$94+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
Sep 24 — Oct 11
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
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 Chicago O'Hare Intl to Kissimmee are usually found in January or February, booked 22 days in advance, depart on a Tuesday or Wednesday and return on a Friday
Cheap flight deals from O'Hare Intl to Kissimmee
Cheapest
Best
Last-minute
One-way
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 August 25, 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 August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/52:46 pm -
1 stop8h 13m
Mon 10/125:20 am -
Nonstop3h 11m
Deal found 8/21![Frontier logo]()
$183
This CheapOair deal was found by Cheapflights users on 8/21. 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 9/123:50 pm -
Nonstop2h 56m
Mon 9/218:10 am -
Nonstop3h 10m
Deal found 8/21![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 10/67:25 am -
1 stop11h 23m
Tue 10/135:20 am -
Nonstop3h 11m
Deal found 8/22![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/177:40 am -
1 stop13h 31m
Tue 10/205:20 am -
Nonstop3h 11m
Deal found 8/21![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:25 am -
1 stop7h 34m
Tue 9/158:51 pm -
Nonstop3h 08m
Deal found 8/23![Frontier logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/97:28 pm -
1 stop20h 41m
Thu 10/296:30 am -
Nonstop3h 16m
Deal found 8/20![Frontier logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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 8/265:59 pm -
Nonstop3h 12m
Tue 9/19:00 pm -
Nonstop3h 08m
Deal found 8/21![Frontier logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/76:20 am -
1 stop14h 39m
Mon 10/125:20 am -
Nonstop3h 11m
Deal found 8/21![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/76:20 am -
1 stop14h 39m
Sat 10/105:20 am -
Nonstop3h 11m
Deal found 8/21![Frontier logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/246:20 am -
1 stop10h 20m
Mon 9/288:51 pm -
Nonstop3h 08m
Deal found 8/21![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Wed 9/93:50 pm -
Nonstop2h 56m
Thu 9/178:51 pm -
Nonstop3h 08m
Deal found 8/24![Frontier logo]()
$193
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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 10/155:54 pm -
Nonstop2h 57m
Mon 10/195:20 am -
Nonstop3h 11m
Deal found 8/21![Frontier logo]()
$194
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 August 25, 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 August 25, 2026.
This Delta deal was found by Cheapflights users on 8/22. 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 1/137:10 am -
1 stop5h 27m
Tue 1/192:45 pm -
1 stop7h 25m
Deal found 8/22![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Thu 12/173:49 pm -
Nonstop2h 55m
Sun 12/277:00 am -
Nonstop3h 18m
Deal found 8/20![United Airlines logo]()
$293
This Sun Country Air deal was found by Cheapflights users on 8/20. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/195:45 pm -
1 stop26h 53m
Mon 12/217:00 am -
1 stop28h 23m
Deal found 8/20![Sun Country Air logo]()
$355
This JetBlue deal was found by Cheapflights users on 8/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:00 pm -
1 stop5h 35m
Fri 9/186:00 pm -
1 stop6h 08m
Deal found 8/23![JetBlue logo]()
$423
This Delta deal was found by Cheapflights users on 8/20. 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 1/303:00 pm -
1 stop5h 38m
Sat 2/67:45 am -
1 stop6h 35m
Deal found 8/20![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 8/21. 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 11/142:44 pm -
1 stop5h 23m
Tue 11/175:40 am -
1 stop7h 40m
Deal found 8/21![Delta logo]()
$257
This Delta deal was found by Cheapflights users on 8/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/263:40 pm -
1 stop4h 21m
Thu 10/298:50 am -
1 stop6h 38m
Deal found 8/23![Delta logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Sat 2/67:45 pm -
Nonstop3h 00m
Sat 2/132:50 pm -
Nonstop3h 01m
Deal found 8/20![United Airlines logo]()
$317
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Thu 9/242:30 pm -
Nonstop2h 58m
Mon 9/289:10 am -
Nonstop3h 10m
Deal found 8/22![United Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 8/23. 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.
Mon 2/154:20 pm -
1 stop7h 24m
Sat 2/207:55 pm -
Nonstop3h 09m
Deal found 8/23![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 8/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:15 pm -
1 stop5h 25m
Thu 11/261:45 pm -
1 stop6h 20m
Deal found 8/23![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 8/21. 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 12/227:45 pm -
Nonstop2h 59m
Sun 12/277:00 am -
Nonstop3h 18m
Deal found 8/21![United Airlines logo]()
$373
Last-minute flights from O'Hare Intl to KissimmeeDiscover last-minute flight deals from O'Hare Intl to Kissimmee. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Kissimmee. Data last updated August 25, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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 8/265:59 pm -
Nonstop3h 12m
Tue 9/19:00 pm -
Nonstop3h 08m
Deal found 8/21![Frontier logo]()
$189
This Expedia deal was found by Cheapflights users on 8/22. 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.
