$103+ Cheap flights from Wisconsin 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
May 30 — Jun 61
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Wisconsin 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 Wisconsin to Key West
Cheapest
Best
Last-minute
One-way
Cheapest flights from Wisconsin to Key WestExplore the most affordable flight options available from Wisconsin to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2026.
Explore the most affordable flight options available from Wisconsin to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop19h 43m
Multiple Airlines
Thu 6/412:05 pm
EYW
- ATW
1 stop10h 47m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop19h 43m
Multiple Airlines
Thu 5/289:24 pm
EYW
- ATW
1 stop26h 24m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$228
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/267:00 am
MKE
- EYW
1 stop8h 07m
American Airlines
Tue 6/25:37 pm
EYW
- MKE
1 stop6h 33m
American Airlines
Deal found 4/26![American Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop19h 43m
Multiple Airlines
Fri 5/292:51 pm
EYW
- ATW
1 stop8h 57m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop22h 17m
Allegiant Air
Thu 6/410:56 am
EYW
- ATW
2 stops22h 50m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$251
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/106:13 am
MKE
- EYW
2 stops11h 36m
American Airlines
Tue 6/161:39 pm
EYW
- MKE
2 stops10h 31m
American Airlines
Deal found 4/28![American Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/2810:11 am
MKE
- EYW
1 stop6h 12m
Delta
Sat 8/17:50 am
EYW
- MKE
1 stop5h 01m
Delta
Deal found 4/28![Delta logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/612:29 pm
MKE
- EYW
2 stops21h 56m
Multiple Airlines
Mon 6/83:25 pm
EYW
- MKE
1 stop17h 33m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$271
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/67:09 am
MKE
- EYW
1 stop6h 00m
Delta
Mon 6/86:24 pm
EYW
- MKE
1 stop6h 35m
Delta
Deal found 4/27![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/2610:13 am
MKE
- EYW
1 stop6h 10m
Delta
Tue 6/22:00 pm
EYW
- MKE
1 stop8h 02m
Delta
Deal found 4/27![Delta logo]()
$280
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/287:25 am
MKE
- EYW
2 stops10h 22m
American Airlines
Sat 8/17:33 pm
EYW
- MKE
1 stop5h 22m
American Airlines
Deal found 4/28![American Airlines logo]()
$285
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2912:43 pm
MKE
- EYW
1 stop6h 06m
Delta
Mon 6/17:30 am
EYW
- MKE
1 stop7h 16m
Delta
Deal found 4/28![Delta logo]()
$295
Best flights from Wisconsin to Key WestDiscover carefully curated flight deals from Wisconsin to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 30, 2026.
Discover carefully curated flight deals from Wisconsin to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop19h 43m
Multiple Airlines
Thu 6/412:05 pm
EYW
- ATW
1 stop10h 47m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop22h 17m
Allegiant Air
Thu 6/410:56 am
EYW
- ATW
2 stops22h 50m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$251
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/2810:11 am
MKE
- EYW
1 stop6h 12m
Delta
Sat 8/17:50 am
EYW
- MKE
1 stop5h 01m
Delta
Deal found 4/28![Delta logo]()
$265
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 10/246:45 am
MSN
- EYW
1 stop7h 21m
United Airlines
Wed 10/284:05 pm
EYW
- MSN
1 stop5h 49m
United Airlines
Deal found 4/28![United Airlines logo]()
$323
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 10/137:05 am
MSN
- EYW
1 stop8h 07m
American Airlines
Sat 10/171:48 pm
EYW
- MSN
1 stop8h 22m
American Airlines
Deal found 4/26![American Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/2912:43 pm
MKE
- EYW
1 stop6h 06m
Delta
Mon 6/17:30 am
EYW
- MKE
1 stop5h 08m
Delta
Deal found 4/26![Delta logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 8/213:17 pm
ATW
- EYW
1 stop22h 45m
Multiple Airlines
Mon 8/241:11 pm
EYW
- ATW
1 stop9h 41m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/282:44 pm
ATW
- EYW
1 stop19h 43m
Multiple Airlines
Sun 5/319:24 pm
EYW
- ATW
1 stop26h 24m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 8/1211:11 am
