$79+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Aug 28 — Sep 41
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 July 29, 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 July 29, 2026.
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:10 pm
CVG
- MDW
2 stops6h 25m
Southwest
Thu 9/178:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 7/27![Southwest logo]()
$172
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:25 pm
CVG
- MDW
1 stop5h 55m
Southwest
Mon 8/243:20 pm
MDW
- CVG
1 stop5h 15m
Southwest
Deal found 7/28![Southwest logo]()
$177
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:53 am
CVG
- ORD
1 stop6h 24m
Delta
Sat 8/225:18 pm
ORD
- CVG
1 stop4h 22m
Delta
Deal found 7/27![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am
CVG
- MDW
2 stops10h 50m
Southwest
Sat 9/123:25 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 7/28![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:50 am
CVG
- MDW
2 stops8h 15m
Southwest
Mon 8/313:20 pm
MDW
- CVG
1 stop5h 15m
Southwest
Deal found 7/28![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:50 am
CVG
- ORD
1 stop5h 27m
Delta
Sun 9/66:59 am
ORD
- CVG
1 stop5h 43m
Delta
Deal found 7/27![Delta logo]()
$182
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:05 am
CVG
- MDW
2 stops9h 25m
Southwest
Mon 9/148:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 7/27![Southwest logo]()
$183
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:50 am
CVG
- ORD
1 stop5h 27m
Delta
Mon 8/175:20 pm
ORD
- CVG
1 stop4h 20m
Delta
Deal found 7/24![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:05 am
CVG
- MDW
2 stops9h 20m
Southwest
Sat 8/222:25 pm
MDW
- CVG
1 stop3h 25m
Southwest
Deal found 7/27![Southwest logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:43 pm
CVG
- ORD
1 stop6h 40m
Frontier
Wed 10/77:28 pm
ORD
- CVG
1 stop15h 15m
Frontier
Deal found 7/26![Frontier logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:26 pm
CVG
- ORD
1 stop8h 33m
Frontier
Tue 8/251:59 pm
ORD
- CVG
1 stop20h 22m
Frontier
Deal found 7/25![Frontier logo]()
$192
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:00 am
CVG
- MDW
2 stops10h 50m
Southwest
Wed 9/21:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 7/27![Southwest logo]()
$193
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 July 29, 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 July 29, 2026.
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/292:23 pm
CVG
- MDW
1 stop5h 10m
Delta
Mon 8/315:45 pm
MDW
- CVG
1 stop3h 55m
Delta
Deal found 7/25![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/277:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Sun 8/306:00 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 7/26![Southwest logo]()
$196
This United Airlines deal was found by Cheapflights users on 7/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:00 am
CVG
- ORD
Nonstop1h 34m
United Airlines
Mon 10/59:40 pm
ORD
- CVG
Nonstop1h 27m
United Airlines
Deal found 7/24![United Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:37 pm
BNA
- RFD
Nonstop1h 32m
Multiple Airlines
Sun 8/239:35 pm
RFD
- BNA
1 stop16h 11m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:34 pm
BNA
- RFD
Nonstop1h 29m
Allegiant Air
Mon 9/2110:22 am
RFD
- BNA
1 stop7h 15m
Allegiant Air
Deal found 7/28![Allegiant Air logo]()
$225
This Contour deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:00 am
BNA
- ORD
1 stop3h 40m
Contour
Wed 8/2611:15 am
ORD
- BNA
1 stop4h 55m
Contour
Deal found 7/26![Contour logo]()
$247
This American Airlines deal was found by Cheapflights users on 7/23. 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.
