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Kissimmee

$52+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 17 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 January 29, 2026.

This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1712:44 pm
ORD
-
MCO
Nonstop2h 47m
Spirit Airlines
Wed 2/186:54 pm
MCO
-
ORD
1 stop5h 53m
Spirit Airlines
Deal found 1/27$102
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
ORD
-
MCO
1 stop5h 49m
Spirit Airlines
Tue 3/33:39 pm
MCO
-
ORD
Nonstop3h 07m
Spirit Airlines
Deal found 1/27$103
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:44 pm
ORD
-
MCO
Nonstop2h 47m
Multiple Airlines
Thu 3/58:20 am
MCO
-
ORD
Nonstop3h 26m
Multiple Airlines
Deal found 1/28$104
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1712:44 pm
ORD
-
MCO
Nonstop2h 47m
Spirit Airlines
Tue 2/242:50 pm
MCO
-
ORD
1 stop9h 57m
Spirit Airlines
Deal found 1/27$105
This Frontier deal was found by Cheapflights users on 1/27. 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.
Thu 3/124:18 pm
ORD
-
MCO
Nonstop3h 05m
Frontier
Tue 3/179:23 pm
MCO
-
ORD
Nonstop3h 15m
Frontier
Deal found 1/27$106
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 2/2310:44 am
ORD
-
MCO
Nonstop2h 50m
Multiple Airlines
Wed 3/41:33 pm
MCO
-
ORD
Nonstop3h 19m
Multiple Airlines
Deal found 1/28$107
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:19 pm
ORD
-
MCO
1 stop5h 14m
Frontier
Thu 3/58:20 am
MCO
-
ORD
Nonstop3h 26m
Frontier
Deal found 1/28$108
This Frontier deal was found by Cheapflights users on 1/26. 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 2/233:50 pm
ORD
-
MCO
Nonstop2h 56m
Frontier
Wed 2/2510:28 am
MCO
-
ORD
1 stop7h 24m
Frontier
Deal found 1/26$109
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/108:30 am
ORD
-
MCO
Nonstop2h 56m
Frontier
Wed 2/111:33 pm
MCO
-
ORD
Nonstop3h 19m
Frontier
Deal found 1/28$110
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/209:07 pm
ORD
-
MCO
Nonstop2h 59m
Multiple Airlines
Wed 2/252:50 pm
MCO
-
ORD
1 stop7h 23m
Multiple Airlines
Deal found 1/27$111
This Super.com deal was found by Cheapflights users on 1/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/273:11 pm
ORD
-
MCO
Nonstop2h 56m
Frontier
Fri 3/66:41 am
MCO
-
ORD
Nonstop3h 25m
Frontier
Deal found 1/28$112
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:44 am
ORD
-
MCO
Nonstop2h 50m
Spirit Airlines
Mon 3/95:34 pm
MCO
-
ORD
Nonstop3h 13m
Spirit Airlines
Deal found 1/27$113

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$102
(CheapOair)

One-way from

$52
(Cheapflightsfares)

Popular in

June

Cheapest in

September

Average price

$237
Provider with most accurate pricing for Chicago (CHI)-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Orlando (ORL) flights.
Search Deals
From Chicago O'Hare Intl to Kissimmee
Search Deals
One-way flight from Chicago O'Hare Intl to Kissimmee
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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 2/28

3:41 pm-7:31 pm

Nonstop2h 50m

Orlando

Wed 3/4

2:50 pm-5:05 pm

Nonstop3h 15m

$168

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 2/27

7:50 pm-11:43 pm

Nonstop2h 53m

Orlando

Tue 3/3

7:00 am-9:18 am

Nonstop3h 18m

$177

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 3/17

12:20 pm-7:38 pm

1 stop6h 18m

Orlando

Mon 3/30

2:30 pm-10:56 pm

1 stop9h 26m

$199

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 3/16

12:20 pm-7:38 pm

1 stop6h 18m

Orlando

Tue 3/17

3:45 pm-10:56 pm

1 stop8h 11m

$217

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 2/20

2:30 pm-6:22 pm

Nonstop2h 52m

Orlando

Mon 2/23

8:43 pm-11:00 pm

Nonstop3h 17m

$237

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 3/15

11:00 am-6:40 pm

1 stop6h 40m

Orlando

Tue 3/17

3:45 pm-10:56 pm

1 stop8h 11m

$240

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 3/15

7:35 pm-11:20 pm

Nonstop2h 45m

Orlando

Wed 3/18

7:30 am-9:45 am

Nonstop3h 15m

$257

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 3/7

2:40 pm-7:45 am

2 stops16h 05m

Orlando

Tue 3/10

10:45 am-5:35 pm

1 stop7h 50m

$293

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 3/24

2:40 pm-8:55 pm

1 stop5h 15m

Orlando

Mon 3/30

9:35 pm-12:50 pm

2 stops16h 15m

$299

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Fri 3/6

2:40 pm-9:00 am

2 stops17h 20m

Orlando

Mon 3/9

7:05 am-12:50 pm

1 stop6h 45m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 24 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 January 23, 2026.

Booking 17 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 January 29, 2026.

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 29% 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 January 24, 2026.

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 January 29, 2026.

The most flights from ORD to K1S are scheduled on a Monday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 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 January 29, 2026.
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
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
8,394 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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
5.7
Fair
3,056 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

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 $168, United Airlines can have you in Kissimmee from Chicago O'Hare Intl Airport in 2h 50m. 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 $32 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $40 and United Airlines from $79 one-way.

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

    Consider Azul (82%), Copa Airlines (81%) or SWISS (78%) 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 $493, our data shows the cheapest flight currently is $39. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $60 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

See prices for flight routes from nearby airports that may be better suited for you.
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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$198FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$62Average$170FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$151Average$292FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$152Average$322FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$377FlexibilityNo cancel feeOn-time71%
DeltaCheapest$169Average$420FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$196Average$311FlexibilityNo cancel feeOn-time62%

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