$50+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SDF
Sep 6 — Sep 131
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 August 7, 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 August 7, 2026.
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/58:00 am -
Nonstop1h 25m
Sun 9/67:30 pm -
Nonstop1h 10m
Deal found 8/4![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 8/6. 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.
Sat 9/55:45 pm -
1 stop3h 55m
Sun 9/66:10 am -
1 stop4h 07m
Deal found 8/6![Delta logo]()
$178
This Cheapflightsfares deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:49 pm -
Nonstop1h 30m
Sun 8/161:23 pm -
Nonstop1h 36m
Deal found 8/3![Allegiant Air logo]()
$179
This Frontier deal was found by Cheapflights users on 8/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:02 pm -
1 stop9h 57m
Mon 10/1212:48 pm -
1 stop10h 10m
Deal found 8/6![Frontier logo]()
$180
This Southwest deal was found by Cheapflights users on 8/6. 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.
Sat 9/53:25 pm -
Nonstop1h 15m
Sat 9/124:55 pm -
Nonstop1h 10m
Deal found 8/6![Southwest logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:30 pm -
Nonstop1h 25m
Fri 10/231:04 pm -
Nonstop1h 32m
Deal found 8/3![Allegiant Air logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 10/912:26 pm -
Nonstop1h 25m
Mon 10/1212:04 pm -
Nonstop1h 32m
Deal found 8/6![Allegiant Air logo]()
$195
This Cheapflightsfares deal was found by Cheapflights users on 8/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:30 pm -
Nonstop1h 25m
Mon 10/1912:04 pm -
Nonstop1h 32m
Deal found 8/6![Allegiant Air logo]()
$199
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/35:55 am -
1 stop5h 20m
Sat 9/52:50 pm -
1 stop6h 45m
Deal found 8/2![Southwest logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 10/2112:03 pm -
2 stops22h 26m
Mon 10/2612:04 pm -
Nonstop1h 32m
Deal found 8/3![Multiple Airlines logo]()
$201
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/165:55 pm -
Nonstop1h 20m
Wed 9/239:05 am -
Nonstop1h 05m
Deal found 8/2![Southwest logo]()
$205
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Thu 8/279:26 pm -
1 stop11h 35m
Sun 8/309:56 am -
1 stop10h 35m
Deal found 8/3![Frontier logo]()
$208
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 August 7, 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 August 7, 2026.
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 10/307:45 am -
Nonstop1h 10m
Sat 11/71:00 pm -
1 stop3h 35m
Deal found 8/3![Southwest logo]()
$191
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/59:24 am -
1 stop6h 17m
Sun 9/612:35 pm -
1 stop4h 22m
Deal found 8/5![Delta logo]()
$237
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 10/17:30 pm -
Nonstop1h 05m
Mon 10/58:20 pm -
Nonstop1h 15m
Deal found 8/2![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 8/6. 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.
Sat 9/128:00 am -
Nonstop1h 25m
Sat 9/194:55 pm -
Nonstop1h 10m
Deal found 8/6![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 8/5. 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.
Sat 9/54:39 pm -
1 stop6h 24m
Mon 9/76:05 am -
1 stop6h 34m
Deal found 8/5![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 8/6. 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.
Tue 9/15:55 pm -
Nonstop1h 15m
Thu 9/37:00 pm -
Nonstop1h 10m
Deal found 8/6![Southwest logo]()
$205
This Southwest deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/212:45 pm -
Nonstop1h 10m
Wed 9/97:15 pm -
Nonstop1h 10m
Deal found 8/3![Southwest logo]()
$205
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 9/299:29 am -
1 stop3h 38m
Sat 10/37:55 am -
1 stop5h 44m
Deal found 8/1![Delta logo]()
$255
This Southwest deal was found by Cheapflights users on 8/6. 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.
Fri 9/46:10 pm -
Nonstop1h 20m
Fri 9/115:25 pm -
1 stop6h 00m
Deal found 8/6![Southwest logo]()
$206
This Delta deal was found by Cheapflights users on 8/5. 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.
