$66+ Cheap flights from Midway (MDW) to Kentucky
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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Jun 11 — Jun 181
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Kentucky with Cheapflights
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Cheapest flights from Midway to KentuckyExplore the most affordable flight options available from Midway to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2026.
Explore the most affordable flight options available from Midway to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 12, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/512:56 pm
MDW
- TYS
Nonstop1h 25m
Allegiant Air
Fri 10/911:14 am
TYS
- MDW
Nonstop1h 32m
Allegiant Air
Deal found 5/11![Allegiant Air logo]()
$139
This Booking.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 7/21:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 5/11![Allegiant Air logo]()
$146
This Cheapflightsfares deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/42:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 6/111:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/8![Allegiant Air logo]()
$150
This Cheapflightsfares deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/252:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/281:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/12![Allegiant Air logo]()
$154
This Cheapflightsfares deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/182:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/211:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/11![Allegiant Air logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/282:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Sun 5/311:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 5/11![Allegiant Air logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/312:47 pm
MDW
- TYS
Nonstop1h 26m
Multiple Airlines
Mon 6/112:55 pm
TYS
- MDW
2 stops34h 07m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/46:00 am
MDW
- TYS
2 stops33h 40m
Multiple Airlines
Thu 6/251:22 pm
TYS
- MDW
Nonstop1h 34m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/96:00 am
MDW
- CVG
1 stop28h 49m
Frontier
Tue 6/1612:24 pm
CVG
- MDW
1 stop10h 47m
Frontier
Deal found 5/12![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/59:23 pm
MDW
- TYS
1 stop23h 15m
Allegiant Air
Sun 6/71:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/7![Allegiant Air logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/312:47 pm
MDW
- TYS
Nonstop1h 26m
Multiple Airlines
Tue 6/211:31 am
TYS
- MDW
2 stops35h 31m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$176
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/912:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Tue 6/169:00 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 5/12![Southwest logo]()
$177
Best flights from Midway to KentuckyDiscover carefully curated flight deals from Midway to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 12, 2026.
Discover carefully curated flight deals from Midway to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 12, 2026.
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 8/278:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Mon 8/317:00 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 5/11![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 7/146:00 am
MDW
- CVG
1 stop5h 28m
Delta
Sat 7/182:10 pm
CVG
- MDW
1 stop4h 57m
Delta
Deal found 5/10![Delta logo]()
$204
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/27:50 am
MDW
- CVG
2 stops8h 15m
Southwest
Thu 6/48:30 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 5/7![Southwest logo]()
$199
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 5/306:23 am
MDW
- CVG
1 stop5h 16m
Delta
Mon 6/14:11 pm
CVG
- MDW
1 stop5h 58m
Delta
Deal found 5/9![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/38:00 am
MDW
- CVG
1 stop3h 40m
Southwest
Sat 6/61:40 pm
CVG
- MDW
2 stops6h 35m
Southwest
Deal found 5/7![Southwest logo]()
$209
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/81:26 pm
MDW
- CVG
1 stop5h 32m
Delta
Mon 6/154:26 pm
CVG
- MDW
1 stop6h 51m
Delta
Deal found 5/11![Delta logo]()
$211
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 7/26:00 am
MDW
- CVG
1 stop4h 19m
Delta
Mon 7/62:15 pm
CVG
- MDW
1 stop5h 16m
Delta
Deal found 5/10![Delta logo]()
$211
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 10/147:45 am
MDW
- CVG
1 stop4h 50m
Southwest
Thu 10/158:10 am
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 5/11![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/297:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Mon 6/18:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 5/9![Southwest logo]()
$232
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/246:15 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Thu 6/48:30 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 5/9![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 5/275:12 pm
MDW
- TRI
1 stop4h 28m
Delta
Sun 5/316:00 am
TRI
- MDW
1 stop5h 00m
Delta
Deal found 5/12![Delta logo]()
$264
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/115:11 pm
MDW
- LEX
1 stop5h 56m
Delta
Sun 6/147:35 am
LEX
- MDW
1 stop6h 11m
Delta
Deal found 5/10![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 8/198:50 am
MDW
- BNA
1 stop3h 20m
Southwest
Tue 8/256:05 am
BNA
- MDW
Nonstop1h 30m
Southwest
Deal found 5/7![Southwest logo]()
$263
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/1712:50 pm
MDW
- LEX
1 stop5h 19m
Delta
Sat 6/205:56 pm
LEX
- MDW
1 stop5h 21m
Delta
Deal found 5/11![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/39:25 am
MDW
- TYS
1 stop6h 45m
Southwest
Tue 6/96:55 pm
TYS
- MDW
1 stop3h 15m
Southwest
Deal found 5/9![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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.
