$58+ Cheap flights from O'Hare Intl (ORD) 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 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
Apr 27 — May 41
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl 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
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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 Chicago O'Hare Intl to Kissimmee are usually found in January or September, booked 42 days in advance, depart on a Tuesday or Saturday and return on a Friday
Cheap flight deals from O'Hare Intl to Kissimmee
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Cheapest flights from O'Hare Intl to KissimmeeExplore the most affordable flight options available from O'Hare Intl to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2026.
Explore the most affordable flight options available from O'Hare Intl to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2026.
This Expedia deal was found by Cheapflights users on 3/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:37 pm
ORD
- MCO
1 stop8h 26m
Frontier
Thu 4/307:15 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Deal found 3/25![Frontier logo]()
$124
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Mon 4/134:21 pm
ORD
- MCO
Nonstop3h 01m
Frontier
Fri 4/172:48 pm
MCO
- ORD
Nonstop3h 21m
Frontier
Deal found 3/27![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Thu 4/165:50 am
ORD
- MCO
1 stop6h 47m
Multiple Airlines
Wed 4/226:22 am
MCO
- ORD
1 stop5h 01m
Multiple Airlines
Deal found 3/26![Multiple Airlines logo]()
$126
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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.
Tue 4/2110:31 am
ORD
- MCO
Nonstop2h 40m
Spirit Airlines
Wed 4/2210:49 pm
MCO
- ORD
1 stop11h 47m
Spirit Airlines
Deal found 3/24![Spirit Airlines logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Tue 5/265:30 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Thu 5/288:58 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Deal found 3/27![Frontier logo]()
$128
This WAYA deal was found by Cheapflights users on 3/24. 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.
Tue 4/146:08 pm
ORD
- MCO
1 stop5h 11m
Multiple Airlines
Wed 4/1511:18 am
MCO
- ORD
1 stop6h 42m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 3/26. 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 4/189:16 am
ORD
- MCO
1 stop5h 13m
Spirit Airlines
Wed 4/226:22 am
MCO
- ORD
1 stop5h 01m
Spirit Airlines
Deal found 3/26![Spirit Airlines logo]()
$130
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 5/24:50 pm
ORD
- MCO
Nonstop2h 43m
Spirit Airlines
Sun 5/109:07 pm
MCO
- ORD
Nonstop3h 00m
Spirit Airlines
Deal found 3/25![Spirit Airlines logo]()
$131
This WAYA deal was found by Cheapflights users on 3/25. 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.
Sat 4/255:50 am
ORD
- MCO
1 stop6h 47m
Multiple Airlines
Sat 5/29:07 pm
MCO
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$132
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Tue 4/149:06 am
ORD
- MCO
Nonstop2h 46m
Spirit Airlines
Sat 4/187:00 am
MCO
- ORD
Nonstop3h 05m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$133
This WAYA deal was found by Cheapflights users on 3/25. 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.
Tue 4/146:08 pm
ORD
- MCO
1 stop5h 11m
Multiple Airlines
Sat 4/186:22 am
MCO
- ORD
1 stop6h 11m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$134
This Priceline deal was found by Cheapflights users on 3/24. 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 4/232:05 pm
ORD
- MCO
Nonstop3h 05m
Multiple Airlines
Mon 4/279:07 pm
MCO
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$135
Best flights from O'Hare Intl to KissimmeeDiscover carefully curated flight deals from O'Hare Intl to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 28, 2026.
Discover carefully curated flight deals from O'Hare Intl to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 28, 2026.
This United Airlines deal was found by Cheapflights users on 3/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/127:23 am
ORD
- MCO
Nonstop2h 57m
United Airlines
Thu 5/147:15 am
MCO
- ORD
Nonstop3h 13m
United Airlines
Deal found 3/23![United Airlines logo]()
$197
This Delta deal was found by Cheapflights users on 3/26. 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.
