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Kissimmee

$58+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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The best prices from Chicago to Kissimmee are usually found in May or April, booked 30 days in advance, depart on a Tuesday or Saturday and return on a Friday

Cheap flight deals from Chicago to Kissimmee

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kissimmee (K1S). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$127
(Cheapflightsfares)

One-way from

$58
(Trip.com)

Popular in

December

Cheapest in

May

Average price

$264
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. 10% potential increase in price ($32 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 January 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 January 21, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/19. 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 2/910:09 amORD - MCO
1 stop13h 32mFrontier
Fri 2/141:34 pmMCO - ORD
1 stop25h 35mFrontier
Deal found 1/19$127
This Cheapflightsfares deal was found by Cheapflights users on 1/20. 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.
Mon 2/1011:33 amMDW - MCO
Nonstop2h 46mFrontier
Wed 2/121:48 pmMCO - MDW
1 stop5h 35mFrontier
Deal found 1/20$127
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/26:06 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Wed 2/56:41 amMCO - ORD
2 stops14h 32mSpirit Airlines
Deal found 1/20$128
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Tue 2/48:00 amORD - MCO
Nonstop2h 50mMultiple Airlines
Sun 2/97:30 amMCO - ORD
Nonstop3h 22mMultiple Airlines
Deal found 1/19$130
This Delta deal was found by Cheapflights users on 1/19. 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.
Tue 4/153:35 pmORD - MCO
1 stop5h 03mDelta
Tue 4/225:30 amMCO - ORD
1 stop7h 39mDelta
Deal found 1/19$217
This Southwest deal was found by Cheapflights users on 1/20. 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.
Wed 2/196:10 pmMDW - MCO
Nonstop2h 40mSouthwest
Wed 2/266:55 amMCO - MDW
1 stop5h 50mSouthwest
Deal found 1/20$243
This JetBlue Airways deal was found by Cheapflights users on 1/20. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/285:15 pmORD - MCO
1 stop7h 10mJetBlue
Fri 4/46:00 amMCO - ORD
1 stop7h 29mJetBlue
Deal found 1/20$261

Find flights from Chicago to Kissimmee within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 1/28

8:00 am-11:50 am

Nonstop2h 50m

Orlando

Thu 2/6

7:05 am-9:27 am

Nonstop3h 22m

$127

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 2/9

10:58 am-2:45 pm

Nonstop2h 47m

Orlando

Wed 2/12

1:48 pm-6:23 pm

1 stop5h 35m

$127

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sun 2/2

12:25 pm-4:12 pm

Nonstop2h 47m

Orlando

Wed 2/5

6:41 am-8:13 pm

2 stops14h 32m

$128

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Thu 2/27

4:21 pm-12:42 am

1 stop7h 21m

Orlando

Wed 3/5

6:00 am-4:31 pm

1 stop11h 31m

$129

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 4/1

1:24 pm-10:05 pm

1 stop7h 41m

Orlando

Tue 4/8

7:18 am-12:27 pm

1 stop6h 09m

$197

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 4/23

3:02 pm-11:16 pm

1 stop7h 14m

Orlando

Tue 4/29

6:20 am-12:30 pm

1 stop7h 10m

$217

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 2/17

8:30 pm-12:10 am

Nonstop2h 40m

Orlando

Wed 2/19

7:10 am-9:05 am

Nonstop2h 55m

$232

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 2/11

11:25 am-7:10 pm

2 stops6h 45m

Orlando

Fri 2/14

3:35 pm-9:30 pm

1 stop6h 55m

$239

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sun 2/23

12:43 pm-4:31 pm

Nonstop2h 48m

$58

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 2/15

4:21 pm-6:32 am

1 stop13h 11m

$59

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 22 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.

Travel insights for flights from Chicago to Kissimmee

Get recent, data-driven insights about flights from Chicago to Kissimmee including ideal travel times, pricing trends, and more.

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 January 17, 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 30 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 January 21, 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 December 16, 2024.

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 at noon 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 January 21, 2025.

The most flights from CHI to K1S are scheduled on a Monday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (45 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 January 21, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Frontier 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
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

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
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

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.

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

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
7.4
Good
3,200 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

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
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Food

7.2

Crew

8.7

Entertainment

7.7

Overall

8.1

Boarding

8.2

Reviews

1 / 10

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 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 $58. Users have also found prices from $70 and $86 on Spirit Airlines and United Airlines, respectively.

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

    Consider Azul (89%), Southwest (89%) or Brussels Airlines (84%) 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 $535 for a flight from Chicago to Kissimmee. The cheapest flight overall is $55 while the most popular route, (Chicago O'Hare Intl - Orlando) is currently priced at $73.

  • 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$39Average$190FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$169FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$112Average$215FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$154Average$353FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$351FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$168Average$400FlexibilityNo cancel feeOn-time63%
DeltaCheapest$195Average$405FlexibilityNo cancel feeOn-timeN/A
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