Fri 6/195:11 pm
MDW
- LEX
1 stop5h 56m
Delta
Sun 6/2110:10 am
LEX
- MDW
1 stop7h 06m
Delta
Deal found 5/9![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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.
Fri 7/1011:05 am
MDW
- TYS
1 stop5h 11m
Delta
Sun 7/125:40 am
TYS
- MDW
1 stop5h 25m
Delta
Deal found 5/11![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/210:10 am
MDW
- BNA
1 stop2h 55m
Southwest
Wed 6/1711:00 am
BNA
- MDW
1 stop4h 55m
Southwest
Deal found 5/8![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/107:45 am
MDW
- SDF
Nonstop1h 20m
Southwest
Wed 6/178:45 am
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 5/11![Southwest logo]()
$275
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 7/86:00 am
MDW
- LEX
1 stop5h 17m
Delta
Sun 7/127:35 am
LEX
- MDW
1 stop6h 03m
Delta
Deal found 5/8![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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.
Fri 7/176:00 am
MDW
- TYS
1 stop4h 05m
Delta
Tue 7/215:40 am
TYS
- MDW
1 stop5h 25m
Delta
Deal found 5/7![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/231:15 pm
MDW
- TYS
2 stops7h 00m
Southwest
Tue 6/308:10 am
TYS
- MDW
1 stop6h 50m
Southwest
Deal found 5/8![Southwest logo]()
$284
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 5/2712:53 pm
MDW
- LEX
1 stop5h 40m
Delta
Mon 6/18:04 am
LEX
- MDW
1 stop5h 38m
Delta
Deal found 5/9![Delta logo]()
$282
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 5/281:30 pm
MDW
- BNA
1 stop5h 25m
Southwest
Mon 6/14:55 pm
BNA
- MDW
1 stop3h 50m
Southwest
Deal found 5/7![Southwest logo]()
$285
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 9/261:00 pm
MDW
- LEX
1 stop3h 10m
Delta
Mon 9/285:55 pm
LEX
- MDW
1 stop4h 51m
Delta
Deal found 5/10![Delta logo]()
$284
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 8/111:00 pm
MDW
- TYS
2 stops4h 55m
Southwest
Fri 8/145:45 pm
TYS
- MDW
1 stop5h 35m
Southwest
Deal found 5/10![Southwest logo]()
$297
This Delta deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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.
Fri 8/710:54 am
MDW
- LEX
1 stop5h 17m
Delta
Sun 8/97:35 am
LEX
- MDW
1 stop6h 04m
Delta
Deal found 5/8![Delta logo]()
$289
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/249:00 am
MDW
- TYS
1 stop7h 00m
Southwest
Sat 6/276:55 pm
TYS
- MDW
1 stop5h 20m
Southwest
Deal found 5/11![Southwest logo]()
$299
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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.
