$58+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
May 1 — May 81
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 85 days in advance, depart on a Tuesday or Saturday and return on a Friday
Cheap flight deals from Chicago to Kissimmee
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Best
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 April 1, 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 April 1, 2026.
This Super.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:14 am
MDW
- MCO
Nonstop2h 49m
Frontier
Fri 4/176:00 am
MCO
- MDW
Nonstop2h 59m
Frontier
Deal found 3/28![Frontier logo]()
$125
This Cheapflightsfares deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:21 pm
ORD
- MCO
Nonstop3h 01m
Frontier
Fri 4/172:48 pm
MCO
- ORD
Nonstop3h 21m
Frontier
Deal found 3/28![Frontier logo]()
$125
This Expedia deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/262:00 pm
MDW
- MCO
Nonstop2h 48m
Frontier
Fri 5/18:30 am
MCO
- MDW
Nonstop2h 58m
Frontier
Deal found 3/28![Frontier logo]()
$126
This Expedia deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:12 am
ORD
- MCO
Nonstop2h 58m
Frontier
Thu 4/1612:45 pm
MCO
- ORD
Nonstop3h 23m
Frontier
Deal found 3/27![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- MCO
Nonstop2h 46m
Frontier
Thu 4/162:56 pm
MCO
- MDW
1 stop5h 35m
Frontier
Deal found 3/28![Frontier logo]()
$127
This CheapOair deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
- MCO
Nonstop3h 01m
Multiple Airlines
Wed 4/156:22 am
MCO
- ORD
1 stop5h 01m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- MCO
Nonstop2h 46m
Frontier
Wed 4/152:40 pm
MCO
- MDW
1 stop8h 34m
Frontier
Deal found 3/28![Frontier logo]()
$128
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/193:55 pm
ORD
- MCO
Nonstop2h 56m
Frontier
Sat 5/238:58 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Deal found 3/30![Frontier logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
MDW
- MCO
Nonstop2h 48m
Frontier
Wed 4/152:40 pm
MCO
- MDW
1 stop5h 51m
Frontier
Deal found 3/31![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:16 am
ORD
- MCO
1 stop5h 13m
Multiple Airlines
Sun 4/269:34 pm
MCO
- ORD
1 stop26h 05m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:31 am
ORD
- MCO
Nonstop2h 40m
Multiple Airlines
Mon 4/279:49 pm
MCO
- ORD
1 stop13h 34m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
MDW
- MCO
1 stop6h 37m
Frontier
Tue 4/211:19 pm
MCO
- MDW
1 stop24h 41m
Frontier
Deal found 3/31![Frontier logo]()
$131
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 April 1, 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 April 1, 2026.
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1212:55 pm
MDW
- MCO
1 stop6h 00m
Southwest
Wed 5/139:00 am
MCO
- MDW
1 stop5h 50m
Southwest
Deal found 4/1![Southwest logo]()
$180
This United Airlines deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:00 pm
ORD
- MCO
Nonstop2h 57m
United Airlines
Mon 6/14:21 pm
MCO
- ORD
Nonstop3h 18m
United Airlines
Deal found 3/31![United Airlines logo]()
$199
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/46:00 am
ORD
- MCO
Nonstop2h 40m
Southwest
Tue 5/57:35 am
MCO
- ORD
Nonstop3h 10m
Southwest
Deal found 3/27![Southwest logo]()
$199
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:15 pm
ORD
- MCO
1 stop5h 44m
United Airlines
Mon 5/186:10 pm
MCO
- ORD
Nonstop3h 12m
United Airlines
Deal found 3/30![United Airlines logo]()
$209
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:20 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 5/205:50 pm
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 3/29![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:35 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Mon 6/810:55 pm
MCO
- MDW
Nonstop2h 45m
Southwest
Deal found 3/29![Southwest logo]()
$199
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:50 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Tue 5/198:55 am
MCO
- MDW
1 stop4h 05m
Southwest
Deal found 3/27![Southwest logo]()
$205
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:10 am
ORD
- MCO
Nonstop2h 59m
United Airlines
Sun 5/107:15 am
MCO
- ORD
Nonstop3h 13m
United Airlines
Deal found 3/28![United Airlines logo]()
$257
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:35 am
MDW
- MCO
Nonstop2h 30m
Southwest
Tue 5/197:15 am
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 3/27![Southwest logo]()
$208
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:05 pm
MDW
- MCO
1 stop4h 35m
Southwest
Wed 5/137:15 am
