$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 11/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Dec 10 — Dec 171
Round-trip
1 adult, Economy
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Find cheap flights from Midway to Kentucky with Cheapflights
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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 November 10, 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 November 10, 2026.
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/38:15 am -
Nonstop1h 15m
Mon 12/77:35 pm -
Nonstop1h 15m
Deal found 11/5![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/39:37 am -
1 stop6h 39m
Mon 12/75:59 pm -
1 stop5h 55m
Deal found 11/5![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:20 pm -
Nonstop1h 15m
Tue 12/152:05 pm -
Nonstop1h 20m
Deal found 11/8![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:55 am -
Nonstop1h 20m
Mon 12/77:35 pm -
Nonstop1h 15m
Deal found 11/9![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:28 am -
1 stop4h 25m
Tue 12/157:05 am -
1 stop5h 59m
Deal found 11/8![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:15 am -
Nonstop1h 15m
Mon 12/147:35 pm -
Nonstop1h 15m
Deal found 11/7![Southwest logo]()
$249
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:08 pm -
1 stop4h 43m
Mon 12/77:05 am -
1 stop5h 59m
Deal found 11/9![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/31:20 pm -
Nonstop1h 15m
Sun 12/67:55 pm -
Nonstop1h 15m
Deal found 11/5![Southwest logo]()
$253
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:28 am -
1 stop4h 44m
Sat 12/510:57 am -
1 stop5h 07m
Deal found 11/9![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/251:05 pm -
1 stop5h 00m
Mon 11/307:05 am -
1 stop4h 19m
Deal found 11/7![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/231:05 pm -
1 stop5h 00m
Fri 11/2710:57 am -
1 stop5h 18m
Deal found 11/7![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/1111:27 am -
1 stop6h 36m
Sun 1/176:00 am -
1 stop5h 00m
Deal found 11/5![Delta logo]()
$407
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 November 10, 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 November 10, 2026.
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/39:37 am -
1 stop6h 39m
Mon 12/75:59 pm -
1 stop5h 55m
Deal found 11/5![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:20 pm -
Nonstop1h 15m
Tue 12/152:05 pm -
Nonstop1h 20m
Deal found 11/8![Southwest logo]()
$219
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/36:00 am -
1 stop6h 00m
Mon 12/77:35 pm -
Nonstop1h 15m
Deal found 11/5![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:28 am -
1 stop4h 25m
Tue 12/157:05 am -
1 stop5h 59m
Deal found 11/8![Delta logo]()
$239
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:25 pm -
1 stop4h 55m
Mon 12/77:35 pm -
Nonstop1h 15m
Deal found 11/9![Southwest logo]()
$244
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:08 pm -
1 stop4h 43m
Mon 12/77:05 am -
1 stop5h 59m
Deal found 11/9![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/31:20 pm -
Nonstop1h 15m
Sun 12/67:55 pm -
Nonstop1h 15m
Deal found 11/5![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/237:40 am -
Nonstop1h 20m
Thu 12/2412:10 pm -
1 stop6h 00m
Deal found 11/6![Southwest logo]()
$254
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/288:25 am -
Nonstop1h 25m
Fri 1/296:20 pm -
Nonstop1h 20m
Deal found 11/8![Southwest logo]()
$259
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/264:13 pm -
1 stop5h 36m
Mon 11/305:59 pm -
1 stop5h 55m
Deal found 11/5![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 3/59:33 am -
1 stop6h 15m
Sat 3/610:50 am -
1 stop6h 46m
Deal found 11/6![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:28 am -
1 stop6h 42m
Sat 12/510:40 am -
1 stop3h 21m
Deal found 11/7![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/35:12 pm -
1 stop5h 52m
Thu 12/106:00 am -
1 stop5h 28m
Deal found 11/5![Delta logo]()
$349
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/231:05 pm -
1 stop5h 00m
Fri 11/2710:57 am -
1 stop5h 18m
Deal found 11/7![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/246:00 am -
1 stop4h 49m
Fri 11/277:35 am -
1 stop4h 50m
Deal found 11/8![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 11/255:13 pm -
1 stop5h 45m
Mon 11/3012:50 pm -
1 stop4h 28m
Deal found 11/6![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:13 pm -
1 stop5h 45m
Fri 11/277:35 am -
1 stop4h 50m
Deal found 11/8![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/216:00 am -
1 stop4h 38m
Sat 1/26:10 am -
1 stop3h 39m
Deal found 11/6![Delta logo]()
$444
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/79:37 am -
2 stops8h 35m
Mon 12/145:59 pm -
1 stop5h 55m
Deal found 11/9![Delta logo]()
$473
Last-minute flights from Midway to KentuckyDiscover last-minute flight deals from Midway to Kentucky. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kentucky. Data last updated November 10, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/1111:27 am -
1 stop6h 36m
Sun 1/176:00 am -
1 stop5h 00m
Deal found 11/5![Delta logo]()
$407
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/231:05 pm -
1 stop5h 00m
Fri 11/2710:57 am -
1 stop5h 18m
Deal found 11/7![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/251:05 pm -
1 stop5h 00m
Mon 11/307:05 am -
1 stop4h 19m
Deal found 11/7![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/211:28 am -
1 stop4h 44m
Sat 12/510:57 am -
1 stop5h 07m
Deal found 11/9![Delta logo]()
$349
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/38:15 am -
Nonstop1h 15m
