$99+ Cheap flights from Midway (MDW) to Kentucky
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Oct 23 — Oct 301
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Kentucky with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 September 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 September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/21. 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 10/127:55 am -
Nonstop1h 15m
Tue 10/132:05 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 9/22. 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 12/91:15 pm -
2 stops7h 55m
Thu 12/102:05 pm -
Nonstop1h 20m
Deal found 9/22![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 9/21. 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 10/246:45 am -
1 stop7h 10m
Sat 10/245:05 pm -
Nonstop1h 20m
Deal found 9/21![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 9/23. 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 10/157:55 am -
Nonstop1h 15m
Mon 10/193:35 pm -
Nonstop1h 15m
Deal found 9/23![Southwest logo]()
$214
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 10/125:31 pm -
1 stop4h 20m
Tue 10/132:36 pm -
1 stop4h 24m
Deal found 9/21![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/18. 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.
Thu 11/56:10 pm -
1 stop5h 15m
Sat 11/77:10 am -
2 stops11h 15m
Deal found 9/18![Southwest logo]()
$228
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:50 am -
Nonstop1h 15m
Tue 10/204:00 pm -
2 stops7h 00m
Deal found 9/21![Southwest logo]()
$229
This Southwest deal was found by Cheapflights users on 9/18. 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.
Fri 10/235:15 am -
1 stop8h 40m
Sat 10/245:05 pm -
Nonstop1h 20m
Deal found 9/18![Southwest logo]()
$230
This Delta deal was found by Cheapflights users on 9/21. 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.
Thu 10/296:04 am -
1 stop4h 54m
Sat 10/317:10 am -
1 stop4h 27m
Deal found 9/21![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:59 am -
1 stop5h 15m
Thu 10/155:59 pm -
1 stop5h 34m
Deal found 9/21![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/306:00 am -
1 stop4h 38m
Sun 1/36:10 am -
1 stop3h 40m
Deal found 9/23![Delta logo]()
$339
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 11/810:42 am -
1 stop23h 04m
Wed 11/115:35 pm -
1 stop16h 47m
Deal found 9/22![Allegiant Air logo]()
$415
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 September 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 September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/21. 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 10/127:55 am -
Nonstop1h 15m
Tue 10/133:55 pm -
1 stop6h 30m
Deal found 9/21![Southwest logo]()
$207
This Delta deal was found by Cheapflights users on 9/18. 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.
Thu 11/56:04 am -
1 stop5h 50m
Sat 11/77:55 am -
1 stop5h 52m
Deal found 9/18![Delta logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 11/810:42 am -
1 stop23h 04m
Wed 11/115:35 pm -
1 stop16h 47m
Deal found 9/22![Allegiant Air logo]()
$415
This Southwest deal was found by Cheapflights users on 9/18. 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.
Thu 11/56:10 pm -
1 stop5h 15m
Sat 11/77:10 am -
2 stops11h 15m
Deal found 9/18![Southwest logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 11/86:16 am -
2 stops11h 18m
Wed 11/115:35 pm -
1 stop16h 47m
Deal found 9/22![Multiple Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:15 am -
1 stop6h 40m
Fri 10/307:15 am -
2 stops8h 40m
Deal found 9/20![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/20. 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.
Thu 10/156:55 pm -
Nonstop1h 15m
Mon 10/193:35 pm -
Nonstop1h 15m
Deal found 9/20![Southwest logo]()
$248
This Delta deal was found by Cheapflights users on 9/21. 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.
Thu 10/296:04 am -
1 stop4h 54m
Sat 10/317:10 am -
1 stop4h 27m
Deal found 9/21![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:59 am -
1 stop5h 15m
Thu 10/155:59 pm -
1 stop5h 34m
Deal found 9/21![Delta logo]()
$334
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/306:00 am -
1 stop4h 38m
Sun 1/36:10 am -
1 stop3h 40m
Deal found 9/23![Delta logo]()
$339
This Southwest deal was found by Cheapflights users on 9/19. 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.
Fri 10/165:15 am -
2 stops10h 10m
Sat 10/175:05 pm -
Nonstop1h 20m
Deal found 9/19![Southwest logo]()
$318
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/209:40 am -
2 stops9h 55m
Fri 10/235:35 am -
1 stop4h 10m
Deal found 9/21![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 9/21. 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.
Fri 10/166:55 pm -
Nonstop1h 15m
Sun 10/185:50 pm -
1 stop7h 20m
Deal found 9/21![Southwest logo]()
$336
This Southwest deal was found by Cheapflights users on 9/18. 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.
Fri 10/96:55 pm -
Nonstop1h 15m
Sun 10/113:25 pm -
Nonstop1h 15m
Deal found 9/18![Southwest logo]()
$375
This Southwest deal was found by Cheapflights users on 9/18. 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.
Sat 10/1011:55 am -
2 stops7h 05m
Mon 10/126:15 pm -
1 stop4h 10m
Deal found 9/18![Southwest logo]()
$379
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:59 am -
1 stop5h 15m
Thu 10/155:59 pm -
1 stop5h 34m
Deal found 9/21![Delta logo]()
$557
This Delta deal was found by Cheapflights users on 9/18. 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.
