$69+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Apr 24 — May 11
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 March 25, 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 March 25, 2026.
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:40 am
MDW
- SDF
Nonstop1h 10m
Southwest
Wed 4/227:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 3/24![Southwest logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 3/22![Allegiant Air logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/312:47 pm
MDW
- TYS
Nonstop1h 26m
Multiple Airlines
Mon 6/110:03 pm
TYS
- MDW
2 stops24h 59m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/259:30 pm
MDW
- TYS
1 stop21h 01m
Allegiant Air
Sun 5/311:22 pm
TYS
- MDW
Nonstop1h 35m
Allegiant Air
Deal found 3/22![Allegiant Air logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:47 pm
MDW
- TYS
Nonstop1h 26m
Multiple Airlines
Mon 6/110:03 pm
TYS
- MDW
2 stops24h 59m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$205
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:45 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Tue 5/197:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 3/24![Southwest logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 5/282:47 pm
MDW
- TYS
Nonstop1h 26m
Multiple Airlines
Sun 5/316:03 pm
TYS
- MDW
2 stops28h 59m
Multiple Airlines
Deal found 3/24![Multiple Airlines logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Thu 4/162:15 pm
MDW
- BNA
2 stops9h 09m
Multiple Airlines
Sat 4/189:30 am
BNA
- MDW
1 stop6h 30m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$212
This Booking.com deal was found by Cheapflights users on 3/20. 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 Booking.com 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
Sun 8/21:22 pm
TYS
- MDW
Nonstop1h 36m
Allegiant Air
Deal found 3/20![Allegiant Air logo]()
$212
This Southwest deal was found by Cheapflights users on 3/23. 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.
Tue 4/218:35 pm
MDW
- BNA
Nonstop1h 25m
Southwest
Tue 4/2811:55 am
BNA
- MDW
Nonstop1h 35m
Southwest
Deal found 3/23![Southwest logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 3/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/282:47 pm
MDW
- TYS
Nonstop1h 26m
Multiple Airlines
Fri 5/2910:03 pm
TYS
- MDW
2 stops24h 59m
Multiple Airlines
Deal found 3/22![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Sat 4/189:14 am
MDW
- BNA
1 stop7h 44m
Multiple Airlines
Tue 4/219:30 am
BNA
- MDW
2 stops12h 44m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$214
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 March 25, 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 March 25, 2026.
This Southwest deal was found by Cheapflights users on 3/23. 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.
Tue 4/219:50 am
MDW
- BNA
Nonstop1h 25m
Southwest
Tue 4/2811:30 am
BNA
- MDW
2 stops5h 25m
Southwest
Deal found 3/23![Southwest logo]()
$228
This Delta deal was found by Cheapflights users on 3/24. 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.
Wed 4/226:00 am
MDW
- TRI
1 stop6h 03m
Delta
Sat 4/255:08 pm
TRI
- MDW
1 stop6h 20m
Delta
Deal found 3/24![Delta logo]()
$249
This Southwest deal was found by Cheapflights users on 3/23. 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.
Thu 4/237:45 am
MDW
- SDF
Nonstop1h 10m
Southwest
Mon 4/278:10 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 3/23![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:59 am
MDW
- TRI
1 stop7h 02m
Delta
Sat 5/304:49 pm
TRI
- MDW
1 stop5h 20m
Delta
Deal found 3/21![Delta logo]()
$249
This Delta deal was found by Cheapflights users on 3/24. 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 5/211:18 am
MDW
- BNA
1 stop5h 32m
Delta
Tue 5/511:19 am
BNA
- MDW
1 stop5h 07m
Delta
Deal found 3/24![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 3/23. 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.
Thu 6/47:15 am
MDW
- BNA
Nonstop1h 25m
Southwest
Mon 6/88:25 pm
BNA
- MDW
Nonstop1h 30m
Southwest
Deal found 3/23![Southwest logo]()
$261
This Delta deal was found by Cheapflights users on 3/22. 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.
Wed 5/65:21 pm
MDW
- LEX
1 stop5h 33m
Delta
Sat 5/163:32 pm
LEX
- MDW
1 stop6h 37m
Delta
Deal found 3/22![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:50 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Wed 5/137:35 pm
CVG
- MDW
Nonstop1h 15m
Southwest
Deal found 3/21![Southwest logo]()
$271
This Delta deal was found by Cheapflights users on 3/20. 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.
