$52+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MCO
maalis 4 — maalis 111
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 July, booked 85 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 helmikuu 2, 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 helmikuu 2, 2026.
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
la 5/92:20 pm
MDW
- MCO
1 stop9h 05m
Frontier
la 5/162:13 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Deal found 2/1![Frontier logo]()
$103
This Expedia deal was found by Cheapflights users on 2/2. 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.
pe 3/612:44 pm
ORD
- MCO
Nonstop2h 47m
Spirit Airlines
ti 3/102:50 pm
MCO
- ORD
1 stop9h 57m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$103
This Super.com deal was found by Cheapflights users on 1/31. 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.
ma 3/29:22 pm
MDW
- MCO
Nonstop2h 47m
Frontier
ma 3/911:05 am
MCO
- MDW
Nonstop3h 03m
Frontier
Deal found 1/31![Frontier logo]()
$104
This Expedia deal was found by Cheapflights users on 2/2. 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.
pe 3/64:23 pm
ORD
- MCO
Nonstop3h 05m
Multiple Airlines
ma 3/93:39 pm
MCO
- ORD
Nonstop3h 07m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$104
This Super.com deal was found by Cheapflights users on 2/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pe 3/69:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
pe 3/139:51 pm
MCO
- MDW
Nonstop3h 00m
Frontier
Deal found 2/1![Frontier logo]()
$105
This Super.com deal was found by Cheapflights users on 2/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pe 3/64:23 pm
ORD
- MCO
Nonstop3h 05m
Frontier
pe 3/139:23 pm
MCO
- ORD
Nonstop3h 15m
Frontier
Deal found 2/1![Frontier logo]()
$105
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to 3/129:10 am
MDW
- MCO
Nonstop2h 45m
Frontier
la 3/147:42 pm
MCO
- MDW
Nonstop3h 03m
Frontier
Deal found 2/1![Frontier logo]()
$106
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/35:15 am
ORD
- MCO
1 stop7h 34m
Spirit Airlines
ti 3/106:00 am
MCO
- ORD
1 stop6h 22m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ke 2/258:30 am
ORD
- MCO
Nonstop2h 56m
Frontier
ma 3/25:01 am
MCO
- ORD
1 stop13h 22m
Frontier
Deal found 2/1![Frontier logo]()
$107
This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/37:30 am
MDW
- MCO
1 stop6h 34m
Frontier
ti 3/104:05 pm
MCO
- MDW
Nonstop3h 08m
Frontier
Deal found 2/1![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
su 3/17:35 am
ORD
- MCO
Nonstop2h 58m
Multiple Airlines
ke 3/46:00 am
MCO
- ORD
1 stop6h 22m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$108
This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pe 3/69:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
la 3/147:42 pm
MCO
- MDW
Nonstop3h 03m
Frontier
Deal found 2/1![Frontier logo]()
$109
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 helmikuu 2, 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 helmikuu 2, 2026.
This Southwest deal was found by Cheapflights users on 1/31. 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.
ti 3/33:15 pm
MDW
- MCO
Nonstop2h 35m
Southwest
la 3/79:55 pm
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 1/31![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/32:46 pm
ORD
- MCO
1 stop6h 12m
Delta
to 3/56:15 am
MCO
- ORD
1 stop4h 59m
Delta
Deal found 2/1![Delta logo]()
$207
This United Airlines deal was found by Cheapflights users on 2/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ke 2/252:30 pm
ORD
- MCO
Nonstop2h 52m
United Airlines
la 2/287:00 am
MCO
- ORD
Nonstop3h 18m
United Airlines
Deal found 2/1![United Airlines logo]()
$247
This Southwest deal was found by Cheapflights users on 1/30. 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.
ti 3/33:45 pm
ORD
- MCO
Nonstop2h 45m
Southwest
la 3/77:30 am
MCO
- ORD
Nonstop3h 15m
Southwest
Deal found 1/30![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 2/1. 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.
ke 3/45:00 am
MDW
- MCO
Nonstop2h 45m
Southwest
ti 3/108:40 pm
MCO
- MDW
Nonstop3h 00m
Southwest
Deal found 2/1![Southwest logo]()
$168
This Southwest deal was found by Cheapflights users on 1/31. 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.
