HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$93+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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

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 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/89:01 pm
MKE
-
EYW
1 stop14h 25m
Multiple Airlines
Thu 3/129:46 am
EYW
-
MKE
1 stop11h 20m
Multiple Airlines
Deal found 1/28$255
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 7/253:53 pm
MKE
-
EYW
1 stop5h 18m
United Airlines
Wed 7/294:05 pm
EYW
-
MKE
1 stop7h 04m
United Airlines
Deal found 1/27$269
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/156:37 pm
MKE
-
EYW
1 stop16h 49m
Multiple Airlines
Thu 2/199:46 am
EYW
-
MKE
1 stop24h 57m
Multiple Airlines
Deal found 1/28$271
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/116:05 am
MKE
-
EYW
2 stops8h 52m
American Airlines
Wed 3/186:49 pm
EYW
-
MKE
1 stop5h 18m
American Airlines
Deal found 1/27$274
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Sat 4/2511:21 am
MKE
-
EYW
2 stops10h 15m
American Airlines
Wed 4/296:45 am
EYW
-
MKE
2 stops9h 03m
American Airlines
Deal found 1/28$279
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 4/2110:05 am
MSN
-
EYW
1 stop7h 10m
American Airlines
Tue 4/286:45 pm
EYW
-
MSN
1 stop5h 52m
American Airlines
Deal found 1/27$283
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 3/108:00 am
ATW
-
EYW
1 stop6h 57m
American Airlines
Tue 3/176:49 pm
EYW
-
ATW
1 stop5h 30m
American Airlines
Deal found 1/27$283
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 9/128:29 am
MKE
-
EYW
1 stop5h 37m
United Airlines
Sat 9/194:05 pm
EYW
-
MKE
1 stop7h 04m
United Airlines
Deal found 1/27$285
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 4/108:00 am
MKE
-
EYW
1 stop6h 57m
United Airlines
Fri 4/173:47 pm
EYW
-
MKE
1 stop7h 28m
United Airlines
Deal found 1/27$288
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 2/145:45 pm
ORD
-
EYW
Nonstop3h 24m
United Airlines
Thu 2/196:35 pm
EYW
-
ORD
1 stop6h 08m
United Airlines
Deal found 1/27$289
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:41 pm
ORD
-
EYW
1 stop15h 56m
Multiple Airlines
Mon 4/132:35 pm
EYW
-
ORD
2 stops21h 09m
Multiple Airlines
Deal found 1/27$290
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:16 pm
ORD
-
EYW
1 stop16h 14m
Multiple Airlines
Sun 3/14:13 pm
EYW
-
ORD
2 stops26h 10m
Multiple Airlines
Deal found 1/28$291

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$255
(Kiwi.com)

One-way from

$93
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$367
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. 7% potential increase in price ($32 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 January 2026
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 January 29, 2026.
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 7/25

3:53 pm-10:11 pm

1 stop5h 18m

Key West

Tue 7/28

4:05 pm-10:09 pm

1 stop7h 04m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Tue 2/24

1:35 pm-7:42 pm

1 stop5h 07m

Key West

Wed 3/4

5:56 pm-11:47 pm

1 stop6h 51m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Fri 4/10

12:11 pm-7:41 pm

1 stop6h 30m

Key West

Fri 4/17

7:33 am-1:52 pm

1 stop7h 19m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Wed 3/11

6:05 am-3:57 pm

2 stops8h 52m

Key West

Wed 3/18

6:49 pm-11:07 pm

1 stop5h 18m

$274

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Fri 4/10

8:00 am-3:57 pm

1 stop6h 57m

Key West

Fri 4/17

3:47 pm-10:15 pm

1 stop7h 28m

$288

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

Sat 2/14

5:45 pm-10:09 pm

Nonstop3h 24m

Key West

Thu 2/19

6:35 pm-11:43 pm

1 stop6h 08m

$289

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 4/23

11:35 am-10:57 pm

2 stops10h 22m

Key West

Sat 5/2

6:45 pm-11:37 pm

1 stop5h 52m

$291

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Wed 4/22

12:32 pm-7:40 pm

1 stop6h 08m

Key West

Tue 4/28

7:33 am-11:27 am

1 stop4h 54m

$293

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Wed 4/22

12:32 pm-7:40 pm

1 stop6h 08m

Key West

Fri 5/1

6:19 pm-11:57 pm

1 stop6h 38m

$293

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

Sat 4/25

6:00 am-3:23 pm

1 stop8h 23m

Key West

Wed 4/29

4:20 pm-10:47 pm

1 stop7h 27m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 60 results
1
2
3
...
6

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 $297). 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 United Airlines, Delta, and American Airlines fly from Wisconsin to Key West in about 5h 07m. The time it takes to get you to your destination can typically vary by up to 3h 45m. Airlines will cover a distance of 1317 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, 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 $297). 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 Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Miami flights
LaGuardia to Fort Lauderdale flights
Newark to West Palm Beach flights
John F Kennedy Intl to West Palm Beach flights
John F Kennedy Intl to Orlando flights
Newark to Orlando flights
John F Kennedy Intl to Tampa flights
LaGuardia to Orlando flights
Newark to Tampa flights
Boston to Fort Lauderdale flights
LaGuardia to Tampa flights
Dulles Intl to Miami flights
Boston to Tampa flights
Boston to Miami flights
Reagan-National to Miami flights
LaGuardia to West Palm Beach flights
Detroit to Orlando flights
Minneapolis to Orlando flights
Detroit to Fort Lauderdale flights
O'Hare Intl to Fort Lauderdale flights
Baltimore to Fort Lauderdale flights
Dulles Intl to Orlando flights
Philadelphia to Miami flights
Boston to Orlando flights
Dulles Intl to Fort Lauderdale flights
Minneapolis to Fort Myers flights
O'Hare Intl to Orlando flights
Baltimore to Miami flights
Detroit to Miami flights
Philadelphia to Fort Lauderdale flights
Philadelphia to Orlando flights
Reagan-National to Orlando flights
Newark to Fort Myers flights
Cleveland to Orlando flights
O'Hare Intl to Miami flights
Philadelphia to Tampa flights
Dallas/Fort Worth to Orlando flights
Boston to West Palm Beach flights
Baltimore to Orlando flights
John F Kennedy Intl to Fort Myers flights
Los Angeles to Miami flights
Los Angeles to Orlando flights
Minneapolis to Tampa flights
Reagan-National to Fort Lauderdale flights
Minneapolis to Miami flights
O'Hare Intl to Tampa flights

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$142Average$271FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$219Average$472FlexibilityNo cancel feeOn-time71%
DeltaCheapest$228Average$433FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$268Average$525FlexibilityNo 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.