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Kissimmee

$34+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Nov 9 — Nov 161
Sat 11/9
Sat 11/16
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 Saturday

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 November 4, 2024.

Popular in

June

Cheapest in

May

Round-trip from

$98
(Frontier)

One-way from

$34
(CheapOair)
High demand for flights, 26% potential price rise
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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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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 November 4, 2024.

This Frontier deal was found by Cheapflights users on 11/3. 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 11/185:33 pmORD - MCO
1 stop6h 20mFrontier
Thu 11/2111:17 amMCO - ORD
Nonstop3h 10mFrontier
Deal found 11/3$108
This Frontier deal was found by Cheapflights users on 11/3. 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 12/92:55 pmMDW - MCO
1 stop9h 53mFrontier
Thu 12/122:36 pmMCO - MDW
1 stop9h 09mFrontier
Deal found 11/3$108
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/188:26 pmORD - MCO
Nonstop3h 03mMultiple Airlines
Fri 11/228:50 amMCO - ORD
Nonstop3h 06mMultiple Airlines
Deal found 11/3$113
This CheapOair deal was found by Cheapflights users on 11/4. 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.
Wed 11/201:09 pmORD - MCO
Nonstop2h 48mSpirit Airlines
Sun 11/248:50 amMCO - ORD
Nonstop3h 06mSpirit Airlines
Deal found 11/4$134
This American Airlines deal was found by Cheapflights users on 11/3. 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.
Tue 12/107:13 pmORD - MCO
Nonstop2h 48mAmerican Airlines
Thu 12/123:57 pmMCO - ORD
Nonstop3h 10mAmerican Airlines
Deal found 11/3$163
This Delta deal was found by Cheapflights users on 11/4. 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.
Wed 12/111:30 pmMDW - MCO
1 stop7h 22mDelta
Sat 12/146:15 amMCO - MDW
1 stop6h 43mDelta
Deal found 11/4$226
This Southwest deal was found by Cheapflights users on 11/3. 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.
Tue 12/32:50 pmMDW - MCO
1 stop4h 15mSouthwest
Thu 12/57:10 amMCO - MDW
Nonstop2h 55mSouthwest
Deal found 11/3$244

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 2,455,398 searches. Data last updated November 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 11/18

8:26 pm-12:29 am

Nonstop3h 03m

$49

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Tue 12/10

9:58 am-10:11 pm

1 stop11h 13m

$60

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 1/7

6:10 pm-9:50 pm

Nonstop2h 40m

$79

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 2/5

10:40 am-2:30 pm

Nonstop2h 50m

$96

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Mon 11/18

8:20 pm-12:16 am

Nonstop2h 56m

$49

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 12/7

5:20 pm-12:05 am

1 stop5h 45m

$98

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 12/6

12:51 pm-12:36 pm

2 stops22h 45m

$110

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 11/27

7:50 pm-10:32 am

1 stop13h 42m

$127

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 3/8

10:56 am-8:35 pm

1 stop8h 39m

$162

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 12/7

5:50 pm-12:05 am

1 stop5h 15m

$98

Flights are sorted by cheapest first

Deals found on 11/4

Showing 1-10 of 23 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 November 1, 2024.

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.

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

Currently, December is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $198). Flying from Chicago to Kissimmee in November is currently the most expensive (average of $255). 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 November 4, 2024.

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 October 27, 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. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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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 November 4, 2024.

The most flights from CHI to K1S are scheduled on a Monday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 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 November 4, 2024.
Get a feel of what it's like to fly with Delta, Southwest 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
5,089 reviews

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.3

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
5,089 reviews
Southwest
8.1
Very good
5,089 reviews

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.3

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
8,829 reviews
Southwest
8.1
Very good
5,089 reviews

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.3

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.

Porter Airlines
7.7
Good
293 reviews
Southwest
8.1
Very good
5,089 reviews

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.3

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
7.5
Good
3,493 reviews
Southwest
8.1
Very good
5,089 reviews

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.3

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
9,226 reviews
Southwest
8.1
Very good
5,089 reviews

Comfort

8.1

Entertainment

7.7

Crew

8.7

Overall

8.1

Food

7.2

Boarding

8.3

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.

  • Can I find flights from Chicago to Kissimmee for under $100 on Cheapflights?

    Yes, there are multiple flights from Chicago to Kissimmee for under $100. The cheapest flight booked recently is on Frontier for just $98, but on average you can expect to pay $159.

  • Are there nonstop flights from Chicago to Kissimmee for under $200 on Cheapflights?

    Cheapflights has at least 7 direct flights from Chicago to Kissimmee under $200. A good price for a nonstop flight from Chicago to Kissimmee is less than $143.

  • Are there last-minute flights available from Chicago to Kissimmee for under $200?

    There are currently 10+ open flights from Chicago to Kissimmee within the next 7 days for less than $200.

  • What days are nonstop flights available from Chicago to Kissimmee?

    Nonstop flights are available for this route on the following days: Tuesday, Wednesday, Thursday, Friday, Saturday.

  • How many flights depart from Chicago to Kissimmee on average per day?

    33 flight departures from Chicago to Kissimmee per day on average.
    Morning (6am - Noon) - 52% of flight departures
    Afternoon (Noon - 6pm) - 24% of flight departures
    Evening (6pm - Midnight) - 24% of flight departures

  • How long is the flight from Chicago to Kissimmee?

    A quick flight from Chicago to Kissimmee can take about 2h 50m. Frontier provides one of the quickest options available for as low as $98. The distance between Chicago and Kissimmee is about 1011 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $34. Users have also found prices from $37 and $79 on Spirit Airlines and Southwest, respectively.

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

    Consider Royal Jordanian (97%), Alaska Airlines (94%) or Spirit Airlines (94%) 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 $601 for a flight from Chicago to Kissimmee. The cheapest flight overall is $60 while the most popular route, (Chicago O'Hare Intl - Orlando) is currently priced at $93.

  • What does ORD to MCO mean?

    Chicago O'Hare Intl Airport is ORD and Orlando Airport is MCO. These codes are created by the International Air Transport Association (IATA) and airlines use them to identify the departing and arrival airports in the flight routes they service. Tampa Airport (TPA), Orlando Sanford Intl Airport (SFB), Daytona Beach Airport (DAB), Melbourne Airport (MLB) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Chicago to Kissimmee that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Kissimmee flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Kissimmee with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Kissimmee flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Kissimmee that allow pets onboard?

    Many airlines flying from Chicago to Kissimmee offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Kissimmee?

    Yes, you can often find last-minute deals on Chicago to Kissimmee flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Kissimmee flight deals updated?

    The Chicago to Kissimmee flight deals you see on this page were last updated on 11/4.

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

    Currently, December is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $198). Flying from Chicago to Kissimmee in November is currently the most expensive (average of $255). 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 Chicago 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 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 2,455,398 searches. Data last updated November 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$23Average$151FlexibilityNo cancel feeOn-time65%
FrontierCheapest$39Average$181FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$106Average$231FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$154Average$321FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$157Average$385FlexibilityNo cancel feeOn-time71%
DeltaCheapest$195Average$412FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$218Average$406FlexibilityNo cancel feeOn-time63%
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