$74+ Cheap flights from Chicago (CHI) 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
Jun 26 — Jul 31
Round-trip
1 adult, Economy
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Find cheap flights from Chicago 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 to Kissimmee are usually found in September or January, booked 18 days in advance, depart on a Tuesday or Thursday and return on a Friday
Cheap flight deals from Chicago to Kissimmee
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Last-minute
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Cheapest flights from Chicago to KissimmeeExplore the most affordable flight options available from Chicago to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 27, 2026.
Explore the most affordable flight options available from Chicago to Kissimmee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/25. 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.
Mon 9/144:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Mon 9/216:05 am
MCO
- ORD
Nonstop3h 16m
Frontier
Deal found 5/25![Frontier logo]()
$158
This deal was found by Cheapflights users on 5/23. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Sat 9/267:10 am
MCO
- ORD
1 stop5h 52m
Frontier
Deal found 5/23![Frontier logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 5/26. 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.
Thu 9/174:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Mon 9/216:05 am
MCO
- ORD
Nonstop3h 16m
Frontier
Deal found 5/26![Frontier logo]()
$161
This Kiwi.com deal was found by Cheapflights users on 5/25. 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.
Thu 9/35:30 pm
ORD
- MCO
Nonstop3h 07m
Frontier
Mon 9/78:54 pm
MCO
- ORD
Nonstop3h 20m
Frontier
Deal found 5/25![Frontier logo]()
$162
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Thu 9/246:05 am
MCO
- ORD
Nonstop3h 16m
Frontier
Deal found 5/24![Frontier logo]()
$163
This Cheapflightsfares deal was found by Cheapflights users on 5/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Tue 6/234:36 pm
MCO
- ORD
1 stop9h 12m
Frontier
Deal found 5/23![Frontier logo]()
$164
This Cheapflightsfares deal was found by Cheapflights users on 5/22. 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 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
Wed 7/158:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 5/22![Frontier logo]()
$165
This Jettzy deal was found by Cheapflights users on 5/23. 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 Jettzy 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
Tue 7/144:36 pm
MCO
- ORD
1 stop9h 13m
Frontier
Deal found 5/23![Frontier logo]()
$166
This Frontier deal was found by Cheapflights users on 5/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Wed 6/179:01 pm
MCO
- ORD
Nonstop3h 18m
Frontier
Deal found 5/26![Frontier logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/23. 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.
Tue 7/75:13 pm
ORD
- MCO
Nonstop3h 12m
Frontier
Wed 7/84:36 pm
MCO
- ORD
1 stop9h 13m
Frontier
Deal found 5/23![Frontier logo]()
$168
This Southwest deal was found by Cheapflights users on 5/26. 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.
Wed 6/175:30 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Tue 6/237:10 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/26![Southwest logo]()
$171
This United Airlines deal was found by Cheapflights users on 5/22. 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.
Tue 7/75:56 pm
ORD
- MCO
Nonstop2h 59m
United Airlines
Tue 7/149:40 am
MCO
- ORD
Nonstop3h 08m
United Airlines
Deal found 5/22![United Airlines logo]()
$171
Best flights from Chicago to KissimmeeDiscover carefully curated flight deals from Chicago to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 27, 2026.
Discover carefully curated flight deals from Chicago to Kissimmee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 27, 2026.
This Southwest deal was found by Cheapflights users on 5/26. 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.
Wed 7/155:30 pm
MDW
- MCO
Nonstop2h 50m
Southwest
Tue 7/216:10 pm
MCO
- MDW
Nonstop3h 00m
Southwest
Deal found 5/26![Southwest logo]()
$171
This Delta deal was found by Cheapflights users on 5/26. 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.
Tue 6/305:30 am
ORD
- MCO
1 stop5h 30m
Delta
Tue 7/71:05 pm
MCO
- ORD
1 stop5h 07m
Delta
Deal found 5/26![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:15 am
MDW
- MCO
Nonstop2h 30m
Southwest
Wed 9/237:15 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 5/22![Southwest logo]()
$187
This Delta deal was found by Cheapflights users on 5/22. 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.
Tue 6/165:11 pm
MDW
- MCO
1 stop4h 40m
Delta
Tue 6/235:30 am
MCO
- MDW
1 stop5h 39m
Delta
Deal found 5/22![Delta logo]()
$197
This Southwest deal was found by Cheapflights users on 5/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:50 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Sat 10/106:20 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/22![Southwest logo]()
$203
This Delta deal was found by Cheapflights users on 5/23. 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.
