$187+ Cheap flights from Wisconsin 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
Nov 29 — Dec 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 October 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 October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/132:57 pm -
1 stop18h 22m
Fri 12/1810:59 am -
1 stop12h 40m
Deal found 10/29![Multiple Airlines logo]()
$265
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 11/278:00 am -
1 stop6h 29m
Thu 12/312:05 pm -
1 stop6h 13m
Deal found 10/28![United Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/133:28 pm -
2 stops20h 44m
Fri 12/183:57 pm -
1 stop7h 33m
Deal found 10/28![Allegiant Air logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/173:37 pm -
1 stop17h 42m
Sun 12/203:10 pm -
1 stop8h 38m
Deal found 10/28![Multiple Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 11/1810:20 am -
1 stop5h 50m
Wed 11/256:08 pm -
1 stop6h 46m
Deal found 10/28![Delta logo]()
$359
This Delta deal was found by Cheapflights users on 10/28. 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 12/135:30 am -
1 stop6h 41m
Tue 1/125:00 pm -
1 stop6h 44m
Deal found 10/28![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 12/155:00 am -
1 stop6h 07m
Wed 12/237:18 pm -
1 stop5h 41m
Deal found 10/29![American Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sun 12/135:00 am -
1 stop6h 07m
Sun 12/207:18 pm -
1 stop5h 41m
Deal found 10/29![American Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 10/27. 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 11/2412:42 pm -
1 stop6h 18m
Tue 12/16:06 pm -
1 stop6h 53m
Deal found 10/27![Delta logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/126:00 pm -
1 stop15h 19m
Mon 11/1610:59 am -
1 stop23h 51m
Deal found 10/28![Breeze Airways logo]()
$391
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/177:00 am -
1 stop7h 23m
Sun 12/204:04 pm -
1 stop6h 36m
Deal found 10/28![United Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 10/25. 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 12/157:40 am -
1 stop8h 06m
Tue 12/221:23 pm -
2 stops7h 37m
Deal found 10/25![American Airlines logo]()
$401
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 October 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 October 30, 2026.
This Delta deal was found by Cheapflights users on 10/28. 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 12/135:30 am -
1 stop6h 41m
Tue 1/125:00 pm -
1 stop6h 44m
Deal found 10/28![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/177:00 am -
1 stop7h 23m
Sun 12/204:04 pm -
1 stop6h 36m
Deal found 10/28![United Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 3/18:10 am -
1 stop6h 31m
Mon 3/86:32 pm -
1 stop5h 36m
Deal found 10/29![American Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 10/29. 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 1/276:05 am -
2 stops8h 59m
Wed 2/35:00 pm -
1 stop6h 11m
Deal found 10/29![Delta logo]()
$364
This Delta deal was found by Cheapflights users on 10/25. 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 11/2511:08 am -
2 stops7h 52m
Wed 12/26:06 pm -
1 stop5h 11m
Deal found 10/25![Delta logo]()
$371
This United Airlines deal was found by Cheapflights users on 10/29. 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 12/235:00 am -
1 stop5h 41m
Tue 12/294:04 pm -
1 stop5h 52m
Deal found 10/29![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/246:45 am -
1 stop8h 19m
Tue 12/14:43 pm -
2 stops8h 09m
Deal found 10/27![American Airlines logo]()
$424
This United Airlines deal was found by Cheapflights users on 10/26. 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.
Wed 12/305:00 am -
1 stop5h 41m
Wed 1/63:15 pm -
1 stop7h 23m
Deal found 10/26![United Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/85:31 am -
2 stops10h 48m
Thu 12/175:16 pm -
1 stop7h 43m
Deal found 10/28![American Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 4/69:42 am -
1 stop7h 34m
Sat 4/102:14 pm -
2 stops10h 17m
Deal found 10/29![American Airlines logo]()
$482
This Delta deal was found by Cheapflights users on 10/25. 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 1/276:32 am -
2 stops8h 32m
Tue 2/22:50 pm -
1 stop8h 21m
Deal found 10/25![Delta logo]()
$483
This United Airlines deal was found by Cheapflights users on 10/26. 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 1/95:00 am -
1 stop6h 16m
Sat 1/1612:59 pm -
1 stop7h 20m
Deal found 10/26![United Airlines logo]()
$524
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Sun 12/136:52 am -
1 stop8h 15m
Tue 1/124:16 pm -
2 stops8h 58m
Deal found 10/25![American Airlines logo]()
$488
This Delta deal was found by Cheapflights users on 10/28. 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 1/176:40 am -
2 stops8h 24m
Fri 1/221:35 pm -
2 stops21h 39m
Deal found 10/28![Delta logo]()
$528
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Sat 2/207:01 am -
2 stops11h 31m
Wed 2/246:15 pm -
1 stop6h 57m
Deal found 10/27![American Airlines logo]()
$488
This United Airlines deal was found by Cheapflights users on 10/29. 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 11/256:25 am -
1 stop8h 04m
Thu 12/1012:05 pm -
1 stop6h 32m
Deal found 10/29![United Airlines logo]()
$539
This Delta deal was found by Cheapflights users on 10/29. 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.
