HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madison

$269+ Cheap flights from Key West to Madison (EYW - MSN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/29. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Key West to Madison 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 Key West to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Madison (MSN). 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 October 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$269
(United Airlines)
Provider with most accurate pricing for Key West-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Madison Truax Field flights.
Search Deals
From Key West to Madison Truax Field
Search Deals

Find flight deals from Key West to Madison

Cheapest flights from Key West to Madison
Explore the most affordable flight options available from Key West to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:22 pmEYW - MSN
1 stop7h 43mUnited Airlines
Mon 1/56:00 amMSN - EYW
1 stop7h 13mUnited Airlines
Deal found 10/29$269
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/298:00 amEYW - MSN
2 stops10h 47mAmerican Airlines
Mon 1/56:00 amMSN - EYW
2 stops9h 44mAmerican Airlines
Deal found 10/29$441

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Madison 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 October 30, 2025.
Use the filters below to find and compare flights from Key West to Madison that are best for you.

Fly from

Key West

Fly to

Madison

Route

Depart

Return

Price

Key WestMadison

EYW - MSN

EYWMSN

Key West

Mon 12/29

12:22 pm-7:05 pm

1 stop7h 43m

Madison Truax Field

Mon 1/5

6:00 am-2:13 pm

1 stop7h 13m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 1/30

4:04 pm-11:41 pm

1 stop8h 37m

Madison Truax Field

Wed 2/4

6:00 am-12:33 pm

1 stop5h 33m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 1/13

4:15 pm-9:05 pm

1 stop5h 50m

Madison Truax Field

Sun 1/18

6:30 am-3:17 pm

1 stop7h 47m

$269

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 2/6

6:08 pm-10:37 pm

1 stop5h 29m

Madison Truax Field

Wed 2/11

7:00 am-7:42 pm

2 stops11h 42m

$274

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 2/13

6:44 pm-11:29 pm

1 stop5h 45m

Madison Truax Field

Thu 2/19

11:22 am-10:59 pm

2 stops10h 37m

$274

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 1/30

1:28 pm-7:15 pm

1 stop6h 47m

Madison Truax Field

Wed 2/4

7:00 am-7:42 pm

2 stops11h 42m

$274

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 1/13

6:06 am-12:46 pm

2 stops7h 40m

Madison Truax Field

Sun 1/18

11:15 am-9:47 pm

2 stops9h 32m

$279

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 2/13

2:25 pm-10:51 pm

1 stop9h 26m

Madison Truax Field

Wed 2/18

6:00 am-3:32 pm

1 stop8h 32m

$329

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 2/12

6:44 pm-11:29 pm

1 stop5h 45m

Madison Truax Field

Wed 2/18

6:00 am-3:32 pm

1 stop8h 32m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Compare providers for flights from Key West to Madison

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 Key West to Madison in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Key West-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-Madison flights, Cheapflights users trust Expedia the most. Expedia 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 Key West-Madison 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 Key West to Madison

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

Related info for your journey

Find useful and relevant information for your journey from Key West to Madison. 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 Key West to Madison?

    A quick flight from Key West to Madison can take about 5h 29m. United Airlines provides one of the quickest options available for as low as $274. Airlines will cover a distance of 1353 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Key West to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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 Key West to Madison

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to O'Hare Intl flights
Tampa to O'Hare Intl flights
Miami to O'Hare Intl flights
Orlando to O'Hare Intl flights
Jacksonville to O'Hare Intl flights
Orlando to Minneapolis flights
Fort Myers to O'Hare Intl flights
Tampa to Minneapolis flights
West Palm Beach to O'Hare Intl flights
Miami to Minneapolis flights
Sarasota to O'Hare Intl flights
Fort Lauderdale to Minneapolis flights
Orlando to Milwaukee flights
Pensacola to O'Hare Intl flights
Fort Myers to Minneapolis flights
Jacksonville to Minneapolis flights
Tampa to Milwaukee flights
Sarasota to Minneapolis flights
Fort Lauderdale to Milwaukee flights
Fort Myers to Milwaukee flights
West Palm Beach to Minneapolis flights
Key West to O'Hare Intl flights
Orlando to Madison flights
Miami to Milwaukee flights
Valparaiso to Minneapolis flights
Jacksonville to Milwaukee flights
Miami to Appleton flights
Orlando to Appleton flights
Miami to Wausau flights
Panama City to O'Hare Intl flights
Valparaiso to O'Hare Intl flights
Daytona Beach to O'Hare Intl flights
Tallahassee to Minneapolis flights
Miami to Madison flights
Pensacola to Minneapolis flights
Fort Myers to Madison flights
Fort Myers to Green Bay flights
Miami to Rhinelander flights
Fort Myers to Appleton flights
Tampa to Madison flights
West Palm Beach to Milwaukee flights
Tallahassee to O'Hare Intl flights
Orlando to Green Bay flights
Tampa to Green Bay flights
Sarasota to Milwaukee flights
Tallahassee to Madison flights
Tampa to Appleton flights
Valparaiso to Milwaukee flights
Panama City to Milwaukee flights
Sarasota to Madison flights

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.