Sat 6/65:30 pm
MDW
- TYS
1 stop5h 31m
Delta
Fri 6/127:30 am
TYS
- MDW
1 stop6h 00m
Delta
Deal found 3/20![Delta logo]()
$269
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/218:35 pm
MDW
- BNA
Nonstop1h 25m
Southwest
Sat 4/255:15 am
BNA
- MDW
Nonstop1h 35m
Southwest
Deal found 3/20![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 3/23. 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.
Thu 5/75:30 am
MDW
- BNA
Nonstop1h 25m
Southwest
Thu 5/149:35 am
BNA
- MDW
1 stop5h 20m
Southwest
Deal found 3/23![Southwest logo]()
$271
This Southwest deal was found by Cheapflights users on 3/22. 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.
Wed 4/295:00 pm
MDW
- CVG
1 stop4h 55m
Southwest
Sun 5/37:15 pm
CVG
- MDW
1 stop6h 05m
Southwest
Deal found 3/22![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 3/20. 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.
Tue 9/151:00 pm
MDW
- SDF
2 stops9h 59m
Delta
Tue 9/2210:43 am
SDF
- MDW
1 stop6h 44m
Delta
Deal found 3/20![Delta logo]()
$300
This Southwest deal was found by Cheapflights users on 3/21. 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.
Sat 4/183:40 pm
MDW
- CVG
Nonstop1h 05m
Southwest
Mon 4/208:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 3/21![Southwest logo]()
$272
This Delta deal was found by Cheapflights users on 3/20. 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.
Wed 9/1610:35 am
MDW
- LEX
1 stop5h 37m
Delta
Tue 9/225:55 pm
LEX
- MDW
1 stop4h 51m
Delta
Deal found 3/20![Delta logo]()
$302
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/181:25 pm
MDW
- SDF
2 stops7h 45m
Southwest
Tue 5/191:35 pm
SDF
- MDW
2 stops7h 35m
Southwest
Deal found 3/24![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:00 am
MDW
- TYS
1 stop4h 17m
Delta
Sat 5/235:35 pm
TYS
- MDW
1 stop4h 34m
Delta
Deal found 3/21![Delta logo]()
$304
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:40 am
MDW
- BNA
1 stop5h 15m
Southwest
Mon 5/186:20 pm
BNA
- MDW
1 stop5h 45m
Southwest
Deal found 3/24![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 3/24. 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.
Fri 5/221:22 pm
MDW
- CVG
2 stops8h 42m
Delta
Mon 5/253:54 pm
CVG
- MDW
1 stop3h 39m
Delta
Deal found 3/24![Delta logo]()
$312
This Southwest deal was found by Cheapflights users on 3/23. 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.
Wed 5/132:35 pm
MDW
- BNA
1 stop5h 10m
Southwest
Fri 5/153:50 pm
BNA
- MDW
1 stop4h 25m
Southwest
Deal found 3/23![Southwest logo]()
$280
This Delta deal was found by Cheapflights users on 3/22. 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.
Wed 5/276:23 am
MDW
- TYS
1 stop3h 46m
Delta
Wed 5/273:30 pm
TYS
- MDW
1 stop6h 39m
Delta
Deal found 3/22![Delta logo]()
$324
This Southwest deal was found by Cheapflights users on 3/22. 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.
Sat 4/256:10 am
MDW
- CVG
1 stop5h 00m
Southwest
Mon 4/278:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 3/22![Southwest logo]()
$282
This Delta deal was found by Cheapflights users on 3/20. 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.
Thu 4/239:27 am
MDW
- SDF
1 stop4h 03m
Delta
Sun 4/266:00 am
SDF
- MDW
1 stop4h 56m
Delta
Deal found 3/20![Delta logo]()
$335
This Southwest deal was found by Cheapflights users on 3/21. 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.
Mon 4/205:30 am
MDW
- TYS
1 stop7h 40m
Southwest
Mon 4/276:45 pm
TYS
- MDW
1 stop5h 45m
Southwest
Deal found 3/21![Southwest logo]()
$284
This Delta deal was found by Cheapflights users on 3/20. 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.
Tue 9/1510:35 am
MDW
- LEX
1 stop5h 37m
Delta
Mon 9/215:55 pm
LEX
- MDW
1 stop4h 51m
Delta
Deal found 3/20![Delta logo]()
$344
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2910:45 am
MDW
- BNA
1 stop5h 30m
Southwest
Sun 5/310:45 pm
BNA
- MDW
Nonstop1h 35m
Southwest
Deal found 3/24![Southwest logo]()
$285
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/227:00 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Mon 5/258:20 pm
CVG
- MDW
Nonstop1h 10m
Southwest
Deal found 3/24![Southwest logo]()
$287
This Delta deal was found by Cheapflights users on 3/22. 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.
