$145+ Cheap flights from Kentucky to Key West (EYW)
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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — EYW
Nov 7 — Nov 141
Round-trip
1 adult, Economy
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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
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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
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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 October 8, 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 October 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:09 pm -
1 stop15h 10m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Breeze Airways logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:09 pm -
1 stop15h 10m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Breeze Airways logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:09 pm -
1 stop15h 10m
Fri 10/3011:59 am -
1 stop22h 12m
Deal found 10/4![Breeze Airways logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:09 pm -
1 stop15h 10m
Fri 10/3011:59 am -
1 stop22h 12m
Deal found 10/4![Breeze Airways logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:25 am -
1 stop7h 22m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:25 am -
1 stop7h 22m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/189:09 pm -
1 stop15h 10m
Thu 10/2212:01 pm -
1 stop8h 28m
Deal found 10/4![Breeze Airways logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:59 pm -
2 stops13h 25m
Fri 11/1311:59 am -
1 stop27h 27m
Deal found 10/7![Breeze Airways logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:25 am -
1 stop7h 22m
Fri 10/3011:59 am -
1 stop22h 12m
Deal found 10/4![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:25 am -
1 stop7h 22m
Fri 10/3011:59 am -
1 stop22h 12m
Deal found 10/4![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:25 am -
1 stop7h 13m
Fri 11/2011:59 am -
1 stop27h 27m
Deal found 10/7![Multiple Airlines logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:59 pm -
2 stops13h 25m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Breeze Airways logo]()
$248
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 October 8, 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 October 8, 2026.
This Breeze Airways deal was found by Cheapflights users on 10/7. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/39:09 pm -
1 stop15h 10m
Thu 1/712:06 pm -
1 stop8h 23m
Deal found 10/7![Breeze Airways logo]()
$229
This American Airlines deal was found by Cheapflights users on 10/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:00 pm -
1 stop7h 33m
Sat 10/315:28 pm -
1 stop6h 17m
Deal found 10/3![American Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 10/6. 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 10/231:59 pm -
1 stop6h 02m
Fri 10/307:40 am -
1 stop5h 14m
Deal found 10/6![Delta logo]()
$389
This United Airlines deal was found by Cheapflights users on 10/5. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:00 am -
1 stop6h 24m
Tue 12/154:10 pm -
1 stop7h 46m
Deal found 10/5![United Airlines logo]()
$531
This Breeze Airways deal was found by Cheapflights users on 10/6. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/159:09 pm -
1 stop15h 10m
Thu 11/1912:01 pm -
1 stop8h 28m
Deal found 10/6![Breeze Airways logo]()
$318
This Breeze Airways deal was found by Cheapflights users on 10/7. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/179:09 pm -
1 stop15h 10m
Sun 12/2012:01 pm -
1 stop8h 28m
Deal found 10/7![Breeze Airways logo]()
$328
This Delta deal was found by Cheapflights users on 10/4. 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 10/216:00 am -
1 stop4h 47m
Fri 10/307:40 am -
1 stop5h 14m
Deal found 10/4![Delta logo]()
$389
This American Airlines deal was found by Cheapflights users on 10/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/185:44 am -
1 stop7h 19m
Mon 11/235:05 pm -
1 stop6h 37m
Deal found 10/8![American Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 10/4. 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.
Mon 10/266:00 am -
1 stop4h 47m
Mon 11/26:11 pm -
1 stop5h 48m
Deal found 10/4![Delta logo]()
$421
This United Airlines deal was found by Cheapflights users on 10/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:08 am -
1 stop7h 03m
Thu 12/315:52 pm -
1 stop6h 07m
Deal found 10/6![United Airlines logo]()
$583
This Delta deal was found by Cheapflights users on 10/5. 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 12/176:00 am -
1 stop4h 48m
Wed 12/307:15 am -
1 stop4h 23m
Deal found 10/5![Delta logo]()
$489
This American Airlines deal was found by Cheapflights users on 10/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:14 am -
2 stops9h 52m
Sat 11/76:26 pm -
1 stop4h 46m
Deal found 10/3![American Airlines logo]()
$734
This American Airlines deal was found by Cheapflights users on 10/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/175:00 am -
2 stops11h 06m
Thu 12/311:23 pm -
2 stops10h 23m
Deal found 10/6![American Airlines logo]()
$802
This Delta deal was found by Cheapflights users on 10/7. 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 10/233:34 pm -
1 stop4h 27m
Tue 10/277:40 am -
1 stop4h 18m
Deal found 10/7![Delta logo]()
$769
Last-minute flights from Kentucky to Key WestDiscover last-minute flight deals from Kentucky to Key West. Data last updated October 8, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Key West. Data last updated October 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/189:09 pm -
1 stop15h 10m
Thu 10/2212:01 pm -
1 stop8h 28m
Deal found 10/4![Breeze Airways logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:09 pm -
1 stop15h 10m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Breeze Airways logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:09 pm -
1 stop15h 10m
Fri 10/3011:59 am -
1 stop22h 12m
Deal found 10/4![Breeze Airways logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:25 am -
1 stop7h 22m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Multiple Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2310:25 am -
1 stop7h 22m
Fri 10/3011:59 am -
1 stop22h 12m
Deal found 10/4![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:59 pm -
2 stops13h 25m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Breeze Airways logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:09 pm -
1 stop15h 10m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Breeze Airways logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/259:09 pm -
1 stop15h 10m
Fri 10/3011:59 am -
1 stop22h 12m
Deal found 10/4![Breeze Airways logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:25 am -
1 stop7h 22m
Thu 10/2912:01 pm -
1 stop8h 28m
Deal found 10/4![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/2610:25 am -
1 stop7h 22m
Fri 10/3011:59 am -
1 stop22h 12m
Deal found 10/4![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:59 pm -
2 stops13h 25m
Fri 11/1311:59 am -
1 stop27h 27m
Deal found 10/7![Breeze Airways logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:25 am -
1 stop7h 13m
Fri 11/2011:59 am -
1 stop27h 27m
Deal found 10/7![Multiple Airlines logo]()
$244
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 October 8, 2026.
