$54+ Cheap flights from Kentucky to Key West (EYW)
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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — EYW
Sep 20 — Sep 271
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Kentucky to Key West 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Kentucky to Key West
Cheapest
Best
Last-minute
One-way
Cheapest flights from Kentucky to Key WestExplore the most affordable flight options available from Kentucky to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Kentucky to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This CheapOair deal was found by Cheapflights users on 8/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:00 am -
Nonstop2h 36m
Fri 9/1812:26 pm -
Nonstop2h 37m
Deal found 8/20![Allegiant Air logo]()
$97
This Booking.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/307:00 am -
Nonstop2h 04m
Mon 11/211:09 am -
Nonstop2h 13m
Deal found 8/17![Allegiant Air logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:00 am -
Nonstop2h 36m
Fri 9/2512:26 pm -
Nonstop2h 37m
Deal found 8/18![Allegiant Air logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:39 pm -
Nonstop2h 34m
Fri 9/45:12 pm -
Nonstop2h 37m
Deal found 8/19![Allegiant Air logo]()
$141
This Booking.com deal was found by Cheapflights users on 8/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:15 am -
Nonstop2h 04m
Fri 10/309:54 am -
Nonstop2h 13m
Deal found 8/19![Allegiant Air logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:20 am -
Nonstop2h 04m
Mon 10/1911:54 am -
Nonstop2h 13m
Deal found 8/18![Allegiant Air logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:00 am -
Nonstop2h 36m
Thu 9/1712:01 pm -
2 stops23h 37m
Deal found 8/18![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:00 am -
Nonstop2h 36m
Fri 9/2512:59 pm -
2 stops22h 39m
Deal found 8/18![Multiple Airlines logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/1410:00 am -
Nonstop2h 36m
Fri 9/1812:59 pm -
2 stops46h 39m
Deal found 8/17![Multiple Airlines logo]()
$165
This Cheapflightsfares deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 8/241:39 pm -
Nonstop2h 34m
Fri 8/285:03 pm -
Nonstop2h 39m
Deal found 8/17![Allegiant Air logo]()
$168
This Gotogate deal was found by Cheapflights users on 8/18. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:15 am -
Nonstop2h 04m
Mon 11/911:54 am -
Nonstop2h 13m
Deal found 8/18![Allegiant Air logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:40 pm -
1 stop15h 39m
Mon 9/1410:59 am -
1 stop22h 49m
Deal found 8/19![Multiple Airlines logo]()
$189
Best flights from Kentucky to Key WestDiscover carefully curated flight deals from Kentucky to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Kentucky to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/169:41 pm -
1 stop11h 21m
Mon 10/1911:54 am -
Nonstop2h 13m
Deal found 8/18![Allegiant Air logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/29:56 pm -
1 stop11h 28m
Tue 10/61:16 pm -
1 stop20h 22m
Deal found 8/17![Multiple Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:40 pm -
1 stop5h 22m
Wed 11/187:35 am -
1 stop3h 54m
Deal found 8/19![Delta logo]()
$319
This United Airlines deal was found by Cheapflights users on 8/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/206:00 am -
2 stops9h 22m
Wed 1/272:30 pm -
1 stop8h 30m
Deal found 8/20![United Airlines logo]()
$388
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1412:16 pm -
1 stop5h 40m
Sat 11/217:18 pm -
1 stop4h 37m
Deal found 8/20![American Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:43 pm -
1 stop21h 55m
Mon 10/269:34 am -
1 stop12h 10m
Deal found 8/18![Allegiant Air logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/54:29 pm -
1 stop17h 56m
Wed 9/912:53 pm -
1 stop24h 58m
Deal found 8/20![Multiple Airlines logo]()
$323
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/173:34 pm -
1 stop4h 27m
Tue 10/207:40 am -
1 stop4h 18m
Deal found 8/16![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 12/812:47 pm -
1 stop7h 15m
Wed 12/167:35 am -
1 stop4h 17m
Deal found 8/17![Delta logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:35 pm -
2 stops11h 49m
Mon 10/1210:59 am -
1 stop10h 45m
Deal found 8/20![Multiple Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/291:04 pm -
1 stop6h 57m
Mon 11/26:11 pm -
1 stop5h 47m
Deal found 8/19![Delta logo]()
$329
This Delta deal was found by Cheapflights users on 8/18. 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.