Fri 5/299:22 am
MDW
- TYS
1 stop3h 58m
Delta
Sat 5/305:40 am
TYS
- MDW
1 stop5h 19m
Delta
Deal found 3/22![Delta logo]()
$369
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/167:50 am
MDW
- SDF
Nonstop1h 15m
Southwest
Sun 5/177:00 am
SDF
- MDW
1 stop4h 15m
Southwest
Deal found 3/24![Southwest logo]()
$290
This Southwest deal was found by Cheapflights users on 3/22. 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.
Wed 5/610:10 am
MDW
- BNA
1 stop2h 55m
Southwest
Sun 5/1010:45 am
BNA
- MDW
1 stop5h 20m
Southwest
Deal found 3/22![Southwest logo]()
$291
Last-minute flights from Midway to KentuckyDiscover last-minute flight deals from Midway to Kentucky. Data last updated March 25, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kentucky. Data last updated March 25, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 3/22. 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.
Sun 4/122:40 pm
MDW
- TYS
1 stop5h 25m
Southwest
Wed 4/155:50 pm
TYS
- MDW
1 stop5h 25m
Southwest
Deal found 3/22![Southwest logo]()
$225
This Southwest deal was found by Cheapflights users on 3/23. 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.
Tue 4/144:50 pm
MDW
- BNA
Nonstop1h 30m
Southwest
Wed 4/158:40 pm
BNA
- MDW
Nonstop1h 35m
Southwest
Deal found 3/23![Southwest logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Wed 4/152:15 pm
MDW
- BNA
2 stops9h 09m
Multiple Airlines
Wed 4/226:43 pm
BNA
- MDW
1 stop12h 43m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Thu 4/162:15 pm
MDW
- BNA
2 stops9h 09m
Multiple Airlines
Sat 4/189:30 am
BNA
- MDW
1 stop6h 30m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$212
This Southwest deal was found by Cheapflights users on 3/23. 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.
Thu 4/167:45 am
MDW
- SDF
Nonstop1h 10m
Southwest
Wed 4/227:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 3/23![Southwest logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Thu 4/162:15 pm
MDW
- BNA
2 stops9h 09m
Multiple Airlines
Wed 4/226:43 pm
BNA
- MDW
1 stop12h 43m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Fri 4/172:15 pm
MDW
- BNA
2 stops9h 09m
Multiple Airlines
Sat 4/189:30 am
BNA
- MDW
1 stop6h 30m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 3/25. 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.
Sat 4/189:14 am
MDW
- BNA
1 stop7h 44m
Multiple Airlines
Tue 4/219:30 am
BNA
- MDW
2 stops12h 44m
Multiple Airlines
Deal found 3/25![Multiple Airlines logo]()
$214
This Frontier deal was found by Cheapflights users on 3/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:14 am
MDW
- BNA
1 stop7h 44m
Frontier
Sun 4/1912:34 pm
BNA
- MDW
1 stop9h 44m
Frontier
Deal found 3/25![Frontier logo]()
$225
This Southwest deal was found by Cheapflights users on 3/23. 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.
Tue 4/218:35 pm
MDW
- BNA
Nonstop1h 25m
Southwest
Tue 4/2811:55 am
BNA
- MDW
Nonstop1h 35m
Southwest
Deal found 3/23![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 3/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:40 am
MDW
- SDF
Nonstop1h 10m
Southwest
Wed 4/227:15 pm
SDF
- MDW
Nonstop1h 15m
Southwest
Deal found 3/24![Southwest logo]()
$177
This Trip.com deal was found by Cheapflights users on 3/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:14 am
MDW
- BNA
1 stop7h 44m
Frontier
Sat 5/25:53 pm
BNA
- MDW
1 stop13h 48m
Frontier
Deal found 3/23![Frontier logo]()
$216
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 March 25, 2026.
Search for one-way flight options from Midway to Kentucky. Find affordable one-way fares based on user searches. Data last updated March 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:04 pm
MDW
- CVG
1 stop22h 00m
Frontier
Deal found 3/23![Frontier logo]()
$69
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/222:15 pm
MDW
- CVG
1 stop26h 18m
Frontier
Deal found 3/24![Frontier logo]()
$72
This Frontier deal was found by Cheapflights users on 3/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
- CVG
1 stop11h 36m
Frontier
Deal found 3/23![Frontier logo]()
$76
This Kiwi.com deal was found by Cheapflights users on 3/24. 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 4/152:15 pm
MDW
- CVG
1 stop26h 18m
Frontier
Deal found 3/24![Frontier logo]()
$77
This Southwest deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 3/20![Southwest logo]()
$79
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- CVG
1 stop28h 41m
Frontier
Deal found 3/23![Frontier logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/122:48 pm
MDW
- TYS
Nonstop1h 30m
Allegiant Air
Deal found 3/23![Allegiant Air logo]()
$83
This Southwest deal was found by Cheapflights users on 3/23. 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.
