MSN - EYW

$187 Find Cheap Flights from Madison to Key West - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$304
Typical prices: $380-$600
Breeze Airways
Wed 2/7Mon 2/12
MSN - EYW • 1 stop
Cheapest one-way
$187
Typical prices: $299-$482
Multiple Airlines
Sat 3/31
MSN - EYW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Madison and Key West. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to book
19 weeks
in advance
Our data shows that travelers who book at least 19 weeks in advance save around 56% compared to booking last minute.
Insights
Insights
When to travel
July
Cheapest • 29% price drop
February
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Newark (EWR)
Cheapest • Avg $398 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 5h 38m (one-way)
Insights
Insights
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We hope you love your trip to Key West!
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Flight Deals

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

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

Recent round-trip flight deals from Madison to Key West

Sun, Feb 7 - Fri, Feb 12
Breeze Airways Logo
6:00 pm - 10:19 amMSN  Madison Truax Field-EYW Key West
15h 19m1 stop Orlando
Breeze Airways Logo
12:59 pm - 9:58 amEYW  Key West-MSN Madison Truax Field
21h 59m1 stop Tampa
$304Breeze Airways
Sun, Jan 10 - Fri, Jan 15
Multiple Airlines Logo
6:00 pm - 10:19 amMSN  Madison Truax Field-EYW Key West
15h 19m1 stop Orlando
Multiple Airlines Logo
3:31 pm - 9:58 amEYW  Key West-MSN Madison Truax Field
19h 27m1 stop Tampa St. Petersburg
$346Multiple Airlines
Tue, Mar 16 - Tue, Mar 23
American Airlines Logo
5:10 am - 11:27 amMSN  Madison Truax Field-EYW Key West
5h 17m1 stop Chicago O'Hare Intl
American Airlines Logo
6:32 pm - 11:08 pmEYW  Key West-MSN Madison Truax Field
5h 36m1 stop Charlotte Douglas
$359American Airlines
Sun, Dec 13 - Tue, Jan 12
American Airlines Logo
5:00 am - 12:07 pmMSN  Madison Truax Field-EYW Key West
6h 07m1 stop Chicago O'Hare Intl
American Airlines Logo
6:26 pm - 11:24 pmEYW  Key West-MSN Madison Truax Field
5h 58m1 stop Charlotte Douglas
$359American Airlines
Sun, Dec 13 - Tue, Jan 12
Delta Logo
5:30 am - 1:11 pmMSN  Madison Truax Field-EYW Key West
6h 41m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:00 pm - 10:44 pmEYW  Key West-MSN Madison Truax Field
6h 44m1 stop Atlanta Hartsfield-Jackson
$359Delta
Sat, Feb 20 - Wed, Feb 24
American Airlines Logo
11:21 am - 6:45 pmMSN  Madison Truax Field-EYW Key West
6h 24m1 stop Charlotte Douglas
American Airlines Logo
6:32 pm - 11:08 pmEYW  Key West-MSN Madison Truax Field
5h 36m1 stop Charlotte Douglas
$389American Airlines
Thu, Nov 12 - Mon, Nov 16
Breeze Airways Logo
6:00 pm - 10:19 amMSN  Madison Truax Field-EYW Key West
15h 19m1 stop Orlando
Breeze Airways Logo
10:59 am - 9:50 amEYW  Key West-MSN Madison Truax Field
23h 51m1 stop Orlando
$391Breeze Airways
Thu, Dec 17 - Sun, Dec 20
United Airlines Logo
7:00 am - 3:23 pmMSN  Madison Truax Field-EYW Key West
7h 23m1 stop Chicago O'Hare Intl
United Airlines Logo
4:04 pm - 9:40 pmEYW  Key West-MSN Madison Truax Field
6h 36m1 stop Chicago O'Hare Intl
$394United Airlines
Thu, Dec 17 - Sun, Dec 20
United Airlines Logo
7:00 am - 3:23 pmMSN  Madison Truax Field-EYW Key West
7h 23m1 stop Chicago O'Hare Intl
United Airlines Logo
1:35 pm - 9:40 pmEYW  Key West-MSN Madison Truax Field
9h 05m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
$425United Airlines
Wed, Nov 25 - Wed, Dec 9
Delta Logo
5:30 am - 12:59 pmMSN  Madison Truax Field-EYW Key West
6h 29m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:06 pm - 10:52 pmEYW  Key West-MSN Madison Truax Field
5h 46m1 stop Atlanta Hartsfield-Jackson
$478Delta
Booking Insights

Price, demand and travel trends for Madison to Key West flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Madison to Key West?

