HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madison

$274+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$274
(American Airlines)
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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 10/16:17 pmEYW - MSN
1 stop5h 53mAmerican Airlines
Wed 10/86:21 amMSN - EYW
2 stops9h 08mAmerican Airlines
Deal found 6/11$274
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Wed 10/18:45 amEYW - MSN
2 stops14h 18mUnited Airlines
Wed 10/812:26 pmMSN - EYW
3 stops28h 39mUnited Airlines
Deal found 6/11$575

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 June 12, 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

Wed 10/1

6:17 pm-11:10 pm

1 stop5h 53m

Madison Truax Field

Wed 10/8

6:21 am-4:29 pm

2 stops9h 08m

$274

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 10/1

8:45 am-10:03 pm

2 stops14h 18m

Madison Truax Field

Wed 10/8

12:26 pm-6:05 pm

3 stops28h 39m

$575

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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.

Cheapflights Insights

Everything you need to know about your flight from Key West to Madison

Rainfall in Madison by month

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

In terms of precipitation, rainfall in Madison ranges from 1.2 - 4.5 inches per month. June is typically the wettest month, when rainfall can reach 4.5 in. January is typically the driest time to visit Madison when rainfall is around 1.2 in.

Temperature in Madison by month

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

If weather is an important factor for your trip to Madison, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated June 12, 2025.
United Airlines
7.4
Good
8,790 reviews

Entertainment

7.0

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,790 reviews
United Airlines
7.4
Good
8,790 reviews

Entertainment

7.0

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,790 reviews

Entertainment

7.0

Crew

8.1

Overall

7.4

Comfort

7.3

Boarding

7.7

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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.

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

    Cheapflights users have booked flights from Key West to Madison round-trip from $274. Another airline that can offer you cheap pricing is United Airlines.

  • 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.

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

    Currently, January is the cheapest month in which you can book a flight from Key West to Madison (average of $338). Flying from Key West to Madison in March is currently the most expensive (average of $422). 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

Traveling to a place near Key West?

Book flights to Key West 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
Orlando to O'Hare Intl flights
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights
Jacksonville to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Tampa to Minneapolis flights
Orlando to Minneapolis flights
Fort Lauderdale to Minneapolis flights
Fort Myers to O'Hare Intl flights
Sarasota to O'Hare Intl flights
Fort Myers to Minneapolis flights
Tampa to Milwaukee flights
Miami to Minneapolis flights
Orlando to Milwaukee flights
Pensacola to O'Hare Intl flights
Jacksonville to Minneapolis flights
Fort Myers to Milwaukee flights
Miami to Milwaukee flights
Fort Lauderdale to Milwaukee flights
Sarasota to Milwaukee flights
West Palm Beach to Minneapolis flights
Jacksonville to Green Bay flights
Sarasota to Minneapolis flights
Jacksonville to Milwaukee flights
Tampa to Madison flights
Panama City to O'Hare Intl flights
Tampa to Green Bay flights
Tallahassee to O'Hare Intl flights
Sarasota to Madison flights
West Palm Beach to Milwaukee flights
Daytona Beach to O'Hare Intl flights
Miami to Madison flights
Melbourne to O'Hare Intl flights
Jacksonville to Appleton flights
Fort Myers to Madison flights
West Palm Beach to Appleton flights
Fort Lauderdale to Madison flights
Sarasota to Appleton flights
Orlando to Appleton flights
Tampa to Appleton flights
West Palm Beach to Madison flights
Valparaiso to O'Hare Intl flights
Fort Myers to Appleton flights
Orlando to Green Bay flights
Orlando to Madison flights
Tampa to Wausau flights
Fort Myers to Green Bay flights
Orlando to Wausau flights
Pensacola to Milwaukee flights

Top airline flying from Key West to Madison

Discover the top airline that operate flights from Key West to Madison. 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$293Average$418FlexibilityNo cancel feeOn-time71%

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.