Tue 10/2010:59 am -
1 stop5h 15m
Fri 10/235:59 pm -
1 stop5h 34m
Deal found 9/18![Delta logo]()
$588
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 10/125:09 pm -
1 stop5h 49m
Thu 10/157:45 am -
1 stop6h 02m
Deal found 9/21![Delta logo]()
$659
Last-minute flights from Midway to KentuckyDiscover last-minute flight deals from Midway to Kentucky. Data last updated September 23, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kentucky. Data last updated September 23, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 9/21. 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.
Sat 9/266:05 am -
1 stop5h 11m
Tue 9/2912:40 pm -
1 stop4h 35m
Deal found 9/21![Delta logo]()
$422
This Delta deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/610:59 am -
1 stop5h 15m
Thu 10/155:59 pm -
1 stop5h 34m
Deal found 9/21![Delta logo]()
$334
This Southwest deal was found by Cheapflights users on 9/21. 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 10/127:55 am -
Nonstop1h 15m
Tue 10/132:05 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 9/21. 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.
Mon 10/125:31 pm -
1 stop4h 20m
Tue 10/132:36 pm -
1 stop4h 24m
Deal found 9/21![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 9/23. 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 10/157:55 am -
Nonstop1h 15m
Mon 10/193:35 pm -
Nonstop1h 15m
Deal found 9/23![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:50 am -
Nonstop1h 15m
Tue 10/204:00 pm -
2 stops7h 00m
Deal found 9/21![Southwest logo]()
$229
This Delta deal was found by Cheapflights users on 9/22. 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 10/216:04 am -
1 stop4h 54m
Mon 10/265:59 pm -
1 stop5h 34m
Deal found 9/22![Delta logo]()
$416
This Southwest deal was found by Cheapflights users on 9/18. 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.
Fri 10/235:15 am -
1 stop8h 40m
Sat 10/245:05 pm -
Nonstop1h 20m
Deal found 9/18![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 9/21. 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 10/246:45 am -
1 stop7h 10m
Sat 10/245:05 pm -
Nonstop1h 20m
Deal found 9/21![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:15 am -
1 stop6h 40m
Fri 10/307:15 am -
2 stops8h 40m
Deal found 9/20![Southwest logo]()
$239
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/277:55 am -
2 stops7h 35m
Tue 10/277:10 pm -
Nonstop1h 15m
Deal found 9/21![Southwest logo]()
$212
This Delta deal was found by Cheapflights users on 9/21. 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.
Thu 10/296:04 am -
1 stop4h 54m
Sat 10/317:10 am -
1 stop4h 27m
Deal found 9/21![Delta logo]()
$319
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 September 23, 2026.
Search for one-way flight options from Midway to Kentucky. Find affordable one-way fares based on user searches. Data last updated September 23, 2026.
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:55 am -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$99
This Delta deal was found by Cheapflights users on 9/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:09 pm -
1 stop5h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 9/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:45 pm -
2 stops4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Southwest logo]()
$114
This Southwest deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:50 am -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Southwest logo]()
$116
This Southwest deal was found by Cheapflights users on 9/22. 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.
Thu 10/2911:05 am -
2 stops10h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$120
This Southwest deal was found by Cheapflights users on 9/22. 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.
Fri 11/66:10 pm -
1 stop5h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$126
This Southwest deal was found by Cheapflights users on 9/20. 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.
Thu 11/267:40 am -
2 stops7h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$131
This Southwest deal was found by Cheapflights users on 9/22. 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.
Thu 10/157:55 am -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$150
This Southwest deal was found by Cheapflights users on 9/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2511:25 am -
Nonstop1h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Southwest logo]()
$163
This Southwest deal was found by Cheapflights users on 9/22. 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 10/212:45 pm -
2 stops4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Southwest logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 10/226:22 am -
2 stops13h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/22![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 9/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/219:23 pm -
2 stops18h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![Multiple Airlines logo]()
$266
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 September 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $197 (Southwest) |
One-way from | $99 (Southwest) |
Popular in | September |
Cheapest in | December |
Average price | $515 |
Good round-trip deal | $311 or less |
Good one-way deal | $186 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 7,457,451 searches. Data last updated September 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
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Sat 11/21
7:55 am-10:15 am
Nonstop1h 20m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
Quickest round-trip
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 10/29
7:55 am-10:10 am
Nonstop1h 15m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Tue 10/27
1:05 pm-3:20 pm
Nonstop1h 15m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$99
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Tue 10/20
5:09 pm-11:59 pm
1 stop5h 50m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Wed 11/18
6:00 am-11:56 am
1 stop4h 56m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Mon 11/23
12:30 pm-6:11 pm
1 stop4h 41m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Tue 11/17
5:13 pm-11:13 pm
1 stop5h 00m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Wed 12/16
5:30 pm-11:02 pm
1 stop4h 32m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Tue 12/22
7:40 am-10:00 am
Nonstop1h 20m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$116
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 11/19
11:30 am-8:40 pm
2 stops8h 10m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$131
Showing 1-10 of 42 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-SDF
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-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 September 23, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 32% on flights from Chicago Midway Airport to Kentucky by exploring options for tickets in the morning.
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 September 19, 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. Thursday 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 September 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.
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Boarding
8.1
Crew
8.6
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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
See prices for flight routes from nearby airports that may be better suited for you.
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 September 23, 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 7,457,451 searches. Data last updated September 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$206 | Average$411 | FlexibilityNo cancel fee | On-time63% |