Cheap flights from Chicago (CHI) to Kissimmee, FL from $29
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 5/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
The best prices from Chicago to Kissimmee are usually found in May or September, booked 30 days in advance, depart on a Tuesday or Wednesday and return on a Wednesday
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 May 11, 2024.
Popular in | March |
|---|---|
Cheapest in | May |
Round-trip from | $182 |
One-way from | $29 |
How far in advance should I book a flight from Chicago to Kissimmee?
To save on the cost of your flight from Chicago to Kissimmee, book at least 31 days before your planned departure. Booking around this time can save you about 27% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $149 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $227.
What is the cheapest month to fly from Chicago to Kissimmee?
The best pricing can be found in the month of May. Prices to Kissimmee from Chicago average $230. You can even find prices in May for less than $230, as users have found deals to Kissimmee from as low as $61. The month of March appears to be one of the more expensive times to travel to Kissimmee from Chicago. Flying in the targeted month can save you up to 36%.
When is the cheapest time to fly from Chicago to Kissimmee (CHI - K1S)?
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.
Cheap Spirit Airlines flights from Chicago to Kissimmee
Explore cheap flight options specifically provided by Spirit Airlines for the route between Chicago and Kissimmee. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
Peruse some of the lowest-priced Spirit Airlines flights we've found from Chicago to Kissimmee. It's recommended that users confirm their flight details before booking.
Cheap Frontier flights from Chicago to Kissimmee
Explore cheap flight options specifically provided by Frontier for the route between Chicago and Kissimmee. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
To aid your search, here are some of the cheapest Frontier flights we've found from Chicago to Kissimmee. Ensure the flight price, dates, time, and airline match your criteria before you book.
Cheap Chicago to Kissimmee flights in May & June 2024
Find cheap flight options from Chicago to Kissimmee specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,684,066 searches. Prices were last updated on May 11, 2024.
The lowest fares we've come across on flights traveling from Chicago to Kissimmee in May and June 2024. For more flight deals, be sure to check back very soon.
Chicago to Kissimmee 2024 flight deals
Discover exclusive flight deals for travel between Chicago and Kissimmee in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
The lowest fares we've come across on flights traveling from Chicago to Kissimmee in May and June 2024. For more flight deals, be sure to check back very soon.
Non-stop flights to Kissimmee from Chicago
Discover non-stop flight options from Chicago to Kissimmee. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
For a quicker trip, book one of these direct flights from Chicago to Kissimmee. Search for alternative flights from Chicago to Kissimmee by utilizing the search form above.
Chicago to Kissimmee flights leaving soon
Find last-minute flight options from Chicago to Kissimmee for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
Consider one of these great deals we found on last-minute flights from Chicago to Kissimmee. Users should be sure to double check the price, date, and time of their last-minute flight.
One-way flights to Kissimmee from Chicago
Search for one-way flight options from Chicago to Kissimmee. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,684,066 searches. Data last updated May 11, 2024.
Users traveling one-way from Chicago to Kissimmee can select one of these great deals. For those needing a return trip from Chicago, there is a search form available above.
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 2,684,066 searches. Data last updated May 11, 2024.
Fly from
Fly to
Budget
$69 - $187
Route
Depart
Return
Price
Chicago MidwayOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 5/22
Nonstop2h 48m
Orlando
Wed 5/29
Nonstop2h 53m
Chicago MidwayOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 8/8
Nonstop2h 41m
Orlando
Mon 8/12
Nonstop2h 48m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 6/5
1 stop7h 51m
Orlando
Wed 6/12
Nonstop3h 14m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 6/5
Nonstop2h 56m
Orlando
Wed 6/12
Nonstop3h 14m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sat 6/1
Nonstop2h 49m
Orlando
Wed 6/12
Nonstop3h 09m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 5/21
Nonstop2h 49m
Orlando
Tue 5/28
1 stop27h 42m
Chicago MidwayOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 5/29
Nonstop2h 48m
Orlando
Sat 6/1
Nonstop2h 58m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Mon 7/1
1 stop12h 49m
Orlando
Fri 7/5
1 stop7h 39m
Chicago O'Hare IntlOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sat 8/3
Nonstop2h 43m
Orlando
Sat 8/10
Nonstop3h 04m
When is the best time to 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 May 10, 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.
When is the cheapest time 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 May 5, 2024.
Average price of flights to Kissimmee by month
Plan your trip from Chicago to Kissimmee by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago to Kissimmee is currently $36 while a round-trip flight costs $104. Price data was last updated on May 5, 2024.
Currently, September is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $182). Flying from Chicago to Kissimmee in March is currently the most expensive (average of $242). 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.
January
$196
February
$202
March
$242
April
$228
May
$206
June
$228
July
$215
August
$196
September
$182
October
$216
November
$221
December
$198
Temperature and rainfall in Kissimmee by month
Plan your trip to Kissimmee by taking into account the average temperature and rainfall totals by month.
ORL Temperature | 60.8 - 84.2 °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 May 11, 2024.
Get a feel of what it's like to fly with Spirit Airlines, Frontier and Sun Country Air 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.
Crew
Comfort
Entertainment
Overall
Boarding
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Crew
Comfort
Entertainment
Overall
Boarding
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Crew
Comfort
Entertainment
Overall
Boarding
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Crew
Comfort
Entertainment
Overall
Boarding
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Crew
Comfort
Entertainment
Overall
Boarding
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Crew
Comfort
Entertainment
Overall
Boarding
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
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.
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Alternative routes for Chicago to KissimmeeSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
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 2,684,066 searches. Data last updated May 11, 2024.
Search flights from Chicago to Kissimmee by cabin class
Find flights from Chicago to Kissimmee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Chicago to Kissimmee
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 May 11, 2024.
| 3%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 49%of flight departures | Morning6 am to noon |
| 48%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
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 May 11, 2024.
| Sunday | 56daily flights |
|---|---|
| Monday | 64daily flights |
| Tuesday | 48daily flights |
| Wednesday | 49daily flights |
| Thursday | 58daily flights |
| Friday | 59daily flights |
| Saturday | 66daily flights |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Fly with Cheapflights
Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Chicago to Kissimmee?
Cheapflights helps you search for flights from Chicago to Kissimmee via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
Why should you use Cheapflights to find cheap flight tickets from Chicago to Kissimmee?
It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Chicago to Kissimmee.
Can Cheapflights find flights from Chicago to Kissimmee with no change fees?
Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago to Kissimmee, users can toggle the no change fees filter when performing a flight search.
Can Cheapflights notify me if prices for flights from Chicago to Kissimmee become cheaper?
Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Kissimmee from Chicago today and book when prices fit your budget.