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$116+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MKE
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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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 September 14, 2025.

Round-trip from

$237
(Kiwi.com)

One-way from

$116
(Kiwi.com)
From Key West to Wisconsin
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One-way flight from Key West to Wisconsin
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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 September 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/268:47 amEYW - ORD
1 stop14h 11mMultiple Airlines
Tue 9/305:46 pmORD - EYW
1 stop15h 21mMultiple Airlines
Deal found 9/13$237
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/138:55 amEYW - ORD
1 stop9h 09mMultiple Airlines
Sat 11/158:00 amORD - EYW
1 stop23h 15mMultiple Airlines
Deal found 9/14$239
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 12/1310:47 amEYW - ORD
1 stop27h 51mMultiple Airlines
Wed 12/1710:18 amORD - EYW
1 stop20h 57mMultiple Airlines
Deal found 9/13$244
This Kiwi.com deal was found by Cheapflights users on 9/12. 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 9/279:52 amEYW - ORD
2 stops25h 39mMultiple Airlines
Tue 9/305:46 pmORD - EYW
1 stop14h 26mMultiple Airlines
Deal found 9/12$251
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 9/2912:32 pmEYW - ORD
1 stop22h 46mMultiple Airlines
Fri 10/34:03 pmORD - EYW
2 stops17h 04mMultiple Airlines
Deal found 9/13$261
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/810:47 amEYW - ORD
1 stop28h 12mMultiple Airlines
Tue 11/1112:37 pmORD - EYW
2 stops20h 30mMultiple Airlines
Deal found 9/14$267
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:01 pmEYW - MKE
1 stop6h 17mDelta
Tue 12/1611:38 amMKE - EYW
1 stop7h 25mDelta
Deal found 9/14$269
This Delta deal was found by Cheapflights users on 9/14. 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 11/86:17 pmEYW - ORD
1 stop6h 41mDelta
Tue 11/115:32 amORD - EYW
1 stop7h 31mDelta
Deal found 9/14$269
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/114:10 pmEYW - MKE
2 stops8h 51mAmerican Airlines
Tue 12/166:01 amMKE - EYW
1 stop8h 23mAmerican Airlines
Deal found 9/14$274
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:10 pmEYW - MSN
1 stop5h 48mDelta
Mon 10/65:30 amMSN - EYW
1 stop6h 32mDelta
Deal found 9/14$294
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/31:59 pmEYW - MSN
2 stops10h 11mAmerican Airlines
Mon 10/66:00 amMSN - EYW
2 stops10h 16mAmerican Airlines
Deal found 9/13$304
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:10 pmEYW - MSN
1 stop5h 48mDelta
Sun 10/55:40 amMSN - EYW
1 stop6h 22mDelta
Deal found 9/14$344

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 September 14, 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

Fri 9/26

8:47 am-9:58 pm

1 stop14h 11m

Chicago O'Hare Intl

Tue 9/30

5:46 pm-10:07 am

1 stop15h 21m

$237

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 12/13

10:47 am-1:38 pm

1 stop27h 51m

Chicago O'Hare Intl

Wed 12/17

10:18 am-8:15 am

1 stop20h 57m

$244

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 9/27

9:52 am-10:31 am

2 stops25h 39m

Chicago O'Hare Intl

Tue 9/30

5:46 pm-9:12 am

1 stop14h 26m

$251

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 9/29

12:32 pm-10:18 am

1 stop22h 46m

Chicago O'Hare Intl

Fri 10/3

4:03 pm-10:07 am

2 stops17h 04m

$261

Key WestChicago

EYW - ORD

EYWORD

Key West

Sat 11/8

10:47 am-1:59 pm

1 stop28h 12m

Chicago O'Hare Intl

Tue 11/11

12:37 pm-10:07 am

2 stops20h 30m

$267

Key WestChicago

EYW - ORD

EYWORD

Key West

Thu 11/13

8:55 am-5:04 pm

1 stop9h 09m

Chicago O'Hare Intl

Sat 11/15

5:45 pm-8:15 am

2 stops13h 30m

$268

Key WestMilwaukee

EYW - MKE

EYWMKE

Key West

Wed 2/25

1:30 pm-8:56 pm

1 stop8h 26m

Milwaukee-Mitchell

Sun 3/1

12:20 pm-7:44 pm

1 stop6h 24m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Mon 1/12

1:30 pm-7:25 pm

1 stop6h 55m

Chicago O'Hare Intl

Tue 1/20

11:19 am-7:44 pm

1 stop7h 25m

$269

Key WestChicago

EYW - ORD

EYWORD

Key West

Fri 12/12

8:55 am-6:44 pm

1 stop10h 49m

Chicago O'Hare Intl

Tue 12/16

10:15 am-10:07 am

2 stops22h 52m

$287

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 10/3

3:12 pm-10:33 pm

1 stop8h 21m

Madison Truax Field

Mon 10/6

6:17 am-2:29 pm

1 stop7h 12m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 41 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.

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 $294, Delta can have you in Wisconsin from Key West in 8h 21m. There are 1353 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 cheapest airlines to fly from Key West to Wisconsin one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $123. However, be on the lookout for offers from Delta and American Airlines, as they are both options that can get you from Key West to Wisconsin for a low price.

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

    Most travelers choose Key West - Chicago O'Hare Intl, Key West - Milwaukee-Mitchell or Key West - Madison Truax Field 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.

  • What is the cheapest month to book a flight from Key West to Wisconsin?

    Currently, February is the cheapest month in which you can book a flight from Key West to Wisconsin (average of $280). Flying from Key West to Wisconsin in June is currently the most expensive (average of $376). 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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Alternative routes for Key West to Wisconsin

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Top airline flying from Key West to Wisconsin

Discover the top airline 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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$403FlexibilityNo cancel feeOn-time71%

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