Thu 9/36:52 pm
TYS
- ORD
Nonstop2h 12m
American Airlines
Sun 9/63:29 pm
ORD
- TYS
Nonstop1h 52m
American Airlines
Deal found 7/23![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:05 pm
BNA
- ORD
2 stops26h 54m
Frontier
Mon 8/319:10 pm
ORD
- BNA
1 stop13h 07m
Frontier
Deal found 7/28![Frontier logo]()
$262
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/298:14 am
CVG
- ORD
1 stop3h 28m
Delta
Mon 8/315:20 pm
ORD
- CVG
1 stop4h 20m
Delta
Deal found 7/25![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:27 am
CVG
- ORD
1 stop5h 15m
Delta
Mon 8/175:20 pm
ORD
- CVG
1 stop4h 20m
Delta
Deal found 7/25![Delta logo]()
$187
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/258:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Tue 9/296:30 am
MDW
- CVG
1 stop6h 10m
Southwest
Deal found 7/27![Southwest logo]()
$206
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:50 pm
SDF
- ORD
Nonstop1h 40m
United Airlines
Mon 10/56:55 am
ORD
- SDF
Nonstop1h 39m
United Airlines
Deal found 7/25![United Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:25 pm
CVG
- MDW
1 stop6h 00m
Southwest
Mon 9/78:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 7/26![Southwest logo]()
$206
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/268:55 am
CVG
- ORD
Nonstop1h 40m
United Airlines
Mon 11/306:50 am
ORD
- CVG
Nonstop1h 30m
United Airlines
Deal found 7/28![United Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:55 pm
BNA
- RFD
3 stops24h 28m
Multiple Airlines
Sun 8/233:59 pm
RFD
- BNA
Nonstop1h 25m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/411:34 am
BNA
- RFD
1 stop24h 17m
Allegiant Air
Sun 9/63:53 pm
RFD
- BNA
Nonstop1h 30m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$246
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:25 pm
CVG
- MDW
1 stop3h 45m
Southwest
Sun 8/236:00 pm
MDW
- CVG
Nonstop1h 15m
Southwest
Deal found 7/27![Southwest logo]()
$206
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/311:10 am
CVG
- ORD
1 stop6h 22m
Delta
Thu 11/57:10 am
ORD
- CVG
1 stop5h 26m
Delta
Deal found 7/27![Delta logo]()
$208
This American Airlines deal was found by Cheapflights users on 7/23. 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.
Fri 10/28:00 am
TYS
- ORD
Nonstop2h 10m
American Airlines
Tue 10/68:20 am
ORD
- TYS
Nonstop1h 45m
American Airlines
Deal found 7/23![American Airlines logo]()
$259
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:20 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Mon 10/57:05 am
MDW
- CVG
1 stop5h 40m
Southwest
Deal found 7/25![Southwest logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:00 am
BNA
- RFD
Nonstop1h 31m
Allegiant Air
Sun 8/1611:37 am
RFD
- BNA
1 stop8h 00m
Allegiant Air
Deal found 7/28![Allegiant Air logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:37 pm
BNA
- RFD
Nonstop1h 32m
Multiple Airlines
Wed 8/262:13 pm
RFD
- BNA
2 stops23h 33m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$253
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:57 pm
LEX
- ORD
Nonstop1h 52m
United Airlines
Sat 9/125:50 pm
ORD
- LEX
Nonstop1h 38m
United Airlines
Deal found 7/27![United Airlines logo]()
$237
This Contour deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:00 am
BNA
- ORD
1 stop3h 40m
Contour
Sun 8/1612:30 pm
ORD
- BNA
1 stop3h 40m
Contour
Deal found 7/28![Contour logo]()
$287
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:23 pm
CVG
- ORD
1 stop5h 06m
Delta
Mon 8/241:59 pm
ORD
- CVG
1 stop4h 55m
Delta
Deal found 7/28![Delta logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/144:36 pm
BNA
- RFD
1 stop15h 49m
Allegiant Air
Sun 8/1611:37 am
RFD
- BNA
1 stop8h 00m
Allegiant Air
Deal found 7/28![Allegiant Air logo]()
$252
This United Airlines deal was found by Cheapflights users on 7/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/219:52 am
LEX
- ORD
Nonstop1h 48m
United Airlines
Fri 8/289:20 pm
ORD
- LEX
Nonstop1h 35m
United Airlines
Deal found 7/24![United Airlines logo]()
$237
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/202:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Mon 8/246:10 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 7/28![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/231:37 pm
BNA
- RFD
Nonstop1h 32m
Multiple Airlines
Sun 8/309:35 pm
RFD
- BNA
1 stop16h 11m
Multiple Airlines
Deal found 7/27![Multiple Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 7/23. 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.