Fri 9/45:10 pm -
1 stop5h 49m
Mon 9/77:35 am -
1 stop6h 04m
Deal found 8/5![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/165:55 pm -
Nonstop1h 20m
Wed 9/233:30 pm -
1 stop6h 20m
Deal found 8/2![Southwest logo]()
$215
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 12/116:00 am -
1 stop4h 52m
Tue 12/157:05 am -
1 stop4h 28m
Deal found 8/3![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/511:15 am -
1 stop5h 05m
Sun 9/67:10 pm -
Nonstop1h 15m
Deal found 8/2![Southwest logo]()
$227
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/264:30 pm -
1 stop5h 12m
Wed 9/3012:40 pm -
1 stop4h 35m
Deal found 8/2![Delta logo]()
$279
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/276:05 am -
1 stop5h 06m
Sun 8/307:35 am -
1 stop6h 04m
Deal found 8/3![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/59:05 am -
2 stops6h 40m
Sun 9/68:05 am -
Nonstop1h 35m
Deal found 8/4![Southwest logo]()
$232
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 12/1011:28 am -
1 stop4h 39m
Sun 12/137:05 am -
1 stop4h 28m
Deal found 8/3![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/169:00 am -
Nonstop1h 20m
Wed 9/238:45 am -
Nonstop1h 15m
Deal found 8/2![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 stop5h 32m
Mon 11/210:06 am -
1 stop6h 11m
Deal found 8/2![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/232:40 pm -
Nonstop1h 25m
Thu 9/243:25 pm -
Nonstop1h 30m
Deal found 8/4![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/166:05 am -
1 stop5h 40m
Wed 9/236:00 am -
1 stop4h 49m
Deal found 8/2![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/245:55 am -
Nonstop1h 25m
Mon 9/288:50 pm -
Nonstop1h 35m
Deal found 8/4![Southwest logo]()
$235
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 8/2610:54 am -
1 stop3h 36m
Sun 8/305:40 am -
1 stop5h 19m
Deal found 8/4![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 10/307:55 am -
1 stop3h 25m
Mon 11/28:05 am -
1 stop5h 50m
Deal found 8/4![Southwest logo]()
$241
This Delta deal was found by Cheapflights users on 8/5. 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.
Mon 10/195:15 pm -
1 stop5h 44m
Mon 10/265:40 am -
1 stop5h 23m
Deal found 8/5![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/6. 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.
Fri 9/43:20 pm -
Nonstop1h 25m
Sun 9/69:15 pm -
Nonstop1h 30m
Deal found 8/6![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2810:54 am -
1 stop3h 36m
Sun 8/307:15 am -
1 stop6h 24m
Deal found 8/3![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 9/197:40 am -
2 stops8h 40m
Sat 9/264:55 pm -
Nonstop1h 20m
Deal found 8/5![Southwest logo]()
$250
This Delta deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/2410:54 am -
1 stop3h 36m
Sat 8/296:00 am -
1 stop5h 10m
Deal found 8/2![Delta logo]()
$279
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/127:55 am -
1 stop3h 35m
Mon 9/1411:10 am -
1 stop3h 20m
Deal found 8/2![Southwest logo]()
$250
Last-minute flights from Midway to KentuckyDiscover last-minute flight deals from Midway to Kentucky. Data last updated August 7, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Kentucky. Data last updated August 7, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:49 pm -
Nonstop1h 30m
Sun 8/161:23 pm -
Nonstop1h 36m
Deal found 8/3![Allegiant Air logo]()
$179
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Thu 8/279:26 pm -
1 stop11h 35m
Sun 8/309:56 am -
1 stop10h 35m
Deal found 8/3![Frontier logo]()
$208
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/38:05 am -
Nonstop1h 20m
Sat 9/58:20 am -
Nonstop1h 05m
Deal found 8/2![Southwest logo]()
$181
This Southwest deal was found by Cheapflights users on 8/6. 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.
Fri 9/48:05 am -
Nonstop1h 20m
Fri 9/117:00 pm -
Nonstop1h 10m
Deal found 8/6![Southwest logo]()
$196
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/58:00 am -
Nonstop1h 25m
Sun 9/67:30 pm -
Nonstop1h 10m
Deal found 8/4![Southwest logo]()
$157
This Delta deal was found by Cheapflights users on 8/6. 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.
Sat 9/55:45 pm -
1 stop3h 55m
Sun 9/66:10 am -
1 stop4h 07m
Deal found 8/6![Delta logo]()
$178
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/511:15 am -
Nonstop1h 25m
Sun 9/69:15 pm -
Nonstop1h 30m
Deal found 8/4![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/57:50 am -
Nonstop1h 20m
Sun 9/610:00 am -
Nonstop1h 10m
Deal found 8/4![Southwest logo]()
$217
This Southwest deal was found by Cheapflights users on 8/5. 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.
Sat 9/55:50 pm -
Nonstop1h 35m
Mon 9/75:40 am -
Nonstop1h 30m
Deal found 8/5![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/6. 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.
Tue 9/81:00 pm -
Nonstop1h 15m
Fri 9/117:10 pm -
Nonstop1h 15m
Deal found 8/6![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/5. 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 9/105:55 am -
1 stop5h 20m
Fri 9/117:05 am -
2 stops9h 25m
Deal found 8/5![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/165:55 pm -
Nonstop1h 20m
Wed 9/239:05 am -
Nonstop1h 05m
Deal found 8/2![Southwest logo]()
$205
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 August 7, 2026.
Search for one-way flight options from Midway to Kentucky. Find affordable one-way fares based on user searches. Data last updated August 7, 2026.