ti 3/33:15 pm
MDW
- MCO
Nonstop2h 35m
Southwest
pe 3/610:50 pm
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 1/31![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 2/246:00 am
MDW
- MCO
1 stop4h 57m
Delta
la 2/2810:00 am
MCO
- MDW
1 stop6h 21m
Delta
Deal found 1/31![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 2/1. 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.
la 3/74:55 pm
MDW
- MCO
Nonstop2h 35m
Southwest
ma 3/910:50 pm
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 2/1![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/246:00 am
MDW
- MCO
1 stop4h 48m
Delta
ti 3/244:15 pm
MCO
- MDW
1 stop7h 16m
Delta
Deal found 2/1![Delta logo]()
$217
This Delta deal was found by Cheapflights users on 1/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/315:30 am
ORD
- MCO
1 stop4h 24m
Delta
ke 4/112:15 pm
MCO
- ORD
1 stop5h 34m
Delta
Deal found 1/31![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 1/31. 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.
la 3/79:00 pm
MDW
- MCO
Nonstop2h 40m
Southwest
ti 3/107:15 am
MCO
- MDW
Nonstop3h 00m
Southwest
Deal found 1/31![Southwest logo]()
$197
This KAYAK deal was found by Cheapflights users on 2/1. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
su 3/158:06 pm
ORD
- MCO
Nonstop2h 53m
United Airlines
ti 3/172:22 pm
MCO
- ORD
Nonstop3h 16m
United Airlines
Deal found 2/1![United Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
su 3/227:10 am
ORD
- MCO
1 stop4h 41m
Delta
ke 3/257:50 pm
MCO
- ORD
1 stop5h 04m
Delta
Deal found 2/1![Delta logo]()
$268
This Southwest deal was found by Cheapflights users on 2/1. 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.
ke 2/2510:00 am
MDW
- MCO
1 stop5h 05m
Southwest
ke 2/257:05 pm
MCO
- MDW
Nonstop2h 55m
Southwest
Deal found 2/1![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 2/1. 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.
la 3/74:55 pm
MDW
- MCO
Nonstop2h 35m
Southwest
la 3/146:25 pm
MCO
- MDW
1 stop5h 15m
Southwest
Deal found 2/1![Southwest logo]()
$227
This Southwest deal was found by Cheapflights users on 1/31. 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.
la 3/78:00 am
ORD
- MCO
1 stop12h 10m
Southwest
la 3/1410:55 pm
MCO
- ORD
2 stops14h 55m
Southwest
Deal found 1/31![Southwest logo]()
$278
This Southwest deal was found by Cheapflights users on 1/31. 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.
la 2/283:45 pm
ORD
- MCO
1 stop6h 10m
Southwest
la 3/710:55 pm
MCO
- ORD
2 stops13h 55m
Southwest
Deal found 1/31![Southwest logo]()
$293
This Southwest deal was found by Cheapflights users on 1/31. 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.
la 4/182:05 pm
ORD
- MCO
1 stop7h 05m
Southwest
ti 4/219:10 pm
MCO
- ORD
2 stops16h 40m
Southwest
Deal found 1/31![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 1/31. 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.
ma 2/165:15 pm
ORD
- MCO
1 stop6h 40m
Southwest
to 2/198:55 pm
MCO
- ORD
2 stops16h 20m
Southwest
Deal found 1/31![Southwest logo]()
$314
Last-minute flights from Chicago to KissimmeeDiscover last-minute flight deals from Chicago to Kissimmee. Data last updated helmikuu 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Kissimmee. Data last updated helmikuu 2, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 2/2. 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.
