HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$112+ 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — EYW
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
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

Keep the following information in mind while searching for Wisconsin to Key West flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$217
(Kiwi.com)

One-way from

$112
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$372
From Wisconsin to Key West
Search Deals
One-way flight from Wisconsin to Key West
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
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 septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
sáb. 10/117:43 pmORD - EYW
1 stop17h 57mMultiple Airlines
mar. 10/1411:45 amEYW - ORD
1 stop23h 23mMultiple Airlines
Deal found 9/15$217
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sáb. 10/117:43 pmORD - EYW
1 stop11h 32mMultiple Airlines
sáb. 10/1810:47 amEYW - ORD
1 stop5h 58mMultiple Airlines
Deal found 9/14$224
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
sáb. 10/257:43 pmORD - EYW
1 stop17h 57mMultiple Airlines
mar. 10/2811:45 amEYW - ORD
1 stop26h 08mMultiple Airlines
Deal found 9/15$227
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
sáb. 10/45:17 pmORD - EYW
1 stop13h 58mMultiple Airlines
vie. 10/108:55 amEYW - ORD
1 stop10h 51mMultiple Airlines
Deal found 9/13$232
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
sáb. 12/137:49 pmORD - EYW
1 stop18h 55mMultiple Airlines
lun. 12/158:55 amEYW - ORD
1 stop9h 09mMultiple Airlines
Deal found 9/15$234
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
jue. 12/116:05 amORD - EYW
1 stop8h 39mMultiple Airlines
lun. 12/158:55 amEYW - ORD
1 stop13h 28mMultiple Airlines
Deal found 9/15$235
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
sáb. 12/137:00 amORD - EYW
1 stop8h 56mMultiple Airlines
mar. 12/1611:45 amEYW - ORD
1 stop26h 53mMultiple Airlines
Deal found 9/15$237
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
mié. 10/156:18 pmORD - EYW
1 stop15h 01mMultiple Airlines
mié. 10/2210:47 amEYW - ORD
1 stop27h 28mMultiple Airlines
Deal found 9/15$238
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom. 10/195:50 amORD - EYW
1 stop26h 27mMultiple Airlines
mié. 10/2210:47 amEYW - ORD
1 stop24h 21mMultiple Airlines
Deal found 9/14$239
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sáb. 11/15:28 pmORD - EYW
1 stop14h 47mMultiple Airlines
sáb. 11/810:47 amEYW - ORD
1 stop28h 12mMultiple Airlines
Deal found 9/14$240
This Kiwi.com deal was found by Cheapflights users on 9/13. 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.
mar. 10/281:56 pmORD - EYW
1 stop19h 11mMultiple Airlines
vie. 10/318:55 amEYW - ORD
1 stop13h 38mMultiple Airlines
Deal found 9/13$244
This Delta deal was found by Cheapflights users on 9/16. 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.
mié. 10/295:30 amGRB - EYW
1 stop4h 57mDelta
vie. 11/76:17 pmEYW - GRB
1 stop5h 35mDelta
Deal found 9/16$260

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 septiembre 16, 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

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

sáb. 10/4

8:00 am-8:15 am

1 stop23h 15m

Key West

vie. 10/10

8:55 am-6:46 pm

1 stop10h 51m

$236

Green BayKey West

GRB - EYW

GRBEYW

Green Bay Austin-Straubel

mié. 10/29

5:30 am-11:27 am

1 stop4h 57m

Key West

vie. 11/7

6:17 pm-10:52 pm

1 stop5h 35m

$260

Green BayKey West

GRB - EYW

GRBEYW

Green Bay Austin-Straubel

sáb. 1/24

12:53 pm-11:59 pm

2 stops10h 06m

Key West

sáb. 1/31

6:31 am-3:50 pm

2 stops10h 19m

$261

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

mié. 11/19

6:00 am-2:04 pm

1 stop7h 04m

Key West

lun. 11/24

3:00 pm-10:45 pm

1 stop8h 45m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

sáb. 10/25

2:04 pm-8:06 pm

1 stop5h 02m

Key West

mié. 10/29

7:40 am-1:09 pm

1 stop6h 29m

$269

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

mié. 11/19

6:00 am-3:28 pm

1 stop8h 28m

Key West

lun. 11/24

4:55 pm-10:28 pm

1 stop6h 33m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

vie. 10/24

2:04 pm-8:06 pm

1 stop5h 02m

Key West

sáb. 11/1

6:17 pm-11:55 pm

1 stop6h 38m

$269

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

sáb. 10/25

7:20 am-4:27 pm

1 stop8h 07m

Key West

mié. 10/29

4:37 pm-10:56 pm

1 stop7h 19m

$269

MilwaukeeKey West

MKE - EYW

MKEEYW

Milwaukee-Mitchell

lun. 12/15

5:45 am-2:06 pm

1 stop7h 21m

Key West

vie. 12/19

6:05 pm-11:56 pm

1 stop6h 51m

$269

ChicagoKey West

ORD - EYW

ORDEYW

Chicago O'Hare Intl

vie. 11/28

11:00 am-3:19 pm

Nonstop3h 19m

Key West

vie. 12/5

3:02 pm-9:07 pm

1 stop7h 05m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 56 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, 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 $491). 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 Delta, American Airlines, and United Airlines fly from Wisconsin to Key West in about 4h 57m. The time it takes to get you to your destination can typically vary by up to 5h 09m. 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 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 $491). 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
Newark to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Orlando flights
LaGuardia to Orlando flights
Boston to Orlando flights
Dallas/Fort Worth to Orlando flights
John F Kennedy Intl to West Palm Beach flights
Dulles Intl to Orlando flights
Philadelphia to Orlando flights
Dulles Intl to Miami flights
Boston to Fort Lauderdale flights
Los Angeles to Orlando flights
Dallas/Fort Worth to Miami flights
O'Hare Intl to Orlando flights
Los Angeles to Miami flights
Baltimore to Fort Lauderdale flights
Newark to West Palm Beach flights
Reagan-National to Miami flights
Newark to Tampa flights
Baltimore to Orlando flights
John F Kennedy Intl to Tampa flights
LaGuardia to Tampa flights
Atlanta to Miami flights
Cleveland to Orlando flights
Philadelphia to Fort Lauderdale flights
Reagan-National to Orlando flights
O'Hare Intl to Miami flights
Seattle to Orlando flights
Hobby to Orlando flights
Denver to Orlando flights
Minneapolis to Orlando flights
O'Hare Intl to Fort Lauderdale flights
Providence to Orlando flights
Boston to Miami flights
LaGuardia to West Palm Beach flights
Detroit to Orlando flights
Baltimore to Miami flights
Dallas/Fort Worth to Fort Lauderdale flights
Philadelphia to Miami flights
Dulles Intl to Tampa flights
Boston to Tampa flights
Atlanta to Fort Lauderdale flights
Detroit to Fort Lauderdale flights
Hartford to Orlando flights
Raleigh to Miami 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 septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$142Average$272FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$219Average$431FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$506FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$268Average$536FlexibilityNo 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.