Mon 12/77:35 pm -
Nonstop1h 15m
Deal found 11/5![Southwest logo]()
$197
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/39:37 am -
1 stop6h 39m
Mon 12/75:59 pm -
1 stop5h 55m
Deal found 11/5![Delta logo]()
$217
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/31:20 pm -
Nonstop1h 15m
Sun 12/67:55 pm -
Nonstop1h 15m
Deal found 11/5![Southwest logo]()
$253
This Southwest deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:55 am -
Nonstop1h 20m
Mon 12/77:35 pm -
Nonstop1h 15m
Deal found 11/9![Southwest logo]()
$234
This Delta deal was found by Cheapflights users on 11/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:08 pm -
1 stop4h 43m
Mon 12/77:05 am -
1 stop5h 59m
Deal found 11/9![Delta logo]()
$252
This Southwest deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:15 am -
Nonstop1h 15m
Mon 12/147:35 pm -
Nonstop1h 15m
Deal found 11/7![Southwest logo]()
$249
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:20 pm -
Nonstop1h 15m
Tue 12/152:05 pm -
Nonstop1h 20m
Deal found 11/8![Southwest logo]()
$219
This Delta deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/811:28 am -
1 stop4h 25m
Tue 12/157:05 am -
1 stop5h 59m
Deal found 11/8![Delta logo]()
$239
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 November 10, 2026.
Search for one-way flight options from Midway to Kentucky. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/261:30 pm -
Nonstop1h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Southwest logo]()
$99
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 11/2611:27 am -
1 stop6h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Delta logo]()
$109
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Sat 12/57:55 am -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Southwest logo]()
$110
This Southwest deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/108:15 am -
Nonstop1h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/8![Southwest logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/910:40 am -
2 stops28h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$132
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/79:37 am -
1 stop3h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Delta logo]()
$135
This Southwest deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/711:30 am -
2 stops8h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Southwest logo]()
$140
This Delta deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/49:37 am -
1 stop6h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![Delta logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/115:02 pm -
2 stops22h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Multiple Airlines logo]()
$149
This Southwest deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/67:45 am -
Nonstop1h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Southwest logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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 12/106:10 pm -
1 stop23h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/5![Allegiant Air logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” 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 12/181:11 pm -
2 stops24h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Multiple Airlines logo]()
$221
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 November 10, 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 | November |
Average price | $316 |
Good round-trip deal | $281 or less |
Good one-way deal | $216 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 November 10, 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
Wed 12/9
6:00 am-2:17 pm
1 stop7h 17m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 11/26
11:27 am-7:14 pm
1 stop6h 47m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$109
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 1/7
5:35 pm-7:55 pm
Nonstop1h 20m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Mon 3/1
7:05 pm-9:25 pm
Nonstop1h 20m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Wed 2/10
5:40 pm-11:25 pm
1 stop4h 45m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
Quickest round-trip
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Thu 12/10
8:15 am-10:30 am
Nonstop1h 15m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Tue 1/5
11:30 am-8:40 pm
2 stops8h 10m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
ChicagoLexington
MDW Chicago Midway - LEX Lexington Blue Grass
MDWLEX
Chicago Midway
Wed 12/9
10:40 am-4:05 pm
2 stops28h 25m
Lexington Blue Grass
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Mon 12/7
9:37 am-2:29 pm
1 stop3h 52m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$135
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Fri 12/4
9:37 am-5:16 pm
1 stop6h 39m
Louisville Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$145
Showing 1-10 of 36 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 November 10, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 36% on flights from Chicago Midway Airport to Kentucky by exploring options for tickets in the morning.
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 November 10, 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.
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Food
7.0
Comfort
8.0
Overall
8.0
Entertainment
7.4
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 November 10, 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 7,457,451 searches. Data last updated November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$191 | Average$411 | FlexibilityNo cancel fee | On-time63% |