MSN - EYW

$114 Find Cheap Flights from Madison to Key West

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Key West departing on 5/30. 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 Key West

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Key West 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 Madison to Key West

KAYAK's recommended round-trip deals from the most popular airlines that fly from Madison to Key West.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
6:45 am - 4:07 pmMSN-EYW
8h 22m1 stop
American Airlines Logo
4:48 pm - 11:50 pmEYW-MSN
8h 02m1 stop
$269American Airlines
Find Deal
Fri, Jul 4 - Tue, Jul 8
American Airlines Logo
6:45 am - 4:07 pmMSN-EYW
8h 22m1 stop
American Airlines Logo
4:48 pm - 11:50 pmEYW-MSN
8h 02m1 stop
$283American Airlines
Find Deal
Fri, Jul 4 - Tue, Jul 8
American Airlines Logo
6:45 am - 4:07 pmMSN-EYW
8h 22m1 stop
American Airlines Logo
4:48 pm - 11:50 pmEYW-MSN
8h 02m1 stop
$306American Airlines
Find Deal
Fri, Jul 4 - Tue, Jul 8
American Airlines Logo
6:45 am - 4:07 pmMSN-EYW
8h 22m1 stop
American Airlines Logo
11:18 am - 9:42 pmEYW-MSN
11h 24m2 stops
$311American Airlines
Find Deal
Fri, Jul 4 - Tue, Jul 8
United Airlines Logo
2:54 pm - 6:05 pmMSN-EYW
26h 11m2 stops
United Airlines Logo
2:45 pm - 1:54 pmEYW-MSN
24h 09m2 stops
$419United Airlines
Find Deal
Fri, Jul 4 - Tue, Jul 8
United Airlines Logo
6:40 am - 8:00 amMSN-EYW
24h 20m3 stops
United Airlines Logo
6:45 pm - 1:54 pmEYW-MSN
20h 09m2 stops
$429United Airlines
Find Deal
Fri, Jul 4 - Tue, Jul 8
Delta Logo
9:28 am - 5:15 pmMSN-EYW
6h 47m2 stops
Delta Logo
7:00 am - 4:33 pmEYW-MSN
10h 33m2 stops
$438Delta
Find Deal
Sun, Aug 31 - Sun, Sep 7
Delta Logo
7:00 am - 8:07 pmMSN-EYW
12h 07m2 stops
Delta Logo
6:25 pm - 11:01 pmEYW-MSN
5h 36m1 stop
$458Delta
Find Deal
Thu, May 15 - Mon, May 19
United Airlines Logo
3:22 pm - 6:05 pmMSN-EYW
25h 43m2 stops
United Airlines Logo
6:45 pm - 9:28 pmEYW-MSN
27h 43m2 stops
$513United Airlines
Find Deal
Thu, May 15 - Mon, May 19
Delta Logo
5:30 am - 12:56 pmMSN-EYW
6h 26m1 stop
Delta Logo
6:25 pm - 11:01 pmEYW-MSN
5h 36m1 stop
$529Delta
Find Deal
Thu, May 15 - Mon, May 19
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KAYAK's insights & trends for Madison to Key West flights

Get data-powered insights and trends into flights from Madison to Key West 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 Madison to Key West?

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

If your flying dates are flexible, you should consider flying to Key West on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Madison to Key West. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Madison to Key West?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Key West, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to Key West is August, where tickets cost $268 (return) on average. On the other hand, the most expensive months are March and October, where the average cost of round-trip tickets is $695 and $537 respectively.

How far in advance should I book a flight from Madison to Key West?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Madison to Key West, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Madison to Key West, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonSeptember
High seasonFebruary
Cheapest flight$114
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Madison to Key West

When to book flights from Madison to Key West

Are your dates flexible? Find out the best times to travel from Madison to Key West 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 Madison to Key West

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

    In the last 3 days, the lowest price for a flight from Madison to Key West was $114 for a one-way ticket and $269 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

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

  • Which is the best airline for flights from Madison to Key West, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Madison to Key West are Delta and United Airlines. With an average price for the route of $597 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $498 and an overall rating of 7.4.

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

    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 Madison to Key West.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Key West from Madison 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 Madison to Key West?

    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 Key West with an airline and back to Madison with another airline. Booking your flights between Madison and EYW 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 Madison to Key West?

    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 Key West from Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top 3 airlines serving from Madison to Key West

 
See real verified KAYAK customer reviews for airlines flying from Madison to Key West. 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 Madison to Key West? 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.
8.0
DeltaOverall score based on 7934 reviews
8.2Boarding
7.9Entertainment
7.9Comfort
7.3Food
8.5Crew
Airline reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

8.0 ExcellentFredrick, Apr 2025GSO - DTW
Read more Delta reviews

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

Pretty standard flight. Delta has a good selection of movies.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

A bit rush for transit. Food and entertainment are not available

Multiple delays and not straight answer from the United team

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

leg space better than expected. two washrooms for one plane isn't enough.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

Would have thought that they would gas up plane before everyone got on board

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Standard. No different than a discount carrier on a short trip.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Crew was late. Baggage was late. 2hs inside the plane waiting fro de-icing and traffic. A 3:30hs flight ended up being almost 6hs inside the airplane.

Checking in at the counter was very disappointing. The lady had a very bad attitude and smart at me. She had no smile, did not greet me by name, or acknowledge me as a valued customer. Poor reflection of the airline.

Miami lounges were overcrowded and we were unable to get in. We only had a short time. But the banks are too tight in all American hubs

I was pleasantly surprised with an upgrade at boarding. I finally had a mostly gluten free food options and a very attentive attendant.

Very poor. Our special services attendant gave us incorrect information. I also was mishandled at landing. There was no wheelchair waiting. I fell deboarding the plane. Appalling!

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

Information on your arrival and departure airports

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