Sat 11/71:59 pm -
1 stop6h 02m
Wed 11/117:35 am -
1 stop4h 21m
Deal found 8/18![Delta logo]()
$333
This United Airlines deal was found by Cheapflights users on 8/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/246:00 am -
2 stops10h 22m
Sat 1/302:30 pm -
1 stop6h 09m
Deal found 8/20![United Airlines logo]()
$445
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:21 am -
2 stops8h 37m
Tue 10/201:43 pm -
2 stops7h 41m
Deal found 8/16![American Airlines logo]()
$457
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/105:21 pm -
2 stops18h 58m
Sun 9/136:11 pm -
1 stop18h 51m
Deal found 8/16![Multiple Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 8/18. 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.
Fri 9/185:40 am -
1 stop5h 06m
Sat 9/196:19 pm -
1 stop4h 08m
Deal found 8/18![Delta logo]()
$334
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/126:00 am -
1 stop7h 11m
Tue 12/154:05 pm -
1 stop6h 25m
Deal found 8/19![United Airlines logo]()
$464
This American Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:00 am -
1 stop7h 11m
Mon 11/165:01 pm -
1 stop7h 38m
Deal found 8/16![American Airlines logo]()
$467
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:18 pm -
1 stop19h 25m
Fri 10/2311:59 am -
2 stops29h 03m
Deal found 8/17![Multiple Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/51:59 pm -
1 stop6h 02m
Tue 11/106:02 pm -
1 stop6h 03m
Deal found 8/17![Delta logo]()
$338
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:53 am -
1 stop5h 02m
Sat 9/54:56 pm -
1 stop8h 03m
Deal found 8/17![American Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/237:05 am -
1 stop5h 48m
Fri 10/306:10 pm -
1 stop5h 49m
Deal found 8/17![Delta logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/214:14 pm -
2 stops19h 07m
Mon 10/269:34 am -
1 stop7h 20m
Deal found 8/18![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:33 pm -
1 stop17h 25m
Mon 9/73:14 pm -
1 stop18h 25m
Deal found 8/20![Allegiant Air logo]()
$574
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:30 am -
3 stops27h 59m
Sat 9/264:00 pm -
1 stop5h 11m
Deal found 8/19![United Airlines logo]()
$525
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/212:09 pm -
1 stop5h 30m
Tue 10/65:28 pm -
1 stop5h 31m
Deal found 8/17![American Airlines logo]()
$496
This Delta deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/211:24 am -
1 stop5h 59m
Mon 10/57:40 am -
1 stop4h 40m
Deal found 8/19![Delta logo]()
$369
This United Airlines deal was found by Cheapflights users on 8/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/78:30 am -
1 stop6h 52m
Mon 1/116:20 pm -
2 stops22h 41m
Deal found 8/20![United Airlines logo]()
$572
This American Airlines deal was found by Cheapflights users on 8/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:06 am -
1 stop6h 59m
Tue 9/87:03 pm -
1 stop4h 48m
Deal found 8/20![American Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/1112:53 pm -
1 stop4h 30m
Tue 9/157:40 am -
1 stop4h 04m
Deal found 8/17![Delta logo]()
$381
Last-minute flights from Kentucky to Key WestDiscover last-minute flight deals from Kentucky to Key West. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Key West. Data last updated August 21, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 8/241:39 pm -
Nonstop2h 34m
Fri 8/285:03 pm -
Nonstop2h 39m
Deal found 8/17![Allegiant Air logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/281:39 pm -
Nonstop2h 34m
Fri 9/45:12 pm -
Nonstop2h 37m
Deal found 8/19![Allegiant Air logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:40 pm -
1 stop15h 39m
Mon 9/1410:59 am -
1 stop22h 49m
Deal found 8/19![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:14 pm -