Sat 4/255:15 am
ORD
- MCO
1 stop4h 28m
Delta
Sat 4/254:20 pm
MCO
- ORD
1 stop4h 56m
Delta
Deal found 3/26![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 3/26. 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 5/91:55 pm
ORD
- MCO
1 stop7h 25m
Southwest
Tue 5/129:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Deal found 3/26![Southwest logo]()
$228
This United Airlines deal was found by Cheapflights users on 3/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/25:56 pm
ORD
- MCO
Nonstop2h 59m
United Airlines
Sat 6/62:25 pm
MCO
- ORD
Nonstop3h 18m
United Airlines
Deal found 3/23![United Airlines logo]()
$211
This Southwest deal was found by Cheapflights users on 3/25. 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 5/1810:30 am
ORD
- MCO
1 stop7h 30m
Southwest
Tue 5/269:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Deal found 3/25![Southwest logo]()
$228
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.
Sun 5/176:00 am
ORD
- MCO
Nonstop2h 40m
Southwest
Wed 5/204:20 pm
MCO
- ORD
Nonstop3h 05m
Southwest
Deal found 3/28![Southwest logo]()
$228
This United Airlines deal was found by Cheapflights users on 3/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:15 pm
ORD
- MCO
Nonstop2h 54m
United Airlines
Sat 5/29:02 am
MCO
- ORD
Nonstop3h 13m
United Airlines
Deal found 3/23![United Airlines logo]()
$232
This Southwest deal was found by Cheapflights users on 3/26. 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 5/112:40 pm
ORD
- MCO
1 stop4h 35m
Southwest
Thu 5/149:55 pm
MCO
- ORD
2 stops15h 55m
Southwest
Deal found 3/26![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 3/27. 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 5/122:40 pm
ORD
- MCO
1 stop4h 50m
Southwest
Tue 5/199:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Deal found 3/27![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 3/27. 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 5/21:55 pm
ORD
- MCO
1 stop4h 50m
Southwest
Tue 5/59:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Deal found 3/27![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 3/25. 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 4/3010:30 am
ORD
- MCO
1 stop7h 30m
Southwest
Sun 5/36:25 am
MCO
- ORD
2 stops10h 05m
Southwest
Deal found 3/25![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 3/26. 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 5/153:05 pm
ORD
- MCO
Nonstop2h 55m
Southwest
Sun 5/177:35 am
MCO
- ORD
Nonstop3h 10m
Southwest
Deal found 3/26![Southwest logo]()
$257
Last-minute flights from O'Hare Intl to KissimmeeDiscover last-minute flight deals from O'Hare Intl to Kissimmee. Data last updated March 28, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Kissimmee. Data last updated March 28, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Mon 4/134:21 pm
ORD
- MCO
Nonstop3h 01m
Frontier
Fri 4/172:48 pm
MCO
- ORD
Nonstop3h 21m
Frontier
Deal found 3/27![Frontier logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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.
Tue 4/1412:45 pm
ORD
- MCO
Nonstop2h 40m
Spirit Airlines
Fri 4/177:00 am
MCO
- ORD
Nonstop3h 05m
Spirit Airlines
Deal found 3/24![Spirit Airlines logo]()
$129
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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.
Tue 4/149:06 am
ORD
- MCO
Nonstop2h 46m
Spirit Airlines
Sat 4/187:00 am
MCO
- ORD
Nonstop3h 05m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$133
This WAYA deal was found by Cheapflights users on 3/25. 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.
Tue 4/146:08 pm
ORD
- MCO
1 stop5h 11m
Multiple Airlines
Sat 4/186:22 am
MCO
- ORD
1 stop6h 11m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Thu 4/165:50 am
ORD
- MCO
1 stop6h 47m
Multiple Airlines
Wed 4/226:22 am
MCO
- ORD
1 stop5h 01m
Multiple Airlines
Deal found 3/26![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 4/176:04 pm
ORD
- MCO
Nonstop3h 06m
Multiple Airlines
Tue 4/2110:58 am
MCO
- ORD
Nonstop3h 02m
Multiple Airlines
Deal found 3/27![Multiple Airlines logo]()
$128
This Cheapflightsfares deal was found by Cheapflights users on 3/26. 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 4/189:16 am
ORD
- MCO
1 stop5h 13m
Spirit Airlines
Wed 4/226:22 am
MCO
- ORD
1 stop5h 01m
Spirit Airlines
Deal found 3/26![Spirit Airlines logo]()
$130
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 4/1911:28 am
ORD
- MCO
1 stop11h 01m
Spirit Airlines
Sat 4/2511:18 am
MCO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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.