MSN
- EYW
1 stop7h 34m
Delta
Wed 8/196:00 pm
EYW
- MSN
1 stop5h 35m
Delta
Deal found 4/25![Delta logo]()
$323
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 8/158:00 am
MSP
- EYW
1 stop6h 06m
United Airlines
Sat 8/224:05 pm
EYW
- MSP
1 stop6h 32m
United Airlines
Deal found 4/26![United Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/156:04 pm
ATW
- EYW
1 stop16h 00m
Allegiant Air
Sun 5/171:57 pm
EYW
- ATW
1 stop24h 45m
Allegiant Air
Deal found 4/26![Allegiant Air logo]()
$388
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/39:49 am
ORD
- EYW
1 stop6h 34m
Delta
Tue 6/92:28 pm
EYW
- ORD
1 stop7h 04m
Delta
Deal found 4/25![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/265:45 am
MSP
- EYW
2 stops12h 25m
American Airlines
Tue 6/211:28 am
EYW
- MSP
2 stops11h 30m
American Airlines
Deal found 4/25![American Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/291:44 pm
ORD
- EYW
1 stop5h 07m
Delta
Sat 8/17:50 am
EYW
- ORD
1 stop7h 35m
Delta
Deal found 4/27![Delta logo]()
$329
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/125:40 am
LSE
- EYW
1 stop5h 58m
American Airlines
Sat 5/162:29 pm
EYW
- LSE
2 stops10h 25m
American Airlines
Deal found 4/27![American Airlines logo]()
$418
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” 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 9/51:15 pm
GRB
- EYW
1 stop7h 56m
United Airlines
Sat 9/124:05 pm
EYW
- GRB
1 stop6h 10m
United Airlines
Deal found 4/30![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/1310:13 am
MKE
- EYW
1 stop6h 10m
Delta
Sat 5/237:30 am
EYW
- MKE
1 stop5h 08m
Delta
Deal found 4/29![Delta logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/229:36 am
ATW
- EYW
2 stops27h 22m
Multiple Airlines
Tue 5/261:14 pm
EYW
- ATW
1 stop24h 43m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/1411:35 am
MSN
- EYW
2 stops10h 23m
American Airlines
Mon 5/186:46 pm
EYW
- MSN
1 stop5h 55m
American Airlines
Deal found 4/27![American Airlines logo]()
$443
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Fri 5/810:43 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Tue 5/124:05 pm
EYW
- ORD
Nonstop3h 55m
United Airlines
Deal found 4/25![United Airlines logo]()
$448
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 7/297:00 am
MSP
- EYW
1 stop5h 29m
Delta
Wed 8/52:24 pm
EYW
- MSP
1 stop8h 10m
Delta
Deal found 4/29![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 7/296:00 am
LSE
- EYW
2 stops12h 06m
American Airlines
Wed 8/52:25 pm
EYW
- LSE
2 stops10h 56m
American Airlines
Deal found 4/29![American Airlines logo]()
$465
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sun 6/149:48 am
ORD
- EYW
1 stop6h 39m
Delta
Mon 6/227:50 am
EYW
- ORD
1 stop7h 26m
Delta
Deal found 4/28![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/121:46 pm
ORD
- EYW
1 stop5h 07m
Delta
Sun 6/147:50 am
EYW
- ORD
1 stop7h 39m
Delta
Deal found 4/27![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/136:34 am
MSN
- EYW
2 stops11h 15m
American Airlines
Sat 6/207:29 pm
EYW
- MSN
1 stop5h 30m
American Airlines
Deal found 4/29![American Airlines logo]()
$500
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 6/36:00 am
ORD
- EYW
1 stop6h 30m
United Airlines
Tue 6/92:26 pm
EYW
- ORD
2 stops19h 40m
United Airlines
Deal found 4/29![United Airlines logo]()
$571
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/210:10 am
MKE
- EYW
1 stop6h 13m
Delta
Sat 5/96:19 pm
EYW
- MKE
1 stop6h 40m
Delta
Deal found 4/25![Delta logo]()
$361
This American Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/145:40 am
ATW
- EYW
1 stop5h 58m
American Airlines
Mon 5/186:46 pm
EYW
- ATW
1 stop5h 54m
American Airlines
Deal found 4/29![American Airlines logo]()
$506
This Delta deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/55:30 am
MKE
- EYW
1 stop7h 14m
Delta
Wed 5/136:19 pm
EYW
- MKE
1 stop6h 34m
Delta
Deal found 4/25![Delta logo]()
$361
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/1610:43 am
ORD
- EYW
Nonstop3h 24m
United Airlines
Tue 5/194:05 pm
EYW
- ORD
Nonstop3h 55m
United Airlines
Deal found 4/26![United Airlines logo]()
$598