Tue 7/76:22 pm
ORD
- MCO
1 stop4h 36m
Delta
Tue 7/144:05 pm
MCO
- ORD
1 stop5h 26m
Delta
Deal found 5/23![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 5/21. 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.
Wed 10/281:15 pm
ORD
- MCO
1 stop7h 23m
Delta
Tue 11/37:50 pm
MCO
- ORD
1 stop5h 00m
Delta
Deal found 5/21![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 5/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:30 am
ORD
- MCO
1 stop4h 27m
Delta
Wed 7/86:05 am
MCO
- ORD
1 stop7h 58m
Delta
Deal found 5/24![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 5/26. 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.
Thu 8/277:50 pm
MDW
- MCO
Nonstop2h 30m
Southwest
Mon 8/3110:00 am
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 5/26![Southwest logo]()
$243
This Delta deal was found by Cheapflights users on 5/22. 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 9/161:15 pm
ORD
- MCO
1 stop7h 33m
Delta
Wed 9/2310:00 am
MCO
- ORD
1 stop5h 19m
Delta
Deal found 5/22![Delta logo]()
$209
This Delta deal was found by Cheapflights users on 5/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:18 pm
MDW
- MCO
1 stop5h 30m
Delta
Tue 8/45:30 am
MCO
- MDW
1 stop5h 29m
Delta
Deal found 5/24![Delta logo]()
$209
This Southwest deal was found by Cheapflights users on 5/26. 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.
Thu 10/227:45 am
MDW
- MCO
1 stop4h 00m
Southwest
Thu 10/297:20 am
MCO
- MDW
2 stops7h 25m
Southwest
Deal found 5/26![Southwest logo]()
$267
This Delta deal was found by Cheapflights users on 5/26. 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.
Mon 8/106:05 am
MDW
- MCO
1 stop4h 55m
Delta
Tue 8/186:15 am
MCO
- MDW
1 stop6h 36m
Delta
Deal found 5/26![Delta logo]()
$210
This Southwest deal was found by Cheapflights users on 5/24. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/245:30 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Sat 6/277:50 am
MCO
- MDW
1 stop5h 15m
Southwest
Deal found 5/24![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 5/26. 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.
Fri 7/31:40 pm
ORD
- MCO
1 stop5h 08m
Delta
Tue 7/73:40 pm
MCO
- ORD
1 stop5h 53m
Delta
Deal found 5/26![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 5/22. 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.
Mon 9/145:30 am
ORD
- MCO
1 stop4h 25m
Delta
Mon 9/213:10 pm
MCO
- ORD
1 stop6h 20m
Delta
Deal found 5/22![Delta logo]()
$223
This Southwest deal was found by Cheapflights users on 5/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:00 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Sun 10/257:55 am
MCO
- MDW
1 stop5h 15m
Southwest
Deal found 5/22![Southwest logo]()
$310
This Delta deal was found by Cheapflights users on 5/22. 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.
Sun 9/61:35 pm
ORD
- MCO
1 stop6h 30m
Delta
Wed 9/97:00 am
MCO
- ORD
1 stop6h 08m
Delta
Deal found 5/22![Delta logo]()
$223
This Delta deal was found by Cheapflights users on 5/23. 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.
Wed 9/911:10 am
ORD
- MCO
1 stop6h 28m
Delta
Mon 9/216:15 am
MCO
- ORD
1 stop4h 54m
Delta
Deal found 5/23![Delta logo]()
$224
This Delta deal was found by Cheapflights users on 5/21. 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.
Mon 9/281:15 pm
ORD
- MCO
1 stop7h 33m
Delta
Thu 10/16:15 am
MCO
- ORD
1 stop4h 49m
Delta
Deal found 5/21![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 5/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:30 pm
MDW
- MCO
1 stop7h 30m
Delta
Thu 9/174:40 pm
MCO
- MDW
1 stop6h 45m
Delta
Deal found 5/24![Delta logo]()
$239
This Delta deal was found by Cheapflights users on 5/22. 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.
Thu 7/21:40 pm
ORD
- MCO
1 stop5h 08m
Delta
Sat 7/46:00 am
MCO
- ORD
1 stop8h 04m
Delta
Deal found 5/22![Delta logo]()
$261
Last-minute flights from Chicago to KissimmeeDiscover last-minute flight deals from Chicago to Kissimmee. Data last updated May 27, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kissimmee. Data last updated May 27, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 5/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Tue 6/234:36 pm
MCO
- ORD
1 stop9h 12m
Frontier
Deal found 5/23![Frontier logo]()
$164
This Frontier deal was found by Cheapflights users on 5/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/164:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Wed 6/179:01 pm
MCO
- ORD
Nonstop3h 18m
Frontier
Deal found 5/26![Frontier logo]()
$167
This Southwest deal was found by Cheapflights users on 5/26. 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.