Tue 5/56:10 pm
MDW
- CVG
Nonstop1h 10m
Southwest
Deal found 3/23![Southwest logo]()
$88
This Delta deal was found by Cheapflights users on 3/20. 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.
Tue 4/215:21 pm
MDW
- CVG
1 stop5h 50m
Delta
Deal found 3/20![Delta logo]()
$89
This Southwest deal was found by Cheapflights users on 3/23. 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.
Wed 4/156:20 pm
MDW
- SDF
Nonstop1h 15m
Southwest
Deal found 3/23![Southwest logo]()
$89
This Frontier deal was found by Cheapflights users on 3/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/184:52 pm
MDW
- CVG
1 stop6h 03m
Frontier
Deal found 3/22![Frontier logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:00 am
MDW
- CVG
1 stop10h 33m
Frontier
Deal found 3/23![Frontier logo]()
$91
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 March 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $177 (Southwest) |
One-way from | $69 (Kiwi.com) |
Popular in | June |
Cheapest in | August |
Average price | $452 |
Good round-trip deal | $297 or less |
Good one-way deal | $127 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 March 25, 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
ChicagoNashville
MDW - BNA
MDWBNA
Chicago Midway
Tue 4/21
9:50 am-11:15 am
Nonstop1h 25m
Nashville Intl
Tue 4/28
11:30 am-4:55 pm
2 stops5h 25m
$228
ChicagoLouisville
MDW - SDF
MDWSDF
Chicago Midway
Thu 4/23
7:45 am-9:55 am
Nonstop1h 10m
Louisville Intl
Mon 4/27
8:10 pm-8:25 pm
Nonstop1h 15m
$244
ChicagoBlountville
MDW - TRI
MDWTRI
Chicago Midway
Wed 4/22
6:00 am-1:03 pm
1 stop6h 03m
Blountville Tri Cities TN/VA
Sat 4/25
5:08 pm-10:28 pm
1 stop6h 20m
$249
ChicagoBlountville
MDW - TRI
MDWTRI
Chicago Midway
Wed 5/27
10:59 am-7:01 pm
1 stop7h 02m
Blountville Tri Cities TN/VA
Sat 5/30
4:49 pm-9:09 pm
1 stop5h 20m
$249
ChicagoNashville
MDW - BNA
MDWBNA
Chicago Midway
Sat 5/2
11:18 am-4:50 pm
1 stop5h 32m
Nashville Intl
Tue 5/5
11:19 am-4:26 pm
1 stop5h 07m
$256
ChicagoNashville
MDW - BNA
MDWBNA
Chicago Midway
Thu 6/4
7:15 am-8:40 am
Nonstop1h 25m
Nashville Intl
Mon 6/8
8:25 pm-9:55 pm
Nonstop1h 30m
$261
ChicagoLexington
MDW - LEX
MDWLEX
Chicago Midway
Wed 5/6
5:21 pm-11:54 pm
1 stop5h 33m
Lexington Blue Grass
Sat 5/16
3:32 pm-9:09 pm
1 stop6h 37m
$269
ChicagoKnoxville
MDW - TYS
MDWTYS
Chicago Midway
Sat 6/6
5:30 pm-12:01 am
1 stop5h 31m
Knoxville McGhee Tyson
Fri 6/12
7:30 am-12:30 pm
1 stop6h 00m
$269
ChicagoCincinnati
MDW - CVG
MDWCVG
Chicago Midway
Wed 5/6
12:50 pm-3:00 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Wed 5/13
7:35 pm-7:50 pm
Nonstop1h 15m
$271
ChicagoNashville
MDW - BNA
MDWBNA
Chicago Midway
Tue 4/21
8:35 pm-10:00 pm
Nonstop1h 25m
Nashville Intl
Sat 4/25
5:15 am-6:50 am
Nonstop1h 35m
$271
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-SDF
MDW-LEX
MDW-BNA
MDW-TYS
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-SDF
MDW-LEX
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 March 25, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 27% 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 March 23, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Kentucky flight should consider departing on Monday evenings 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 March 25, 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.
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
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
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Midway and Kentucky flights
Browse other Midway and Kentucky flight options. Last updated on March 25, 2026.
Popular flight searches
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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 March 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$124 | Average$255 | FlexibilityNo cancel fee | On-time63% |