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Kissimmee

$48+ Cheap flights from Cleveland (CLE) 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — MCO
Nov 16 — Nov 231
Sun 11/16
Sun 11/23
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Kissimmee are usually found in September or January, booked 13 days in advance, depart on a Tuesday or Monday and return on a Thursday

Find flight deals from Cleveland to Kissimmee

Cheapest flights from Cleveland to Kissimmee
Explore the most affordable flight options available from Cleveland to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 17, 2025.

This Frontier deal was found by Cheapflights users on 10/17. 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.
Fri 10/248:25 amCLE - MCO
Nonstop2h 26mFrontier
Sat 11/18:30 pmMCO - CLE
Nonstop2h 36mFrontier
Deal found 10/17$116
This Frontier deal was found by Cheapflights users on 10/17. 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 10/252:14 pmCLE - MCO
Nonstop2h 29mFrontier
Sun 11/27:30 amMCO - CLE
Nonstop2h 39mFrontier
Deal found 10/17$117
This Frontier deal was found by Cheapflights users on 10/16. 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 11/17:14 pmCLE - MCO
Nonstop2h 33mFrontier
Tue 11/411:38 amMCO - CLE
1 stop9h 34mFrontier
Deal found 10/16$118
This Mytrip deal was found by Cheapflights users on 10/17. 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.
Sat 11/17:14 pmCLE - MCO
Nonstop2h 33mFrontier
Mon 11/38:59 pmMCO - CLE
1 stop16h 32mFrontier
Deal found 10/17$119
This CheapOair deal was found by Cheapflights users on 10/16. 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.
Sun 12/147:17 pmCLE - MCO
Nonstop2h 42mFrontier
Fri 12/195:05 amMCO - CLE
Nonstop2h 38mFrontier
Deal found 10/16$120
This Frontier deal was found by Cheapflights users on 10/15. 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.
Sun 11/95:49 pmCLE - MCO
1 stop11h 55mFrontier
Fri 11/1410:04 pmMCO - CLE
Nonstop2h 34mFrontier
Deal found 10/15$121
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/87:20 amCLE - MCO
1 stop6h 15mMultiple Airlines
Thu 11/1310:04 pmMCO - CLE
Nonstop2h 34mMultiple Airlines
Deal found 10/16$122
This Kiwi.com deal was found by Cheapflights users on 10/16. 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.
Sun 11/95:49 pmCLE - MCO
1 stop11h 55mFrontier
Thu 11/1310:04 pmMCO - CLE
Nonstop2h 34mFrontier
Deal found 10/16$124
This Frontier deal was found by Cheapflights users on 10/15. 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 11/104:55 pmCLE - MCO
Nonstop2h 35mFrontier
Mon 11/1010:04 pmMCO - CLE
Nonstop2h 34mFrontier
Deal found 10/15$125
This Frontier deal was found by Cheapflights users on 10/16. 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.
Fri 10/315:45 pmCLE - MCO
Nonstop2h 32mFrontier
Tue 11/46:59 pmMCO - CLE
Nonstop2h 36mFrontier
Deal found 10/16$126
This Cheapflightsfares deal was found by Cheapflights users on 10/16. 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.
Thu 10/231:46 pmCLE - MCO
Nonstop2h 23mFrontier
Sat 10/258:15 amMCO - CLE
Nonstop2h 34mFrontier
Deal found 10/16$127

Cheap flight deals from Cleveland to Kissimmee

Keep the following information in mind while searching for Cleveland to Kissimmee flight deals. Data was last updated October 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$116
(Kiwi.com)

One-way from

$48
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$194
Provider with most accurate pricing for Cleveland Hopkins Intl-Orlando (ORL) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Orlando (ORL) flights.
Search Deals
From Cleveland Hopkins Intl to Kissimmee
Search Deals
One-way flight from Cleveland Hopkins Intl to Kissimmee
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cleveland 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 October 17, 2025.
Use the filters below to find and compare flights from Cleveland to Kissimmee that are best for you.