Last-minute flights from Wisconsin to Key WestDiscover last-minute flight deals from Wisconsin to Key West. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Key West. Data last updated April 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop19h 43m
Multiple Airlines
Thu 6/412:05 pm
EYW
- ATW
1 stop10h 47m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop19h 43m
Multiple Airlines
Thu 5/289:24 pm
EYW
- ATW
1 stop26h 24m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop19h 43m
Multiple Airlines
Fri 5/292:51 pm
EYW
- ATW
1 stop8h 57m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop22h 17m
Allegiant Air
Thu 6/410:56 am
EYW
- ATW
2 stops22h 50m
Allegiant Air
Deal found 4/28![Allegiant Air logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/248:30 am
ORD
- EYW
1 stop27h 01m
Multiple Airlines
Thu 5/289:24 pm
EYW
- ORD
1 stop26h 49m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/2511:22 am
ORD
- EYW
Nonstop3h 27m
American Airlines
Mon 6/17:29 pm
EYW
- ORD
1 stop5h 36m
American Airlines
Deal found 4/27![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/267:00 am
MKE
- EYW
1 stop8h 07m
American Airlines
Tue 6/25:37 pm
EYW
- MKE
1 stop6h 33m
American Airlines
Deal found 4/26![American Airlines logo]()
$231
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/2610:13 am
MKE
- EYW
1 stop6h 10m
Delta
Tue 6/22:00 pm
EYW
- MKE
1 stop8h 02m
Delta
Deal found 4/27![Delta logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Tue 5/266:40 am
MSP
- EYW
1 stop27h 26m
Multiple Airlines
Tue 6/21:14 pm
EYW
- MSP
2 stops50h 50m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/288:46 am
MKE
- EYW
1 stop25h 41m
Multiple Airlines
Mon 6/112:07 pm
EYW
- MKE
1 stop20h 54m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$304
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2912:43 pm
MKE
- EYW
1 stop6h 06m
Delta
Mon 6/17:30 am
EYW
- MKE
1 stop7h 16m
Delta
Deal found 4/28![Delta logo]()
$295
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/297:30 am
MKE
- EYW
2 stops10h 19m
American Airlines
Mon 6/17:29 pm
EYW
- MKE
1 stop5h 32m
American Airlines
Deal found 4/28![American Airlines logo]()
$305
One-way flights from Wisconsin to Key WestSearch for one-way flight options from Wisconsin to Key West. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
Search for one-way flight options from Wisconsin to Key West. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/242:44 pm
ATW
- EYW
1 stop19h 43m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Tue 5/268:05 am
ORD
- EYW
2 stops26h 01m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/241:50 pm
ORD
- EYW
2 stops20h 37m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/31:50 pm
ORD
- EYW
2 stops24h 32m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/237:00 am
ATW
- EYW
1 stop27h 25m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Tue 6/97:52 am
ORD
- EYW
2 stops26h 14m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$136
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Tue 6/231:29 pm
ORD
- EYW
2 stops20h 37m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/276:55 am
ORD
- EYW
2 stops27h 30m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 5/206:06 pm
ATW
- EYW
1 stop18h 18m
Allegiant Air
Deal found 4/25![Allegiant Air logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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.
Tue 6/161:29 pm
ORD
- EYW
2 stops20h 37m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/256:55 am
ORD
- EYW
2 stops28h 39m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 6/57:52 pm
ORD
- EYW
2 stops42h 30m
Multiple Airlines
Deal found 4/27![Multiple Airlines logo]()
$154
Find flight deals from Wisconsin to Key West
Keep the following information in mind while searching for Wisconsin to Key West flight deals. Data was last updated April 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $205 (Kiwi.com) |
One-way from | $103 (Kiwi.com) |
Popular in | April |
Cheapest in | July |
Average price | $480 |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin 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 2,558,603 searches. Data last updated April 30, 2026.