Wed 6/175:30 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Tue 6/237:10 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 5/26![Southwest logo]()
$171
This American Airlines deal was found by Cheapflights users on 5/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/175:04 pm
ORD
- MCO
Nonstop2h 53m
American Airlines
Tue 6/236:30 am
MCO
- ORD
Nonstop3h 09m
American Airlines
Deal found 5/26![American Airlines logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 5/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/174:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Tue 6/234:36 pm
MCO
- ORD
1 stop9h 12m
Frontier
Deal found 5/23![Frontier logo]()
$173
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/174:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Wed 6/249:30 am
MCO
- ORD
1 stop7h 23m
Frontier
Deal found 5/24![Frontier logo]()
$175
This United Airlines deal was found by Cheapflights users on 5/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:02 am
ORD
- MCO
Nonstop2h 43m
United Airlines
Wed 6/242:25 pm
MCO
- ORD
Nonstop3h 18m
United Airlines
Deal found 5/26![United Airlines logo]()
$180
This Trip.com deal was found by Cheapflights users on 5/22. 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.
Tue 6/234:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Tue 6/306:30 pm
MCO
- ORD
1 stop11h 37m
Frontier
Deal found 5/22![Frontier logo]()
$181
This Priceline deal was found by Cheapflights users on 5/26. 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 Priceline 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
Tue 7/76:16 pm
MCO
- ORD
1 stop12h 21m
Frontier
Deal found 5/26![Frontier logo]()
$166
This Super.com deal was found by Cheapflights users on 5/24. 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.
Tue 6/304:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Wed 7/88:59 pm
MCO
- ORD
Nonstop3h 11m
Frontier
Deal found 5/24![Frontier logo]()
$174
This Southwest deal was found by Cheapflights users on 5/25. 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.
Tue 6/308:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Tue 7/144:40 pm
MCO
- MDW
1 stop4h 10m
Southwest
Deal found 5/25![Southwest logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 5/26. 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.
Tue 6/304:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Sat 7/49:51 am
MCO
- ORD
1 stop10h 59m
Frontier
Deal found 5/26![Frontier logo]()
$178
One-way flights from Chicago to KissimmeeSearch for one-way flight options from Chicago to Kissimmee. Find affordable one-way fares based on user searches. Data last updated May 27, 2026.
Search for one-way flight options from Chicago to Kissimmee. Find affordable one-way fares based on user searches. Data last updated May 27, 2026.
This Frontier deal was found by Cheapflights users on 5/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/14:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 5/23![Frontier logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 10/224:49 pm
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 5/24![Frontier logo]()
$77
This Super.com deal was found by Cheapflights users on 5/24. 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.
Tue 6/234:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 5/24![Frontier logo]()
$81
This Southwest deal was found by Cheapflights users on 5/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/168:10 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Deal found 5/22![Southwest logo]()
$86
This United Airlines deal was found by Cheapflights users on 5/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:00 am
ORD
- MCO
Nonstop2h 40m
United Airlines
Deal found 5/26![United Airlines logo]()
$86
This American Airlines deal was found by Cheapflights users on 5/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:45 am
ORD
- MCO
Nonstop2h 38m
American Airlines
Deal found 5/22![American Airlines logo]()
$87
This Super.com deal was found by Cheapflights users on 5/25. 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.
Thu 9/179:26 am
ORD
- MCO
Nonstop2h 49m
Frontier
Deal found 5/25![Frontier logo]()
$88
This Southwest deal was found by Cheapflights users on 5/26. 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.
Wed 7/293:00 pm
MDW
- MCO
1 stop3h 55m
Southwest
Deal found 5/26![Southwest logo]()
$91
This United Airlines deal was found by Cheapflights users on 5/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:25 am
ORD
- MCO
1 stop6h 22m
United Airlines
Deal found 5/26![United Airlines logo]()
$91
This Super.com deal was found by Cheapflights users on 5/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/204:59 pm
ORD
- MCO
Nonstop3h 02m
Frontier
Deal found 5/26![Frontier logo]()
$93
This Southwest deal was found by Cheapflights users on 5/26. 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.
