$86+ 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 8/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — MCO
Jul 8 — Jul 151
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 September, booked 22 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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Best
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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 June 8, 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 June 8, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/3. 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 8/285:30 pm
ORD
- MCO
Nonstop3h 07m
Frontier
Mon 8/318:54 pm
MCO
- ORD
Nonstop3h 20m
Frontier
Deal found 6/3![Frontier logo]()
$168
This Frontier deal was found by Cheapflights users on 6/3. 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 8/155:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Wed 8/198:45 am
MCO
- ORD
1 stop8h 25m
Frontier
Deal found 6/3![Frontier logo]()
$169
This Frontier deal was found by Cheapflights users on 6/6. 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 8/175:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Tue 8/258:54 pm
MCO
- ORD
Nonstop3h 20m
Frontier
Deal found 6/6![Frontier logo]()
$170
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 8/177:05 am
ORD
- MCO
1 stop6h 18m
Frontier
Thu 8/208:54 pm
MCO
- ORD
Nonstop3h 20m
Frontier
Deal found 6/4![Frontier logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 6/4. 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 7/19:48 pm
ORD
- MCO
1 stop30h 50m
Frontier
Wed 7/158:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/4![Frontier logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 6/4. 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 9/85:30 pm
ORD
- MCO
Nonstop3h 07m
Frontier
Tue 9/159:47 pm
MCO
- ORD
Nonstop3h 08m
Frontier
Deal found 6/4![Frontier logo]()
$174
This Frontier deal was found by Cheapflights users on 6/4. 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 11/36:00 am
ORD
- MCO
1 stop10h 19m
Frontier
Wed 11/119:42 pm
MCO
- ORD
Nonstop3h 08m
Frontier
Deal found 6/4![Frontier logo]()
$175
This Frontier deal was found by Cheapflights users on 6/7. 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 9/149:26 am
ORD
- MCO
Nonstop2h 49m
Frontier
Tue 9/159:47 pm
MCO
- ORD
Nonstop3h 08m
Frontier
Deal found 6/7![Frontier logo]()
$176
This Super.com deal was found by Cheapflights users on 6/4. 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 8/165:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Thu 8/208:54 pm
MCO
- ORD
Nonstop3h 20m
Frontier
Deal found 6/4![Frontier logo]()
$177
This Frontier deal was found by Cheapflights users on 6/7. 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 8/35:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Sun 8/238:54 pm
MCO
- ORD
Nonstop3h 20m
Frontier
Deal found 6/7![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 6/7. 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 8/165:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Sun 8/238:54 pm
MCO
- ORD
Nonstop3h 20m
Frontier
Deal found 6/7![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 6/7. 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 9/224:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Mon 9/286:05 am
MCO
- ORD
Nonstop3h 16m
Frontier
Deal found 6/7![Frontier logo]()
$180
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 June 8, 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 June 8, 2026.
This Delta deal was found by Cheapflights users on 6/6. 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.
Tue 8/115:28 am
ORD
- MCO
1 stop4h 29m
Delta
Wed 8/125:30 am
MCO
- ORD
1 stop4h 53m
Delta
Deal found 6/6![Delta logo]()
$229
This United Airlines deal was found by Cheapflights users on 6/3. 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 8/182:10 pm
ORD
- MCO
Nonstop2h 52m
United Airlines
Fri 8/217:40 am
MCO
- ORD
Nonstop3h 05m
United Airlines
Deal found 6/3![United Airlines logo]()
$274
This Cheapflightsfares deal was found by Cheapflights users on 6/3. 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 6/194:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Mon 6/225:40 am
MCO
- ORD
1 stop11h 13m
Frontier
Deal found 6/3![Frontier logo]()
$340
This Delta deal was found by Cheapflights users on 6/3. 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 7/89:45 am
ORD
- MCO
1 stop5h 55m
Delta
Wed 7/154:05 pm
MCO
- ORD
1 stop5h 26m
Delta
Deal found 6/3![Delta logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 7/225:46 pm
ORD
- MCO
2 stops25h 04m
Frontier
Fri 7/313:18 pm
MCO
- ORD
1 stop5h 35m
Frontier
Deal found 6/3![Frontier logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/8. 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 7/116:00 am
ORD
- MCO
Nonstop2h 40m
United Airlines
Sat 7/117:40 pm
MCO
- ORD
Nonstop3h 20m
United Airlines
Deal found 6/8![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 6/7. 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.
Fri 6/265:30 am
ORD
- MCO
1 stop4h 27m
Delta
Sat 7/46:00 am
MCO
- ORD
1 stop8h 04m
Delta
Deal found 6/7![Delta logo]()
$401
This United Airlines deal was found by Cheapflights users on 6/5. 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 7/28:40 am
ORD
- MCO
1 stop5h 18m
United Airlines
Sun 7/57:09 am
MCO
- ORD
Nonstop3h 09m
United Airlines
Deal found 6/5![United Airlines logo]()
$407
This United Airlines deal was found by Cheapflights users on 6/8. 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 7/97:20 am
ORD
- MCO
Nonstop2h 55m
United Airlines
Thu 7/97:40 pm
MCO
- ORD
Nonstop3h 20m
United Airlines
Deal found 6/8![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 6/7. 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 6/132:35 pm
ORD
- MCO
1 stop5h 41m
Delta
Wed 6/176:45 pm
MCO
- ORD
1 stop6h 14m
Delta
Deal found 6/7![Delta logo]()
$429
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Fri 8/219:02 am
ORD
- MCO
Nonstop2h 57m
United Airlines
Fri 8/216:00 pm
MCO
- ORD
Nonstop3h 13m
United Airlines
Deal found 6/7![United Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 6/122:00 pm
ORD
- MCO
Nonstop2h 57m
United Airlines
Wed 6/179:40 am
MCO
- ORD
Nonstop3h 08m
United Airlines
Deal found 6/8![United Airlines logo]()
$432
Last-minute flights from O'Hare Intl to KissimmeeDiscover last-minute flight deals from O'Hare Intl to Kissimmee. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Kissimmee. Data last updated June 8, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/4. 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 7/19:48 pm
ORD
- MCO
1 stop30h 50m
Frontier
Wed 7/158:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/4![Frontier logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 6/7. 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 7/75:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Mon 7/137:00 am
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/7![Frontier logo]()
$183
This Frontier deal was found by Cheapflights users on 6/7. 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 7/75:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Sun 7/128:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/7![Frontier logo]()
$185
This Frontier deal was found by Cheapflights users on 6/3. 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 7/81:50 pm
ORD
- MCO
1 stop7h 25m
Frontier
Wed 7/158:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/3![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 7/225:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Fri 7/318:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/5![Frontier logo]()
$170
This Expedia deal was found by Cheapflights users on 6/4. 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.
