EYW - MSN

$159 Find Cheap Flights from Key West to Madison - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$478
Typical prices: $375-$440
Delta
Mon 2/5Tue 2/6
EYW - MSN • 1 stop
Cheapest one-way
$159
Typical prices: $248-$385
Breeze Airways
Thu 1/4
EYW - MSN • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Key West and Madison. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
May
Cheapest • 17% price drop
April
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Chicago O'Hare Intl (ORD)
Cheapest • Avg $370 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 5h 31m (one-way)
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Insights
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Flight Deals

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

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

Recent round-trip flight deals from Key West to Madison

Fri, Feb 5 - Sat, Feb 6
Delta Logo
11:48 am - 4:32 pmEYW  Key West-MSN Madison Truax Field
5h 44m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:01 pm - 8:48 pmMSN  Madison Truax Field-EYW Key West
6h 47m1 stop Atlanta Hartsfield-Jackson
$478Delta
Fri, Feb 5 - Sat, Feb 6
American Airlines Logo
5:58 pm - 12:14 amEYW  Key West-MSN Madison Truax Field
7h 16m1 stop Chicago O'Hare Intl
American Airlines Logo
6:00 am - 4:09 pmMSN  Madison Truax Field-EYW Key West
9h 09m1 stop Washington, D.C. Reagan-National
$483American Airlines
Fri, Feb 5 - Sat, Feb 6
American Airlines Logo
5:58 pm - 12:14 amEYW  Key West-MSN Madison Truax Field
7h 16m1 stop Chicago O'Hare Intl
American Airlines Logo
6:00 am - 5:54 pmMSN  Madison Truax Field-EYW Key West
10h 54m2 stops Washington, D.C. Reagan-National Charlotte Douglas
$488American Airlines
Fri, Feb 5 - Sat, Feb 6
American Airlines Logo
11:32 am - 8:02 pmEYW  Key West-MSN Madison Truax Field
9h 30m2 stops Miami Chicago O'Hare Intl
American Airlines Logo
6:00 am - 5:54 pmMSN  Madison Truax Field-EYW Key West
10h 54m2 stops Washington, D.C. Reagan-National Charlotte Douglas
$738American Airlines
Fri, Feb 5 - Sat, Feb 6
American Airlines Logo
11:32 am - 9:19 pmEYW  Key West-MSN Madison Truax Field
10h 47m2 stops Miami New York LaGuardia
American Airlines Logo
6:00 am - 5:54 pmMSN  Madison Truax Field-EYW Key West
10h 54m2 stops Washington, D.C. Reagan-National Charlotte Douglas
$752American Airlines
Booking Insights

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

Round-trip flights from Key West to Madison typically range from $375 to $440. The lowest price found in the past 5 days was $478, on Delta.

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Key details for Key West to Madison flights

Cheapest flight

$159
The most popular month to fly with an average 5% increase in travelers.
One-way 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

Your Key West to Madison 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 Key West to Madison?

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

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

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

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

    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 Key West to Madison flight?

    Round-trip flights from Key West to Madison range from $375 to $440, with an average of $408 over the past 12 months. Anything below $375 counts as a good deal.

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

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route varied from about $478 to $752. That means the highest observed fare was about 57% higher than the lowest one.

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

    One-way fares from Key West to Madison are currently in line with typical prices for this route. Average one-way fares are about $327.

  • What car rental options are available at Madison Truax Field Airport (MSN)?

    Madison Truax Field Airport (MSN) hosts 5 major car rental companies, with daily rates averaging $86 for economy cars. Top options include:

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

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

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

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

    Connecting flights from Key West to Madison most commonly pass through:

    • Atlanta Hartsfield-Jackson (ATL) - 64% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 36% of one-stop connections

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

    Yes. Flexible dates can save you up to 35% on flights from Key West to Madison. Thursday is the cheapest departure day at $348 round-trip on average, while Wednesday is the most expensive at $534, a difference of $186.

    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 Key West to Madison?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 5h 31m, compared with 6h 50m via Chicago O'Hare Intl (ORD).

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

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

Your guide to booking Key West to Madison 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 Thursday departure and avoid flying on Wednesday. On this route, Thursday flights average $348, about $186 less than Wednesday fares (35% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Key West to Madison trip for May. Fares historically average $341 round-trip in that month - typically $243 less than the most expensive month, which is June (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Madison Truax Field Airport.

    • Doubletree by Hilton East Madison East
    • Best Western East Towne Suites
    • Rodeway Inn and Suites Madison East

More options for your flight from Key West to Madison

Complete your trip to Madison with a hotel stay or car rental

Car rentals in Madison
Hotels in Madison
Vacations in Madison