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$95+ Cheap flights from Key West (EYW) to Wisconsin

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MKE
nov. 29 — dic. 61
sáb. 11/29
sáb. 12/6
1 adult, Economy
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Find flight deals from Key West to Wisconsin

Cheapest flights from Key West to Wisconsin
Explore the most affordable flight options available from Key West to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 30, 2025.

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.
jue. 11/139:36 pmEYW - ORD
1 stop26h 30mMultiple Airlines
dom. 11/165:25 amORD - EYW
1 stop14h 21mMultiple Airlines
Deal found 10/28$193
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.
sáb. 11/222:24 pmEYW - ORD
1 stop10h 05mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$200
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.
dom. 11/238:55 amEYW - ORD
1 stop10h 04mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$201
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.
lun. 11/248:55 amEYW - ORD
1 stop9h 20mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$204
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.
vie. 11/218:55 amEYW - ORD
1 stop8h 08mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$211
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.
jue. 11/2710:59 amEYW - ORD
1 stop12h 37mMultiple Airlines
sáb. 11/296:48 amORD - EYW
1 stop24h 27mMultiple Airlines
Deal found 10/29$213
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.
sáb. 11/222:24 pmEYW - ORD
1 stop10h 05mSpirit Airlines
mié. 12/33:43 pmORD - EYW
1 stop18h 37mSpirit Airlines
Deal found 10/29$221
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.
jue. 11/138:55 amEYW - ORD
1 stop15h 11mMultiple Airlines
lun. 11/171:50 pmORD - EYW
2 stops20h 15mMultiple Airlines
Deal found 10/29$222
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.
mar. 11/2510:59 amEYW - ORD
1 stop11h 48mMultiple Airlines
jue. 11/273:37 pmORD - EYW
1 stop16h 40mMultiple Airlines
Deal found 10/29$223
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.
jue. 11/2710:59 amEYW - ORD
1 stop12h 37mMultiple Airlines
mar. 12/24:22 pmORD - EYW
2 stops16h 45mMultiple Airlines
Deal found 10/29$226
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.
sáb. 11/222:24 pmEYW - ORD
1 stop10h 05mMultiple Airlines
sáb. 11/296:48 amORD - EYW
1 stop24h 27mMultiple Airlines
Deal found 10/29$230
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.
lun. 12/2912:22 pmEYW - MSN
1 stop7h 43mUnited Airlines
lun. 1/56:00 amMSN - EYW
1 stop7h 13mUnited Airlines
Deal found 10/29$269

Cheap flight deals from Key West to Wisconsin

Keep the following information in mind while searching for Key West to Wisconsin flight deals. Data was last updated octubre 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$193
(Kiwi.com)

One-way from

$95
(Kiwi.com)
Provider with most accurate pricing for Key West-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Milwaukee-Mitchell flights.
Search Deals
From Key West to Wisconsin
Search Deals
One-way flight from Key West to Wisconsin
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Wisconsin 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 octubre 30, 2025.
Use the filters below to find and compare flights from Key West to Wisconsin that are best for you.

Fly from

Key West

Fly to

Wisconsin

Route

Depart

Return

Price

Key WestChicago

EYW - ORD

EYWORD

Key West

jue. 11/27

10:59 am-10:36 pm

1 stop12h 37m

Chicago O'Hare Intl

mar. 12/2

12:32 pm-10:07 am

1 stop20h 35m

$229

Key WestChicago

EYW - ORD

EYWORD

Key West

sáb. 11/22

2:24 pm-11:29 pm

1 stop10h 05m

Chicago O'Hare Intl

mié. 12/3

8:00 am-8:15 am

2 stops23h 15m

$243

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 11/21

8:55 am-4:03 pm

1 stop8h 08m

Chicago O'Hare Intl

mar. 12/2

12:32 pm-10:07 am

1 stop20h 35m

$257

Key WestMilwaukee

EYW - MKE

EYWMKE

Key West

mié. 2/25

7:00 am-12:18 pm

1 stop6h 18m

Milwaukee-Mitchell

dom. 3/1

12:20 pm-7:44 pm

1 stop6h 24m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

lun. 12/29

12:22 pm-7:05 pm

1 stop7h 43m

Madison Truax Field

lun. 1/5

6:00 am-2:13 pm

1 stop7h 13m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

vie. 1/30

4:04 pm-11:41 pm

1 stop8h 37m

Madison Truax Field

mié. 2/4

6:00 am-12:33 pm

1 stop5h 33m

$269

Key WestMilwaukee

EYW - MKE

EYWMKE

Key West

vie. 2/6

7:10 am-11:10 am

1 stop5h 00m

Milwaukee-Mitchell

dom. 2/8

7:00 am-1:48 pm

1 stop5h 48m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

mar. 1/13

4:15 pm-9:05 pm

1 stop5h 50m

Madison Truax Field

dom. 1/18

6:30 am-3:17 pm

1 stop7h 47m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

mar. 11/25

6:18 pm-12:02 am

1 stop6h 44m

Chicago O'Hare Intl

mar. 12/2

1:20 pm-8:06 pm

1 stop5h 46m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

vie. 2/13

7:00 am-1:23 pm

1 stop7h 23m

Chicago O'Hare Intl

mar. 2/17

9:30 am-5:13 pm

1 stop6h 43m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 56 results
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Best time to book a flight from Key West to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Key West 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 Key West to Wisconsin
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated octubre 30, 2025.
Read through reviews of airlines operating flights from Key West to Wisconsin, such as Delta and American Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Key West to Wisconsin. 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 from for flights from Key West to Wisconsin?

    Key West (EYW) is the airport you will fly out of if you book a flight from Key West to Wisconsin. It is only a 2.6 mi journey to Key West (EYW) from Key West’s city center.

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

    For as low as $269, Delta can have you in Wisconsin from Key West in 6h 18m. There are 1317 mi between Key West and Wisconsin. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Most travelers choose Key West - Chicago O'Hare Intl, Key West - Madison Truax Field or Key West - Minneapolis St Paul when deciding on the best route from Key West to Wisconsin.

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

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

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

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

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

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

See more FAQs

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Top 2 airlines flying from Key West to Wisconsin

Discover the top 2 airlines that operate flights from Key West to Wisconsin. 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 octubre 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$283Average$343FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$348Average$403FlexibilityNo cancel feeOn-time71%

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