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Kissimmee

$50+ Cheap flights from Chicago (CHI) 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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Apr 16 — Apr 231
Wed 4/16
Wed 4/23
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kissimmee are usually found in May or April, booked 85 days in advance, depart on a Tuesday or Saturday and return on a Friday

Cheap flight deals from Chicago to Kissimmee

Keep the following information in mind while searching for Chicago to Kissimmee flight deals. Data was last updated April 11, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$106
(Agoda.com)

One-way from

$50
(Cheapflightsfares)

Popular in

March

Cheapest in

May

Average price

$232
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 (CHI) to Kissimmee
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One-way flight from Chicago (CHI) to Kissimmee
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Highest demand for flights based on searches. 5% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 Chicago to Kissimmee

Cheapest flights from Chicago to Kissimmee
Explore the most affordable flight options available from Chicago to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/10. 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.
Sat 5/34:15 pmORD - MCO
Nonstop3h 03mMultiple Airlines
Sat 5/109:25 pmMCO - ORD
Nonstop3h 04mMultiple Airlines
Deal found 4/10$108
This Booking.com deal was found by Cheapflights users on 4/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/197:47 amORD - MCO
Nonstop2h 39mSpirit Airlines
Sat 5/245:55 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
Deal found 4/10$112
This Frontier deal was found by Cheapflights users on 4/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/199:25 amORD - MCO
Nonstop2h 56mFrontier
Sat 4/194:45 pmMCO - ORD
Nonstop3h 19mFrontier
Deal found 4/10$114
This Cheapflightsfares deal was found by Cheapflights users on 4/10. 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.
Sun 6/19:12 pmMDW - MCO
Nonstop2h 41mFrontier
Thu 6/56:22 pmMCO - MDW
Nonstop2h 55mFrontier
Deal found 4/10$125
This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/286:00 amORD - MCO
Nonstop2h 47mUnited Airlines
Wed 7/212:16 pmMCO - ORD
Nonstop3h 07mUnited Airlines
Deal found 4/10$188
This Southwest deal was found by Cheapflights users on 4/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/59:10 amMDW - MCO
1 stop4h 40mSouthwest
Wed 7/95:25 pmMCO - MDW
Nonstop3h 00mSouthwest
Deal found 4/10$194
This American Airlines deal was found by Cheapflights users on 4/9. 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 5/316:38 pmORD - MCO
Nonstop2h 50mAmerican Airlines
Tue 6/311:45 amMCO - ORD
Nonstop3h 05mAmerican Airlines
Deal found 4/9$199
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/251:08 pmMDW - MCO
1 stop4h 46mDelta
Sun 6/15:30 amMCO - MDW
1 stop5h 10mDelta
Deal found 4/10$228
This Delta deal was found by Cheapflights users on 4/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/167:59 pmORD - MCO
1 stop4h 20mDelta
Sat 6/286:15 amMCO - ORD
1 stop4h 54mDelta
Deal found 4/10$237

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago 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 11, 2025.
Use the filters below to find and compare flights from Chicago to Kissimmee that are best for you.

Fly from

Chicago

Fly to

Kissimmee

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 5/3

4:15 pm-8:18 pm

Nonstop3h 03m

Orlando

Sat 5/10

9:25 pm-11:29 pm

Nonstop3h 04m

$108

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 5/19

7:47 am-11:26 am

Nonstop2h 39m

Orlando

Sat 5/24

5:55 pm-8:03 pm

Nonstop3h 08m

$112

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 4/19

9:25 am-1:21 pm

Nonstop2h 56m

Orlando

Sat 4/19

4:45 pm-7:04 pm

Nonstop3h 19m

$114

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 6/1

9:12 pm-12:53 am

Nonstop2h 41m

Orlando

Thu 6/5

6:22 pm-8:17 pm

Nonstop2h 55m

$125

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 6/28

6:00 am-9:47 am

Nonstop2h 47m

Orlando

Wed 7/2

12:16 pm-2:23 pm

Nonstop3h 07m

$188

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 7/5

9:10 am-2:50 pm

1 stop4h 40m

Orlando

Wed 7/9

5:25 pm-7:25 pm

Nonstop3h 00m

$194

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 5/31

6:38 pm-10:28 pm

Nonstop2h 50m

Orlando

Tue 6/3

11:45 am-1:50 pm

Nonstop3h 05m

$199

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 5/25

1:08 pm-6:54 pm

1 stop4h 46m

Orlando

Sun 6/1

5:30 am-9:40 am

1 stop5h 10m

$228

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 6/16

7:59 pm-1:19 am

1 stop4h 20m

Orlando

Sat 6/28

6:15 am-10:09 am

1 stop4h 54m

$237

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 6/6

8:36 pm-12:45 am

2 stops27h 09m

Orlando

Sun 6/8

9:42 pm-7:46 pm

2 stops23h 04m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Showing 1-10 of 24 results
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Best time to book a flight from Chicago to Kissimmee

Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Chicago 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 to Kissimmee

How far ahead should I book a flight from Chicago to Kissimmee?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Kissimmee. Price data was last updated on April 4, 2025.

The price you pay for your flight from Chicago to Kissimmee may vary depending on when you book. For the best chance of a lower fare, look to book 85 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Kissimmee?

Currently, May is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $206). Flying from Chicago 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 CHI to K1S?

Find hourly flight availability from Chicago 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 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Kissimmee as you normally would.

What is the cheapest day to fly from Chicago to Kissimmee?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Kissimmee. Price data was last updated on March 30, 2025.

Travelers seeking maximum savings on their Chicago to Kissimmee flight should consider departing on Tuesday afternoons 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.

Weekly flight availability from Chicago to Kissimmee

Explore weekly flight availability from Chicago 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 11, 2025.

The most flights from CHI to K1S are scheduled on a Thursday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 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 11, 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
9,851 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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
9,851 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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
9,851 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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
7,910 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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
8,636 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Crew

8.5

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Entertainment

7.1

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 Chicago 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 to Kissimmee one-way?

    For one-way options, check prices for Frontier. According to our data, you can fly for as low as $50. Users have also found prices from $51 and $89 on Spirit Airlines and Southwest, respectively.

  • What are the most reliable airlines from Chicago 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 to Kissimmee.

  • What are the cheapest flights from Chicago to Kissimmee?

    On average you can expect to pay $490 for a flight from Chicago to Kissimmee. The cheapest flight overall is $43 while the most popular route, (Chicago O'Hare Intl - Orlando) is currently priced at $97.

  • Can I find deals for flights from Chicago to Kissimmee that include hotel bookings?

    Yes. In addition to deals on Chicago to Kissimmee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kissimmee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kissimmee.

  • Can I find deals for business class flights from Chicago to Kissimmee?

    Yes. Cheapflights offers flight deals from Chicago 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 to Kissimmee?

    Currently, May is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $206). Flying from Chicago 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 7 airlines flying from Chicago to Kissimmee

Discover the top 7 airlines that operate flights from Chicago 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$41Average$196FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$65Average$173FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$106Average$204FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$128Average$344FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$160Average$361FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$180Average$404FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$389FlexibilityNo cancel feeOn-timeN/A

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