HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$109+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Key West with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Wisconsin to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Wisconsin (USWI) 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 January 21, 2025.

Round-trip from

$209
(American Airlines)

One-way from

$109
(Delta)
From Wisconsin to Key West
Search Deals
One-way flight from Wisconsin to Key West
Search Deals

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 January 21, 2025.

This American Airlines deal was found by Cheapflights users on 1/20. 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 4/16:00 amMSN - EYW
1 stop8h 25mAmerican Airlines
Wed 4/94:54 pmEYW - MSN
1 stop6h 55mAmerican Airlines
Deal found 1/20$209
This Delta deal was found by Cheapflights users on 1/20. 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.
Wed 2/2612:38 pmMKE - EYW
1 stop6h 33mDelta
Wed 3/57:00 amEYW - MKE
1 stop5h 30mDelta
Deal found 1/20$249
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/266:20 amMKE - EYW
2 stops8h 34mAmerican Airlines
Wed 3/53:08 pmEYW - MKE
1 stop7h 59mAmerican Airlines
Deal found 1/20$254
This Mytrip deal was found by Cheapflights users on 1/21. 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.
Sat 1/253:26 pmATW - EYW
1 stop15h 47mAllegiant Air
Sat 2/15:34 pmEYW - ATW
1 stop5h 55mAllegiant Air
Deal found 1/21$277
This American Airlines deal was found by Cheapflights users on 1/20. 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 2/258:06 amORD - EYW
Nonstop3h 21mAmerican Airlines
Tue 3/48:02 amEYW - ORD
1 stop5h 22mAmerican Airlines
Deal found 1/20$279
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Sat 3/15:45 pmORD - EYW
1 stop14h 40mMultiple Airlines
Wed 3/53:06 pmEYW - ORD
2 stops11h 12mMultiple Airlines
Deal found 1/20$286
This Delta deal was found by Cheapflights users on 1/20. 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 2/45:20 amMSP - EYW
1 stop5h 18mDelta
Tue 2/116:16 pmEYW - MSP
1 stop7h 14mDelta
Deal found 1/20$288
This Delta deal was found by Cheapflights users on 1/20. 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 10/106:00 amORD - EYW
1 stop6h 09mDelta
Wed 10/157:00 amEYW - ORD
1 stop6h 09mDelta
Deal found 1/20$289
This American Airlines deal was found by Cheapflights users on 1/20. 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 5/31:52 pmMSP - EYW
1 stop5h 19mAmerican Airlines
Wed 5/77:33 pmEYW - MSP
1 stop5h 18mAmerican Airlines
Deal found 1/20$289
This United Airlines deal was found by Cheapflights users on 1/20. 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 3/310:59 amORD - EYW
Nonstop3h 12mUnited Airlines
Wed 3/123:59 pmEYW - ORD
Nonstop3h 41mUnited Airlines
Deal found 1/20$294
This Mytrip deal was found by Cheapflights users on 1/19. 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.
Sun 3/24:00 pmMSP - EYW
1 stop16h 03mMultiple Airlines
Thu 3/68:53 amEYW - MSP
1 stop14h 45mMultiple Airlines
Deal found 1/19$302
This American Airlines deal was found by Cheapflights users on 1/20. 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 1/286:10 amATW - EYW
1 stop8h 33mAmerican Airlines
Wed 2/58:09 amEYW - ATW
2 stops11h 20mAmerican Airlines
Deal found 1/20$304

Find flights from Wisconsin to Key West within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 4/1

