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Key West

$90+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. 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 12/247:55 amORD - EYW
Nonstop3h 39mUnited Airlines
Wed 12/315:10 pmEYW - ORD
1 stop7h 34mUnited Airlines
Deal found 12/10$286
This United Airlines deal was found by Cheapflights users on 12/10. 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 12/307:55 amORD - EYW
Nonstop3h 39mUnited Airlines
Thu 1/156:05 pmEYW - ORD
1 stop6h 34mUnited Airlines
Deal found 12/10$289
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/178:00 amORD - EYW
2 stops23h 15mMultiple Airlines
Sun 12/218:55 amEYW - ORD
1 stop24h 52mMultiple Airlines
Deal found 12/10$295
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/306:50 amORD - EYW
2 stops29h 40mMultiple Airlines
Thu 1/1510:06 amEYW - ORD
1 stop10h 35mMultiple Airlines
Deal found 12/10$303
This United Airlines deal was found by Cheapflights users on 12/10. 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 12/318:51 amORD - EYW
1 stop6h 38mUnited Airlines
Wed 1/74:15 pmEYW - ORD
Nonstop3h 33mUnited Airlines
Deal found 12/10$304
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/313:26 pmORD - EYW
1 stop18h 54mSpirit Airlines
Mon 1/52:30 pmEYW - ORD
2 stops30h 34mSpirit Airlines
Deal found 12/10$325
This American Airlines deal was found by Cheapflights users on 12/9. 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 12/318:00 amORD - EYW
1 stop6h 33mAmerican Airlines
Wed 1/77:08 amEYW - ORD
1 stop5h 27mAmerican Airlines
Deal found 12/9$326
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/186:00 amORD - EYW
2 stops29h 30mMultiple Airlines
Tue 1/612:20 pmEYW - ORD
1 stop23h 54mMultiple Airlines
Deal found 12/10$337
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/203:39 pmATW - EYW
1 stop15h 36mMultiple Airlines
Sat 12/2710:35 pmEYW - ATW
1 stop16h 48mMultiple Airlines
Deal found 12/11$343
This United Airlines deal was found by Cheapflights users on 12/11. 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 12/237:55 amORD - EYW
Nonstop3h 39mUnited Airlines
Mon 12/2912:22 pmEYW - ORD
Nonstop3h 45mUnited Airlines
Deal found 12/11$345
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/163:35 pmMSN - EYW
1 stop5h 11mAmerican Airlines
Fri 12/264:40 pmEYW - MSN
1 stop8h 19mAmerican Airlines
Deal found 12/10$364
This United Airlines deal was found by Cheapflights users on 12/11. 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 12/186:40 amMSN - EYW
2 stops8h 49mUnited Airlines
Thu 12/253:09 pmEYW - MSN
1 stop8h 48mUnited Airlines
Deal found 12/11$379

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$243
(Kiwi.com)

One-way from

$90
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$478
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. 3% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 12, 2025.
Use the filters below to find and compare flights from Wisconsin to Key West that are best for you.

Fly from

Wisconsin

Fly to

Key West

Route

Depart

Return

Price

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 1/17

12:51 pm-11:56 pm

2 stops10h 05m

Key West

Thu 1/22

4:37 pm-11:35 pm

2 stops7h 58m

$257

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 1/10

10:17 am-9:47 pm

2 stops10h 30m

Key West

Sat 1/17

6:06 am-3:20 pm

2 stops10h 14m

$257

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 1/8

7:20 am-3:25 pm

1 stop7h 05m

Key West

Thu 1/15

2:44 pm-10:59 pm

1 stop9h 15m

$257

Green BayKey West

GRB - EYW

GRBEYW

Green Bay Austin-Straubel

Mon 1/19

5:00 am-11:25 am

1 stop5h 25m

Key West

Tue 1/27

6:06 pm-10:30 pm

1 stop5h 24m

$260

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 1/10

5:00 am-11:26 am

1 stop5h 26m

Key West

Sat 1/17

4:15 pm-8:48 pm

1 stop5h 33m

$261

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Fri 1/23

12:17 pm-7:40 pm

1 stop6h 23m

Key West

Tue 1/27

7:10 am-1:48 pm

1 stop7h 38m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Tue 3/3

1:35 pm-7:42 pm

1 stop5h 07m

Key West

Tue 3/10

6:25 pm-11:51 pm

1 stop6h 26m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sun 2/1

12:17 pm-7:40 pm

1 stop6h 23m

Key West

Thu 2/12

6:07 pm-11:48 pm

1 stop6h 41m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Mon 2/2

6:40 am-4:24 pm

1 stop8h 44m

Key West

Sat 2/7

5:35 pm-10:17 pm

1 stop5h 42m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sun 1/25

7:00 am-3:17 pm

1 stop7h 17m

Key West

Sat 1/31

2:05 pm-10:56 pm

2 stops9h 51m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 60 results
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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, May is the cheapest month in which you can book a flight from Wisconsin to Key West (average of $158). Flying from Wisconsin to Key West in June is currently the most expensive (average of $314). 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.

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 American Airlines, Delta, and United Airlines fly from Wisconsin to Key West in about 5h 25m. The time it takes to get you to your destination can typically vary by up to 4h 40m. Airlines will cover a distance of 1422 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Wisconsin to Key West one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $159. However, be on the lookout for offers from Delta and United Airlines, as they are both options that can get you from Wisconsin to Key West for a low price.

  • 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 Appleton Intl - 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, May is the cheapest month in which you can book a flight from Wisconsin to Key West (average of $158). Flying from Wisconsin to Key West in June is currently the most expensive (average of $314). 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 Wisconsin to Key West

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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$142Average$272FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$219Average$489FlexibilityNo cancel feeOn-time71%
DeltaCheapest$228Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$268Average$539FlexibilityNo cancel feeOn-time69%

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