Tue 6/235:30 pm
MDW
- MCO
Nonstop2h 45m
Southwest
Deal found 5/26![Southwest logo]()
$95
This American Airlines deal was found by Cheapflights users on 5/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:45 pm
ORD
- MCO
Nonstop2h 51m
American Airlines
Deal found 5/24![American Airlines logo]()
$95
Find flight deals from Chicago to Kissimmee
Keep the following information in mind while searching for Chicago to Kissimmee flight deals. Data was last updated May 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $158 (Kiwi.com) |
One-way from | $74 (Frontier) |
Popular in | March |
Cheapest in | September |
Average price | $268 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 May 27, 2026.
Use the filters below to find and compare flights from Chicago to Kissimmee that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 7/15
5:30 pm-9:20 pm
Nonstop2h 50m
Orlando
Tue 7/21
6:10 pm-8:10 pm
Nonstop3h 00m
$171
Quickest round-trip
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 9/17
7:15 am-10:45 am
Nonstop2h 30m
Orlando
Wed 9/23
7:15 pm-9:00 pm
Nonstop2h 45m
$187
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 6/30
5:30 am-12:00 pm
1 stop5h 30m
Orlando
Tue 7/7
1:05 pm-5:12 pm
1 stop5h 07m
$197
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Tue 6/16
5:11 pm-10:51 pm
1 stop4h 40m
Orlando
Tue 6/23
5:30 am-10:09 am
1 stop5h 39m
$197
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Mon 10/5
8:50 pm-12:25 am
Nonstop2h 35m
Orlando
Sat 10/10
6:20 am-8:10 am
Nonstop2h 50m
$203
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 7/7
6:22 pm-11:58 pm
1 stop4h 36m
Orlando
Tue 7/14
4:05 pm-8:31 pm
1 stop5h 26m
$209
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 10/28
1:15 pm-9:38 pm
1 stop7h 23m
Orlando
Tue 11/3
7:50 pm-11:50 pm
1 stop5h 00m
$209
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Tue 6/30
5:30 am-10:57 am
1 stop4h 27m
Orlando
Wed 7/8
6:05 am-1:03 pm
1 stop7h 58m
$209
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Wed 9/16
1:15 pm-9:48 pm
1 stop7h 33m
Orlando
Wed 9/23
10:00 am-2:19 pm
1 stop5h 19m
$209
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 7/29
1:18 pm-7:48 pm
1 stop5h 30m
Orlando
Tue 8/4
5:30 am-9:59 am
1 stop5h 29m
$209
Showing 1-10 of 45 resultsSorted by cheapest first
Best time to book a flight from Chicago to Kissimmee
Have a flexible travel schedule? Discover the best time to fly to Kissimmee from Chicago with our price prediction graph.
MDW-MCO
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 to Kissimmee
CHI-K1S
MDW-MCO
ORD-MCO
What is the cheapest time of day to fly from CHI to K1S?
Find hourly flight availability from Chicago 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 May 27, 2026.
When flying from Chicago to Kissimmee, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 20% versus a flight at noon.
Weekly flight availability from Chicago to Kissimmee
Explore weekly flight availability from Chicago 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 May 27, 2026.
The most flights from CHI to K1S are scheduled on a Monday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).
How much does it cost to fly round-trip from Chicago to Kissimmee?
What is the cheapest day to fly from Chicago to Kissimmee?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Kissimmee. Price data was last updated on May 23, 2026.
Travelers seeking maximum savings on their Chicago 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.
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 May 27, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican Airlines from Chicago to Kissimmee. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Spirit Airlines
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Comfort
8.0
Boarding
8.1
Food
7.0
Crew
8.6
Entertainment
7.5
Overall
7.9
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago 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 Chicago to Kissimmee
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Complete your trip
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Find flights from Chicago to Kissimmee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Kissimmee flights
Browse other Chicago and Kissimmee flight options. Last updated on May 27, 2026.
Other flights from Chicago
Browse through other flights departing from Chicago. Flights are based on user searches made on Cheapflights and were last updated on May 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Kissimmee flights
Consider these flights traveling from Chicago to Kissimmee.
Top 8 airlines flying from Chicago to Kissimmee
Discover the top 8 airlines that operate flights from Chicago 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 May 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$196 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$77 | Average$180 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$109 | Average$258 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$114 | Average$221 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$147 | Average$288 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$148 | Average$331 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$368 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$339 | FlexibilityNo cancel fee | On-time69% |