Wed 7/225:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Sun 8/98:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/4![Frontier logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 6/3. 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 7/257:05 am
ORD
- MCO
1 stop6h 18m
Frontier
Fri 7/318:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/3![Frontier logo]()
$181
This Expedia deal was found by Cheapflights users on 6/6. 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.
Sun 7/265:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Sat 8/18:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/6![Frontier logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 6/4. 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 7/275:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Sat 8/18:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/4![Frontier logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 6/4. 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 7/275:46 pm
ORD
- MCO
1 stop22h 20m
Frontier
Fri 7/318:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/4![Frontier logo]()
$186
This CheapOair deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/289:28 am
ORD
- MCO
1 stop13h 37m
Frontier
Fri 7/318:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 6/4![Frontier logo]()
$169
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 June 8, 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 June 8, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/8. 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 8/105:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/8![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 8/151:50 pm
ORD
- MCO
1 stop15h 50m
Frontier
Deal found 6/4![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 8/191:50 pm
ORD
- MCO
1 stop7h 19m
Frontier
Deal found 6/4![Frontier logo]()
$95
This Super.com deal was found by Cheapflights users on 6/4. 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.
Fri 7/245:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/4![Frontier logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 6/4. 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 7/175:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/4![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 6/4. 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 7/115:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Deal found 6/4![Frontier logo]()
$102
This Super.com deal was found by Cheapflights users on 6/8. 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.
Tue 6/304:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 6/8![Frontier logo]()
$103
This American Airlines deal was found by Cheapflights users on 6/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:45 pm
ORD
- MCO
Nonstop2h 51m
American Airlines
Deal found 6/4![American Airlines logo]()
$105
This United Airlines deal was found by Cheapflights users on 6/8. 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 8/2612:56 pm
ORD
- MCO
1 stop6h 02m
United Airlines
Deal found 6/8![United Airlines logo]()
$106
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 June 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $169 (Frontier) |
One-way from | $86 (Cheapflightsfares) |
Popular in | March |
Cheapest in | January |
Average price | $346 |
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 June 8, 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 - MCO
ORDMCO
Chicago O'Hare Intl
Tue 8/11
5:28 am-10:57 am
1 stop4h 29m
Orlando
Wed 8/12
5:30 am-9:23 am
1 stop4h 53m
$229
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 7/8
9:45 am-4:40 pm
1 stop5h 55m
Orlando
Wed 7/15
4:05 pm-8:31 pm
1 stop5h 26m
$229
Quickest round-trip
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 8/18
2:10 pm-6:02 pm
Nonstop2h 52m
Orlando
Fri 8/21
7:40 am-9:45 am
Nonstop3h 05m
$274
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Fri 6/19
4:59 pm-9:01 pm
Nonstop3h 02m
Orlando
Mon 6/22
5:40 am-3:53 pm
1 stop11h 13m
$340
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 7/22
5:46 pm-7:50 pm
2 stops25h 04m
Orlando
Fri 7/31
3:18 pm-7:53 pm
1 stop5h 35m
$344
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sat 7/11
6:00 am-9:40 am
Nonstop2h 40m
Orlando
Sat 7/11
7:40 pm-10:00 pm
Nonstop3h 20m
$377
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Fri 6/26
5:30 am-10:57 am
1 stop4h 27m
Orlando
Sat 7/4
6:00 am-1:04 pm
1 stop8h 04m
$401
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Thu 7/2
8:40 am-2:58 pm
1 stop5h 18m
Orlando
Sun 7/5
7:09 am-9:18 am
Nonstop3h 09m
$407
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Thu 7/9
7:20 am-11:15 am
Nonstop2h 55m
Orlando
Thu 7/9
7:40 pm-10:00 pm
Nonstop3h 20m
$419
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Fri 8/21
9:02 am-12:59 pm
Nonstop2h 57m
Orlando
Fri 8/21
6:00 pm-8:13 pm
Nonstop3h 13m
$419
Showing 1-10 of 24 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 June 8, 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 19% on your trip compared to booking a flight at noon.
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 June 8, 2026.
The most flights from ORD to K1S are scheduled on a Monday (69 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (48 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to Kissimmee?
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 June 8, 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 June 8, 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.
Entertainment
7.5
Crew
8.6
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Entertainment
7.5
Crew
8.6
Overall
7.9
Food
7.0
Comfort
8.0
Boarding
8.1
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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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 June 8, 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 June 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
O'Hare Intl to Kissimmee flights
Consider these flights traveling from O'Hare Intl to Kissimmee.
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 2,558,603 searches. Data last updated June 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$210 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$109 | Average$257 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$147 | Average$296 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$147 | Average$313 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$340 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$162 | Average$397 | FlexibilityNo cancel fee | On-time71% |