$70+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
May 24 — May 311
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 April 24, 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 April 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Thu 4/309:50 am
STL
- BNA
1 stop3h 58m
Southern / Mokulele
Deal found 4/22![Southern / Mokulele logo]()
$171
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1211:16 am
SDF
- ORD
Nonstop1h 40m
American Airlines
Tue 5/196:57 pm
ORD
- SDF
Nonstop1h 33m
American Airlines
Deal found 4/22![American Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/203:30 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Wed 5/277:40 am
MDW
- SDF
Nonstop1h 10m
Southwest
Deal found 4/20![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/198:55 am
SDF
- MDW
Nonstop1h 20m
Southwest
Tue 5/2612:50 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 4/19![Southwest logo]()
$178
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:09 pm
BNA
- STL
1 stop6h 48m
Frontier
Mon 6/18:08 pm
STL
- BNA
1 stop22h 14m
Frontier
Deal found 4/20![Frontier logo]()
$181
This Kissandfly.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/22![Southern / Mokulele logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 stop20h 09m
Frontier
Sat 5/301:50 pm
ORD
- CVG
1 stop20h 14m
Frontier
Deal found 4/19![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/810:33 am
SDF
- ORD
1 stop14h 26m
Multiple Airlines
Sun 5/103:44 pm
ORD
- SDF
1 stop16h 44m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 5/187:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/24![Southwest logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/1912:54 pm
CVG
- ORD
1 stop20h 09m
Frontier
Mon 6/226:55 am
ORD
- CVG
1 stop27h 19m
Frontier
Deal found 4/20![Frontier logo]()
$191
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/198:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Tue 5/2610:15 am
MDW
- CVG
2 stops10h 00m
Southwest
Deal found 4/20![Southwest logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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
1 stop20h 09m
Frontier
Tue 6/161:50 pm
ORD
- CVG
1 stop20h 59m
Frontier
Deal found 4/19![Frontier logo]()
$192
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 April 24, 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 April 24, 2026.
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:00 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Sat 5/307:40 am
MDW
- CVG
Nonstop1h 05m
Southwest
Deal found 4/23![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:20 am
BNA
- STL
1 stop6h 02m
Delta
Tue 5/2610:49 am
STL
- BNA
1 stop6h 42m
Delta
Deal found 4/21![Delta logo]()
$217
This Contour deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:00 am
BNA
- ORD
1 stop3h 30m
Contour
Sun 6/712:20 pm
ORD
- BNA
1 stop3h 50m
Contour
Deal found 4/22![Contour logo]()
$217
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:00 am
TRI
- ORD
Nonstop2h 02m
United Airlines
Mon 7/69:40 pm
ORD
- TRI
Nonstop1h 49m
United Airlines
Deal found 4/19![United Airlines logo]()
$229
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/28:00 am
TRI
- ORD
Nonstop2h 10m
American Airlines
Sun 7/59:07 pm
ORD
- TRI
Nonstop1h 52m
American Airlines
Deal found 4/20![American Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/82:35 pm
BNA
- STL
1 stop4h 01m
Multiple Airlines
Mon 6/158:08 pm
STL
- BNA
2 stops15h 52m
Multiple Airlines
Deal found 4/24![Multiple Airlines logo]()
$274
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/197:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Tue 5/2610:15 am
MDW
- SDF
2 stops9h 50m
Southwest
Deal found 4/19![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Sat 5/237:40 am
MDW
- CVG
Nonstop1h 05m
Southwest
Deal found 4/21![Southwest logo]()
$193
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:00 am
TRI
- ORD
Nonstop2h 02m
United Airlines
Sun 6/287:25 am
ORD
- TRI
Nonstop1h 53m
United Airlines
Deal found 4/21![United Airlines logo]()
$229
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/28:00 am
TRI
- ORD
Nonstop2h 10m
American Airlines
Sat 7/119:07 pm
ORD
- TRI
Nonstop1h 52m
American Airlines
Deal found 4/19![American Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/34:28 pm
SDF
- ORD
1 stop5h 52m
Delta
Sat 6/63:47 pm
ORD
- SDF
1 stop7h 05m
Delta
Deal found 4/23![Delta logo]()
$230
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 6/88:25 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Wed 6/105:30 pm
MDW
- CVG
1 stop4h 35m
Southwest
Deal found 4/20![Southwest logo]()
$204
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/1110:53 am
TRI
- ORD
Nonstop2h 02m
United Airlines
Mon 6/152:15 pm
ORD
- TRI
Nonstop1h 51m
United Airlines
Deal found 4/19![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:50 am
SDF
- ORD
1 stop6h 06m
Delta
Tue 5/267:00 am
ORD
- SDF
1 stop5h 51m
Delta
Deal found 4/22![Delta logo]()
$230
This American Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/28:25 pm
TRI
- ORD
1 stop4h 34m
American Airlines
Mon 7/69:07 pm
ORD
- TRI
Nonstop1h 52m
American Airlines
Deal found 4/20![American Airlines logo]()
$249