2 stops17h 10m
Mon 9/1410:59 am -
1 stop22h 49m
Deal found 8/19![Multiple Airlines logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:40 pm -
1 stop15h 39m
Mon 9/1410:59 am -
1 stop22h 49m
Deal found 8/19![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/129:43 am -
1 stop23h 36m
Fri 9/1810:59 am -
1 stop22h 49m
Deal found 8/17![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:40 pm -
1 stop15h 39m
Thu 9/1712:01 pm -
2 stops32h 36m
Deal found 8/20![Multiple Airlines logo]()
$211
This CheapOair deal was found by Cheapflights users on 8/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:00 am -
Nonstop2h 36m
Fri 9/1812:26 pm -
Nonstop2h 37m
Deal found 8/20![Allegiant Air logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1410:00 am -
Nonstop2h 36m
Thu 9/1712:01 pm -
2 stops23h 37m
Deal found 8/18![Multiple Airlines logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 9/1410:00 am -
Nonstop2h 36m
Fri 9/1812:59 pm -
2 stops46h 39m
Deal found 8/17![Multiple Airlines logo]()
$165
This Cheapflightsfares deal was found by Cheapflights users on 8/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:00 am -
Nonstop2h 36m
Fri 9/2512:26 pm -
Nonstop2h 37m
Deal found 8/18![Allegiant Air logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:00 am -
Nonstop2h 36m
Fri 9/2512:59 pm -
2 stops22h 39m
Deal found 8/18![Multiple Airlines logo]()
$160
One-way flights from Kentucky to Key WestSearch for one-way flight options from Kentucky to Key West. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Kentucky to Key West. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:00 am -
Nonstop2h 04m
Deal found 8/20![Allegiant Air logo]()
$54
This FlightHub deal was found by Cheapflights users on 8/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:00 am -
Nonstop2h 04m
Deal found 8/20![Allegiant Air logo]()
$71
This CheapOair deal was found by Cheapflights users on 8/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2810:00 am -
Nonstop2h 36m
Deal found 8/19![Allegiant Air logo]()
$87
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2312:43 pm -
2 stops20h 41m
Deal found 8/20![Multiple Airlines logo]()
$104
This Jetabroad deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/78:30 am -
Nonstop2h 43m
Deal found 8/17![Allegiant Air logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 11/259:00 am -
Nonstop2h 32m
Deal found 8/17![Allegiant Air logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/22:28 pm -
Nonstop2h 39m
Deal found 8/19![Allegiant Air logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/285:40 pm -
3 stops38h 44m
Deal found 8/18![Multiple Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/299:09 pm -
1 stop15h 10m
Deal found 8/17![Breeze Airways logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 11/812:48 pm -
2 stops47h 48m
Deal found 8/16![Multiple Airlines logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1711:55 am -
2 stops22h 24m
Deal found 8/17![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” 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 10/1612:43 pm -
2 stops20h 41m
Deal found 8/17![Multiple Airlines logo]()
$129
Find flight deals from Kentucky to Key West
Keep the following information in mind while searching for Kentucky to Key West flight deals. Data was last updated August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $97 (CheapOair) |
One-way from | $54 (Kiwi.com) |
Popular in | November |
Cheapest in | February |
Average price | $381 |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Key West 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 August 21, 2026.