Tue 8/46:32 pm
TYS
- ORD
Nonstop2h 18m
American Airlines
Tue 9/110:00 am
ORD
- TYS
Nonstop1h 46m
American Airlines
Deal found 7/23![American Airlines logo]()
$304
Last-minute flights from Kentucky to IllinoisDiscover last-minute flight deals from Kentucky to Illinois. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Illinois. Data last updated July 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:18 pm
CVG
- ORD
1 stop8h 35m
Frontier
Mon 8/171:50 pm
ORD
- CVG
1 stop20h 31m
Frontier
Deal found 7/24![Frontier logo]()
$194
This Cheapflightsfares deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:23 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Sun 8/162:49 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 7/28![Allegiant Air logo]()
$197
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1511:50 am
CVG
- ORD
1 stop5h 27m
Delta
Mon 8/175:20 pm
ORD
- CVG
1 stop4h 20m
Delta
Deal found 7/24![Delta logo]()
$187
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:53 am
CVG
- ORD
1 stop6h 24m
Delta
Sat 8/225:18 pm
ORD
- CVG
1 stop4h 22m
Delta
Deal found 7/27![Delta logo]()
$177
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:25 pm
CVG
- MDW
1 stop5h 55m
Southwest
Mon 8/243:20 pm
MDW
- CVG
1 stop5h 15m
Southwest
Deal found 7/28![Southwest logo]()
$177
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/224:55 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Wed 8/261:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 7/26![Southwest logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:26 pm
CVG
- ORD
1 stop8h 33m
Frontier
Tue 8/251:59 pm
ORD
- CVG
1 stop20h 22m
Frontier
Deal found 7/25![Frontier logo]()
$192
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:00 am
CVG
- MDW
2 stops10h 50m
Southwest
Wed 9/21:00 pm
MDW
- CVG
2 stops6h 50m
Southwest
Deal found 7/27![Southwest logo]()
$193
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/278:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Sun 8/309:15 am
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 7/27![Southwest logo]()
$196
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:29 pm
CVG
- ORD
Nonstop1h 34m
United Airlines
Sun 8/306:09 pm
ORD
- CVG
Nonstop1h 34m
United Airlines
Deal found 7/27![United Airlines logo]()
$196
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:50 am
CVG
- MDW
2 stops8h 15m
Southwest
Mon 8/313:20 pm
MDW
- CVG
1 stop5h 15m
Southwest
Deal found 7/28![Southwest logo]()
$182
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:50 am
CVG
- ORD
1 stop5h 27m
Delta
Sun 9/66:59 am
ORD
- CVG
1 stop5h 43m
Delta
Deal found 7/27![Delta 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 July 29, 2026.
