MSN - EYW

$223 Find Cheap Flights from Madison to Key West - Compare and Save

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 12/15. 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, 0 bags

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Everything you should know

Cheapest round-trip
$333
Typical prices: $336-$502
Delta
Tue 10/27Wed 11/4
MSN - EYW • 1 stop
Cheapest one-way
$240
Breeze Airways
Tue 12/15
MSN - EYW • 2 stops
Top airlines
Cheapest • from $254 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Madison and Key West. You'll need at least 1 connection.
Insights
Insights
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Insights
Top layover airports
Cheapest • Avg $401 (round-trip)
Shortest trip • 5h 43m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 19% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 11% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Key West!
Flight Deals
Booking Insights
Flight Deals

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

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Key West

Tue, Oct 27 - Wed, Nov 4
Delta Logo
11:28 am - 7:51 pm
MSN
-
EYW
7h 23m
1 stop
Delta Logo
6:11 pm - 10:53 pm
EYW
-
MSN
5h 42m
1 stop
$333Delta
Tue, Oct 27 - Tue, Nov 3
Delta Logo
11:28 am - 7:51 pm
MSN
-
EYW
7h 23m
1 stop
Delta Logo
6:11 pm - 10:53 pm
EYW
-
MSN
5h 42m
1 stop
$333Delta
Wed, Oct 28 - Wed, Nov 4
Delta Logo
11:28 am - 5:16 pm
MSN
-
EYW
4h 48m
1 stop
Delta Logo
6:11 pm - 10:53 pm
EYW
-
MSN
5h 42m
1 stop
$333Delta
Tue, Nov 3 - Sat, Nov 7
American Airlines Logo
9:28 am - 4:30 pm
MSN
-
EYW
6h 02m
1 stop
American Airlines Logo
4:45 pm - 12:13 am
EYW
-
MSN
8h 28m
1 stop
$336American Airlines
Tue, Nov 3 - Sun, Nov 8
American Airlines Logo
9:28 am - 4:30 pm
MSN
-
EYW
6h 02m
1 stop
American Airlines Logo
5:01 pm - 12:13 am
EYW
-
MSN
8h 12m
1 stop
$341American Airlines
Tue, Nov 3 - Sat, Nov 7
American Airlines Logo
9:28 am - 4:30 pm
MSN
-
EYW
6h 02m
1 stop
American Airlines Logo
4:45 pm - 12:13 am
EYW
-
MSN
8h 28m
1 stop
$341American Airlines
Fri, Aug 7 - Tue, Aug 11
Breeze Airways Logo
6:50 pm - 11:25 am
MSN
-
EYW
39h 35m
2 stops
Breeze Airways Logo
1:14 pm - 9:47 am
EYW
-
MSN
21h 33m
1 stop
$365Breeze Airways
Wed, Nov 18 - Wed, Nov 25
United Airlines Logo
6:09 am - 1:59 pm
MSN
-
EYW
6h 50m
1 stop
United Airlines Logo
2:55 pm - 11:37 pm
EYW
-
MSN
9h 42m
1 stop
$418United Airlines
Tue, Nov 17 - Wed, Nov 25
United Airlines Logo
6:09 am - 1:59 pm
MSN
-
EYW
6h 50m
1 stop
United Airlines Logo
2:55 pm - 11:37 pm
EYW
-
MSN
9h 42m
1 stop
$418United Airlines
Thu, Aug 27 - Fri, Sep 4
Multiple Airlines Logo
7:55 pm - 11:27 am
MSN
-
EYW
14h 32m
2 stops
Multiple Airlines Logo
1:11 pm - 9:47 am
EYW
-
MSN
21h 36m
1 stop
$456Multiple Airlines
Booking Insights

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 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 September, where tickets cost $408 (return) on average. On the other hand, the most expensive months are June and December, where the average cost of round-trip tickets is $578 and $535 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 4 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low season

June

Cheapest flight

$223
Best time to beat the crowds but there is an average 25% increase in price.
Most popular time to fly and prices are also 1% lower on average.
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 5 days, the lowest price for a flight from Madison to Key West was $223 for a one-way ticket and $254 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?

    Star Alliance, SkyTeam, and oneworld are the airline alliances operating flights between Madison and Key West, with Star Alliance 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 $428 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $438 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.

Reviews of the 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.
7.8
DeltaOverall score based on 8482 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

6.0 GoodLaura, Jul 2026
JFK - MCO
Read more Delta reviews

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

Flight was delayed and then "they did not have time to load food". No snack or drink at all for 1.5 how flight. Somebody wasn't prepared.

It is usually very pleasant. Good service for the price, international flights are even better

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

The experience with United Airlines was excellent; however, the experience with Houston Intercontinental Airport (IAH) was horrible. Although our flight departed from Terminal B, we had to go through security in Terminal C and then get on a train for travel to Terminal B. Additionally, there was significant walking required to get to the boarding location.

Flight was delayed 5 hours. Updates kept changing. Sears were extremely cramped. Very little leg room. Flight attendant was rushing through with drinks and hit me in the knee either the cart and didn’t apologize. They gave a 15 dollar voucher in airport which doesn’t buy. Much and it was so late that choices were limited.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

Quick flight. No time to stress over it. Over before it begins.

Very good, boarded and took off on time and landed early

Delayed boarding because a flight attendant couldn't find the gate...sat on the plane for over an hour at the gate because AA couldn't get one of the planes behind us to move

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

The departure and arrival was on time. The fact that I could load my boarding tickets on the American airlines app.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

We sat on the plane for 1 hour because the airline was short handed could not be unloading.

Our flight was changed from Madison to DC to Madison to Charlotte.

Boarding was relatively fast and easy and the crew was attentive throughout.

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

Information on your arrival and departure airports