This CheapOair deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/191:26 pm -
Nonstop1h 25m
Deal found 8/3![Allegiant Air logo]()
$50
This Super.com deal was found by Cheapflights users on 8/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:49 pm -
Nonstop1h 30m
Deal found 8/5![Allegiant Air logo]()
$69
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/118:05 am -
Nonstop1h 20m
Deal found 8/4![Southwest logo]()
$79
This CheapOair deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/232:26 pm -
Nonstop1h 25m
Deal found 8/3![Allegiant Air logo]()
$82
This Cheapflightsfares deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/512:56 pm -
Nonstop1h 25m
Deal found 8/2![Allegiant Air logo]()
$83
This CheapOair deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:30 pm -
Nonstop1h 27m
Deal found 8/3![Allegiant Air logo]()
$87
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/59:24 am -
1 stop3h 18m
Deal found 8/4![Delta logo]()
$89
This Super.com deal was found by Cheapflights users on 8/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2812:54 pm -
1 stop5h 29m
Deal found 8/6![Frontier logo]()
$99
This CheapOair deal was found by Cheapflights users on 8/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:24 pm -
Nonstop1h 25m
Deal found 8/6![Allegiant Air logo]()
$99
This Southwest deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/78:05 am -
Nonstop1h 20m
Deal found 8/4![Southwest logo]()
$103
This Frontier deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Fri 10/212:54 pm -
1 stop5h 29m
Deal found 8/2![Frontier logo]()
$106
This Southwest deal was found by Cheapflights users on 8/6. 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.
Sat 9/53:15 pm -
Nonstop1h 15m
Deal found 8/6![Southwest logo]()
$109
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 August 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $157 (Southwest) |
One-way from | $50 (CheapOair) |
Popular in | May |
Cheapest in | December |
Average price | $315 |
Good round-trip deal | $291 or less |
Good one-way deal | $179 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 August 7, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kentucky that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoCincinnati
MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky
MDWCVG
Chicago Midway
Fri 10/30
7:45 am-9:55 am
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Sat 11/7
1:00 pm-3:35 pm
1 stop3h 35m
$191
Quickest round-trip
ChicagoCincinnati
MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky
MDWCVG
Chicago Midway
Thu 10/1
7:30 pm-9:35 pm
Nonstop1h 05m
Cincinnati Cinci./N. Kentucky
Mon 10/5
8:20 pm-8:35 pm
Nonstop1h 15m
$205
ChicagoCincinnati
MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky
MDWCVG
Chicago Midway
Sat 9/12
8:00 am-10:25 am
Nonstop1h 25m
Cincinnati Cinci./N. Kentucky
Sat 9/19
4:55 pm-5:05 pm
Nonstop1h 10m
$205
ChicagoCincinnati
MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky
MDWCVG
Chicago Midway
Tue 9/1
5:55 pm-8:10 pm
Nonstop1h 15m
Cincinnati Cinci./N. Kentucky
Thu 9/3
7:00 pm-7:10 pm
Nonstop1h 10m
$205
ChicagoCincinnati
MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky
MDWCVG
Chicago Midway
Wed 9/2
12:45 pm-2:55 pm
Nonstop1h 10m
Cincinnati Cinci./N. Kentucky
Wed 9/9
7:15 pm-7:25 pm
Nonstop1h 10m
$205
ChicagoCincinnati
MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky
MDWCVG
Chicago Midway
Fri 9/4
6:10 pm-8:30 pm
Nonstop1h 20m
Cincinnati Cinci./N. Kentucky
Fri 9/11
5:25 pm-10:25 pm
1 stop6h 00m
$206
ChicagoCincinnati
MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky
MDWCVG
Chicago Midway
Wed 9/16
5:55 pm-8:15 pm
Nonstop1h 20m
Cincinnati Cinci./N. Kentucky
Wed 9/23
3:30 pm-8:50 pm
1 stop6h 20m
$215
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Sat 9/5
11:15 am-5:20 pm
1 stop5h 05m
Louisville Intl
Sun 9/6
7:10 pm-7:25 pm
Nonstop1h 15m
$227
ChicagoNashville
MDW Chicago Midway - BNA Nashville Intl
MDWBNA
Chicago Midway
Sat 9/5
9:05 am-3:45 pm
2 stops6h 40m
Nashville Intl
Sun 9/6
8:05 am-9:40 am
Nonstop1h 35m
$232
ChicagoLouisville
MDW Chicago Midway - SDF Louisville Intl
MDWSDF
Chicago Midway
Wed 9/16
9:00 am-11:20 am
Nonstop1h 20m
Louisville Intl
Wed 9/23
8:45 am-9:00 am
Nonstop1h 15m
$235
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-LEX
MDW-SDF
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-LEX
MDW-SDF
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 August 7, 2026.
Unlike in the evening, when flights are generally more expensive, you can save up to 21% on flights from Chicago Midway Airport to Kentucky by exploring options for tickets at noon.
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 August 1, 2026.
Travelers seeking maximum savings on their Chicago Midway Airport to Kentucky flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Kentucky
Get insights into the airlines that provide service to Kentucky. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kentucky. Reviews last updated August 7, 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
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Overall
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
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Complete your trip
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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 August 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Kentucky flights
Consider these flights traveling from Midway to Kentucky.
Top airline flying from Midway to Kentucky
Discover the top airline that operate flights from Midway to Kentucky. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$129 | Average$360 | FlexibilityNo cancel fee | On-time63% |