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Kissimmee

Cheap flights from O'Hare Intl (ORD) to Kissimmee, FL

ORD — MCO
Nov 23 — Nov 301
Mon 11/23
Mon 11/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Kissimmee are usually found in January or February, booked 68 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Find flight deals from O'Hare Intl to Kissimmee

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

June

Cheapest in

January

Average price

$390
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.
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Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Kissimmee

What is the cheapest time of day to fly from ORD to K1S?

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 afternoon. If you’re flexible enough to do this you can expect to save up to 11% on your trip compared to booking a flight in the morning.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Kissimmee?

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Kissimmee flight should consider departing on Sunday evenings when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Kissimmee

Get a feel of what it's like to fly with Southwest,Delta, andUnited 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
4,221 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.
Southwest
7.9
Good
4,221 reviews
Southwest
7.9
Good
4,221 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.
Delta
7.8
Good
8,678 reviews
Southwest
7.9
Good
4,221 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.
United Airlines
7.3
Good
10,432 reviews
Southwest
7.9
Good
4,221 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.
American Airlines
7.0
Good
12,192 reviews
Southwest
7.9
Good
4,221 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.
Frontier
5.5
Fair
2,519 reviews
Southwest
7.9
Good
4,221 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Overall

7.9

Entertainment

7.4

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Related info for your journey

  • 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 $42 on Frontier. Other airlines that offer cheap prices include Southwest from $78 and American Airlines from $94 one-way.

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

    Consider Sun Country Air (100%), Copa Airlines (90%) or Azul (85%) 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 $567, our data shows the cheapest flight currently is $109. When looking at the most popular route, (Chicago O'Hare Intl - Orlando), you can expect to pay $85 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Top 6 airlines flying from O'Hare Intl to Kissimmee

AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$63Average$236FlexibilityNo cancel feeOn-time62%
DeltaCheapest$109Average$312FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$147Average$288FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$168Average$333FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$174Average$381FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$190Average$425FlexibilityNo cancel feeOn-time71%

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