Tue 4/2110:31 am
ORD
- MCO
Nonstop2h 40m
Spirit Airlines
Wed 4/2210:49 pm
MCO
- ORD
1 stop11h 47m
Spirit Airlines
Deal found 3/24![Spirit Airlines logo]()
$127
This Priceline deal was found by Cheapflights users on 3/24. 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 4/232:05 pm
ORD
- MCO
Nonstop3h 05m
Multiple Airlines
Mon 4/279:07 pm
MCO
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$135
This Expedia deal was found by Cheapflights users on 3/25. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:37 pm
ORD
- MCO
1 stop8h 26m
Frontier
Thu 4/307:15 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Deal found 3/25![Frontier logo]()
$124
This WAYA deal was found by Cheapflights users on 3/25. 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.
Sat 4/255:50 am
ORD
- MCO
1 stop6h 47m
Multiple Airlines
Sat 5/29:07 pm
MCO
- ORD
Nonstop3h 00m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$132
One-way flights from O'Hare Intl to KissimmeeSearch for one-way flight options from O'Hare Intl to Kissimmee. Find affordable one-way fares based on user searches. Data last updated March 28, 2026.
Search for one-way flight options from O'Hare Intl to Kissimmee. Find affordable one-way fares based on user searches. Data last updated March 28, 2026.
This Super.com deal was found by Cheapflights users on 3/24. 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.
Sun 4/124:21 pm
ORD
- MCO
Nonstop3h 01m
Frontier
Deal found 3/24![Frontier logo]()
$58
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 4/2911:28 am
ORD
- MCO
1 stop7h 35m
Spirit Airlines
Deal found 3/27![Spirit Airlines logo]()
$59
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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 5/24:50 pm
ORD
- MCO
Nonstop2h 43m
Spirit Airlines
Deal found 3/25![Spirit Airlines logo]()
$60
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 4/146:08 pm
ORD
- MCO
1 stop15h 16m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$61
This Super.com deal was found by Cheapflights users on 3/23. 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.
Mon 4/206:00 am
ORD
- MCO
Nonstop2h 57m
Frontier
Deal found 3/23![Frontier logo]()
$62
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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 5/105:30 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 3/24![Frontier logo]()
$63
This Super.com deal was found by Cheapflights users on 3/24. 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 4/44:21 pm
ORD
- MCO
Nonstop3h 06m
Frontier
Deal found 3/24![Frontier logo]()
$64
This Priceline deal was found by Cheapflights users on 3/24. 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.
Sat 4/49:06 am
ORD
- MCO
Nonstop2h 46m
Spirit Airlines
Deal found 3/24![Spirit Airlines logo]()
$65
This WAYA deal was found by Cheapflights users on 3/25. 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.
Wed 4/226:08 pm
ORD
- MCO
1 stop5h 11m
Frontier
Deal found 3/25![Frontier logo]()
$66
This Cheapflightsfares deal was found by Cheapflights users on 3/24. 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 5/1511:51 am
ORD
- MCO
1 stop4h 45m
Spirit Airlines
Deal found 3/24![Spirit Airlines logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Thu 4/165:50 am
ORD
- MCO
1 stop17h 29m
Frontier
Deal found 3/24![Frontier logo]()
$68
Find flight deals from O'Hare Intl to Kissimmee
Keep the following information in mind while searching for O'Hare Intl to Kissimmee flight deals. Data was last updated March 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $124 (Expedia) |
One-way from | $58 (Super.com) |
Popular in | March |
Cheapest in | January |
Average price | $359 |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 March 28, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Kissimmee that are best for you.
