$57+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — MCO
May 2 — May 91
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Kissimmee with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Kissimmee are usually found in September or August, booked 65 days in advance, depart on a Tuesday or Wednesday and return on a Friday
Cheap flight deals from Cleveland to Kissimmee
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Last-minute
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Cheapest flights from Cleveland to KissimmeeExplore 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 April 2, 2026.
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 April 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Fri 7/39:42 pm
CLE
- MCO
Nonstop2h 32m
Frontier
Sat 7/115:01 am
MCO
- CLE
Nonstop2h 37m
Frontier
Deal found 3/31![Frontier logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Sat 5/162:14 pm
CLE
- MCO
Nonstop2h 37m
Frontier
Sun 5/249:52 pm
MCO
- CLE
Nonstop2h 38m
Frontier
Deal found 3/31![Frontier logo]()
$106
This Frontier deal was found by Cheapflights users on 3/29. 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 4/2410:00 pm
CLE
- MCO
Nonstop2h 36m
Frontier
Thu 4/306:13 pm
MCO
- CLE
Nonstop2h 42m
Frontier
Deal found 3/29![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/208:50 am
CLE
- MCO
Nonstop2h 31m
Frontier
Mon 4/209:49 pm
MCO
- CLE
1 stop9h 55m
Frontier
Deal found 3/31![Frontier logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Wed 5/139:57 pm
CLE
- MCO
Nonstop2h 35m
Frontier
Wed 5/205:40 am
MCO
- CLE
1 stop8h 42m
Frontier
Deal found 3/31![Frontier logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Sat 5/309:57 pm
CLE
- MCO
Nonstop2h 35m
Frontier
Sat 6/65:01 am
MCO
- CLE
Nonstop2h 33m
Frontier
Deal found 3/31![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 3/30. 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 7/59:42 pm
CLE
- MCO
Nonstop2h 32m
Frontier
Tue 7/147:50 pm
MCO
- CLE
Nonstop2h 45m
Frontier
Deal found 3/30![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 3/29. 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.
Tue 5/269:57 pm
CLE
- MCO
Nonstop2h 35m
Frontier
Thu 5/2810:30 am
MCO
- CLE
Nonstop2h 39m
Frontier
Deal found 3/29![Frontier logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 5/108:47 pm
CLE
- MCO
1 stop10h 46m
Frontier
Thu 5/145:01 am
MCO
- CLE
Nonstop2h 33m
Frontier
Deal found 3/30![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Wed 4/152:46 pm
CLE
- MCO
Nonstop2h 40m
Frontier
Fri 4/249:49 pm
MCO
- CLE
1 stop12h 54m
Frontier
Deal found 3/31![Frontier logo]()
$114
This Super.com deal was found by Cheapflights users on 3/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/119:42 pm
CLE
- MCO
Nonstop2h 32m
Frontier
Sat 7/185:01 am
MCO
- CLE
Nonstop2h 37m
Frontier
Deal found 3/31![Frontier logo]()
$115
This Frontier deal was found by Cheapflights users on 3/30. 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 7/59:42 pm
CLE
- MCO
Nonstop2h 32m
Frontier
Thu 7/95:49 pm
MCO
- CLE
Nonstop2h 48m
Frontier
Deal found 3/30![Frontier logo]()
$116
Best flights from Cleveland to KissimmeeDiscover carefully curated flight deals from Cleveland to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 2, 2026.
Discover carefully curated flight deals from Cleveland to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 2, 2026.
This Delta deal was found by Cheapflights users on 3/30. 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 5/1312:45 pm
CLE
- MCO
1 stop4h 25m
Delta
Sat 5/168:00 am
MCO
- CLE
1 stop5h 03m
Delta
Deal found 3/30![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 3/30. 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.
