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Key West

$107+ Cheap flights from Milwaukee to Key West (MKE - 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
Jan 27 — Feb 31
Tue 1/27
Tue 2/3
1 adult, Economy
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Cheap flight deals from Milwaukee to Key West

Cheapest flights from Milwaukee to Key West
Explore the most affordable flight options available from Milwaukee to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 28, 2025.

This American Airlines deal was found by Cheapflights users on 12/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:52 pmMKE - EYW
2 stops7h 52mAmerican Airlines
Sun 1/46:26 pmEYW - MKE
1 stop7h 18mAmerican Airlines
Deal found 12/27$410
This United Airlines deal was found by Cheapflights users on 12/25. 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.
Sat 12/275:00 amMKE - EYW
1 stop6h 34mUnited Airlines
Wed 1/74:15 pmEYW - MKE
1 stop7h 41mUnited Airlines
Deal found 12/25$427
This American Airlines deal was found by Cheapflights users on 12/26. 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 12/311:52 pmMKE - EYW
2 stops7h 52mAmerican Airlines
Thu 1/14:40 pmEYW - MKE
1 stop8h 18mAmerican Airlines
Deal found 12/26$440
This Kiwi.com deal was found by Cheapflights users on 12/26. 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 12/318:15 pmMKE - EYW
1 stop11h 00mMultiple Airlines
Sun 1/48:55 amEYW - MKE
2 stops25h 58mMultiple Airlines
Deal found 12/26$447
This United Airlines deal was found by Cheapflights users on 12/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/295:00 amMKE - EYW
1 stop6h 34mUnited Airlines
Thu 1/112:22 pmEYW - MKE
1 stop5h 45mUnited Airlines
Deal found 12/27$469
This American Airlines deal was found by Cheapflights users on 12/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/291:52 pmMKE - EYW
2 stops7h 52mAmerican Airlines
Thu 1/112:55 pmEYW - MKE
2 stops7h 43mAmerican Airlines
Deal found 12/27$479

Find flight deals from Milwaukee to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$241
(Kiwi.com)

One-way from

$107
(Kiwi.com)

Popular in

March

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 Milwaukee-Mitchell to Key West
Search Deals
One-way flight from Milwaukee-Mitchell to Key West
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 Milwaukee 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 28, 2025.
Use the filters below to find and compare flights from Milwaukee to Key West that are best for you.

Fly from

Milwaukee

Fly to

Key West

Route

Depart

Return

Price

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-11:57 pm

1 stop6h 32m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Fri 1/30

12:17 pm-7:40 pm

1 stop6h 23m

Key West

Wed 2/4

6:06 pm-11:46 pm

1 stop6h 40m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Tue 2/24

10:10 am-5:01 pm

1 stop5h 51m

Key West

Thu 3/5

5:56 pm-11:47 pm

1 stop6h 51m

$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

7:10 am-11:13 am

1 stop5h 03m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sun 3/1

6:39 pm-12:26 pm

1 stop16h 47m

Key West

Sun 3/8

9:46 am-10:03 am

2 stops25h 17m

$270

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 1/17

9:30 am-9:47 pm

2 stops11h 17m

Key West

Thu 1/22

4:04 pm-11:35 pm

1 stop8h 31m

$274

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Thu 1/22

10:17 am-9:47 pm

2 stops10h 30m

Key West

Thu 1/29

2:00 pm-8:24 pm

1 stop7h 24m

$274

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Mon 1/26

10:17 am-9:47 pm

2 stops10h 30m

Key West

Mon 2/2

6:06 am-3:20 pm

2 stops10h 14m

$279

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Mon 2/23

12:20 pm-7:42 pm

1 stop6h 22m

Key West

Wed 3/4

7:10 am-12:31 pm

1 stop6h 21m

$293

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Tue 2/24

1:35 pm-7:42 pm

1 stop5h 07m

Key West

Wed 3/4

7:10 am-12:31 pm

1 stop6h 21m

$293

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/26

Showing 1-10 of 15 results
1
2

Compare providers for flights from Milwaukee to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Milwaukee to Key West in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Milwaukee-Key West flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Milwaukee-Key West flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Milwaukee-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-Key West flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Milwaukee-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Milwaukee to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Milwaukee 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 Milwaukee to Key West

How far ahead should I book a flight from Milwaukee to Key West?

Use this chart to determine the optimal time to book a round-trip flight from Milwaukee to Key West. Price data was last updated on December 26, 2025.

To ensure you get the cheapest price possible for a flight from Milwaukee to Key West, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, August is the cheapest month in which you can book a flight from Milwaukee to Key West (average of $225). Flying from Milwaukee to Key West in June is currently the most expensive (average of $302). 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.

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 December 28, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Milwaukee to Key West to help guide your decision. 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
8,019 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
8,019 reviews
Delta
7.9
Good
8,019 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
9,113 reviews
Delta
7.9
Good
8,019 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
11,072 reviews
Delta
7.9
Good
8,019 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Milwaukee to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    There are many flights that can get you from Milwaukee to Key West in 5h 07m. Fly via Delta to get the fastest option. The distance from Milwaukee to Key West is about 1317 mi.

  • What are the cheapest airlines flying from Milwaukee to Key West round-trip?

    According to our current data, American Airlines ($248), Delta ($248), and United Airlines ($268) offers the cheapest pricing from Milwaukee to Key West. American Airlines is currently priced 36% below the average price you’ll pay for this route.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee 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 Milwaukee to Key West?

    Currently, August is the cheapest month in which you can book a flight from Milwaukee to Key West (average of $225). Flying from Milwaukee to Key West in June is currently the most expensive (average of $302). 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 3 airlines flying from Milwaukee to Key West

Discover the top 3 airlines that operate flights from Milwaukee 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$386FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$249Average$392FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$268Average$482FlexibilityNo cancel feeOn-time69%

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