 6/17

1:05 pm-4:59 pm

1 stop4h 54m

$217

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 6/19

6:00 am-9:47 am

Nonstop2h 47m

Orlando

Wed 6/25

12:16 pm-2:23 pm

Nonstop3h 07m

$247

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 5/13

7:47 am-11:26 am

Nonstop2h 39m

$50

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 5/15

4:15 pm-8:18 pm

Nonstop3h 03m

$56

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 6/21

5:50 pm-9:46 pm

Nonstop2h 56m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

Showing 1-10 of 16 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 April 11, 2025.

Booking 70 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 April 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 March 30, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport 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 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 April 15, 2025.

The most flights from ORD to K1S are scheduled on a Monday (49 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (35 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 April 15, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta 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.
Alaska Airlines
8.0
Very good
9,871 reviews

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,871 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,279 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,918 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,871 reviews

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,658 reviews
Alaska Airlines
8.0
Very good
9,871 reviews

Comfort

7.9

Entertainment

7.1

Food

7.1

Overall

8.0

Boarding

8.2

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 $48 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $54 and United Airlines from $89 one-way.

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

    Consider Azul (85%), Copa Airlines (84%) or Air Canada (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 $465, our data shows the cheapest flight currently is $48. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $98 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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$41Average$180FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$170FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$158Average$350FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$362FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$416FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$196Average$397FlexibilityNo cancel feeOn-time63%

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