MSN - EYW

$273 Find Cheap Flights from Madison to Key West - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$280
Typical prices: $357-$580
Multiple Airlines
Thu 11/1Tue 11/6
MSN - EYW • 1 stop
Cheapest one-way
$273
Typical prices: $248-$471
Breeze Airways
Tue 1/16
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
22 weeks
in advance
Our data shows that travelers who book at least 22 weeks in advance save around 63% compared to booking last minute.
Insights
Insights
When to travel
July
Cheapest • 26% price drop
February
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Newark (EWR)
Cheapest • Avg $401 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 5h 38m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Key West!
Flight Deals
Booking Insights
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, Nov 1 - Fri, Nov 6
Multiple Airlines Logo
6:00 pm - 8:44 amMSN  Madison Truax Field-EYW Key West
13h 44m1 stop Orlando
Multiple Airlines Logo
12:59 pm - 9:58 amEYW  Key West-MSN Madison Truax Field
21h 59m1 stop Tampa
$280Multiple Airlines
Tue, Jan 26 - Tue, Feb 2
Delta Logo
11:11 am - 7:43 pmMSN  Madison Truax Field-EYW Key West
7h 32m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:30 pm - 8:11 pmEYW  Key West-MSN Madison Truax Field
6h 41m1 stop New York LaGuardia
$333Delta
Sun, Nov 1 - Thu, Nov 5
Multiple Airlines Logo
6:00 pm - 8:44 amMSN  Madison Truax Field-EYW Key West
13h 44m1 stop Orlando
Multiple Airlines Logo
10:59 am - 5:20 pmEYW  Key West-MSN Madison Truax Field
7h 21m1 stop Orlando
$335Multiple Airlines
Thu, Dec 10 - Mon, Dec 14
Breeze Airways Logo
6:10 pm - 10:19 amMSN  Madison Truax Field-EYW Key West
15h 09m1 stop Orlando
Breeze Airways Logo
10:59 am - 9:50 amEYW  Key West-MSN Madison Truax Field
23h 51m1 stop Orlando
$341Breeze Airways
Sun, Dec 6 - Wed, Dec 16
American Airlines Logo
6:55 am - 4:02 pmMSN  Madison Truax Field-EYW Key West
8h 07m1 stop Charlotte Douglas
American Airlines Logo
6:25 pm - 11:12 pmEYW  Key West-MSN Madison Truax Field
5h 47m1 stop Chicago O'Hare Intl
$345American Airlines
Sun, Dec 6 - Wed, Dec 16
American Airlines Logo
5:00 am - 11:54 amMSN  Madison Truax Field-EYW Key West
5h 54m1 stop Chicago O'Hare Intl
American Airlines Logo
6:25 pm - 12:13 amEYW  Key West-MSN Madison Truax Field
6h 48m1 stop Chicago O'Hare Intl
$345American Airlines
Sat, Nov 7 - Fri, Nov 13
Delta Logo
1:37 pm - 8:01 pmMSN  Madison Truax Field-EYW Key West
5h 24m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 pm - 10:50 pmEYW  Key West-MSN Madison Truax Field
5h 45m1 stop Atlanta Hartsfield-Jackson
$345Delta
Mon, Jan 25 - Tue, Feb 2
Delta Logo
11:11 am - 5:11 pmMSN  Madison Truax Field-EYW Key West
5h 00m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:30 pm - 8:11 pmEYW  Key West-MSN Madison Truax Field
6h 41m1 stop New York LaGuardia
$345Delta
Fri, Jan 8 - Sat, Jan 9
United Airlines Logo
6:00 am - 3:12 pmMSN  Madison Truax Field-EYW Key West
8h 12m1 stop Chicago O'Hare Intl
United Airlines Logo
5:51 pm - 11:10 pmEYW  Key West-MSN Madison Truax Field
6h 19m1 stop Chicago O'Hare Intl
$356United Airlines
Wed, Mar 3 - Wed, Mar 10
United Airlines Logo
5:10 am - 5:02 pmMSN  Madison Truax Field-EYW Key West
10h 52m2 stops Chicago O'Hare Intl Newark
United Airlines Logo
4:00 pm - 11:03 pmEYW  Key West-MSN Madison Truax Field
8h 03m1 stop Chicago O'Hare Intl
$373United Airlines
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 from Madison to Key West with more confidence.

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

Tuesday is the cheapest day of the week to fly from Madison to Key West, it is 14% cheaper than the average day. Monday is the most expensive day with flight prices 35% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is 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 prices from Madison to Key West the cheapest?

Flights from Madison to Key West are cheapest 22 weeks before departure. Booking in this window typically costs about 63% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Find deals

Key details for Madison to Key West flights

Low season

July

Cheapest flight

$273
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 3% 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

Your Madison to Key West flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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).

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

    Only Economy Class is available on flights from Madison to Key West.

  • 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) - 36% of one-stop connections
    • Charlotte Douglas (CLT) - 31% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 27% of one-stop connections
    • Dallas/Fort Worth (DFW) - 3% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

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

    Yes. Being flexible with your travel dates can save you up to 37% on the Madison to Key West route. Tuesday is the cheapest departure day at $384 round-trip on average, while Monday is the most expensive at $605, a difference of $221. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • 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.

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

    Last-minute fares on this route - booked within 2 weeks of departure - run 61% above the route average of $445. Book 22 weeks before departure for the lowest fares.

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

    A nonstop flight from Madison to Key West takes 0h 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.

  • 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 $280 to $1,883. That means the highest observed fare was about 7x 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 $318, which is 12% below the typical average for this route.

  • 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 13m 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 car rental options are available at Key West Airport (EYW)?

    Key West Airport (EYW) hosts 5 major car rental companies, with daily rates starting from around $29 for economy cars. Top options include:
    • Dollar
    • Hertz
    • Budget
    • Enterprise Rent-A-Car
    • Alamo

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

    Round-trip flights from Madison to Key West range from $357 to $580, with an average of $445 over the past 12 months. Anything below $357 counts as a good deal.

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 can be flexible, aim for a Tuesday departure instead of Monday. On this route, Tuesday flights average $384 - about $221 less than Monday (37% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 22 weeks before you fly. On this route, that window historically saves about 63% 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.
    - Havana Cabana at Key West
    - Fairfield Inn & Suites by Marriott Key West at The Keys Collection
    - Parrot Key Hotel & Villas

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