Fly from

Cleveland

Fly to

Kissimmee

Route

Depart

Return

Price

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Tue 1/13

2:35 pm-7:40 pm

1 stop5h 05m

Orlando

Tue 1/20

6:15 am-11:03 am

1 stop4h 48m

$197

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Thu 1/29

7:13 pm-12:46 am

1 stop5h 33m

Orlando

Tue 2/3

11:05 am-1:40 pm

Nonstop2h 35m

$215

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Tue 12/9

11:40 am-6:00 pm

1 stop6h 20m

Orlando

Wed 12/10

3:30 pm-9:05 pm

2 stops5h 35m

$222

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Tue 11/11

1:10 pm-7:15 pm

2 stops6h 05m

Orlando

Mon 11/17

11:45 am-5:35 pm

1 stop5h 50m

$222

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Sat 11/8

6:50 pm-10:59 pm

1 stop4h 09m

Orlando

Fri 11/14

7:52 pm-12:38 am

1 stop4h 46m

$237

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Fri 11/14

7:05 pm-12:25 am

1 stop5h 20m

Orlando

Mon 11/17

11:45 am-5:35 pm

1 stop5h 50m

$237

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Wed 11/12

5:00 pm-9:48 pm

1 stop4h 48m

Orlando

Fri 11/14

11:20 am-3:56 pm

1 stop4h 36m

$237

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Fri 12/12

3:25 pm-10:05 pm

2 stops6h 40m

Orlando

Mon 12/15

3:30 pm-9:05 pm

2 stops5h 35m

$246

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Sun 11/2

5:00 am-8:55 am

1 stop3h 55m

Orlando

Sat 11/8

5:30 am-11:35 am

1 stop6h 05m

$257

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Fri 2/20

7:20 pm-12:50 am

1 stop5h 30m

Orlando

Mon 2/23

8:45 am-5:15 pm

2 stops8h 30m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 21 results
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Best time to book a flight from Cleveland to Kissimmee

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

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

Use this chart to determine the optimal time to book a round-trip flight from Cleveland to Kissimmee. Price data was last updated on October 10, 2025.

To ensure you get the cheapest price possible for a flight from Cleveland to Kissimmee, you should look to book at least 13 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, February is the cheapest month in which you can book a flight from Cleveland to Kissimmee (average of $56). Flying from Cleveland to Kissimmee in June is currently the most expensive (average of $86). 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 CLE to K1S?

Find hourly flight availability from Cleveland 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 October 17, 2025.

It’s optimal to fly from Cleveland to Kissimmee in the evening. By choosing this option you can save up to 26% on the cost of your flight, compared to a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Cleveland to Kissimmee. Price data was last updated on October 12, 2025.

Travelers seeking maximum savings on their Cleveland to Kissimmee flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Cleveland to Kissimmee

Explore weekly flight availability from Cleveland 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 October 17, 2025.

The most flights from CLE to K1S are scheduled on a Wednesday (9 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 on average).

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 October 17, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Cleveland 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
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,987 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,036 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,102 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,134 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Cleveland to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Cleveland to Kissimmee?

    Located just 10.1 mi from the city center, Cleveland Hopkins Intl is the airport most travelers will use when flying to Kissimmee from Cleveland. Booking flights from Hopkins Intl (CLE) to Kissimmee should be relatively easy as there are 6 daily outbound flights to Kissimmee from 8 different airlines.

  • How long is the flight from Cleveland to Kissimmee?

    Delta, United Airlines, and Southwest can get you from Cleveland to Kissimmee in just under 5h 05m. Your travel time can differ by up to 1h 15m. There are 897 mi between Cleveland and Kissimmee. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Before booking your flight to Kissimmee from Cleveland, check out the most reliable airlines to get you to your destination on time: Azul (98%), United Airlines (97%), Avianca( 94%).

  • What are the cheapest flights from Cleveland to Kissimmee?

    The cheapest flight price from Cleveland to Kissimmee is $49. On average you can expect to pay $344. The most popular route, (Cleveland Hopkins Intl - Orlando), can usually be booked for $68.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Cleveland 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 Cleveland to Kissimmee?

    Currently, February is the cheapest month in which you can book a flight from Cleveland to Kissimmee (average of $56). Flying from Cleveland to Kissimmee in June is currently the most expensive (average of $86). 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.

See more FAQs

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Top 8 airlines flying from Cleveland to Kissimmee

Discover the top 8 airlines that operate flights from Cleveland 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 October 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$41Average$265FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$52Average$162FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$188FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$104Average$178FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$160Average$338FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$178Average$356FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$178Average$333FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$351FlexibilityNo cancel feeOn-timeN/A

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