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Tue 5/268:00 am
MDW
- CVG
1 stop3h 40m
Southwest
Deal found 4/23![Southwest logo]()
$208
This United Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
TRI
- ORD
Nonstop2h 02m
United Airlines
Mon 7/279:40 pm
ORD
- TRI
Nonstop1h 49m
United Airlines
Deal found 4/23![United Airlines logo]()
$229
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/38:10 am
SDF
- MDW
1 stop4h 46m
Delta
Sat 6/65:30 pm
MDW
- SDF
1 stop5h 29m
Delta
Deal found 4/21![Delta logo]()
$230
This Contour deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/23![Contour logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/238:20 pm
BNA
- STL
2 stops18h 11m
Multiple Airlines
Mon 5/257:20 pm
STL
- BNA
1 stop13h 43m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$299
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/228:25 pm
TRI
- ORD
1 stop4h 34m
American Airlines
Mon 7/279:07 pm
ORD
- TRI
Nonstop1h 52m
American Airlines
Deal found 4/23![American Airlines logo]()
$249
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:00 am
TRI
- ORD
Nonstop2h 02m
United Airlines
Sat 6/277:25 am
ORD
- TRI
Nonstop1h 53m
United Airlines
Deal found 4/21![United Airlines logo]()
$229
This Southwest deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Thu 6/47:05 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/23![Southwest logo]()
$211
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
SDF
- ORD
1 stop7h 08m
Delta
Fri 8/288:15 am
ORD
- SDF
1 stop4h 33m
Delta
Deal found 4/23![Delta logo]()
$234
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/235:47 pm
SDF
- MDW
1 stop4h 22m
Delta
Tue 5/261:22 pm
MDW
- SDF
2 stops10h 03m
Delta
Deal found 4/23![Delta logo]()
$235
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/193:40 pm
BNA
- STL
1 stop4h 15m
Southwest
Tue 5/2611:35 am
STL
- BNA
Nonstop1h 10m
Southwest
Deal found 4/21![Southwest logo]()
$214
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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.
Fri 5/156:00 am
LEX
- ORD
1 stop5h 11m
American Airlines
Sun 5/248:06 am
ORD
- LEX
Nonstop1h 36m
American Airlines
Deal found 4/19![American Airlines logo]()
$259
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
CVG
- ORD
Nonstop1h 35m
United Airlines
Wed 5/2010:44 am
ORD
- CVG
Nonstop1h 23m
United Airlines
Deal found 4/21![United Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/197:00 am
SDF
- ORD
1 stop6h 50m
Southwest
Tue 5/262:40 pm
ORD
- SDF
1 stop5h 25m
Southwest
Deal found 4/19![Southwest logo]()
$215
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/218:10 pm
LEX
- ORD
1 stop4h 49m
American Airlines
Wed 5/276:55 am
ORD
- LEX
1 stop4h 43m
American Airlines
Deal found 4/24![American Airlines logo]()
$269
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated April 24, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated April 24, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Thu 4/309:50 am
STL
- BNA
1 stop3h 58m
Southern / Mokulele
Deal found 4/22![Southern / Mokulele logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/810:33 am
SDF
- ORD
1 stop14h 26m
Multiple Airlines
Sun 5/103:44 pm
ORD
- SDF
1 stop16h 44m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$191
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1211:16 am
SDF
- ORD
Nonstop1h 40m
American Airlines
Tue 5/196:57 pm
ORD
- SDF
Nonstop1h 33m
American Airlines
Deal found 4/22![American Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Mon 5/187:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 4/24![Southwest logo]()
$191
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:36 am
CVG
- ORD
Nonstop1h 45m
American Airlines
Mon 5/187:14 pm
ORD
- CVG
Nonstop1h 30m
American Airlines
Deal found 4/24![American Airlines logo]()
$191
This Southwest deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/198:55 am
SDF
- MDW
Nonstop1h 20m
Southwest
Tue 5/2612:50 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 4/19![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/198:35 am
CVG
- MDW
Nonstop1h 10m
Southwest
Tue 5/2610:15 am
MDW
- CVG
2 stops10h 00m
Southwest
Deal found 4/20![Southwest logo]()
$192
This Southwest deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/203:30 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Wed 5/277:40 am
MDW
- SDF
Nonstop1h 10m
Southwest
Deal found 4/20![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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
1 stop20h 09m
Frontier
Tue 6/161:50 pm
ORD
- CVG
1 stop20h 59m
Frontier
Deal found 4/19![Frontier logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 stop20h 09m
Frontier
Sat 5/301:50 pm
ORD
- CVG
1 stop20h 14m
Frontier
Deal found 4/19![Frontier logo]()
$190
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:09 pm
BNA
- STL
1 stop6h 48m
Frontier
Mon 6/18:08 pm
STL
- BNA
1 stop22h 14m
Frontier
Deal found 4/20![Frontier logo]()
$181
This Kissandfly.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 4/22![Southern / Mokulele logo]()
$182
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 April 24, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated April 24, 2026.
