$49+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
jul. 23 — jul. 301
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 juni 23, 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 juni 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 7/92:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/121:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$140
This Trip.com deal was found by Cheapflights users on 6/20. 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.
to. 7/232:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/261:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$142
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 7/162:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/191:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$146
This Cheapflightsfares deal was found by Cheapflights users on 6/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 7/192:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
to. 7/231:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/22![Allegiant Air logo]()
$155
This Southwest deal was found by Cheapflights users on 6/23. 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.
ti. 7/146:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
lø. 7/187:10 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/23![Southwest logo]()
$157
This Mytrip deal was found by Cheapflights users on 6/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 8/62:49 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
to. 8/131:23 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/22![Allegiant Air logo]()
$160
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 8/22:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 8/91:23 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$163
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 7/122:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/191:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/21![Allegiant Air logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 7/192:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/261:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/21![Allegiant Air logo]()
$171
This Southwest deal was found by Cheapflights users on 6/19. 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.
ti. 7/2112:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
ti. 7/287:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Deal found 6/19![Southwest logo]()
$172
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 7/122:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
to. 7/161:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$175
This Southwest deal was found by Cheapflights users on 6/23. 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.
lø. 8/88:00 am
MDW
- CVG
Nonstop1h 25m
Southwest
ma. 8/108:10 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 6/23![Southwest logo]()
$176
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 juni 23, 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 juni 23, 2026.
This Southwest deal was found by Cheapflights users on 6/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 7/146:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
lø. 7/189:15 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 6/22![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 6/21. 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.
ti. 7/149:19 am
MDW
- CVG
1 stop4h 57m
Delta
lø. 7/182:15 pm
CVG
- MDW
1 stop4h 52m
Delta
Deal found 6/21![Delta logo]()
$228
This Southwest deal was found by Cheapflights users on 6/23. 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.
ti. 8/185:55 pm
MDW
- CVG
Nonstop1h 15m
Southwest
ti. 8/257:15 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/23![Southwest logo]()
$157
This Southwest deal was found by Cheapflights users on 6/19. 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.
ti. 7/215:30 pm
MDW
- CVG
1 stop4h 40m
Southwest
ti. 7/287:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Deal found 6/19![Southwest logo]()
$182
This Southwest deal was found by Cheapflights users on 6/21. 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.
lø. 8/88:00 am
MDW
- CVG
Nonstop1h 25m
Southwest
ma. 8/107:05 am
CVG
- MDW
1 stop4h 55m
Southwest
Deal found 6/21![Southwest logo]()
$186
This Delta deal was found by Cheapflights users on 6/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 8/1310:54 am
MDW
- LEX
1 stop5h 17m
Delta
sø. 8/166:00 am
LEX
- MDW
1 stop4h 59m
Delta
Deal found 6/19![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/20. 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.
to. 9/107:30 am
MDW
- CVG
1 stop5h 05m
Southwest
ma. 9/145:25 pm
CVG
- MDW
1 stop5h 55m
Southwest
Deal found 6/20![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 6/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
fr. 8/76:05 am
MDW
- LEX
1 stop5h 06m
Delta
sø. 8/96:00 am
LEX
- MDW
1 stop6h 51m
Delta
Deal found 6/20![Delta logo]()
$269
This Delta deal was found by Cheapflights users on 6/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 10/2210:35 am
MDW
- LEX
1 stop5h 35m
Delta
sø. 10/256:00 am
LEX
- MDW
1 stop4h 52m
Delta
Deal found 6/20![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/20. 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.
lø. 7/187:40 am
MDW
- SDF
Nonstop1h 20m
Southwest
lø. 7/2511:50 am
SDF
- MDW
Nonstop1h 10m
Southwest
Deal found 6/20![Southwest logo]()
$223
This Delta deal was found by Cheapflights users on 6/22. 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.
lø. 8/296:05 am
MDW
- LEX
1 stop5h 06m
Delta
sø. 8/306:00 am
LEX
- MDW
1 stop4h 59m
Delta
Deal found 6/22![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/20. 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.
lø. 8/83:15 pm
MDW
- SDF
Nonstop1h 10m
Southwest
ma. 8/107:10 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 6/20![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 6/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 7/146:00 am
MDW
- TRI
1 stop5h 56m
Delta
ti. 7/286:00 am
TRI
- MDW
1 stop5h 05m
Delta
Deal found 6/19![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/20. 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.
on. 10/76:00 am
MDW
- TYS
1 stop6h 05m
Southwest
on. 10/144:05 pm
TYS
- MDW
1 stop8h 15m
Southwest
Deal found 6/20![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 6/22. 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.
to. 7/236:00 am
MDW
- TYS
1 stop6h 16m
Delta
lø. 7/257:15 am
TYS
- MDW
1 stop6h 23m
Delta
Deal found 6/22![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 6/20. 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.
lø. 7/186:30 am
MDW
- TYS
1 stop5h 25m
Southwest
lø. 7/251:35 pm
TYS
- MDW
1 stop10h 30m
Southwest
Deal found 6/20![Southwest logo]()
$242
This Delta deal was found by Cheapflights users on 6/21. 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.