Fri 5/225:10 pm
MDW
- LEX
1 stop5h 49m
Delta
Sun 5/243:32 pm
LEX
- MDW
1 stop6h 37m
Delta
Deal found 5/7![Delta logo]()
$299
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/65:50 pm
MDW
- SDF
Nonstop1h 10m
Southwest
Sun 6/78:00 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 5/8![Southwest logo]()
$301
Last-minute flights from Midway to KentuckyDiscover last-minute flight deals from Midway to Kentucky. Data last updated May 12, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kentucky. Data last updated May 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/259:30 pm
MDW
- TYS
1 stop21h 01m
Allegiant Air
Thu 5/281:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 5/10![Allegiant Air logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/282:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Sun 5/311:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 5/11![Allegiant Air logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/312:47 pm
MDW
- TYS
Nonstop1h 26m
Multiple Airlines
Mon 6/112:55 pm
TYS
- MDW
2 stops34h 07m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/312:47 pm
MDW
- TYS
Nonstop1h 26m
Multiple Airlines
Tue 6/211:31 am
TYS
- MDW
2 stops35h 31m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/42:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 6/111:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/8![Allegiant Air logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/46:00 am
MDW
- TYS
2 stops33h 40m
Multiple Airlines
Thu 6/251:22 pm
TYS
- MDW
Nonstop1h 34m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/59:23 pm
MDW
- TYS
1 stop23h 15m
Allegiant Air
Sun 6/71:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/7![Allegiant Air logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/96:00 am
MDW
- CVG
1 stop28h 49m
Frontier
Tue 6/1612:24 pm
CVG
- MDW
1 stop10h 47m
Frontier
Deal found 5/12![Frontier logo]()
$173
This Southwest deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/912:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Tue 6/169:00 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 5/12![Southwest logo]()
$177
This Cheapflightsfares deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/182:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/211:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/11![Allegiant Air logo]()
$155
This Booking.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/252:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Thu 7/21:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 5/11![Allegiant Air logo]()
$146
This Cheapflightsfares deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/252:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Sun 6/281:22 pm
TYS
- MDW
Nonstop1h 34m
Allegiant Air
Deal found 5/12![Allegiant Air logo]()
$154
One-way flights from Midway to KentuckySearch for one-way flight options from Midway to Kentucky. Find affordable one-way fares based on user searches. Data last updated May 12, 2026.
Search for one-way flight options from Midway to Kentucky. Find affordable one-way fares based on user searches. Data last updated May 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/912:27 pm
MDW
- CVG
1 stop22h 22m
Frontier
Deal found 5/8![Frontier logo]()
$66
This Kiwi.com deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 10/22:24 pm
MDW
- TYS
Nonstop1h 25m
Allegiant Air
Deal found 5/10![Allegiant Air logo]()
$67
This Kiwi.com deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 7/411:59 am
MDW
- CVG
1 stop22h 14m
Frontier
Deal found 5/9![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/212:27 pm
MDW
- CVG
1 stop22h 14m
Frontier
Deal found 5/11![Frontier logo]()
$70
This Trip.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 5/212:47 pm
MDW
- TYS
Nonstop1h 26m
Allegiant Air
Deal found 5/11![Allegiant Air logo]()
$73
This Cheapflightsfares deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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.