Search for one-way flight options from Kentucky to Illinois. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/108:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 7/27![Southwest logo]()
$79
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:30 am
CVG
- ORD
Nonstop1h 40m
American Airlines
Deal found 7/26![American Airlines logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2612:48 pm
CVG
- MDW
1 stop23h 10m
Frontier
Deal found 7/25![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2612:48 pm
CVG
- ORD
1 stop24h 14m
Frontier
Deal found 7/25![Frontier logo]()
$81
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:30 am
CVG
- ORD
1 stop29h 20m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/282:01 pm
CVG
- ORD
1 stop26h 19m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$84
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/254:10 pm
CVG
- ORD
1 stop5h 20m
Delta
Deal found 7/28![Delta logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/61:23 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 7/26![Allegiant Air logo]()
$94
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:14 am
CVG
- ORD
1 stop3h 28m
Delta
Deal found 7/24![Delta logo]()
$94
This Super.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:23 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 7/27![Allegiant Air logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:26 pm
CVG
- ORD
1 stop8h 33m
Frontier
Deal found 7/28![Frontier logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Wed 10/214:14 pm
TYS
- ORD
1 stop24h 12m
Multiple Airlines
Deal found 7/24![Multiple Airlines logo]()
$99
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 July 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $172 (Southwest) |
One-way from | $79 (Southwest) |
Popular in | January |
Cheapest in | November |
Average price | $337 |
Good round-trip deal | $163 or less |
Good one-way deal | $214 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 July 29, 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
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Sat 8/29
2:23 pm-6:33 pm
1 stop5h 10m
Chicago Midway
Mon 8/31
5:45 pm-10:40 pm
1 stop3h 55m
$187
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Sat 8/29
8:14 am-10:42 am
1 stop3h 28m
Chicago O'Hare Intl
Mon 8/31
5:20 pm-10:40 pm
1 stop4h 20m
$187
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Sat 8/15
6:27 am-10:42 am
1 stop5h 15m
Chicago O'Hare Intl
Mon 8/17
5:20 pm-10:40 pm
1 stop4h 20m
$187
Quickest round-trip
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Thu 8/27
7:00 pm-7:10 pm
Nonstop1h 10m
Chicago Midway
Sun 8/30
6:00 pm-8:15 pm
Nonstop1h 15m
$196
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Fri 10/2
7:00 am-7:34 am
Nonstop1h 34m
Chicago O'Hare Intl
Mon 10/5
9:40 pm-12:07 am
Nonstop1h 27m
$196
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Fri 9/25
8:10 am-8:15 am
Nonstop1h 05m
Chicago Midway
Tue 9/29
6:30 am-1:40 pm
1 stop6h 10m
$206
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Fri 9/4
5:25 pm-10:25 pm
1 stop6h 00m
Chicago Midway
Mon 9/7
8:05 am-10:25 am
Nonstop1h 20m
$206
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Thu 8/20
5:25 pm-8:10 pm
1 stop3h 45m
Chicago Midway
Sun 8/23
6:00 pm-8:15 pm
Nonstop1h 15m
$206
CincinnatiChicago
CVG - MDW
CVGMDW
Cincinnati Cinci./N. Kentucky
Fri 10/2
8:20 pm-8:35 pm
Nonstop1h 15m
Chicago Midway
Mon 10/5
7:05 am-1:45 pm
1 stop5h 40m
$206
CincinnatiChicago
CVG - ORD
CVGORD
Cincinnati Cinci./N. Kentucky
Tue 11/3
11:10 am-4:32 pm
1 stop6h 22m
Chicago O'Hare Intl
Thu 11/5
7:10 am-1:36 pm
1 stop5h 26m
$208
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.
CVG-MDW
CVG-ORD
BNA-RFD
BNA-ORD
TYS-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
CVG-MDW
CVG-ORD
BNA-RFD
BNA-ORD
What is the cheapest month to book a flight from Kentucky to Illinois?
Currently, October is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $228). Flying from Kentucky to Illinois in June is currently the most expensive (average of $367). 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 July 29, 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 34% on your trip compared to booking a flight in the evening.
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 July 29, 2026.
The most flights from USKY to USIL are scheduled on a Tuesday (39 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (18 on average).
How much does it cost to fly round-trip from Kentucky to Illinois?
Airfare is below average for this route at the moment.
Kentucky to Illinois flights typically cost between $227 and $349 in September.The cheapest round-trip price found within the last 5 days was $217 on United Airlines (Sep 10-Sep 12).
How far ahead should I book a flight from Kentucky to Illinois?
The best time to book flights from Kentucky to Illinois is 78 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 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 July 25, 2026.
Travelers seeking maximum savings on their Kentucky to Illinois flight should consider departing on Sunday mornings when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
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 July 29, 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.
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Comfort
8.0
Entertainment
7.5
Overall
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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 July 29, 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 July 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$77 | Average$272 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$104 | Average$170 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$288 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$127 | Average$288 | FlexibilityNo cancel fee | On-time71% |