Round-trip flights from Madison to Key West typically range from $380 to $600. The lowest price found in the past 5 days was $304, on Breeze Airways.

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

Based on deals KAYAK users found in the last 12 months, Tuesday is the cheapest day of the week to fly from Madison to Key West. It’s 13% cheaper than the average day, while Monday is the most expensive, with prices 30% higher.

What’s the cheapest month to fly from Madison to Key West?

•July is the cheapest month to fly from Madison to Key West at $328 round-trip.
•September ($646) and June ($578) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 96% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Madison to Key West the cheapest?

Flights from Madison to Key West are cheapest 19 weeks before departure. Booking in this window typically costs about 56% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for Madison to Key West flights

Low season

July

Cheapest flight

$187
Beat the crowds with an average 85% drop in travelers.
The most popular month to fly with an average 96% increase in travelers.
One-way 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

Your Madison to Key West flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Madison to Key West?

    Two cabin classes are available on flights from Madison to Key West:

    • Economy Class
    • First Class

  • How long is a flight from Madison to Key West?

    A nonstop flight from Madison to Key West takes 00m, covering 1,353 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Madison to Key West flight?

    Round-trip flights from Madison to Key West range from $380 to $600, with an average of $464 over the past 12 months. Anything below $380 counts as a good deal.

  • How expensive are last-minute Madison to Key West flights?

    Last-minute fares on this route (booked within two weeks of departure) run 61% above the $464 route average. Book 19 weeks before departure for the lowest fares.

  • Have flight prices from Madison to Key West changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $304 to $1,919. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Madison to Key West looking right now?

    One-way fares from Madison to Key West are currently lower than usual. Average one-way flight prices are about $368, which is 5% below the typical average for this route.

  • What car rental options are available at Key West Airport (EYW)?

    Key West Airport (EYW) hosts 5 major car rental companies, with daily rates averaging $67 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Budget
    • Enterprise Rent-A-Car
    • Alamo

  • Which airports can I use when flying from Madison to Key West?

    Flights from Madison to Key West usually depart from Madison Truax Field (MSN) and arrive at Key West (EYW).

  • Which airports do connecting flights from Madison to Key West pass through?

    One-stop flights from Madison to Key West most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 34% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 34% of one-stop connections
    • Charlotte Douglas (CLT) - 26% of one-stop connections
    • Dallas/Fort Worth (DFW) - 3% of one-stop connections

  • Can I save money by using flexible dates for flights from Madison to Key West?

    Yes. Flexible dates can save you up to 34% on flights from Madison to Key West. Tuesday is the cheapest departure day at $405 round-trip on average, while Monday is the most expensive at $605, a difference of $200.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Madison to Key West?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 5h 38m, compared with 5h 48m via Washington, D.C. Reagan-National (DCA) and 6h 11m via Chicago O'Hare Intl (ORD).

  • What is the time difference between Madison and Key West?

    Key West is 1 hour ahead of Madison (Eastern Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Key West?

    Some of the most popular sights in Key West are Duval Street, Key West Historic District and Mallory Square. These are among the most viewed places in Key West on KAYAK.

Your guide to booking Madison to Key West flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Tuesday departure and avoid flying on Monday. On this route, Tuesday flights average $405, about $200 less than Monday fares (33% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 19 weeks before you fly. On this route, that window historically saves about 56% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Madison to Key West trip for July. Fares historically average $328 round-trip in that month - typically $318 less than the most expensive month, which is September (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Key West Airport.

    • Parrot Key Hotel & Villas
    • Margaritaville Beach House Key West
    • Havana Cabana at Key West

More options for your flight from Madison to Key West

Complete your trip to Key West with a hotel stay or car rental

Car rentals in Key West
Hotels in Key West
Vacations in Key West