Use the filters below to find and compare flights from Wisconsin to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
AppletonKey West
ATW - EYW
ATWEYW
Appleton Intl
Sun 5/24
2:44 pm-11:27 am
1 stop19h 43m
Key West
Thu 6/4
12:05 pm-9:52 pm
1 stop10h 47m
$207
AppletonKey West
ATW - EYW
ATWEYW
Appleton Intl
Sun 5/24
2:44 pm-2:01 pm
1 stop22h 17m
Key West
Thu 6/4
10:56 am-8:46 am
2 stops22h 50m
$251
MilwaukeeKey West
MKE - EYW
MKEEYW
Milwaukee-Mitchell
Tue 7/28
10:11 am-5:23 pm
1 stop6h 12m
Key West
Sat 8/1
7:50 am-11:51 am
1 stop5h 01m
$265
MilwaukeeKey West
MKE - EYW
MKEEYW
Milwaukee-Mitchell
Fri 5/29
12:43 pm-7:49 pm
1 stop6h 06m
Key West
Mon 6/1
7:30 am-11:38 am
1 stop5h 08m
$295
AppletonKey West
ATW - EYW
ATWEYW
Appleton Intl
Fri 8/21
3:17 pm-3:02 pm
1 stop22h 45m
Key West
Mon 8/24
1:11 pm-9:52 pm
1 stop9h 41m
$305
AppletonKey West
ATW - EYW
ATWEYW
Appleton Intl
Thu 5/28
2:44 pm-11:27 am
1 stop19h 43m
Key West
Sun 5/31
9:24 pm-10:48 pm
1 stop26h 24m
$321
MadisonKey West
MSN - EYW
MSNEYW
Madison Truax Field
Sat 10/24
6:45 am-3:06 pm
1 stop7h 21m
Key West
Wed 10/28
4:05 pm-8:54 pm
1 stop5h 49m
$323
MadisonKey West
MSN - EYW
MSNEYW
Madison Truax Field
Wed 8/12
11:11 am-7:45 pm
1 stop7h 34m
Key West
Wed 8/19
6:00 pm-10:35 pm
1 stop5h 35m
$323
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 6/3
9:49 am-5:23 pm
1 stop6h 34m
Key West
Tue 6/9
2:28 pm-8:32 pm
1 stop7h 04m
$329
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 7/29
1:44 pm-7:51 pm
1 stop5h 07m
Key West
Sat 8/1
7:50 am-2:25 pm
1 stop7h 35m
$329
Showing 1-10 of 57 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Wisconsin with our price prediction graph.
ATW-EYW
MKE-EYW
MSP-EYW
ORD-EYW
GRB-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 Wisconsin to Key West
USWI-EYW
ATW-EYW
MKE-EYW
MSP-EYW
ORD-EYW
How far ahead should I book a flight from Wisconsin to Key West?
The price you pay for your flight from Wisconsin to Key West may vary depending on when you book. For the best chance of a lower fare, look to book 68 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Wisconsin to Key West?
Currently, April is the cheapest month in which you can book a flight from Wisconsin to Key West (average of $142). Flying from Wisconsin to Key West in June is currently the most expensive (average of $318). 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 Wisconsin to Key West?
Related info for your journey
Find useful and relevant information for your journey from Wisconsin 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 Wisconsin 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 Wisconsin to Key West by cabin class
Find flights from Wisconsin 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 April 30, 2026.
Wisconsin and Key West flights
Browse other Wisconsin and Key West flight options. Last updated on April 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Wisconsin to Key West flights
Consider these flights traveling from Wisconsin to Key West.
Top 4 airlines flying from Wisconsin to Key West
Discover the top 4 airlines that operate flights from Wisconsin 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 2,558,603 searches. Data last updated April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$272 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$230 | Average$410 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$268 | Average$478 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$290 | Average$441 | FlexibilityNo cancel fee | On-time69% |