6:00 am-3:25 pm

1 stop8h 25m

Key West

Wed 4/9

4:54 pm-10:49 pm

1 stop6h 55m

$209

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Wed 2/26

12:38 pm-8:11 pm

1 stop6h 33m

Key West

Wed 3/5

7:00 am-11:30 am

1 stop5h 30m

$249

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Wed 2/26

6:20 am-3:54 pm

2 stops8h 34m

Key West

Wed 3/5

3:08 pm-10:07 pm

1 stop7h 59m

$254

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 2/25

8:06 am-12:27 pm

Nonstop3h 21m

Key West

Tue 3/4

7:29 pm-11:55 pm

1 stop5h 26m

$279

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 3/1

5:45 pm-9:25 am

1 stop14h 40m

Key West

Wed 3/5

3:06 pm-1:18 am

2 stops11h 12m

$286

MinneapolisKey West

MSP - EYW

MSPEYW

Minneapolis St Paul

Tue 2/4

5:20 am-11:38 am

1 stop5h 18m

Key West

Tue 2/11

6:16 pm-12:30 am

1 stop7h 14m

$288

MinneapolisKey West

MSP - EYW

MSPEYW

Minneapolis St Paul

Sat 5/3

1:52 pm-8:11 pm

1 stop5h 19m

Key West

Wed 5/7

5:21 pm-12:19 am

1 stop7h 58m

$289

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Tue 2/25

6:00 am-8:11 pm

2 stops13h 11m

Key West

Wed 2/26

6:14 pm-11:49 pm

1 stop6h 35m

$290

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Mon 3/3

10:59 am-3:11 pm

Nonstop3h 12m

Key West

Wed 3/12

3:59 pm-6:40 pm

Nonstop3h 41m

$294

AppletonKey West

ATW - EYW

ATWEYW

Appleton Intl

Sat 2/1

3:26 pm-8:13 am

1 stop15h 47m

Key West

Sat 2/8

5:12 pm-10:29 pm

1 stop6h 17m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 41 results
1
2
3
...
5

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.

Travel insights for flights from Wisconsin to Key West

Get recent, data-driven insights about flights from Wisconsin to Key West including ideal travel times, pricing trends, and more.

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 $531). 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.

What is the cheapest time of day to fly from WI to EYW?

Find hourly flight availability from Wisconsin to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 21, 2025.

When flying from Wisconsin to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Key West by month

Plan your trip to Key West by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

Plan your trip to Key West by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

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 January 21, 2025.
To help decide which airline to fly from Wisconsin to Key West, see what other customers have to say about Delta, American Airlines and United Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,706 reviews

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,706 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,521 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,985 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Allegiant Air
7.4
Good
801 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,706 reviews

Boarding

8.2

Food

7.1

Comfort

7.9

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 10

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 Delta, with whom users have recently found tickets for as low as $109. However, be on the lookout for offers from American Airlines 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, 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 $531). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wisconsin to Key West

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Miami flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
LaGuardia to Fort Lauderdale flights
Newark to Fort Lauderdale flights
LaGuardia to Miami flights
Newark to Miami flights
Newark to Orlando flights
Reagan-National to Miami flights
LaGuardia to Orlando flights
Boston to Fort Lauderdale flights
Dulles Intl to Miami flights
John F Kennedy Intl to West Palm Beach flights
Boston to Orlando flights
O'Hare Intl to Orlando flights
Dulles Intl to Orlando flights
Philadelphia to Orlando flights
Dallas/Fort Worth to Orlando flights
O'Hare Intl to Miami flights
Baltimore to Orlando flights
Newark to West Palm Beach flights
Newark to Tampa flights
O'Hare Intl to Fort Lauderdale flights
Boston to Miami flights
Detroit to Orlando flights
Los Angeles to Miami flights
Atlanta to Miami flights
LaGuardia to Tampa flights
Minneapolis to Orlando flights
Baltimore to Fort Lauderdale flights
Reagan-National to Orlando flights
Los Angeles to Orlando flights
O'Hare Intl to Tampa flights
LaGuardia to West Palm Beach flights
John F Kennedy Intl to Tampa flights
Baltimore to Miami flights
Philadelphia to Fort Lauderdale flights
Newark to Fort Myers flights
Detroit to Fort Lauderdale flights
Detroit to Miami flights
Dulles Intl to Fort Lauderdale flights
Los Angeles to Fort Lauderdale flights
Philadelphia to Miami flights
Minneapolis to Fort Lauderdale flights
Cleveland to Orlando flights
Dulles Intl to Tampa flights
Philadelphia to Tampa flights
Dallas/Fort Worth to Fort Lauderdale flights
Reagan-National to Fort Lauderdale flights
Boston to West Palm Beach flights

Top 3 airlines flying from Wisconsin to Key West

Discover the top 3 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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$237Average$521FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$238Average$480FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$319Average$524FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.