EYW - MSN

$274 Find Cheap Flights from Key West to Madison

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Madison departing on 10/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Madison

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Madison, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Madison, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Key West to Madison (EYW-MSN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Madison that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Key West to Madison

Wed, Oct 1 - Wed, Oct 8
American Airlines Logo
6:17 pm - 11:10 pmEYW-MSN
5h 53m1 stop
American Airlines Logo
6:21 am - 4:29 pmMSN-EYW
9h 08m2 stops
$274American Airlines
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Wed, Oct 1 - Wed, Oct 8
American Airlines Logo
1:59 pm - 11:10 pmEYW-MSN
10h 11m2 stops
American Airlines Logo
6:00 am - 4:29 pmMSN-EYW
9h 29m2 stops
$279American Airlines
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Wed, Oct 1 - Wed, Oct 8
American Airlines Logo
3:45 pm - 11:10 pmEYW-MSN
8h 25m1 stop
American Airlines Logo
6:35 am - 1:47 pmMSN-EYW
6h 12m1 stop
$373American Airlines
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Thu, Jun 26 - Mon, Jul 7
American Airlines Logo
4:49 pm - 11:59 pmEYW-MSN
8h 10m1 stop
American Airlines Logo
6:27 am - 1:51 pmMSN-EYW
6h 24m1 stop
$522American Airlines
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Thu, Jun 26 - Mon, Jul 7
American Airlines Logo
1:24 pm - 11:59 pmEYW-MSN
11h 35m2 stops
American Airlines Logo
6:27 am - 1:51 pmMSN-EYW
6h 24m1 stop
$560American Airlines
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Wed, Oct 1 - Wed, Oct 8
United Airlines Logo
8:45 am - 10:03 pmEYW-MSN
14h 18m2 stops
United Airlines Logo
12:26 pm - 6:05 pmMSN-EYW
28h 39m3 stops
$575United Airlines
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Thu, Jun 26 - Mon, Jul 7
American Airlines Logo
1:24 pm - 11:59 pmEYW-MSN
11h 35m2 stops
American Airlines Logo
6:27 am - 4:18 pmMSN-EYW
8h 51m2 stops
$712American Airlines
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Useful Info

KAYAK's insights & trends for Key West to Madison flights

Get data-powered insights and trends into flights from Key West to Madison to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Key West to Madison?

The average price of all round-trip flights from Key West to Madison clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Key West to Madison, look for departures on Fridays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Madison, Wednesday is the cheapest day to fly and Saturday is the most expensive.

Find deals

Good to know

Cheapest flight$274
Flight from Key West to Madison

When to book flights from Key West to Madison

Are your dates flexible? Find out the best times to travel from Key West to Madison based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Key West to Madison

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

    In the last 3 days, the lowest price for a flight from Key West to Madison was $274 for a round-trip ticket.

  • Do I need a passport to fly between Key West and Madison?

    A passport is not required to fly from Key West to Madison.

  • Which aircraft models fly most regularly from Key West to Madison?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Key West to Madison?

    oneworld, and Star Alliance are the airline alliances operating flights between Key West and Madison, with oneworld being the most commonly used for this route.

  • How does KAYAK find such low prices on flights from Key West to Madison?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Madison.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Madison?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from Key West is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Key West to Madison?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Madison with an airline and back to Key West with another airline. Booking your flights between Key West and MSN can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Madison?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Madison from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top airline flying from Key West to Madison

 
See real verified KAYAK customer reviews for airlines flying from Key West to Madison. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Key West to Madison? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 10000 reviews
6.5Food
7.5Boarding
7.2Comfort
6.9Entertainment
8.0Crew
Airline reviews

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

2.0 MediocreJose David, Jun 2025MIA - DTW
Read more American Airlines reviews

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Crew professional. Easy bag drop off. On time. Good entertainment.

Flight was late and missed connecting flight. They could have better accommodated, but instead did an overnight and had to arrive the next afternoon.

The boarding crew was incredibly helpful getting me on an earlier flight

They have lost any customer service care and support. Terrible airline now and been for awhile.

The flight was delayed leaving Miami. When we arrived in Charlotte, we were unable to park at our scheduled gate. We had to wait another 30-45 minutes before we could park at a different gate. All in all, we were delayed by almost two hours arriving in Charlotte.

the pilot that landed this flight in Philadelphia did an amazing job, the weather was absolutely terrible and we landed safely.

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

Information on your arrival and departure airports

Key West (EYW)
Madison (MSN)

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