$69+ Cheap flights from Kentucky to Illinois
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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Jun 4 — Jun 111
Round-trip
1 adult, Economy
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Cheapest flights from Kentucky to IllinoisExplore the most affordable flight options available from Kentucky to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
Explore the most affordable flight options available from Kentucky to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 5, 2026.
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/11:30 pm
BNA
- STL
Nonstop1h 15m
Southwest
Wed 7/810:15 am
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 5/5![Southwest logo]()
$137
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:54 pm
BNA
- STL
1 stop5h 02m
Delta
Tue 7/76:00 am
STL
- BNA
1 stop4h 09m
Delta
Deal found 5/5![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:40 am
BNA
- STL
1 stop4h 50m
Southwest
Tue 6/93:10 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 5/3![Southwest logo]()
$174
This Kissandfly.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:30 am
BNA
- STL
1 stop3h 51m
Southern / Mokulele
Mon 6/12:00 pm
STL
- BNA
1 stop4h 03m
Southern / Mokulele
Deal found 5/4![Southern / Mokulele logo]()
$182
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:55 am
BNA
- STL
Nonstop1h 20m
Southwest
Thu 6/47:15 pm
STL
- BNA
Nonstop1h 05m
Southwest
Deal found 5/5![Southwest logo]()
$191
This Southwest deal was found by Cheapflights users on 5/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Wed 5/276:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 5/2![Southwest logo]()
$192
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
CVG
- ORD
Nonstop1h 34m
American Airlines
Mon 6/13:27 pm
ORD
- CVG
Nonstop1h 29m
American Airlines
Deal found 5/3![American Airlines logo]()
$193
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:48 am
CVG
- ORD
1 stop5h 28m
Delta
Tue 5/265:19 pm
ORD
- CVG
1 stop4h 10m
Delta
Deal found 4/30![Delta logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:46 pm
CVG
- ORD
1 stop7h 43m
Frontier
Thu 6/111:29 pm
ORD
- CVG
1 stop21h 20m
Frontier
Deal found 5/4![Frontier logo]()
$195
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 pm
CVG
- ORD
1 stop6h 59m
Delta
Wed 6/37:00 am
ORD
- CVG
2 stops8h 37m
Delta
Deal found 4/30![Delta logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:46 pm
CVG
- ORD
2 stops24h 51m
Frontier
Thu 5/281:50 pm
ORD
- CVG
1 stop20h 51m
Frontier
Deal found 5/2![Frontier logo]()
$200
This Southwest deal was found by Cheapflights users on 4/30. 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.
Thu 5/286:50 pm
CVG
- MDW
1 stop5h 40m
Southwest
Thu 6/41:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/30![Southwest logo]()
$201
Best flights from Kentucky to IllinoisDiscover carefully curated flight deals from Kentucky to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
Discover carefully curated flight deals from Kentucky to Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 5, 2026.
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:54 pm
BNA
- STL
1 stop5h 02m
Delta
Tue 7/76:00 am
STL
- BNA
1 stop4h 09m
Delta
Deal found 5/5![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Wed 6/2412:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 5/3![Southwest logo]()
$192
This Southern / Mokulele deal was found by Cheapflights users on 5/1. 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 Southern / Mokulele is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/212:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Fri 5/227:20 pm
STL
- BNA
1 stop13h 43m
Southern / Mokulele
Deal found 5/1![Southern / Mokulele logo]()
$212
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:54 am
TRI
- ORD
Nonstop2h 11m
American Airlines
Sat 7/119:07 pm
ORD
- TRI
Nonstop1h 50m
American Airlines
Deal found 5/5![American Airlines logo]()
$229
This United Airlines deal was found by Cheapflights users on 5/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:15 am
LEX
- ORD
Nonstop1h 50m
United Airlines
Sun 5/247:00 am
ORD
- LEX
Nonstop1h 30m
United Airlines
Deal found 5/2![United Airlines logo]()
$249
This Contour deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/178:00 am
BNA
- ORD
1 stop3h 30m
Contour
Sun 6/2112:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 5/4![Contour logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
Sun 5/1710:33 am
SDF
- ORD
2 stops22h 22m
Multiple Airlines
Tue 5/195:05 am
ORD
- SDF
1 stop29h 29m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:54 pm
BNA
- STL
1 stop5h 02m
Delta
Wed 7/89:24 am
STL
- BNA
1 stop6h 02m
Delta
Deal found 5/5![Delta logo]()
$157
This Southwest deal was found by Cheapflights users on 5/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:50 pm
CVG
- MDW
2 stops5h 20m
Southwest
Thu 5/281:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 5/2![Southwest logo]()
$206
This Southern / Mokulele deal was found by Cheapflights users on 5/1. 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 Southern / Mokulele is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/292:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Tue 6/307:20 pm
STL
- BNA
1 stop13h 43m
Southern / Mokulele
Deal found 5/1![Southern / Mokulele logo]()
$212
This Delta deal was found by Cheapflights users on 5/1. 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.
