HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kissimmee

$55+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl to Kissimmee with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago O'Hare Intl to Kissimmee are usually found in May 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 junio 12, 2025.

Round-trip from

$122
(Cheapflightsfares)

One-way from

$55
(FlightHub)

Popular in

March

Cheapest in

May

Average price

$340
From Chicago O'Hare Intl to Kissimmee
Search Deals
One-way flight from Chicago O'Hare Intl to Kissimmee
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 junio 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
mié. 7/27:56 amORD - MCO
Nonstop2h 44mSpirit Airlines
mié. 7/99:38 pmMCO - ORD
1 stop11h 12mSpirit Airlines
Deal found 6/10$122
This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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.
jue. 8/287:46 pmORD - MCO
Nonstop3h 06mFrontier
vie. 8/294:18 pmMCO - ORD
Nonstop3h 23mFrontier
Deal found 6/12$126
This American Airlines deal was found by Cheapflights users on 6/10. 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.
mar. 11/41:15 pmORD - MCO
Nonstop2h 37mAmerican Airlines
mar. 11/47:20 pmMCO - ORD
Nonstop3h 04mAmerican Airlines
Deal found 6/10$152
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
sáb. 8/24:37 pmORD - MCO
Nonstop2h 47mMultiple Airlines
dom. 8/101:22 pmMCO - ORD
Nonstop3h 21mMultiple Airlines
Deal found 6/10$164
This Delta deal was found by Cheapflights users on 6/11. 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.
sáb. 7/267:00 amORD - MCO
1 stop6h 27mDelta
sáb. 8/27:00 amMCO - ORD
1 stop6h 33mDelta
Deal found 6/11$197
This Southwest deal was found by Cheapflights users on 6/11. 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.
jue. 8/281:50 pmORD - MCO
2 stops8h 40mSouthwest
lun. 9/19:50 amMCO - ORD
Nonstop3h 00mSouthwest
Deal found 6/11$212

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 junio 12, 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

mié. 7/2

7:56 am-11:40 am

Nonstop2h 44m

Orlando

mié. 7/9

9:38 pm-7:50 am

1 stop11h 12m

$122

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

jue. 8/28

7:46 pm-11:52 pm

Nonstop3h 06m

Orlando

vie. 8/29

4:18 pm-6:41 pm

Nonstop3h 23m

$126

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

mar. 11/4

1:15 pm-4:52 pm

Nonstop2h 37m

Orlando

mar. 11/4

7:20 pm-9:24 pm

Nonstop3h 04m

$152

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

sáb. 8/2

4:37 pm-8:24 pm

Nonstop2h 47m

Orlando

dom. 8/10

1:22 pm-3:43 pm

Nonstop3h 21m

$164

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

sáb. 7/26

7:00 am-12:05 pm

1 stop4h 05m

Orlando

mié. 7/30

5:45 pm-9:30 pm

1 stop4h 45m

$197

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

jue. 8/28

1:50 pm-11:30 pm

2 stops8h 40m

Orlando

lun. 9/1

9:50 am-11:50 am

Nonstop3h 00m

$212

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

jue. 7/31

6:00 am-9:47 am

Nonstop2h 47m

Orlando

jue. 7/31

4:11 pm-6:25 pm

Nonstop3h 14m

$258

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

lun. 6/30

7:39 pm-7:18 am

1 stop10h 39m

$55

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

mar. 10/14

4:53 pm-8:40 pm

Nonstop2h 47m

$78

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

mar. 8/5

9:15 am-1:10 pm

Nonstop2h 55m

$80

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 16 results
1
2

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 June 9, 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 junio 12, 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 June 8, 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 junio 12, 2025.

The most flights from ORD to K1S are scheduled on a Thursday (60 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (42 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 junio 12, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines 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.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

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.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

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.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

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
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.0

Comfort

8.0

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.

  • 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 $55 on Spirit Airlines. Other airlines that offer cheap prices include American Airlines from $78 and United Airlines from $80 one-way.

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

    Consider Copa Airlines (92%), United Airlines (89%) or Azul (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 $538, our data shows the cheapest flight currently is $49. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $106 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Orlando flights
Midway to Miami flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Jacksonville flights
Midway to Tampa flights
Midway to Fort Lauderdale flights
O'Hare Intl to Key West flights
O'Hare Intl to Pensacola flights
O'Hare Intl to Panama City flights
O'Hare Intl to West Palm Beach flights
Midway to Fort Myers flights
Midway to Sarasota flights
Midway to West Palm Beach flights
Midway to Jacksonville flights
Midway to Key West flights
Midway to Panama City flights
O'Hare Intl to Daytona Beach flights
Rockford to Orlando Sanford Intl flights
O'Hare Intl to Valparaiso flights
O'Hare Intl to St Petersburg flights
Midway to Pensacola flights
Midway to Orlando Sanford Intl flights
Rockford to St Petersburg flights
Midway to Daytona Beach flights
O'Hare Intl to Gainesville flights
Midway to Melbourne flights
O'Hare Intl to Melbourne flights
O'Hare Intl to Orlando Sanford Intl flights
Midway to Gainesville flights
O'Hare Intl to Punta Gorda flights
O'Hare Intl to Tallahassee flights
Midway to Valparaiso flights
Midway to Punta Gorda flights
Rockford to Punta Gorda flights
Midway to Tallahassee flights
Midway to Valdosta flights
O'Hare Intl to Valdosta flights
O'Hare Intl to Destin flights

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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$44Average$175FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$64Average$174FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$155Average$347FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$362FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$413FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$196Average$389FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.