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 3/27![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/204:50 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Tue 5/263:00 pm
MCO
- MDW
1 stop5h 25m
Southwest
Deal found 3/30![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:15 pm
ORD
- MCO
Nonstop2h 45m
Southwest
Mon 5/119:55 pm
MCO
- ORD
2 stops15h 55m
Southwest
Deal found 4/1![Southwest logo]()
$220
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:05 am
MDW
- MCO
Nonstop2h 30m
Southwest
Thu 5/710:10 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 3/27![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:55 pm
ORD
- MCO
1 stop4h 50m
Southwest
Tue 5/59:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Deal found 3/27![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:30 am
ORD
- MCO
1 stop7h 30m
Southwest
Thu 5/289:55 pm
MCO
- ORD
2 stops15h 55m
Southwest
Deal found 3/31![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/239:55 am
ORD
- MCO
1 stop8h 00m
Southwest
Wed 5/279:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Deal found 3/27![Southwest logo]()
$235
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:35 pm
MDW
- MCO
Nonstop2h 35m
Southwest
Wed 4/2911:55 am
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 3/27![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/235:30 am
MDW
- MCO
1 stop5h 15m
Southwest
Sun 4/268:20 pm
MCO
- MDW
1 stop5h 00m
Southwest
Deal found 3/31![Southwest logo]()
$268
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:40 pm
ORD
- MCO
1 stop4h 50m
Southwest
Wed 5/209:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Deal found 3/29![Southwest logo]()
$279
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/294:50 pm
MDW
- MCO
Nonstop2h 40m
Southwest
Wed 5/61:25 pm
MCO
- MDW
Nonstop2h 50m
Southwest
Deal found 3/31![Southwest logo]()
$283
This Southwest deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:40 pm
ORD
- MCO
2 stops8h 25m
Southwest
Mon 4/209:55 pm
MCO
- ORD
2 stops15h 55m
Southwest
Deal found 3/27![Southwest logo]()
$284
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:40 pm
ORD
- MCO
2 stops8h 25m
Southwest
Sun 5/310:55 pm
MCO
- ORD
2 stops14h 55m
Southwest
Deal found 3/29![Southwest logo]()
$343
Last-minute flights from Chicago to KissimmeeDiscover last-minute flight deals from Chicago to Kissimmee. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kissimmee. Data last updated April 1, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
- MCO
Nonstop3h 01m
Multiple Airlines
Wed 4/156:22 am
MCO
- ORD
1 stop5h 01m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:00 am
MDW
- MCO
Nonstop2h 48m
Frontier
Wed 4/152:40 pm
MCO
- MDW
1 stop5h 51m
Frontier
Deal found 3/31![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- MCO
Nonstop2h 46m
Frontier
Thu 4/162:56 pm
MCO
- MDW
1 stop5h 35m
Frontier
Deal found 3/28![Frontier logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
MDW
- MCO
Nonstop2h 46m
Frontier
Wed 4/152:40 pm
MCO
- MDW
1 stop8h 34m
Frontier
Deal found 3/28![Frontier logo]()
$128
This Cheapflightsfares deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:21 pm
ORD
- MCO
Nonstop3h 01m
Frontier
Fri 4/172:48 pm
MCO
- ORD
Nonstop3h 21m
Frontier
Deal found 3/28![Frontier logo]()
$125
This Expedia deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:12 am
ORD
- MCO
Nonstop2h 58m
Frontier
Thu 4/1612:45 pm
MCO
- ORD
Nonstop3h 23m
Frontier
Deal found 3/27![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/169:14 am
MDW
- MCO
Nonstop2h 49m
Frontier
Fri 4/176:00 am
MCO
- MDW
Nonstop2h 59m
Frontier
Deal found 3/28![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
MDW
- MCO
1 stop6h 37m
Frontier
Tue 4/211:19 pm
MCO
- MDW
1 stop24h 41m
Frontier
Deal found 3/31![Frontier logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:16 am
ORD
- MCO
1 stop5h 13m
Multiple Airlines
Sun 4/269:34 pm
MCO
- ORD
1 stop26h 05m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$129
This Mytrip deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:15 pm
ORD
- MCO
2 stops19h 14m
Spirit Airlines
Sat 4/2511:18 am
MCO
- ORD
1 stop10h 54m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:31 am
ORD
- MCO
Nonstop2h 40m
Multiple Airlines
Mon 4/279:49 pm
MCO
- ORD
1 stop13h 34m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$130
This Frontier deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/262:00 pm
MDW
- MCO
Nonstop2h 48m
Frontier
Sat 5/22:13 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Deal found 3/28![Frontier logo]()
$126
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 April 1, 2026.