ti 2/1712:44 pm
ORD
- MCO
Nonstop2h 47m
Spirit Airlines
to 2/196:54 pm
MCO
- ORD
1 stop5h 53m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$104
This CheapOair deal was found by Cheapflights users on 1/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 2/1710:44 am
ORD
- MCO
Nonstop2h 50m
Spirit Airlines
ke 2/252:50 pm
MCO
- ORD
1 stop9h 57m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 2/178:30 am
ORD
- MCO
Nonstop2h 56m
Frontier
la 2/219:57 pm
MCO
- ORD
1 stop10h 37m
Frontier
Deal found 2/1![Frontier logo]()
$111
This Expedia deal was found by Cheapflights users on 1/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pe 2/209:07 pm
ORD
- MCO
Nonstop2h 59m
Multiple Airlines
ti 2/242:50 pm
MCO
- ORD
1 stop7h 23m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
la 2/218:15 am
ORD
- MCO
Nonstop2h 56m
Frontier
to 2/268:20 am
MCO
- ORD
Nonstop3h 26m
Frontier
Deal found 2/1![Frontier logo]()
$106
This Priceline deal was found by Cheapflights users on 1/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
la 2/219:15 am
MDW
- MCO
1 stop10h 32m
Frontier
to 2/2612:20 pm
MCO
- MDW
Nonstop3h 06m
Frontier
Deal found 1/31![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 2/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 2/233:50 pm
ORD
- MCO
Nonstop2h 56m
Frontier
ke 2/2510:28 am
MCO
- ORD
1 stop7h 24m
Frontier
Deal found 2/1![Frontier logo]()
$109
This CheapOair deal was found by Cheapflights users on 1/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 2/233:50 pm
ORD
- MCO
Nonstop2h 56m
Multiple Airlines
pe 2/272:50 pm
MCO
- ORD
1 stop7h 23m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 2/1. 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.
ti 2/2410:44 am
ORD
- MCO
Nonstop2h 50m
Spirit Airlines
ti 3/35:34 pm
MCO
- ORD
Nonstop3h 13m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ke 2/258:30 am
ORD
- MCO
Nonstop2h 56m
Frontier
ma 3/25:01 am
MCO
- ORD
1 stop13h 22m
Frontier
Deal found 2/1![Frontier logo]()
$107
This Expedia deal was found by Cheapflights users on 2/2. 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.
ke 2/255:15 am
ORD
- MCO
1 stop7h 34m
Spirit Airlines
to 3/52:50 pm
MCO
- ORD
1 stop7h 23m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$108
This Super.com deal was found by Cheapflights users on 1/31. 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.
la 2/288:00 am
MDW
- MCO
Nonstop2h 49m
Frontier
ma 3/911:05 am
MCO
- MDW
Nonstop3h 03m
Frontier
Deal found 1/31![Frontier logo]()
$105
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 helmikuu 2, 2026.
Search for one-way flight options from Chicago to Kissimmee. Find affordable one-way fares based on user searches. Data last updated helmikuu 2, 2026.
This WAYA deal was found by Cheapflights users on 1/31. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti 3/311:56 am
ORD
- MCO
1 stop7h 11m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$52
This Cheapflightsfares deal was found by Cheapflights users on 1/31. 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.
ti 2/178:30 am
ORD
- MCO
Nonstop2h 56m
Frontier
Deal found 1/31![Frontier logo]()
$53
This Priceline deal was found by Cheapflights users on 2/2. 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.
ma 3/167:25 am
MDW
- MCO
Nonstop2h 50m
Frontier
Deal found 2/2![Frontier logo]()
$54
This Cheapflightsfares deal was found by Cheapflights users on 2/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma 2/911:51 am
ORD
- MCO
Nonstop2h 53m
Frontier
Deal found 2/1![Frontier logo]()
$55
This Super.com deal was found by Cheapflights users on 1/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pe 3/64:23 pm
ORD
- MCO
Nonstop3h 05m
Frontier
Deal found 1/30![Frontier logo]()
$56
This Super.com deal was found by Cheapflights users on 1/31. 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.
su 4/129:00 am
MDW
- MCO
Nonstop2h 49m
Frontier
Deal found 1/31![Frontier logo]()
$56
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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.
ti 4/74:36 pm
ORD
- MCO
1 stop6h 14m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$57
This CheapOair deal was found by Cheapflights users on 2/2. 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.