ma. 8/179:24 am
MDW
- BNA
1 stop3h 49m
Delta
lø. 8/222:13 pm
BNA
- MDW
1 stop4h 20m
Delta
Deal found 6/21![Delta logo]()
$271
This Southwest deal was found by Cheapflights users on 6/23. 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.
on. 7/1512:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
ma. 7/208:25 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/23![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 6/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
on. 7/2211:25 am
MDW
- BNA
1 stop4h 55m
Southwest
on. 7/293:25 pm
BNA
- MDW
1 stop4h 45m
Southwest
Deal found 6/22![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 6/22. 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.
ma. 7/2011:05 am
MDW
- LEX
1 stop5h 05m
Delta
ma. 7/275:56 pm
LEX
- MDW
1 stop5h 19m
Delta
Deal found 6/22![Delta logo]()
$314
This Southwest deal was found by Cheapflights users on 6/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 8/111:30 am
MDW
- BNA
1 stop5h 30m
Southwest
on. 8/510:10 am
BNA
- MDW
1 stop4h 05m
Southwest
Deal found 6/22![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 6/21. 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.
to. 8/2010:54 am
MDW
- BNA
1 stop3h 54m
Delta
fr. 8/212:10 pm
BNA
- MDW
1 stop4h 23m
Delta
Deal found 6/21![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 8/2510:10 am
MDW
- TYS
2 stops7h 45m
Southwest
lø. 8/2912:30 pm
TYS
- MDW
2 stops7h 50m
Southwest
Deal found 6/18![Southwest logo]()
$257
This Delta deal was found by Cheapflights users on 6/22. 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.
to. 9/105:45 pm
MDW
- BNA
1 stop4h 33m
Delta
sø. 9/136:00 am
BNA
- MDW
1 stop6h 39m
Delta
Deal found 6/22![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 6/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 8/87:40 am
MDW
- SDF
2 stops8h 35m
Southwest
to. 8/203:20 pm
SDF
- MDW
2 stops7h 35m
Southwest
Deal found 6/22![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 6/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lø. 8/16:00 am
MDW
- LEX
1 stop5h 17m
Delta
lø. 8/86:00 am
LEX
- MDW
1 stop5h 10m
Delta
Deal found 6/19![Delta logo]()
$329
This Southwest deal was found by Cheapflights users on 6/19. 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.
lø. 8/226:50 am
MDW
- TYS
1 stop8h 20m
Southwest
sø. 8/238:30 am
TYS
- MDW
1 stop6h 15m
Southwest
Deal found 6/19![Southwest logo]()
$268
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
fr. 9/251:14 pm
MDW
- LEX
1 stop3h 06m
Delta
sø. 9/2712:40 pm
LEX
- MDW
1 stop4h 31m
Delta
Deal found 6/18![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 6/21. 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.
fr. 8/287:25 am
MDW
- TYS
1 stop5h 00m
Southwest
sø. 8/305:55 pm
TYS
- MDW
1 stop6h 00m
Southwest
Deal found 6/21![Southwest logo]()
$269
This Delta deal was found by Cheapflights users on 6/21. 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.
fr. 7/315:10 pm
MDW
- LEX
1 stop5h 45m
Delta
sø. 8/25:56 pm
LEX
- MDW
1 stop5h 20m
Delta
Deal found 6/21![Delta logo]()
$354
Last-minute flights from Midway to KentuckyDiscover last-minute flight deals from Midway to Kentucky. Data last updated juni 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kentucky. Data last updated juni 23, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
sø. 7/52:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
to. 7/91:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 7/92:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/121:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$140
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 7/122:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/191:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/21![Allegiant Air logo]()
$166
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 7/122:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
to. 7/161:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$175
This Southwest deal was found by Cheapflights users on 6/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 7/146:15 pm
MDW
- CVG
Nonstop1h 15m
Southwest
lø. 7/189:15 am
CVG
- MDW
Nonstop1h 05m
Southwest
Deal found 6/22![Southwest logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 7/162:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/191:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$146
This Southwest deal was found by Cheapflights users on 6/20. 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.
lø. 7/1811:30 am
MDW
- SDF
Nonstop1h 10m
Southwest
lø. 7/187:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 6/20![Southwest logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 6/22. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 7/192:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
to. 7/231:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/22![Allegiant Air logo]()
$155
This Cheapflightsfares deal was found by Cheapflights users on 6/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 7/192:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/261:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/21![Allegiant Air logo]()
$171
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 7/207:05 pm
MDW
- CVG
Nonstop1h 15m
Southwest
on. 7/227:40 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 6/18![Southwest logo]()
$215
This Southwest deal was found by Cheapflights users on 6/19. 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.
ti. 7/2112:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
ti. 7/287:00 am
CVG
- MDW
2 stops7h 35m
Southwest
Deal found 6/19![Southwest logo]()
$172
This Trip.com deal was found by Cheapflights users on 6/20. 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.
to. 7/232:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
sø. 7/261:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$142
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 juni 23, 2026.