Mon 11/305:30 am -
1 stop6h 29m
Sat 12/56:06 pm -
1 stop5h 11m
Deal found 10/29![Delta logo]()
$531
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 3/117:01 am -
1 stop5h 36m
Tue 3/236:32 pm -
1 stop5h 36m
Deal found 10/28![American Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 10/26. 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.
Wed 12/235:00 am -
1 stop5h 41m
Tue 1/53:15 pm -
1 stop7h 23m
Deal found 10/26![United Airlines logo]()
$548
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 1/135:15 am -
1 stop9h 49m
Wed 1/207:30 am -
2 stops10h 06m
Deal found 10/28![Delta logo]()
$583
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Sat 1/306:05 am -
1 stop7h 08m
Wed 2/33:15 pm -
1 stop7h 23m
Deal found 10/29![United Airlines logo]()
$588
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 1/46:25 pm -
1 stop16h 26m
Fri 1/85:58 pm -
1 stop18h 00m
Deal found 10/29![American Airlines logo]()
$591
This United Airlines deal was found by Cheapflights users on 10/26. 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 12/125:00 am -
1 stop5h 24m
Tue 12/1512:05 pm -
1 stop7h 43m
Deal found 10/26![United Airlines logo]()
$600
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 2/197:00 am -
2 stops11h 43m
Mon 2/226:00 pm -
1 stop5h 45m
Deal found 10/29![Delta logo]()
$634
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Mon 1/186:24 am -
2 stops10h 02m
Mon 1/186:48 pm -
1 stop6h 11m
Deal found 10/25![American Airlines logo]()
$603
This United Airlines deal was found by Cheapflights users on 10/26. 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.
Tue 3/165:30 am -
2 stops9h 25m
Wed 3/244:45 pm -
2 stops31h 07m
Deal found 10/26![United Airlines logo]()
$606
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Fri 2/195:21 am -
2 stops12h 19m
Mon 2/228:02 pm -
2 stops14h 36m
Deal found 10/25![American Airlines logo]()
$631
This Delta deal was found by Cheapflights users on 10/26. 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.
Tue 11/1010:20 am -
1 stop5h 50m
Sat 11/147:30 am -
1 stop5h 07m
Deal found 10/26![Delta logo]()
$699
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 12/132:38 pm -
3 stops22h 58m
Sun 12/204:04 pm -
1 stop8h 07m
Deal found 10/28![United Airlines logo]()
$666
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Sat 1/91:12 pm -
1 stop21h 29m
Sat 1/166:26 pm -
2 stops16h 14m
Deal found 10/25![American Airlines logo]()
$639
Last-minute flights from Wisconsin to Key WestDiscover last-minute flight deals from Wisconsin to Key West. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Key West. Data last updated October 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/95:44 pm -
2 stops17h 52m
Fri 11/138:25 am -
1 stop26h 37m
Deal found 10/26![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/126:00 pm -
1 stop15h 19m
Mon 11/1610:59 am -
1 stop23h 51m
Deal found 10/28![Breeze Airways logo]()
$391
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 11/1312:42 pm -
1 stop6h 18m
Tue 11/177:30 am -
1 stop5h 07m
Deal found 10/29![Delta logo]()
$420
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Fri 11/1312:24 pm -
1 stop5h 23m
Tue 11/176:35 pm -
1 stop6h 08m
Deal found 10/26![American Airlines logo]()
$454
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 11/1810:20 am -
1 stop5h 50m
Wed 11/256:08 pm -
1 stop6h 46m
Deal found 10/28![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/187:17 am -
2 stops8h 58m
Wed 11/255:05 pm -
1 stop6h 35m
Deal found 10/28![American Airlines logo]()
$424
This Delta deal was found by Cheapflights users on 10/27. 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 11/2412:42 pm -
1 stop6h 18m
Tue 12/16:06 pm -
1 stop6h 53m
Deal found 10/27![Delta logo]()
$379
This Delta deal was found by Cheapflights users on 10/25. 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 11/2511:08 am -
2 stops7h 52m
Wed 12/26:06 pm -
1 stop5h 11m
Deal found 10/25![Delta logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/253:34 pm -
1 stop17h 05m
Wed 12/24:40 pm -
1 stop21h 55m
Deal found 10/25![Allegiant Air logo]()
$411
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 11/278:00 am -
1 stop6h 29m
Thu 12/312:05 pm -
1 stop6h 13m
Deal found 10/28![United Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/276:11 pm -
2 stops42h 32m
Thu 12/37:22 pm -
1 stop22h 04m
Deal found 10/28![Multiple Airlines logo]()
$454
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/285:01 am -
1 stop5h 45m
Sat 12/55:01 pm -
1 stop6h 35m
Deal found 10/28![American Airlines logo]()
$449
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 October 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 October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Wed 3/3110:31 am -
1 stop26h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Wed 11/256:11 pm -
2 stops40h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/276:45 am -
