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Key West

$142+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap 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 July 30, 2025.

Round-trip from

$234
(Delta)

One-way from

$152
(Mytrip)

Popular in

March

Cheapest in

August

Average price

$323
From Wisconsin to Key West
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One-way flight from Wisconsin to Key West
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Highest demand for flights based on searches. 13% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find 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 July 30, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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.
Tue 8/265:31 amGRB - EYW
1 stop6h 34mDelta
Sat 8/306:20 pmEYW - GRB
1 stop6h 02mDelta
Deal found 7/28$234
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Mon 12/1510:50 amORD - EYW
Nonstop3h 19mUnited Airlines
Sat 12/204:05 pmEYW - ORD
Nonstop3h 25mUnited Airlines
Deal found 7/28$249
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 9/2712:13 pmMKE - EYW
1 stop6h 54mDelta
Wed 10/17:00 amEYW - MKE
1 stop7h 54mDelta
Deal found 7/27$249
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:43 amMKE - EYW
1 stop6h 27mAmerican Airlines
Sat 12/1312:07 pmEYW - MKE
2 stops10h 02mAmerican Airlines
Deal found 7/30$254
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 12/1611:19 amORD - EYW
1 stop4h 53mDelta
Sat 12/206:02 pmEYW - ORD
1 stop6h 56mDelta
Deal found 7/29$268
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:33 amMSN - EYW
1 stop7h 22mAmerican Airlines
Mon 11/242:39 pmEYW - MSN
1 stop8h 15mAmerican Airlines
Deal found 7/30$269
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 8/265:34 amATW - EYW
1 stop6h 31mDelta
Sat 8/306:20 pmEYW - ATW
1 stop5h 33mDelta
Deal found 7/29$269
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:30 amATW - EYW
2 stops11h 52mAmerican Airlines
Fri 11/76:33 pmEYW - ATW
1 stop5h 52mAmerican Airlines
Deal found 7/30$274
This Mytrip deal was found by Cheapflights users on 7/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:00 amORD - EYW
1 stop11h 46mMultiple Airlines
Sun 11/162:25 pmEYW - ORD
1 stop7h 35mMultiple Airlines
Deal found 7/29$287
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:05 amORD - EYW
1 stop7h 25mSpirit Airlines
Mon 11/102:25 pmEYW - ORD
1 stop10h 17mSpirit Airlines
Deal found 7/30$303
This American Airlines deal was found by Cheapflights users on 7/28. 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 10/316:45 amORD - EYW
1 stop8h 28mAmerican Airlines
Wed 11/51:52 pmEYW - ORD
Nonstop3h 40mAmerican Airlines
Deal found 7/28$313
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 8/231:20 pmMSN - EYW
1 stop5h 52mDelta
Tue 8/266:20 pmEYW - MSN
1 stop5h 42mDelta
Deal found 7/27$324

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 July 30, 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

Green BayKey West

GRB - EYW

GRBEYW

Green Bay Austin-Straubel

Tue 8/26

5:31 am-1:05 pm

1 stop6h 34m

Key West

Sat 8/30

6:20 pm-11:22 pm

1 stop6h 02m

$234

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 9/27

12:13 pm-8:07 pm

1 stop6h 54m

Key West

Wed 10/1

7:00 am-1:54 pm

1 stop7h 54m

$249

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 12/6

8:43 am-4:10 pm

1 stop6h 27m

Key West

Sat 12/13

12:07 pm-9:09 pm

2 stops10h 02m

$254

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 11/19

6:33 am-2:55 pm

1 stop7h 22m

Key West

Mon 11/24

2:39 pm-9:54 pm

1 stop8h 15m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 8/27

1:30 pm-8:12 pm

1 stop5h 42m

Key West

Wed 9/3

6:20 pm-10:37 pm

1 stop5h 17m

$269

AppletonKey West

ATW - EYW

ATWEYW

Appleton Intl

Tue 8/26

5:34 am-1:05 pm

1 stop6h 31m

Key West

Sat 8/30

6:20 pm-10:53 pm

1 stop5h 33m

$269

AppletonKey West

ATW - EYW

ATWEYW

Appleton Intl

Wed 10/1

6:33 am-6:59 pm

2 stops11h 26m

Key West

Tue 10/7

4:37 pm-11:43 pm

2 stops8h 06m

$309

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Wed 8/27

8:12 pm-5:01 pm

2 stops19h 49m

Key West

Thu 9/4

12:29 pm-10:48 pm

2 stops11h 19m

$318

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 8/30

8:20 am-3:19 pm

1 stop5h 59m

Key West

Wed 9/3

12:24 pm-5:23 pm

1 stop5h 59m

$323

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 8/23

1:20 pm-8:12 pm

1 stop5h 52m

Key West

Tue 8/26

6:20 pm-11:02 pm

1 stop5h 42m

$324

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 38 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, August is the cheapest month in which you can book a flight from Wisconsin to Key West (average of $328). Flying from Wisconsin to Key West in March is currently the most expensive (average of $492). 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?

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated July 30, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Wisconsin to Key West. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.
Spirit Airlines
6.3
Okay
8,048 reviews
Delta
8.0
Very good
7,980 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

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.

  • 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 $169. 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 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, August is the cheapest month in which you can book a flight from Wisconsin to Key West (average of $328). Flying from Wisconsin to Key West in March is currently the most expensive (average of $492). 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$142Average$273FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$219Average$473FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$552FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$268Average$535FlexibilityNo cancel feeOn-time69%

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