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Key West

$119+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
Sep 3 — Sep 101
Thu 9/3
Thu 9/10
1 adult, Economy
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Cheap flight deals from Wisconsin to Key West

Cheapest flights from Wisconsin to Key West
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 August 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:44 pm
ORD
-
EYW
1 stop14h 41m
Multiple Airlines
Wed 9/910:04 am
EYW
-
ORD
2 stops9h 19m
Multiple Airlines
Deal found 8/2$254
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:59 pm
ORD
-
EYW
1 stop16h 26m
Multiple Airlines
Wed 9/211:46 am
EYW
-
ORD
2 stops9h 22m
Multiple Airlines
Deal found 8/1$256
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/265:59 pm
ORD
-
EYW
1 stop16h 26m
Multiple Airlines
Tue 9/11:14 pm
EYW
-
ORD
2 stops31h 54m
Multiple Airlines
Deal found 8/1$257
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:50 pm
ORD
-
EYW
1 stop17h 29m
Multiple Airlines
Sat 9/1910:04 am
EYW
-
ORD
2 stops9h 19m
Multiple Airlines
Deal found 7/30$258
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/225:59 pm
ORD
-
EYW
1 stop16h 26m
Multiple Airlines
Wed 8/2611:46 am
EYW
-
ORD
2 stops9h 22m
Multiple Airlines
Deal found 7/31$269
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:44 am
ORD
-
EYW
2 stops34h 50m
Multiple Airlines
Mon 8/3112:07 pm
EYW
-
ORD
1 stop12h 01m
Multiple Airlines
Deal found 8/1$270
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:28 pm
ORD
-
EYW
2 stops36h 56m
Multiple Airlines
Thu 9/1710:59 am
EYW
-
ORD
1 stop13h 00m
Multiple Airlines
Deal found 8/2$271
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:50 pm
ORD
-
EYW
1 stop17h 29m
Multiple Airlines
Wed 9/3010:04 am
EYW
-
ORD
2 stops9h 19m
Multiple Airlines
Deal found 8/1$273
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/249:20 am
ORD
-
EYW
2 stops25h 01m
Multiple Airlines
Thu 10/2910:59 am
EYW
-
ORD
1 stop13h 51m
Multiple Airlines
Deal found 7/31$274
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am
ORD
-
EYW
2 stops33h 22m
Multiple Airlines
Mon 8/3112:07 pm
EYW
-
ORD
1 stop12h 01m
Multiple Airlines
Deal found 8/1$275
This Kiwi.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:17 pm
ATW
-
EYW
1 stop18h 10m
Multiple Airlines
Mon 8/312:54 pm
EYW
-
ATW
1 stop8h 28m
Multiple Airlines
Deal found 8/1$277
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:44 am
ATW
-
EYW
1 stop23h 41m
Multiple Airlines
Fri 9/1110:59 am
EYW
-
ATW
1 stop11h 01m
Multiple Airlines
Deal found 7/30$278

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 August 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$254
(Kiwi.com)

One-way from

$119
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$374
Provider with most accurate pricing for Milwaukee-Mitchell-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Key West flights.
Search Deals
From Wisconsin to Key West
Search Deals
One-way flight from Wisconsin to Key West
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

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 August 4, 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

Price

Cheapest round-trip

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 9/12

12:45 pm-8:00 pm

1 stop6h 15m

Key West

Sat 9/19

7:40 am-11:40 am

1 stop5h 00m

$281

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 10/3

12:45 pm-8:00 pm

1 stop6h 15m

Key West

Wed 10/7

7:40 am-1:54 pm

1 stop7h 14m

$281

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sun 9/6

12:51 pm-7:57 pm

1 stop6h 06m

Key West

Wed 9/9

7:40 am-1:50 pm

1 stop7h 10m

$281

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Wed 10/28

12:36 pm-8:01 pm

1 stop6h 25m

Key West

Mon 11/2

6:11 pm-11:53 pm

1 stop6h 42m

$310

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 9/5

12:47 pm-7:57 pm

1 stop6h 10m

Key West

Wed 9/9

7:40 am-1:50 pm

1 stop7h 10m

$310

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 10/15

6:00 pm-7:44 am

1 stop12h 44m

Key West

Mon 10/19

2:54 pm-9:50 am

1 stop19h 56m

$320

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Wed 10/14

12:36 pm-8:01 pm

1 stop6h 25m

Key West

Tue 10/20

7:40 am-11:29 am

1 stop4h 49m

$325

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Tue 8/25

7:03 am-1:00 pm

1 stop4h 57m

Key West

Sat 8/29

7:40 am-11:39 am

1 stop4h 59m

$330

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 8/29

7:55 pm-11:25 am

1 stop14h 30m

Key West

Tue 9/8

1:14 pm-9:53 am

1 stop21h 39m

$331

AppletonKey West

ATW - EYW

ATWEYW

Appleton Intl

Sat 9/5

11:09 am-7:57 pm

2 stops7h 48m

Key West

Fri 9/11

6:19 pm-10:45 pm

1 stop5h 26m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/2

Showing 1-10 of 60 resultsSorted by cheapest first
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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.
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

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 $339). Flying from Wisconsin to Key West in June is currently the most expensive (average of $494). 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 $284 and $489 in September.
The cheapest round-trip price found within the last 5 days was $281 on Delta (Sep 12-Sep 19).

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 69 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.

  • What airport do you fly into for flights to Key West from Wisconsin?

    Most people fly into Key West (EYW) if they book a flight to Key West from Wisconsin. Key West is conveniently located just 2.6 mi from Key West’s city center.

  • How long is the flight from Wisconsin to Key West?

    Airlines like Delta, Breeze Airways, and American Airlines fly from Wisconsin to Key West in about 5h 57m. The time it takes to get you to your destination can typically vary by up to 8h 33m. Airlines will cover a distance of 1353 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Wisconsin to Key West?

    The most popular route from Wisconsin to Key West is Chicago O'Hare Intl - Key West. You may also consider Minneapolis St Paul - Key West or Milwaukee-Mitchell - Key West.

  • Can I find deals for flights from Wisconsin to Key West that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Key West.

  • Can I find deals for business class flights from Wisconsin to Key West?

    Yes. Cheapflights offers flight deals from Wisconsin to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $339). Flying from Wisconsin to Key West in June is currently the most expensive (average of $494). 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.

See more FAQs

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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 August 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$142Average$288FlexibilityNo cancel feeOn-time88%
DeltaCheapest$230Average$444FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$268Average$441FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$485FlexibilityNo cancel feeOn-time71%

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