1 stop8h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![American Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Thu 12/246:10 pm -
1 stop15h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Breeze Airways logo]()
$311
This United Airlines deal was found by Cheapflights users on 10/25. 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 11/276:10 am -
1 stop6h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![United Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/258:00 am -
1 stop6h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![United Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/29. 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 3/318:10 am -
1 stop6h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Fri 1/85:07 am -
2 stops9h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![American Airlines logo]()
$344
This United Airlines deal was found by Cheapflights users on 10/29. 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 12/95:51 am -
1 stop8h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![United Airlines logo]()
$383
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Fri 11/277:05 am -
2 stops8h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![American Airlines logo]()
$385
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Wed 3/316:45 am -
2 stops9h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![United Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/272:40 pm -
3 stops20h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Multiple Airlines logo]()
$411
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 October 30, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $265 (Kiwi.com) |
One-way from | $187 (Kiwi.com) |
Popular in | October |
Cheapest in | September |
Average price | $506 |
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 7,457,451 searches. Data last updated October 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
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Wed 3/31
10:31 am-2:26 pm
1 stop26h 55m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$187
MilwaukeeKey West
MKE Milwaukee-Mitchell - EYW Key West
MKEEYW
Milwaukee-Mitchell
Wed 11/25
6:11 pm-11:19 am
2 stops40h 08m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$194
MilwaukeeKey West
MKE Milwaukee-Mitchell - EYW Key West
MKEEYW
Milwaukee-Mitchell
Fri 11/27
6:45 am-4:04 pm
1 stop8h 19m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$267
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Thu 12/24
6:10 pm-10:19 am
1 stop15h 09m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$311
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Fri 11/27
6:10 am-1:52 pm
1 stop6h 42m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$334
MilwaukeeKey West
MKE Milwaukee-Mitchell - EYW Key West
MKEEYW
Milwaukee-Mitchell
Fri 1/8
7:00 am-4:04 pm
1 stop8h 04m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$339
MilwaukeeKey West
MKE Milwaukee-Mitchell - EYW Key West
MKEEYW
Milwaukee-Mitchell
Wed 11/25
8:00 am-3:29 pm
1 stop6h 29m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$339
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Wed 3/31
8:10 am-3:41 pm
1 stop6h 31m
Key West
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$339
MadisonKey West
MSN Madison Truax Field - EYW Key West
MSNEYW
Madison Truax Field
Sun 12/13
5:30 am-1:11 pm
1 stop6h 41m
Key West
Tue 1/12
5:00 pm-10:44 pm
1 stop6h 44m
$359
AppletonKey West
ATW Appleton Intl - EYW Key West
ATWEYW
Appleton Intl
Wed 1/27
6:05 am-4:04 pm
2 stops8h 59m
Key West
Wed 2/3
5:00 pm-10:11 pm
1 stop6h 11m
$364
Showing 1-10 of 47 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
MSN-EYW
CWA-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
MSN-EYW
CWA-EYW
What is the cheapest month to book a flight from Wisconsin to Key West?
Currently, September is the cheapest month in which you can book a flight from Wisconsin to Key West (average of $362). Flying from Wisconsin to Key West in November is currently the most expensive (average of $500). 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?
Airfare is below average for this route at the moment.
Wisconsin to Key West flights typically cost between $447 and $548 in November.The cheapest round-trip price found within the last 5 days was $313 on United Airlines (Nov 27-Dec 3).
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.
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 October 30, 2026.
Wisconsin and Key West flights
Browse other Wisconsin and Key West flight options. Last updated on October 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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$142 | Average$310 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$230 | Average$456 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$268 | Average$525 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$270 | Average$424 | FlexibilityNo cancel fee | On-time69% |