Sun 7/262:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 5/10![Allegiant Air logo]()
$76
This Cheapflightsfares deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/22:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 5/7![Allegiant Air logo]()
$83
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/46:00 am
MDW
- CVG
1 stop28h 41m
Frontier
Deal found 5/12![Frontier logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 6/116:00 am
MDW
- CVG
1 stop28h 49m
Frontier
Deal found 5/12![Frontier logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 5/12. Clicking the “Pick Dates” 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 7/86:00 am
MDW
- CVG
1 stop28h 13m
Frontier
Deal found 5/12![Frontier logo]()
$88
This Southwest deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/26:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 5/11![Southwest logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 5/11. Clicking the “Pick Dates” 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 6/182:46 pm
MDW
- TYS
Nonstop1h 28m
Allegiant Air
Deal found 5/11![Allegiant Air logo]()
$89
Find flight deals from Midway to Kentucky
Keep the following information in mind while searching for Midway to Kentucky flight deals. Data was last updated May 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $139 (Cheapflightsfares) |
One-way from | $66 (Kiwi.com) |
Popular in | March |
Cheapest in | August |
Average price | $395 |
Good round-trip deal | $301 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Midway to Kentucky 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 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Thu 8/27
8:05 am-10:25 am
Nonstop1h 20m
Cincinnati Cinci./N. Kentucky
Mon 8/31
7:00 pm-7:10 pm
Nonstop1h 10m
$191
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Tue 6/2
7:50 am-5:05 pm
2 stops8h 15m
Cincinnati Cinci./N. Kentucky
Thu 6/4
8:30 pm-8:40 pm
Nonstop1h 10m
$199
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Tue 7/14
6:00 am-12:28 pm
1 stop5h 28m
Cincinnati Cinci./N. Kentucky
Sat 7/18
2:10 pm-6:07 pm
1 stop4h 57m
$204
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 6/3
8:00 am-12:40 pm
1 stop3h 40m
Cincinnati Cinci./N. Kentucky
Sat 6/6
1:40 pm-7:15 pm
2 stops6h 35m
$209
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Sat 5/30
6:23 am-12:39 pm
1 stop5h 16m
Cincinnati Cinci./N. Kentucky
Mon 6/1
4:11 pm-9:09 pm
1 stop5h 58m
$211
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Mon 6/8
1:26 pm-7:58 pm
1 stop5h 32m
Cincinnati Cinci./N. Kentucky
Mon 6/15
4:26 pm-10:17 pm
1 stop6h 51m
$211
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Thu 7/2
6:00 am-11:19 am
1 stop4h 19m
Cincinnati Cinci./N. Kentucky
Mon 7/6
2:15 pm-6:31 pm
1 stop5h 16m
$211
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 10/14
7:45 am-1:35 pm
1 stop4h 50m
Cincinnati Cinci./N. Kentucky
Thu 10/15
8:10 am-8:20 am
Nonstop1h 10m
$229
Quickest round-trip
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Fri 5/29
7:00 pm-9:10 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Mon 6/1
8:20 pm-8:30 pm
Nonstop1h 10m
$232
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Sun 5/24
6:15 pm-8:25 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Thu 6/4
8:30 pm-8:40 pm
Nonstop1h 10m
$232
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Midway to Kentucky
Have a flexible travel schedule? Discover the best time to fly to Kentucky from Midway with our price prediction graph.
MDW-CVG
MDW-TRI
MDW-TYS
MDW-BNA
MDW-LEX
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago Midway Airport to Kentucky
MDW-USKY
MDW-CVG
MDW-TRI
MDW-TYS
MDW-BNA
What is the cheapest time of day to fly from MDW to KY?
Find hourly flight availability from Midway to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 12, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 41% on flights from Chicago Midway Airport to Kentucky by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Chicago Midway Airport to Kentucky?
Use this chart to determine the cheapest time to fly round-trip from Midway to Kentucky. Price data was last updated on May 9, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Kentucky flight should consider departing on Tuesday afternoons 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.
How much does it cost to fly round-trip from Chicago Midway Airport to Kentucky?
Reviews of airlines servicing Kentucky
Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated May 12, 2026.
Peruse reviews from past customers who have flown with Southwest from Chicago Midway Airport to Kentucky to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Comfort
8.0
Food
7.0
Overall
8.0
Crew
8.6
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 Midway to Kentucky. 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 Midway to Kentucky
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Complete your trip
Complete your trip to Kentucky by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Midway to Kentucky by cabin class
Find flights from Midway to Kentucky, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Midway and Kentucky flights
Browse other Midway and Kentucky flight options. Last updated on May 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Kentucky flights
Consider these flights traveling from Midway to Kentucky.
Top airline flying from Midway to Kentucky
Discover the top airline that operate flights from Midway to Kentucky. 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$124 | Average$249 | FlexibilityNo cancel fee | On-time63% |