Thu 4/165:40 am
CLE
- MCO
2 stops8h 00m
Southwest
Wed 4/229:10 am
MCO
- CLE
1 stop4h 50m
Southwest
Deal found 3/30![Southwest logo]()
$321
This JetBlue deal was found by Cheapflights users on 3/29. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
CLE
- MCO
1 stop6h 35m
JetBlue
Thu 4/305:10 pm
MCO
- CLE
1 stop6h 40m
JetBlue
Deal found 3/29![JetBlue logo]()
$327
This Delta deal was found by Cheapflights users on 3/31. 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.
Thu 6/47:46 pm
CLE
- MCO
1 stop4h 13m
Delta
Wed 6/106:45 pm
MCO
- CLE
1 stop6h 11m
Delta
Deal found 3/31![Delta logo]()
$274
This Southwest deal was found by Cheapflights users on 3/28. 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.
Mon 5/412:40 pm
CLE
- MCO
2 stops6h 35m
Southwest
Mon 5/410:20 pm
MCO
- CLE
1 stop11h 35m
Southwest
Deal found 3/28![Southwest logo]()
$332
This Southwest deal was found by Cheapflights users on 3/29. 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.
Fri 5/13:45 pm
CLE
- MCO
2 stops7h 15m
Southwest
Sun 5/108:40 am
MCO
- CLE
2 stops6h 50m
Southwest
Deal found 3/29![Southwest logo]()
$337
This Southwest deal was found by Cheapflights users on 4/1. 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.
Fri 5/153:45 pm
CLE
- MCO
2 stops7h 15m
Southwest
Fri 5/222:00 pm
MCO
- CLE
2 stops7h 15m
Southwest
Deal found 4/1![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 3/31. 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.
Thu 4/1612:55 pm
CLE
- MCO
2 stops7h 05m
Southwest
Mon 4/204:25 pm
MCO
- CLE
2 stops5h 50m
Southwest
Deal found 3/31![Southwest logo]()
$387
This Southwest deal was found by Cheapflights users on 4/1. 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.
Sat 6/63:35 pm
CLE
- MCO
2 stops6h 55m
Southwest
Sat 6/134:10 pm
MCO
- CLE
2 stops7h 05m
Southwest
Deal found 4/1![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 3/30. 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.
Mon 5/253:45 pm
CLE
- MCO
2 stops7h 15m
Southwest
Fri 5/292:20 pm
MCO
- CLE
2 stops6h 55m
Southwest
Deal found 3/30![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 4/1. 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.
Sun 5/247:10 am
CLE
- MCO
2 stops8h 00m
Southwest
Sun 5/318:30 am
MCO
- CLE
2 stops7h 00m
Southwest
Deal found 4/1![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 4/1. 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.
Mon 6/154:45 pm
CLE
- MCO
2 stops6h 40m
Southwest
Mon 6/2211:10 am
MCO
- CLE
2 stops8h 25m
Southwest
Deal found 4/1![Southwest logo]()
$419
Last-minute flights from Cleveland to KissimmeeDiscover last-minute flight deals from Cleveland to Kissimmee. Data last updated April 2, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Kissimmee. Data last updated April 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Wed 4/152:46 pm
CLE
- MCO
Nonstop2h 40m
Frontier
Fri 4/249:49 pm
MCO
- CLE
1 stop12h 54m
Frontier
Deal found 3/31![Frontier logo]()
$114
This Super.com deal was found by Cheapflights users on 3/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:31 pm
CLE
- MCO
Nonstop2h 36m
Frontier
Sat 4/2512:36 pm
MCO
- CLE
Nonstop2h 44m
Frontier
Deal found 3/30![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/208:50 am
CLE
- MCO
Nonstop2h 31m
Frontier
Mon 4/209:49 pm
MCO
- CLE
1 stop9h 55m
Frontier
Deal found 3/31![Frontier logo]()
$108
This Frontier deal was found by Cheapflights users on 3/29. 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 4/2410:00 pm
CLE
- MCO
Nonstop2h 36m
Frontier
Thu 4/306:13 pm
MCO
- CLE
Nonstop2h 42m
Frontier
Deal found 3/29![Frontier logo]()
$107
This WAYA deal was found by Cheapflights users on 3/31. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:57 pm
CLE