Use the filters below to find and compare flights from Kentucky to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
KnoxvilleKey West
TYS Knoxville McGhee Tyson - EYW Key West
TYSEYW
Knoxville McGhee Tyson
Fri 10/16
9:41 pm-9:02 am
1 stop11h 21m
Key West
Mon 10/19
11:54 am-2:07 pm
Nonstop2h 13m
$206
KnoxvilleKey West
TYS Knoxville McGhee Tyson - EYW Key West
TYSEYW
Knoxville McGhee Tyson
Wed 10/21
2:43 pm-12:38 pm
1 stop21h 55m
Key West
Mon 10/26
9:34 am-9:44 pm
1 stop12h 10m
$282
KnoxvilleKey West
TYS Knoxville McGhee Tyson - EYW Key West
TYSEYW
Knoxville McGhee Tyson
Fri 10/2
9:56 pm-9:24 am
1 stop11h 28m
Key West
Tue 10/6
1:16 pm-9:38 am
1 stop20h 22m
$315
KnoxvilleKey West
TYS Knoxville McGhee Tyson - EYW Key West
TYSEYW
Knoxville McGhee Tyson
Fri 11/13
2:40 pm-8:02 pm
1 stop5h 22m
Key West
Wed 11/18
7:35 am-11:29 am
1 stop3h 54m
$319
EvansvilleKey West
EVV Evansville Dress Regional - EYW Key West
EVVEYW
Evansville Dress Regional
Sat 9/5
4:29 pm-11:25 am
1 stop17h 56m
Key West
Wed 9/9
12:53 pm-12:51 pm
1 stop24h 58m
$323
LexingtonKey West
LEX Lexington Blue Grass - EYW Key West
LEXEYW
Lexington Blue Grass
Sat 10/17
3:34 pm-8:01 pm
1 stop4h 27m
Key West
Tue 10/20
7:40 am-11:58 am
1 stop4h 18m
$329
LexingtonKey West
LEX Lexington Blue Grass - EYW Key West
LEXEYW
Lexington Blue Grass
Tue 12/8
12:47 pm-8:02 pm
1 stop7h 15m
Key West
Wed 12/16
7:35 am-11:52 am
1 stop4h 17m
$329
LexingtonKey West
LEX Lexington Blue Grass - EYW Key West
LEXEYW
Lexington Blue Grass
Thu 10/29
1:04 pm-8:01 pm
1 stop6h 57m
Key West
Mon 11/2
6:11 pm-11:58 pm
1 stop5h 47m
$329
LouisvilleKey West
SDF Louisville Intl - EYW Key West
SDFEYW
Louisville Intl
Sat 11/7
1:59 pm-8:01 pm
1 stop6h 02m
Key West
Wed 11/11
7:35 am-11:56 am
1 stop4h 21m
$333
KnoxvilleKey West
TYS Knoxville McGhee Tyson - EYW Key West
TYSEYW
Knoxville McGhee Tyson
Fri 9/18
5:40 am-10:46 am
1 stop5h 06m
Key West
Sat 9/19
6:19 pm-10:27 pm
1 stop4h 08m
$334
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Kentucky with our price prediction graph.
TYS-EYW
BNA-EYW
HTS-EYW
EVV-EYW
LEX-EYW
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 Kentucky to Key West
USKY-EYW
TYS-EYW
BNA-EYW
HTS-EYW
EVV-EYW
What is the cheapest month to book a flight from Kentucky to Key West?
Currently, January is the cheapest month in which you can book a flight from Kentucky to Key West (average of $368). Flying from Kentucky to Key West in November is currently the most expensive (average of $589). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Kentucky to Key West?
Airfare is below average for this route at the moment.
Kentucky to Key West flights typically cost between $320 and $542 in November.The cheapest round-trip price found within the last 5 days was $205 on Breeze Airways (Nov 15-Nov 19).
How far ahead should I book a flight from Kentucky to Key West?
Booking 36 days in advance of your planned departure date is, on average, the best time to get cheap flights from Kentucky to Key West. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Key West flight routes
Other flight options
Popular flights
Top destinations
Alternative routes for Kentucky to Key West
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Key West by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Key West by cabin class
Find flights from Kentucky to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Key West
Explore flights to Key West departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 21, 2026.
Kentucky and Key West flights
Browse other Kentucky and Key West flight options. Last updated on August 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Kentucky to Key West flights
Consider these flights traveling from Kentucky to Key West.
Top 3 airlines flying from Kentucky to Key West
Discover the top 3 airlines that operate flights from Kentucky to Key West. 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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$389 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$278 | Average$535 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$282 | Average$424 | FlexibilityNo cancel fee | On-timeN/A |