Mon 5/256:20 am
CVG
- ORD
1 stop6h 27m
Delta
Tue 5/265:19 pm
ORD
- CVG
1 stop4h 10m
Delta
Deal found 5/1![Delta logo]()
$194
This American Airlines deal was found by Cheapflights users on 5/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:54 am
TRI
- ORD
Nonstop2h 11m
American Airlines
Sun 7/59:25 pm
ORD
- TRI
Nonstop1h 50m
American Airlines
Deal found 5/2![American Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 pm
CVG
- ORD
1 stop6h 59m
Delta
Wed 6/37:00 am
ORD
- CVG
2 stops8h 37m
Delta
Deal found 4/30![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 5/1. 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 6/96:25 am
BNA
- STL
Nonstop1h 20m
Southwest
Tue 6/91:45 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 5/1![Southwest logo]()
$223
This United Airlines deal was found by Cheapflights users on 5/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Sun 7/56:55 am
ORD
- TYS
Nonstop1h 48m
United Airlines
Deal found 5/2![United Airlines logo]()
$249
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:16 pm
TRI
- ORD
1 stop6h 35m
American Airlines
Sat 7/259:07 pm
ORD
- TRI
Nonstop1h 50m
American Airlines
Deal found 5/1![American Airlines logo]()
$249
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/233:00 pm
CVG
- ORD
1 stop6h 24m
Delta
Thu 5/283:47 pm
ORD
- CVG
1 stop6h 11m
Delta
Deal found 5/2![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 5/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/169:45 pm
BNA
- STL
Nonstop1h 15m
Southwest
Tue 6/236:15 pm
STL
- BNA
1 stop4h 10m
Southwest
Deal found 5/2![Southwest logo]()
$233
This Contour deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:00 am
BNA
- ORD
1 stop3h 30m
Contour
Sun 6/712:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 5/4![Contour logo]()
$282
This United Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:15 am
LEX
- ORD
Nonstop1h 50m
United Airlines
Mon 5/255:51 pm
ORD
- LEX
Nonstop1h 37m
United Airlines
Deal found 5/4![United Airlines logo]()
$264
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 6/26:00 am
BNA
- STL
1 stop6h 11m
United Airlines
Wed 6/36:00 am
STL
- BNA
1 stop4h 34m
United Airlines
Deal found 4/30![United Airlines logo]()
$271
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/149:00 am
BNA
- STL
1 stop5h 45m
Southwest
Wed 6/175:40 am
STL
- BNA
2 stops5h 35m
Southwest
Deal found 5/4![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 5/1. 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.
Tue 6/95:10 am
BNA
- STL
1 stop4h 36m
Delta
Tue 6/93:57 pm
STL
- BNA
1 stop4h 43m
Delta
Deal found 5/1![Delta logo]()
$228
This Southwest deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:40 pm
BNA
- MDW
Nonstop1h 35m
Southwest
Tue 6/96:30 am
MDW
- BNA
2 stops7h 05m
Southwest
Deal found 5/4![Southwest logo]()
$248
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:51 am
SDF
- ORD
Nonstop1h 49m
American Airlines
Sun 6/78:00 am
ORD
- SDF
Nonstop1h 35m
American Airlines
Deal found 4/30![American Airlines logo]()
$301
This United Airlines deal was found by Cheapflights users on 5/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:00 am
LEX
- ORD
Nonstop1h 50m
United Airlines
Sun 5/179:30 pm
ORD
- LEX
Nonstop1h 29m
United Airlines
Deal found 5/2![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 5/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
CVG
- ORD
1 stop6h 31m
Delta
Tue 6/307:01 am
ORD
- CVG
1 stop5h 34m
Delta
Deal found 5/2![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/16:35 pm
CVG
- MDW
1 stop5h 35m
Southwest
Fri 7/107:00 pm
MDW
- CVG
1 stop4h 25m
Southwest
Deal found 5/5![Southwest logo]()
$249
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Fri 7/316:30 am
TYS
- ORD
Nonstop1h 59m
United Airlines
Sun 8/26:45 am
ORD
- TYS
Nonstop1h 48m
United Airlines
Deal found 4/30![United Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:54 pm
BNA
- STL
1 stop5h 02m
Delta
Sat 6/208:00 am
STL
- BNA
1 stop3h 33m
Delta
Deal found 5/4![Delta logo]()
$238
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated May 5, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:46 pm
