EYW - MSN

$288 Find Cheap Flights from Key West to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Madison departing on 6/20. 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.
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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

 
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.

Recent round-trip flight deals from Key West to Madison

KAYAK's recommended round-trip deals from the most popular airlines that fly from Key West to Madison.
Discover the best prices for you by selecting your travel dates on KAYAK.
Delta Logo
6:27 pm - 10:34 pmEYW-MSN
5h 07m1 stop
Delta Logo
5:45 am - 1:09 pmMSN-EYW
6h 24m1 stop
$324Delta
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Tue, Jul 15 - Mon, Aug 11
Delta Logo
7:00 am - 4:21 pmEYW-MSN
10h 21m2 stops
Delta Logo
11:11 am - 5:15 pmMSN-EYW
5h 04m1 stop
$329Delta
Find Deal
Tue, Jul 15 - Wed, Aug 13
Delta Logo
7:00 am - 4:21 pmEYW-MSN
10h 21m2 stops
Delta Logo
7:00 am - 5:15 pmMSN-EYW
9h 15m2 stops
$334Delta
Find Deal
Tue, Jul 15 - Wed, Aug 13
Delta Logo
6:27 pm - 10:34 pmEYW-MSN
5h 07m1 stop
Delta Logo
11:11 am - 7:46 pmMSN-EYW
7h 35m1 stop
$349Delta
Find Deal
Tue, Jul 15 - Tue, Aug 12
American Airlines Logo
11:18 am - 7:56 pmEYW-MSN
9h 38m2 stops
American Airlines Logo
6:20 am - 1:51 pmMSN-EYW
6h 31m1 stop
$381American Airlines
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Mon, Jul 14 - Tue, Aug 12
American Airlines Logo
11:18 am - 7:56 pmEYW-MSN
9h 38m2 stops
American Airlines Logo
6:00 am - 4:21 pmMSN-EYW
9h 21m2 stops
$386American Airlines
Find Deal
Mon, Jul 14 - Tue, Aug 12
United Airlines Logo
6:45 pm - 1:54 pmEYW-MSN
20h 09m2 stops
United Airlines Logo
2:35 pm - 8:00 amMSN-EYW
16h 25m2 stops
$406United Airlines
Find Deal
Mon, Jul 14 - Wed, Aug 13
American Airlines Logo
4:48 pm - 11:50 pmEYW-MSN
8h 02m1 stop
American Airlines Logo
6:46 am - 4:08 pmMSN-EYW
8h 22m1 stop
$453American Airlines
Find Deal
Mon, Jul 14 - Tue, Aug 12
United Airlines Logo
6:45 pm - 11:43 amEYW-MSN
17h 58m2 stops
United Airlines Logo
2:35 pm - 2:00 pmMSN-EYW
22h 25m2 stops
$476United Airlines
Find Deal
Mon, Jul 14 - Mon, Aug 11
United Airlines Logo
8:45 am - 8:15 pmEYW-MSN
12h 30m2 stops
United Airlines Logo
6:35 am - 6:05 pmMSN-EYW
10h 30m2 stops
$589United Airlines
Find Deal
Tue, Jul 15 - Mon, Aug 11
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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.

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Good to know

Low seasonApril
High seasonApril
Cheapest flight$288
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 29% lower on average.
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 $288 for a one-way ticket and $324 for a round-trip.

  • 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, Star Alliance, and SkyTeam are the airline alliances operating flights between Key West and Madison, with SkyTeam 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
7.2Comfort
7.5Boarding
6.9Entertainment
8.0Crew
6.5Food
Airline reviews

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.

2.0 MediocreAnonymous, Apr 2025RSW - DFW
Read more American Airlines reviews

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.

Per usual, flight status, staff courtesy and professionalism were excellent

The seats were crammed and the guy in front of me wouldn't stop reclining. If AA is cramming extra rows in, they need to take away the reclining in coach. My knees were smashed for 4 1/2 hours and I was very close to confronting the passenger in front of me.

AA can't control the weather. But the airplane was hot and stuffy while stuck on the runway with a broken entertainment system.

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

Information on your arrival and departure airports

Madison (MSN)
Key West (EYW)

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