- MCO
Nonstop2h 31m
Frontier
Wed 4/296:00 am
MCO
- CLE
1 stop8h 26m
Frontier
Deal found 3/31![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 3/31. 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 5/110:00 pm
CLE
- MCO
Nonstop2h 36m
Frontier
Sat 5/305:01 am
MCO
- CLE
Nonstop2h 33m
Frontier
Deal found 3/31![Frontier logo]()
$116
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 5/108:47 pm
CLE
- MCO
1 stop10h 46m
Frontier
Thu 5/145:01 am
MCO
- CLE
Nonstop2h 33m
Frontier
Deal found 3/30![Frontier logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Wed 5/139:57 pm
CLE
- MCO
Nonstop2h 35m
Frontier
Wed 5/205:40 am
MCO
- CLE
1 stop8h 42m
Frontier
Deal found 3/31![Frontier logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Sat 5/162:14 pm
CLE
- MCO
Nonstop2h 37m
Frontier
Sun 5/249:52 pm
MCO
- CLE
Nonstop2h 38m
Frontier
Deal found 3/31![Frontier logo]()
$106
This Frontier deal was found by Cheapflights users on 3/29. 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 5/239:57 pm
CLE
- MCO
Nonstop2h 35m
Frontier
Fri 5/298:30 pm
MCO
- CLE
Nonstop2h 41m
Frontier
Deal found 3/29![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 3/29. 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.
Tue 5/269:57 pm
CLE
- MCO
Nonstop2h 35m
Frontier
Thu 5/2810:30 am
MCO
- CLE
Nonstop2h 39m
Frontier
Deal found 3/29![Frontier logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Sat 5/309:57 pm
CLE
- MCO
Nonstop2h 35m
Frontier
Sat 6/65:01 am
MCO
- CLE
Nonstop2h 33m
Frontier
Deal found 3/31![Frontier logo]()
$110
One-way flights from Cleveland to KissimmeeSearch for one-way flight options from Cleveland to Kissimmee. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
Search for one-way flight options from Cleveland to Kissimmee. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
This Super.com deal was found by Cheapflights users on 3/28. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/85:20 pm
CLE
- MCO
Nonstop2h 38m
Frontier
Deal found 3/28![Frontier logo]()
$57
This Frontier deal was found by Cheapflights users on 3/29. 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 5/276:30 am
CLE
- MCO
Nonstop2h 36m
Frontier
Deal found 3/29![Frontier logo]()
$58
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/278:25 pm
CLE
- MCO
1 stop14h 20m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$61
This Super.com deal was found by Cheapflights users on 3/31. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:52 pm
CLE
- MCO
Nonstop2h 48m
Frontier
Deal found 3/31![Frontier logo]()
$62
This Frontier deal was found by Cheapflights users on 3/31. 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 6/299:42 pm
CLE
- MCO
Nonstop2h 32m
Frontier
Deal found 3/31![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Wed 4/293:33 pm
CLE
- MCO
1 stop8h 46m
Frontier
Deal found 3/31![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/288:55 pm
CLE
- MCO
1 stop18h 34m
Multiple Airlines
Deal found 3/28![Multiple Airlines logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Fri 4/2411:05 am
CLE
- MCO
1 stop20h 34m
Frontier
Deal found 3/31![Frontier logo]()
$67
This Frontier deal was found by Cheapflights users on 3/31. 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 5/13:46 pm
CLE
- MCO
1 stop4h 50m
Frontier
Deal found 3/31![Frontier logo]()
$70
Find flight deals from Cleveland to Kissimmee
Keep the following information in mind while searching for Cleveland to Kissimmee flight deals. Data was last updated April 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $105 (Kiwi.com) |
One-way from | $57 (Super.com) |
Popular in | February |
Cheapest in | September |
Average price | $231 |
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 April 2, 2026.