Search for one-way flight options from Midway to Kentucky. Find affordable one-way fares based on user searches. Data last updated juni 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
to. 8/132:49 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/20![Allegiant Air logo]()
$49
This Kiwi.com deal was found by Cheapflights users on 6/21. 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.
to. 7/232:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/21![Allegiant Air logo]()
$62
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sø. 7/122:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$67
This Super.com deal was found by Cheapflights users on 6/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
to. 7/92:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/21![Allegiant Air logo]()
$70
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
on. 7/2212:45 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 6/18![Southwest logo]()
$79
This Delta deal was found by Cheapflights users on 6/22. 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.
on. 9/169:29 am
MDW
- CVG
1 stop2h 59m
Delta
Deal found 6/22![Delta logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
sø. 8/22:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/19![Allegiant Air logo]()
$92
This Southwest deal was found by Cheapflights users on 6/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ti. 8/41:05 pm
MDW
- CVG
2 stops6h 45m
Southwest
Deal found 6/22![Southwest logo]()
$94
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ma. 9/78:05 am
MDW
- CVG
Nonstop1h 20m
Southwest
Deal found 6/18![Southwest logo]()
$98
This Cheapflightsfares deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
sø. 8/92:49 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 6/18![Allegiant Air logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 6/19. 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.
ma. 9/1412:03 pm
MDW
- CVG
1 stop22h 40m
Frontier
Deal found 6/19![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 6/21. 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.
ma. 9/2112:03 pm
MDW
- CVG
1 stop22h 40m
Frontier
Deal found 6/21![Frontier logo]()
$104
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 juni 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $140 (Cheapflightsfares) |
One-way from | $49 (Kiwi.com) |
Popular in | May |
Cheapest in | August |
Average price | $489 |
Good round-trip deal | $315 or less |
Good one-way deal | $227 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 juni 23, 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
Quickest round-trip
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
ti. 7/14
6:15 pm-8:30 pm
Nonstop1h 15m
Cincinnati Cinci./N. Kentucky
lø. 7/18
9:15 am-9:20 am
Nonstop1h 05m
$157
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
ti. 8/18
5:55 pm-8:10 pm
Nonstop1h 15m
Cincinnati Cinci./N. Kentucky
ti. 8/25
7:15 pm-7:25 pm
Nonstop1h 10m
$157
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
ti. 7/21
5:30 pm-11:10 pm
1 stop4h 40m
Cincinnati Cinci./N. Kentucky
ti. 7/28
7:00 am-1:35 pm
2 stops7h 35m
$182
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
lø. 8/8
8:00 am-10:25 am
Nonstop1h 25m
Cincinnati Cinci./N. Kentucky
ma. 8/10
7:05 am-11:00 am
1 stop4h 55m
$186
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
to. 9/10
7:30 am-1:35 pm
1 stop5h 05m
Cincinnati Cinci./N. Kentucky
ma. 9/14
5:25 pm-10:20 pm
1 stop5h 55m
$215
ChicagoLouisville
MDW - SDF
MDWSDF
Chicago Midway
lø. 7/18
7:40 am-10:00 am
Nonstop1h 20m
Louisville Intl
lø. 7/25
11:50 am-12:00 pm
Nonstop1h 10m
$223
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
ti. 7/14
9:19 am-3:16 pm
1 stop4h 57m
Cincinnati Cinci./N. Kentucky
lø. 7/18
2:15 pm-6:07 pm
1 stop4h 52m
$228
ChicagoLouisville
MDW - SDF
MDWSDF
Chicago Midway
lø. 8/8
3:15 pm-5:25 pm
Nonstop1h 10m
Louisville Intl
ma. 8/10
7:10 pm-7:25 pm
Nonstop1h 15m
$235
ChicagoKnoxville
MDW - TYS
MDWTYS
Chicago Midway
on. 10/7
6:00 am-1:05 pm
1 stop6h 05m
Knoxville McGhee Tyson
on. 10/14
4:05 pm-11:20 pm
1 stop8h 15m
$237
ChicagoKnoxville
MDW - TYS
MDWTYS
Chicago Midway
lø. 7/18
6:30 am-12:55 pm
1 stop5h 25m
Knoxville McGhee Tyson
lø. 7/25
1:35 pm-11:05 pm
1 stop10h 30m
$242
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-TYS
MDW-SDF
MDW-LEX
MDW-TRI
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-TYS
MDW-SDF
MDW-LEX
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 juni 23, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 55% 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 June 20, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Kentucky flight should consider departing on Saturday at noon 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 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 juni 23, 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.
Food
7.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Comfort
8.0
Crew
8.6
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Entertainment
7.5
Overall
7.9
Boarding
8.1
Comfort
8.0
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 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.
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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 juni 23, 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 juni 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$124 | Average$295 | FlexibilityNo cancel fee | On-time63% |