Search for one-way flight options from Chicago to Kissimmee. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Super.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
- MCO
Nonstop3h 01m
Frontier
Deal found 3/31![Frontier logo]()
$58
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:28 am
ORD
- MCO
1 stop7h 35m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$59
This Expedia deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2011:28 am
ORD
- MCO
1 stop11h 01m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$60
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/217:30 am
MDW
- MCO
1 stop14h 56m
Frontier
Deal found 3/30![Frontier logo]()
$64
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/287:30 am
MDW
- MCO
1 stop14h 56m
Frontier
Deal found 3/29![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/124:05 pm
ORD
- MCO
1 stop30h 12m
Frontier
Deal found 3/31![Frontier logo]()
$65
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2711:28 am
ORD
- MCO
1 stop21h 59m
Multiple Airlines
Deal found 4/1![Multiple Airlines logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/204:14 pm
MDW
- MCO
1 stop21h 23m
Frontier
Deal found 3/30![Frontier logo]()
$67
This Mytrip deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:16 am
ORD
- MCO
1 stop5h 13m
Spirit Airlines
Deal found 3/29![Spirit Airlines logo]()
$67
This Super.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/95:01 am
MDW
- MCO
Nonstop2h 46m
Frontier
Deal found 3/29![Frontier logo]()
$68
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/139:06 am
ORD
- MCO
Nonstop2h 46m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$68
This Super.com deal was found by Cheapflights users on 3/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:07 pm
MDW
- MCO
1 stop7h 14m
Frontier
Deal found 3/27![Frontier logo]()
$69
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 April 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $125 (Cheapflightsfares) |
One-way from | $58 (Super.com) |
Popular in | March |
Cheapest in | September |
Average price | $246 |
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 April 1, 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
Tue 5/12
12:55 pm-7:55 pm
1 stop6h 00m
Orlando
Wed 5/13
9:00 am-1:50 pm
1 stop5h 50m
$180
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Thu 5/28
2:00 pm-5:57 pm
Nonstop2h 57m
Orlando
Mon 6/1
4:21 pm-6:39 pm
Nonstop3h 18m
$199
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Mon 5/4
6:00 am-9:40 am
Nonstop2h 40m
Orlando
Tue 5/5
7:35 am-9:45 am
Nonstop3h 10m
$199
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 5/13
6:20 pm-9:55 pm
Nonstop2h 35m
Orlando
Wed 5/20
5:50 pm-7:45 pm
Nonstop2h 55m
$199
Quickest round-trip
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Mon 6/1
8:35 pm-12:10 am
Nonstop2h 35m
Orlando
Mon 6/8
10:55 pm-12:40 am
Nonstop2h 45m
$199
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Tue 5/12
4:50 pm-8:30 pm
Nonstop2h 40m
Orlando
Tue 5/19
8:55 am-12:00 pm
1 stop4h 05m
$205
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Thu 5/14
5:35 am-9:05 am
Nonstop2h 30m
Orlando
Tue 5/19
7:15 am-9:10 am
Nonstop2h 55m
$208
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
Sat 5/16
6:15 pm-12:59 am
1 stop5h 44m
Orlando
Mon 5/18
6:10 pm-8:22 pm
Nonstop3h 12m
$209
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 5/6
1:05 pm-6:40 pm
1 stop4h 35m
Orlando
Wed 5/13
7:15 am-9:10 am
Nonstop2h 55m
$209
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Wed 5/20
4:50 pm-8:30 pm
Nonstop2h 40m
Orlando
Tue 5/26
3:00 pm-7:25 pm
1 stop5h 25m
$209
Showing 1-10 of 43 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
How far ahead should I book a flight from Chicago to Kissimmee?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Kissimmee. Price data was last updated on March 13, 2026.
The price you pay for your flight from Chicago to Kissimmee may vary depending on when you book. For the best chance of a lower fare, look to book 85 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago to Kissimmee?
Currently, January is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $58). Flying from Chicago to Kissimmee in June is currently the most expensive (average of $108). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from 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 April 1, 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 21% versus a flight at noon.
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 March 28, 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.
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 April 1, 2026.
The most flights from CHI to K1S are scheduled on a Wednesday (72 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).
How much does it cost to fly round-trip from Chicago to Kissimmee?
Reviews of airlines servicing Kissimmee
Get insights into the airlines that provide service to Kissimmee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kissimmee. Reviews last updated April 1, 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.
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Crew
8.6
Boarding
8.1
Overall
8.0
Comfort
8.0
Entertainment
7.5
Food
7.0
Reviews
1 / 20
6.0
GoodScott,Feb 2026
HOU - FLL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Kissimmee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Chicago 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 Chicago to Kissimmee by cabin class
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 April 1, 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 April 1, 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 April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$192 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$76 | Average$175 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$87 | Average$205 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$445 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$312 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$153 | Average$326 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$156 | Average$365 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$157 | Average$326 | FlexibilityNo cancel fee | On-time69% |