CVG
- ORD
2 stops24h 51m
Frontier
Thu 5/281:50 pm
ORD
- CVG
1 stop20h 51m
Frontier
Deal found 5/2![Frontier logo]()
$200
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/255:48 am
CVG
- ORD
1 stop5h 28m
Delta
Tue 5/265:19 pm
ORD
- CVG
1 stop4h 10m
Delta
Deal found 4/30![Delta logo]()
$194
This Southwest deal was found by Cheapflights users on 5/2. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Wed 5/276:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 5/2![Southwest logo]()
$192
This Kissandfly.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:30 am
BNA
- STL
1 stop3h 51m
Southern / Mokulele
Mon 6/12:00 pm
STL
- BNA
1 stop4h 03m
Southern / Mokulele
Deal found 5/4![Southern / Mokulele logo]()
$182
This Southwest deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2811:55 am
BNA
- STL
Nonstop1h 20m
Southwest
Thu 6/47:15 pm
STL
- BNA
Nonstop1h 05m
Southwest
Deal found 5/5![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 am
CVG
- ORD
Nonstop1h 34m
American Airlines
Mon 6/13:27 pm
ORD
- CVG
Nonstop1h 29m
American Airlines
Deal found 5/3![American Airlines logo]()
$193
This Southwest deal was found by Cheapflights users on 4/30. 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.
Thu 5/286:50 pm
CVG
- MDW
1 stop5h 40m
Southwest
Thu 6/41:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/30![Southwest logo]()
$201
This Delta deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/13:00 pm
CVG
- ORD
1 stop4h 35m
Delta
Wed 6/36:24 am
ORD
- CVG
2 stops7h 50m
Delta
Deal found 5/4![Delta logo]()
$199
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/65:40 am
BNA
- STL
1 stop4h 50m
Southwest
Tue 6/93:10 pm
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 5/3![Southwest logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:46 pm
CVG
- ORD
1 stop7h 43m
Frontier
Thu 6/111:29 pm
ORD
- CVG
1 stop21h 20m
Frontier
Deal found 5/4![Frontier logo]()
$195
This Southwest deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Wed 6/244:10 pm
MDW
- CVG
1 stop5h 55m
Southwest
Deal found 5/3![Southwest logo]()
$202
This Delta deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:54 pm
BNA
- STL
1 stop5h 02m
Delta
Wed 7/89:24 am
STL
- BNA
1 stop6h 02m
Delta
Deal found 5/5![Delta logo]()
$157
One-way flights from Kentucky to IllinoisSearch for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Southwest deal was found by Cheapflights users on 5/1. 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.
Wed 5/276:00 pm
BNA
- STL
Nonstop1h 15m
Southwest
Deal found 5/1![Southwest logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:46 pm
CVG
- MDW
1 stop10h 16m
Frontier
Deal found 5/5![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:12 pm
CVG
- MDW
1 stop10h 50m
Frontier
Deal found 5/5![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:46 pm
CVG
- ORD
1 stop7h 55m
Frontier
Deal found 5/5![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:46 pm
CVG
- MDW
1 stop23h 26m
Frontier
Deal found 5/4![Frontier logo]()
$71
This Trip.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/139:30 am
BNA
- STL
1 stop6h 31m
Southern / Mokulele
Deal found 5/4![Southern / Mokulele logo]()
$74
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Wed 5/2712:46 pm
CVG
- MDW
1 stop10h 16m
Frontier
Deal found 5/1![Frontier logo]()
$74
This Trip.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/112:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Deal found 5/5![Southern / Mokulele logo]()
$75
This Trip.com deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/182:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Deal found 5/4![Southern / Mokulele logo]()
$76
This Travelocity deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/2412:12 pm
CVG
- MDW
1 stop10h 50m
Frontier
Deal found 5/3![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Tue 5/2612:12 pm
CVG
- ORD
1 stop20h 43m
Frontier
Deal found 5/1![Frontier logo]()
$76
This Delta deal was found by Cheapflights users on 5/1. 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.