pe 3/69:51 pm
MDW
- MCO
Nonstop2h 47m
Frontier
Deal found 2/2![Frontier logo]()
$57
This Cheapflightsfares deal was found by Cheapflights users on 1/31. 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.
la 2/288:16 pm
ORD
- MCO
1 stop10h 23m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$58
This Trip.com deal was found by Cheapflights users on 2/1. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ke 4/226:31 am
ORD
- MCO
1 stop8h 32m
Frontier
Deal found 2/1![Frontier logo]()
$59
This Trip.com deal was found by Cheapflights users on 1/31. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
pe 4/108:30 pm
MDW
- MCO
Nonstop2h 51m
Frontier
Deal found 1/31![Frontier logo]()
$59
This Super.com deal was found by Cheapflights users on 2/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
la 4/412:45 pm
ORD
- MCO
Nonstop2h 40m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$60
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 helmikuu 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $103 (Frontier) |
One-way from | $52 (WAYA) |
Popular in | March |
Cheapest in | September |
Average price | $264 |
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 helmikuu 2, 2026.
Use the filters below to find and compare flights from Chicago to Kissimmee that are best for you.
Fly from
Chicago
Fly to
Kissimmee
Route
Depart
Return
Price
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
ti 3/3
3:15 pm-6:50 pm
Nonstop2h 35m
Orlando
la 3/7
9:55 pm-11:50 pm
Nonstop2h 55m
$157
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
ti 3/3
3:45 pm-7:30 pm
Nonstop2h 45m
Orlando
la 3/7
7:30 am-9:45 am
Nonstop3h 15m
$157
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
ke 3/4
5:00 am-8:45 am
Nonstop2h 45m
Orlando
ti 3/10
8:40 pm-10:40 pm
Nonstop3h 00m
$168
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
ti 3/3
3:15 pm-6:50 pm
Nonstop2h 35m
Orlando
pe 3/6
10:50 pm-12:45 am
Nonstop2h 55m
$177
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
la 3/7
4:55 pm-8:30 pm
Nonstop2h 35m
Orlando
ma 3/9
10:50 pm-12:45 am
Nonstop2h 55m
$177
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
la 3/7
9:00 pm-12:40 am
Nonstop2h 40m
Orlando
ti 3/10
7:15 am-9:15 am
Nonstop3h 00m
$197
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
ti 3/3
2:46 pm-9:58 pm
1 stop6h 12m
Orlando
to 3/5
6:15 am-10:14 am
1 stop4h 59m
$207
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
ti 2/24
6:00 am-11:57 am
1 stop4h 57m
Orlando
la 2/28
10:00 am-3:21 pm
1 stop6h 21m
$217
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
ti 3/24
6:00 am-11:48 am
1 stop4h 48m
Orlando
ti 3/24
4:15 pm-10:31 pm
1 stop7h 16m
$217
ChicagoOrlando
ORD - MCO
ORDMCO
Chicago O'Hare Intl
ti 3/31
5:30 am-10:54 am
1 stop4h 24m
Orlando
ke 4/1
12:15 pm-4:49 pm
1 stop5h 34m
$217
Showing 1-10 of 41 results
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.
ORD-MCO
MDW-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
ORD-MCO
MDW-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 January 30, 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, March is the cheapest month in which you can book a flight from Chicago to Kissimmee (average of $53). 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 helmikuu 2, 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 18% 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 January 31, 2026.
Travelers seeking maximum savings on their Chicago to Kissimmee flight should consider departing on Wednesday 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 helmikuu 2, 2026.
The most flights from CHI to K1S are scheduled on a Friday (73 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (44 on average).
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 helmikuu 2, 2026.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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.
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Boarding
8.1
Entertainment
7.5
Food
7.0
Crew
8.6
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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.
Alternative routes for Chicago to Kissimmee
See prices for flight routes from nearby airports that may be better suited for you.
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 helmikuu 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$35 | Average$157 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$48 | Average$203 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$87 | Average$180 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$98 | Average$452 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$300 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$151 | Average$331 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$155 | Average$324 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$156 | Average$348 | FlexibilityNo cancel fee | On-time71% |