Fly from
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Route
Depart
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Cheapest round-trip
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 5/12
7:23 am-11:20 am
Nonstop2h 57m
Orlando
Thu 5/14
7:15 am-9:28 am
Nonstop3h 13m
$197
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 6/2
5:56 pm-9:55 pm
Nonstop2h 59m
Orlando
Sat 6/6
2:25 pm-4:43 pm
Nonstop3h 18m
$211
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sat 4/25
5:15 am-10:43 am
1 stop4h 28m
Orlando
Sat 4/25
4:20 pm-8:16 pm
1 stop4h 56m
$217
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sat 5/9
1:55 pm-10:20 pm
1 stop7h 25m
Orlando
Tue 5/12
9:10 pm-12:50 pm
2 stops16h 40m
$228
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Mon 5/18
10:30 am-7:00 pm
1 stop7h 30m
Orlando
Tue 5/26
9:10 pm-12:50 pm
2 stops16h 40m
$228
Quickest round-trip
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sun 5/17
6:00 am-9:40 am
Nonstop2h 40m
Orlando
Wed 5/20
4:20 pm-6:25 pm
Nonstop3h 05m
$228
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Mon 5/11
2:40 pm-8:15 pm
1 stop4h 35m
Orlando
Thu 5/14
9:55 pm-12:50 pm
2 stops15h 55m
$228
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 5/12
2:40 pm-8:30 pm
1 stop4h 50m
Orlando
Tue 5/19
9:10 pm-12:50 pm
2 stops16h 40m
$230
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sat 5/2
1:55 pm-7:45 pm
1 stop4h 50m
Orlando
Tue 5/5
9:10 pm-12:50 pm
2 stops16h 40m
$230
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 4/29
4:15 pm-8:09 pm
Nonstop2h 54m
Orlando
Sat 5/2
9:02 am-11:15 am
Nonstop3h 13m
$232
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Kissimmee
Have a flexible travel schedule? Discover the best time to fly to Kissimmee from O'Hare Intl with our price prediction graph.
ORD-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 Chicago O'Hare Intl Airport to Kissimmee
ORD-K1S
ORD-MCO
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Kissimmee?
Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Kissimmee. Price data was last updated on March 13, 2026.
Booking 29 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago O'Hare Intl Airport to Kissimmee. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Kissimmee?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kissimmee (average of $59). Flying from Chicago O'Hare Intl Airport to Kissimmee in June is currently the most expensive (average of $108). 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 ORD to K1S?
Find hourly flight availability from O'Hare Intl 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 March 28, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Kissimmee in the evening. If you’re flexible enough to do this you can expect to save up to 20% on your trip compared to booking a flight at noon.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Kissimmee?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Kissimmee. Price data was last updated on March 28, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Kissimmee flight should consider departing on Sunday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago O'Hare Intl Airport to Kissimmee
Explore weekly flight availability from O'Hare Intl 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 March 28, 2026.
The most flights from ORD to K1S are scheduled on a Friday (68 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (14 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport 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 March 28, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport 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.
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Food
7.0
Boarding
8.1
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl 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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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for O'Hare Intl to Kissimmee
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Complete your trip
Complete your trip to Kissimmee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Kissimmee by cabin class
Find flights from O'Hare Intl to Kissimmee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Kissimmee flights
Browse other O'Hare Intl and Kissimmee flight options. Last updated on March 28, 2026.
Other flights from O'Hare Intl
Browse through other flights departing from O'Hare Intl. Flights are based on user searches made on Cheapflights and were last updated on March 28, 2026.
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O'Hare Intl to Kissimmee flights
Consider these flights traveling from O'Hare Intl to Kissimmee.
Top 7 airlines flying from O'Hare Intl to Kissimmee
Discover the top 7 airlines that operate flights from O'Hare Intl 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 March 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$76 | Average$175 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$119 | Average$312 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$153 | Average$297 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$157 | Average$326 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$159 | Average$387 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$169 | Average$416 | FlexibilityNo cancel fee | On-timeN/A |