Tue 5/266:43 pm
BNA
- STL
1 stop5h 16m
Delta
Deal found 5/1![Delta logo]()
$79
Find flight deals from Kentucky to Illinois
Keep the following information in mind while searching for Kentucky to Illinois flight deals. Data was last updated May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $137 (Southwest) |
One-way from | $69 (Southwest) |
Popular in | January |
Cheapest in | November |
Average price | $308 |
Good round-trip deal | $126 or less |
Good one-way deal | $58 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Illinois 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 5, 2026.
Use the filters below to find and compare flights from Kentucky to Illinois that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Wed 7/1
6:54 pm-11:56 pm
1 stop5h 02m
Lambert-St Louis
Tue 7/7
6:00 am-10:09 am
1 stop4h 09m
$157
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Tue 6/30
6:54 pm-11:56 pm
1 stop5h 02m
Lambert-St Louis
Wed 7/8
9:24 am-3:26 pm
1 stop6h 02m
$157
Quickest round-trip
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Wed 6/17
7:40 pm-7:50 pm
Nonstop1h 10m
Chicago Midway
Wed 6/24
12:45 pm-2:55 pm
Nonstop1h 10m
$192
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Mon 5/25
6:20 am-11:47 am
1 stop6h 27m
Chicago O'Hare Intl
Tue 5/26
5:19 pm-10:29 pm
1 stop4h 10m
$194
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Mon 6/1
6:00 pm-11:59 pm
1 stop6h 59m
Chicago O'Hare Intl
Wed 6/3
7:00 am-4:37 pm
2 stops8h 37m
$199
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 5/23
12:50 pm-5:10 pm
2 stops5h 20m
Chicago Midway
Thu 5/28
1:00 pm-3:10 pm
Nonstop1h 10m
$206
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Sat 5/23
3:00 pm-8:24 pm
1 stop6h 24m
Chicago O'Hare Intl
Thu 5/28
3:47 pm-10:58 pm
1 stop6h 11m
$211
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Thu 5/21
2:35 pm-6:36 pm
1 stop4h 01m
Lambert-St Louis
Fri 5/22
7:20 pm-9:03 am
1 stop13h 43m
$212
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Mon 6/29
2:35 pm-6:36 pm
1 stop4h 01m
Lambert-St Louis
Tue 6/30
7:20 pm-9:03 am
1 stop13h 43m
$212
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Tue 6/9
6:25 am-7:45 am
Nonstop1h 20m
Lambert-St Louis
Tue 6/9
1:45 pm-2:55 pm
Nonstop1h 10m
$223
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Kentucky with our price prediction graph.
BNA-STL
CVG-MDW
TRI-ORD
LEX-ORD
BNA-ORD
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 Kentucky to Illinois
USKY-USIL
BNA-STL
CVG-MDW
TRI-ORD
LEX-ORD
How far ahead should I book a flight from Kentucky to Illinois?
The best time to book flights from Kentucky to Illinois is 73 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Kentucky to Illinois?
Currently, April is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $58). Flying from Kentucky to Illinois in February is currently the most expensive (average of $118). 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 KY to IL?
Find hourly flight availability from Kentucky to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 5, 2026.
A simple way to save on the total cost of your ticket is to fly from Kentucky to Illinois in the morning. If you’re flexible enough to do this you can expect to save up to 32% on your trip compared to booking a flight in the evening.
What is the cheapest day to fly from Kentucky to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Kentucky to Illinois. Price data was last updated on May 2, 2026.
Travelers seeking maximum savings on their Kentucky to Illinois flight should consider departing on Saturday at noon when fares are most often at their lowest. Monday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Kentucky to Illinois
Explore weekly flight availability from Kentucky to Illinois. 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 5, 2026.
The most flights from USKY to USIL are scheduled on a Monday (52 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (24 on average).
How much does it cost to fly round-trip from Kentucky to Illinois?
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated May 5, 2026.
Read through reviews of airlines operating flights from Kentucky to Illinois, such as Southwest,Contour, andUnited Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Overall
7.9
Food
7.0
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Illinois. 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
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Alternative routes for Kentucky to Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Illinois by cabin class
Find flights from Kentucky to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Illinois flights
Browse other Kentucky and Illinois flight options. Last updated on May 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Illinois
Find the right flight back to Kentucky after your stay in Illinois
Kentucky to Illinois flights
Consider these flights traveling from Kentucky to Illinois.
Top 4 airlines flying from Kentucky to Illinois
Discover the top 4 airlines that operate flights from Kentucky to Illinois. 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$97 | Average$271 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$97 | Average$230 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$108 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$280 | FlexibilityNo cancel fee | On-time69% |