Kissimmee

$59+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — MCO
Aug 25 — Sep 11
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Kissimmee are usually found in September or October, booked 24 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

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 August 20, 2025.

Round-trip from

$108
(Priceline)

One-way from

$59
(Cheapflightsfares)

Popular in

November

Cheapest in

September

Average price

$191
From Cleveland Hopkins Intl to Kissimmee
One-way flight from Cleveland Hopkins Intl to Kissimmee
Highest demand for flights based on searches. 5% potential increase in price ($14 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Average for round-trip flights in August 2025

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 August 20, 2025.

This Priceline deal was found by Cheapflights users on 8/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:00 amCLE - MCO
Nonstop2h 34mFrontier
Sat 9/1311:40 amMCO - CLE
Nonstop2h 35mFrontier
Deal found 8/19$108
This CheapOair deal was found by Cheapflights users on 8/18. 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.
Tue 9/168:00 amCLE - MCO
Nonstop2h 26mFrontier
Fri 9/196:15 pmMCO - CLE
Nonstop2h 40mFrontier
Deal found 8/18$109
This Frontier deal was found by Cheapflights users on 8/18. 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.
Wed 10/12:00 pmCLE - MCO
Nonstop2h 38mFrontier
Wed 10/157:00 pmMCO - CLE
Nonstop2h 39mFrontier
Deal found 8/18$110
This CheapOair deal was found by Cheapflights users on 8/18. 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 9/178:00 amCLE - MCO
Nonstop2h 26mFrontier
Sun 9/218:00 amMCO - CLE
1 stop5h 31mFrontier
Deal found 8/18$111
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 10/125:30 amCLE - MCO
Nonstop2h 32mFrontier
Mon 10/205:30 amMCO - CLE
1 stop5h 17mFrontier
Deal found 8/18$112
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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.
Fri 10/245:30 amCLE - MCO
Nonstop2h 32mFrontier
Fri 10/317:42 pmMCO - CLE
1 stop5h 12mFrontier
Deal found 8/18$113
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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 10/265:45 pmCLE - MCO
Nonstop2h 32mFrontier
Thu 10/307:30 amMCO - CLE
Nonstop2h 39mFrontier
Deal found 8/19$115
This Cheapflightsfares deal was found by Cheapflights users on 8/19. 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 10/59:50 pmCLE - MCO
Nonstop2h 22mFrontier
Wed 10/81:48 pmMCO - CLE
Nonstop2h 37mFrontier
Deal found 8/19$117
This CheapOair deal was found by Cheapflights users on 8/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/305:31 pmCLE - MCO
Nonstop2h 39mFrontier
Mon 9/89:01 amMCO - CLE
1 stop11h 25mFrontier
Deal found 8/19$118
This Cheapflightsfares deal was found by Cheapflights users on 8/18. 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 9/259:50 pmCLE - MCO
Nonstop2h 22mFrontier
Mon 9/296:15 pmMCO - CLE
Nonstop2h 40mFrontier
Deal found 8/18$119
This CheapOair deal was found by Cheapflights users on 8/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2811:52 amCLE - MCO
1 stop11h 43mFrontier
Sun 8/3110:39 amMCO - CLE
Nonstop2h 40mFrontier
Deal found 8/19$120

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 August 20, 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

Wed 9/17

2:00 pm-4:38 pm

Nonstop2h 38m

Orlando

Wed 9/24

4:04 pm-1:31 pm

1 stop21h 27m

$111

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Sat 10/18

11:34 am-2:04 pm

Nonstop2h 30m

Orlando

Tue 10/21

11:04 am-5:26 pm

1 stop6h 22m

$111

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Thu 9/18

9:50 pm-12:12 am

Nonstop2h 22m

Orlando

Mon 9/22

7:38 pm-12:43 am

1 stop5h 05m

$112

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Thu 9/25

9:50 pm-12:12 am

Nonstop2h 22m

Orlando

Mon 9/29

8:00 am-1:31 pm

1 stop5h 31m

$112

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Thu 9/4

9:50 pm-12:12 am

Nonstop2h 22m

Orlando

Sun 9/7

8:00 am-1:31 pm

1 stop5h 31m

$112

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Fri 10/24

8:25 am-10:51 am

Nonstop2h 26m

Orlando

Fri 10/31

7:42 pm-12:54 am

1 stop5h 12m

$112

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Sun 10/12

5:30 am-8:02 am

Nonstop2h 32m

Orlando

Sat 10/18

8:15 pm-10:51 pm

Nonstop2h 36m

$112

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Thu 9/18

9:50 pm-12:12 am

Nonstop2h 22m

Orlando

Sun 9/21

8:00 am-1:31 pm

1 stop5h 31m

$113

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Thu 9/11

5:53 pm-8:36 pm

Nonstop2h 43m

Orlando

Thu 9/18

8:00 am-1:31 pm

1 stop5h 31m

$113

ClevelandOrlando

CLE - MCO

CLEMCO

Cleveland Hopkins Intl

Fri 9/5

9:50 pm-12:12 am

Nonstop2h 22m

Orlando

Mon 9/8

6:00 am-10:39 am

1 stop4h 39m

$113

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 19 results
1
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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 August 8, 2025.

To ensure you get the cheapest price possible for a flight from Cleveland to Kissimmee, you should look to book at least 24 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, May is the cheapest month in which you can book a flight from Cleveland to Kissimmee (average of $206). Flying from Cleveland 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 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 August 20, 2025.

When flying from Cleveland to Kissimmee, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 August 17, 2025.

Travelers seeking maximum savings on their Cleveland to Kissimmee flight should consider departing on Monday at noon when fares are most often at their lowest. Saturday at noon 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 August 20, 2025.

The most flights from CLE to K1S are scheduled on a Wednesday (6 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Cleveland to Kissimmee?

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 August 20, 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.

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Overall

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 4 daily outbound flights to Kissimmee from 8 different airlines.

  • How long is the flight from Cleveland to Kissimmee?

    Frontier can get you from Cleveland to Kissimmee in just under 2h 38m. Your travel time will be generally consistent. There are 897 mi between Cleveland and Kissimmee. Most flights are nonstop.

  • 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: Avianca (92%), Copa Airlines (92%), Azul( 86%).

  • What are the cheapest flights from Cleveland to Kissimmee?

    The cheapest flight price from Cleveland to Kissimmee is $50. On average you can expect to pay $407. The most popular route, (Cleveland Hopkins Intl - Orlando), can usually be booked for $78.

  • 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, May is the cheapest month in which you can book a flight from Cleveland to Kissimmee (average of $206). Flying from Cleveland 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.

See more FAQs

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Alternative routes for Cleveland to Kissimmee

See prices for flight routes from nearby airports that may be better suited for you.

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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$41Average$166FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$52Average$134FlexibilityNo cancel feeOn-time65%
FrontierCheapest$78Average$181FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$81Average$160FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$159Average$349FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$191Average$350FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$195Average$355FlexibilityNo cancel feeOn-time71%
DeltaCheapest$196Average$347FlexibilityNo cancel feeOn-timeN/A

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