This Frontier deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:02 pm
BNA
- STL
1 stop7h 19m
Frontier
Deal found 4/20![Frontier logo]()
$70
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1812:46 pm
CVG
- MDW
1 stop23h 23m
Frontier
Deal found 4/21![Frontier logo]()
$71
This Trip.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/69:30 am
BNA
- STL
1 stop6h 31m
Southern / Mokulele
Deal found 4/22![Southern / Mokulele logo]()
$74
This Trip.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 4/302:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Deal found 4/20![Southern / Mokulele logo]()
$75
This Frontier deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/152:08 pm
BNA
- STL
1 stop10h 13m
Frontier
Deal found 4/23![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/1812:46 pm
CVG
- ORD
1 stop20h 09m
Frontier
Deal found 4/20![Frontier logo]()
$76
This Expedia deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:00 am
CVG
- ORD
1 stop17h 13m
Frontier
Deal found 4/19![Frontier logo]()
$78
This Trip.com deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Deal found 4/24![Southern / Mokulele logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/192:35 pm
BNA
- STL
1 stop4h 01m
Southern / Mokulele
Deal found 4/21![Southern / Mokulele logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/1812:52 pm
CVG
- MDW
1 stop10h 19m
Frontier
Deal found 4/19![Frontier logo]()
$86
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/2012:54 pm
CVG
- MDW
1 stop23h 18m
Frontier
Deal found 4/20![Frontier logo]()
$88
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:59 pm
CVG
- ORD
Nonstop1h 42m
American Airlines
Deal found 4/22![American Airlines logo]()
$88
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 April 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (American Airlines) |
One-way from | $70 (Frontier) |
Popular in | January |
Cheapest in | November |
Average price | $332 |
Good round-trip deal | $107 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 April 24, 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
Quickest round-trip
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 5/23
5:00 pm-5:15 pm
Nonstop1h 15m
Chicago Midway
Sat 5/30
7:40 am-9:45 am
Nonstop1h 05m
$191
LouisvilleChicago
SDF - MDW
SDFMDW
Louisville Intl
Tue 5/19
7:15 pm-7:30 pm
Nonstop1h 15m
Chicago Midway
Tue 5/26
10:15 am-9:05 pm
2 stops9h 50m
$193
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Wed 5/20
7:35 pm-7:50 pm
Nonstop1h 15m
Chicago Midway
Sat 5/23
7:40 am-9:45 am
Nonstop1h 05m
$193
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Mon 6/8
8:25 pm-8:35 pm
Nonstop1h 10m
Chicago Midway
Wed 6/10
5:30 pm-11:05 pm
1 stop4h 35m
$204
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 5/23
12:50 pm-5:10 pm
2 stops5h 20m
Chicago Midway
Tue 5/26
8:00 am-12:40 pm
1 stop3h 40m
$208
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Mon 6/1
8:20 pm-8:30 pm
Nonstop1h 10m
Chicago Midway
Thu 6/4
7:05 pm-9:15 pm
Nonstop1h 10m
$211
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Tue 5/19
3:40 pm-7:55 pm
1 stop4h 15m
Lambert-St Louis
Tue 5/26
11:35 am-12:45 pm
Nonstop1h 10m
$214
LouisvilleChicago
SDF - ORD
SDFORD
Louisville Intl
Tue 5/19
7:00 am-12:50 pm
1 stop6h 50m
Chicago O'Hare Intl
Tue 5/26
2:40 pm-9:05 pm
1 stop5h 25m
$215
NashvilleSt. Louis
BNA - STL
BNASTL
Nashville Intl
Tue 5/19
6:20 am-12:22 pm
1 stop6h 02m
Lambert-St Louis
Tue 5/26
10:49 am-5:31 pm
1 stop6h 42m
$217
NashvilleChicago
BNA - ORD
BNAORD
Nashville Intl
Thu 6/4
8:00 am-11:30 am
1 stop3h 30m
Chicago O'Hare Intl
Sun 6/7
12:20 pm-4:10 pm
1 stop3h 50m
$217
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
SDF-ORD
SDF-MDW
CVG-ORD
CVG-MDW
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
SDF-ORD
SDF-MDW
CVG-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 April 24, 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 33% 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 April 18, 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. Wednesday afternoons 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 April 24, 2026.
The most flights from USKY to USIL are scheduled on a Monday (46 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 April 24, 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.
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Overall
8.0
Boarding
8.1
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.
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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 April 24, 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 April 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$225 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$97 | Average$265 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$108 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$114 | Average$265 | FlexibilityNo cancel fee | On-time69% |