Search for one-way flight options from Kentucky to Key West. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/1411:45 am -
1 stop25h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Allegiant Air logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 10/6. 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.
Mon 10/1910:25 am -
1 stop7h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/159:20 am -
1 stop22h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Allegiant Air logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/162:33 pm -
3 stops44h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 10/159:11 pm -
2 stops36h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$265
This American Airlines deal was found by Cheapflights users on 10/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:00 am -
2 stops8h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/112:37 pm -
1 stop28h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Allegiant Air logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/124:34 pm -
3 stops40h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 10/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/118:59 pm -
2 stops15h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Multiple Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 10/4. 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.
Mon 10/121:04 pm -
1 stop6h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Delta logo]()
$470
This American Airlines deal was found by Cheapflights users on 10/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:00 am -
2 stops8h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![American Airlines logo]()
$475
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 October 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $181 (Kiwi.com) |
One-way from | $145 (Kiwi.com) |
Popular in | November |
Cheapest in | January |
Average price | $480 |
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 October 8, 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
LexingtonKey West
LEX Lexington Blue Grass - EYW Key West
LEXEYW
Lexington Blue Grass
Wed 10/14
11:45 am-12:47 pm
1 stop25h 02m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$145
LexingtonKey West
LEX Lexington Blue Grass - EYW Key West
LEXEYW
Lexington Blue Grass
Thu 10/15
9:20 am-7:44 am
1 stop22h 24m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$166
LouisvilleKey West
SDF Louisville Intl - EYW Key West
SDFEYW
Louisville Intl
Mon 10/19
7:35 pm-9:24 am
2 stops37h 49m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$203
LouisvilleKey West
SDF Louisville Intl - EYW Key West
SDFEYW
Louisville Intl
Sun 1/3
9:09 pm-12:19 pm
1 stop15h 10m
Key West
Thu 1/7
12:06 pm-8:29 pm
1 stop8h 23m
$229
LexingtonKey West
LEX Lexington Blue Grass - EYW Key West
LEXEYW
Lexington Blue Grass
Fri 10/16
2:33 pm-11:21 am
3 stops44h 48m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$257
LouisvilleKey West
SDF Louisville Intl - EYW Key West
SDFEYW
Louisville Intl
Sun 11/15
9:09 pm-12:19 pm
1 stop15h 10m
Key West
Thu 11/19
12:01 pm-8:29 pm
1 stop8h 28m
$318
LouisvilleKey West
SDF Louisville Intl - EYW Key West
SDFEYW
Louisville Intl
Thu 12/17
9:09 pm-12:19 pm
1 stop15h 10m
Key West
Sun 12/20
12:01 pm-8:29 pm
1 stop8h 28m
$328
LouisvilleKey West
SDF Louisville Intl - EYW Key West
SDFEYW
Louisville Intl
Sat 10/24
12:00 pm-7:33 pm
1 stop7h 33m
Key West
Sat 10/31
5:28 pm-11:45 pm
1 stop6h 17m
$363
LouisvilleKey West
SDF Louisville Intl - EYW Key West
SDFEYW
Louisville Intl
Fri 10/23
1:59 pm-8:01 pm
1 stop6h 02m
Key West
Fri 10/30
7:40 am-12:54 pm
1 stop5h 14m
$389
LouisvilleKey West
SDF Louisville Intl - EYW Key West
SDFEYW
Louisville Intl
Wed 10/21
6:00 am-10:47 am
1 stop4h 47m
Key West
Fri 10/30
7:40 am-12:54 pm
1 stop5h 14m
$389
Showing 1-10 of 22 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.
LEX-EYW
SDF-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
LEX-EYW
SDF-EYW
What is the cheapest month to book a flight from Kentucky to Key West?
Currently, February is the cheapest month in which you can book a flight from Kentucky to Key West (average of $367). Flying from Kentucky to Key West in April is currently the most expensive (average of $585). 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 $363 and $603 in October.The cheapest round-trip price found within the last 5 days was $181 on Breeze Airways (Oct 22-Oct 29).
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.
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Alternative routes for Kentucky to Key West
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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 October 8, 2026.
Kentucky and Key West flights
Browse other Kentucky and Key West flight options. Last updated on October 8, 2026.
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Kentucky to Key West flights
Consider these flights traveling from Kentucky to Key West.
Top 2 airlines flying from Kentucky to Key West
Discover the top 2 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 October 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$278 | Average$543 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$298 | Average$463 | FlexibilityNo cancel fee | On-timeN/A |