Sat 9/57:44 pm -
Nonstop2h 45m
Mon 9/148:10 am -
Nonstop3h 10m
Deal found 8/22![Frontier logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/97:28 pm -
1 stop20h 41m
Thu 10/296:30 am -
Nonstop3h 16m
Deal found 8/20![Frontier logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Wed 9/93:50 pm -
Nonstop2h 56m
Thu 9/178:51 pm -
Nonstop3h 08m
Deal found 8/24![Frontier logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:28 pm -
1 stop11h 41m
Sat 9/128:51 pm -
Nonstop3h 08m
Deal found 8/23![Frontier logo]()
$191
This CheapOair deal was found by Cheapflights users on 8/21. 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 9/123:50 pm -
Nonstop2h 56m
Mon 9/218:10 am -
Nonstop3h 10m
Deal found 8/21![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:25 am -
1 stop7h 34m
Mon 9/288:51 pm -
Nonstop3h 08m
Deal found 8/23![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Sat 9/123:50 pm -
Nonstop2h 56m
Mon 9/146:12 am -
1 stop6h 28m
Deal found 8/24![Frontier logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:25 am -
1 stop7h 34m
Tue 9/158:51 pm -
Nonstop3h 08m
Deal found 8/23![Frontier logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 8/21. 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 9/123:50 pm -
Nonstop2h 56m
Sat 9/198:51 pm -
Nonstop3h 08m
Deal found 8/21![Frontier logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:20 am -
1 stop14h 39m
Thu 10/18:51 pm -
Nonstop3h 08m
Deal found 8/23![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 9/246:20 am -
1 stop10h 20m
Mon 9/288:51 pm -
Nonstop3h 08m
Deal found 8/21![Frontier logo]()
$192
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 August 25, 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 August 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/1912:56 pm -
1 stop7h 47m
Deal found 8/20![Frontier logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Fri 9/253:50 pm -
Nonstop2h 56m
Deal found 8/24![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Fri 10/238:11 pm -
Nonstop2h 57m
Deal found 8/25![Frontier logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:56 pm -
1 stop7h 47m
Deal found 8/23![Frontier logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 8/25. 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.
Tue 9/17:44 pm -
Nonstop2h 45m
Deal found 8/25![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 8/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:50 pm -
Nonstop2h 56m
Deal found 8/25![Frontier logo]()
$102
This Priceline deal was found by Cheapflights users on 8/21. 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.
Tue 10/139:00 am -
Nonstop2h 49m
Deal found 8/21![Frontier logo]()
$103
This Trip.com deal was found by Cheapflights users on 8/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:28 pm -
1 stop20h 41m
Deal found 8/22![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/102:46 pm -
1 stop8h 13m
Deal found 8/20![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 8/21. 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 9/57:44 pm -
Nonstop2h 45m
Deal found 8/21![Frontier logo]()
$107
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 August 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $183 (Kiwi.com) |
One-way from | $94 (Kiwi.com) |
Popular in | June |
Cheapest in | January |
Average price | $325 |
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 7,457,451 searches. Data last updated August 25, 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
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Wed 1/13
7:10 am-1:37 pm
1 stop5h 27m
Orlando
Tue 1/19
2:45 pm-9:10 pm
1 stop7h 25m
$257
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Sat 1/30
3:00 pm-9:38 pm
1 stop5h 38m
Orlando
Sat 2/6
7:45 am-1:20 pm
1 stop6h 35m
$257
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Sat 11/14
2:44 pm-9:07 pm
1 stop5h 23m
Orlando
Tue 11/17
5:40 am-12:20 pm
1 stop7h 40m
$257
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Mon 10/26
3:40 pm-9:01 pm
1 stop4h 21m
Orlando
Thu 10/29
8:50 am-2:28 pm
1 stop6h 38m
$257
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Thu 12/17
3:49 pm-7:44 pm
Nonstop2h 55m
Orlando
Sun 12/27
7:00 am-9:18 am
Nonstop3h 18m
$293
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Sat 11/21
6:15 pm-12:40 am
1 stop5h 25m
Orlando
Thu 11/26
1:45 pm-7:05 pm
1 stop6h 20m
$313
Quickest round-trip
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Sat 2/6
7:45 pm-11:45 pm
Nonstop3h 00m
Orlando
Sat 2/13
2:50 pm-4:51 pm
Nonstop3h 01m
$317
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Thu 9/24
2:30 pm-6:28 pm
Nonstop2h 58m
Orlando
Mon 9/28
9:10 am-11:20 am
Nonstop3h 10m
$318
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Mon 2/15
4:20 pm-12:44 am
1 stop7h 24m
Orlando
Sat 2/20
7:55 pm-10:04 pm
Nonstop3h 09m
$327
ChicagoOrlando
ORD Chicago O'Hare Intl - MCO Orlando
ORDMCO
Chicago O'Hare Intl
Sat 12/19
5:45 pm-9:38 pm
1 stop26h 53m
Orlando
Mon 12/21
7:00 am-10:23 am
1 stop28h 23m
$355
Showing 1-10 of 23 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
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 August 25, 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 16% on your trip compared to booking a flight in the morning.
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 August 25, 2026.
The most flights from ORD to K1S are scheduled on a Monday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Kissimmee?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to Kissimmee flights typically cost between $218 and $368 in October.The cheapest round-trip price found within the last 5 days was $183 on Frontier (Oct 5-Oct 12).
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 August 22, 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. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 25, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited 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.
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
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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O'Hare Intl and Kissimmee flights
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Top 6 airlines flying from O'Hare Intl to Kissimmee
Discover the top 6 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 7,457,451 searches. Data last updated August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$59 | Average$221 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$109 | Average$308 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$146 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$164 | Average$349 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$165 | Average$316 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$173 | Average$412 | FlexibilityNo cancel fee | On-time71% |