Use the filters below to find and compare flights from Cleveland to Kissimmee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Wed 5/13
12:45 pm-5:10 pm
1 stop4h 25m
Orlando
Sat 5/16
8:00 am-1:03 pm
1 stop5h 03m
$237
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Thu 6/4
7:46 pm-11:59 pm
1 stop4h 13m
Orlando
Wed 6/10
6:45 pm-12:56 am
1 stop6h 11m
$274
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Thu 4/16
5:40 am-1:40 pm
2 stops8h 00m
Orlando
Wed 4/22
9:10 am-2:00 pm
1 stop4h 50m
$321
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Mon 4/27
6:00 am-12:35 pm
1 stop6h 35m
Orlando
Thu 4/30
5:10 pm-11:50 pm
1 stop6h 40m
$327
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Mon 5/4
12:40 pm-7:15 pm
2 stops6h 35m
Orlando
Mon 5/4
10:20 pm-9:55 am
1 stop11h 35m
$332
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Fri 5/1
3:45 pm-11:00 pm
2 stops7h 15m
Orlando
Sun 5/10
8:40 am-3:30 pm
2 stops6h 50m
$337
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Fri 5/15
3:45 pm-11:00 pm
2 stops7h 15m
Orlando
Fri 5/22
2:00 pm-9:15 pm
2 stops7h 15m
$353
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Thu 4/16
12:55 pm-8:00 pm
2 stops7h 05m
Orlando
Mon 4/20
4:25 pm-10:15 pm
2 stops5h 50m
$387
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Sat 6/6
3:35 pm-10:30 pm
2 stops6h 55m
Orlando
Sat 6/13
4:10 pm-11:15 pm
2 stops7h 05m
$419
ClevelandOrlando
CLE - MCO
CLEMCO
Cleveland Hopkins Intl
Mon 5/25
3:45 pm-11:00 pm
2 stops7h 15m
Orlando
Fri 5/29
2:20 pm-9:15 pm
2 stops6h 55m
$419
Showing 1-10 of 21 resultsSorted by cheapest first
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.
CLE-MCO
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
CLE-K1S
CLE-MCO
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 March 13, 2026.
To ensure you get the cheapest price possible for a flight from Cleveland to Kissimmee, you should look to book at least 65 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, January is the cheapest month in which you can book a flight from Cleveland to Kissimmee (average of $58). Flying from Cleveland to Kissimmee in March is currently the most expensive (average of $92). 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 April 2, 2026.
It’s optimal to fly from Cleveland to Kissimmee in the evening. By choosing this option you can save up to 18% on the cost of your flight, compared to a flight in the morning.
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 March 28, 2026.
Travelers seeking maximum savings on their Cleveland to Kissimmee flight should consider departing on Wednesday at noon 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 April 2, 2026.
The most flights from CLE to K1S are scheduled on a Wednesday (14 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (4 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 April 2, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited 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.
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
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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.
Complete your trip
Complete your trip to Kissimmee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Cleveland to Kissimmee by cabin class
Find flights from Cleveland to Kissimmee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Cleveland and Kissimmee flights
Browse other Cleveland and Kissimmee flight options. Last updated on April 2, 2026.
Other flights from Cleveland
Browse through other flights departing from Cleveland. Flights are based on user searches made on Cheapflights and were last updated on April 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Cleveland to Kissimmee flights
Consider these flights traveling from Cleveland to Kissimmee.
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 April 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$61 | Average$132 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$80 | Average$197 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$94 | Average$282 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$110 | Average$187 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$139 | Average$364 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$152 | Average$318 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$178 | Average$355 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$178 | Average$330 | FlexibilityNo cancel fee | On-time63% |