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

Compare Madison to Key West International flight deals

Find the cheapest month or even day of the year to fly to Key West International

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Flight deals from Madison to Key West International

Looking for a cheap last-minute deal or the best return flight from Madison Airport to Key West International Airport? If you want to travel next month, return fares start from $479. Find the lowest prices on one-way and return tickets right here.
Key West.$459 per passenger.Departing Tue, 22 Sep, returning Tue, 29 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Madison on Tue, 22 Sep, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Tue, 29 Sep, arriving in Madison.Price includes taxes and charges.From $459, select.
Key West.$460 per passenger.Departing Sat, 5 Dec, returning Wed, 9 Dec.Return flight with United.Outbound indirect flight with United, departs from Madison on Sat, 5 Dec, arriving in Key West International.Inbound indirect flight with United, departs from Key West International on Wed, 9 Dec, arriving in Madison.Price includes taxes and charges.From $460, select.
Key West.$479 per passenger.Departing Sat, 22 Aug, returning Fri, 28 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Madison on Sat, 22 Aug, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Fri, 28 Aug, arriving in Madison.Price includes taxes and charges.From $479, select.
Key West.$514 per passenger.Departing Sun, 16 May, returning Sat, 22 May.Return flight with United.Outbound indirect flight with United, departs from Madison on Sun, 16 May, arriving in Key West International.Inbound indirect flight with United, departs from Key West International on Sat, 22 May, arriving in Madison.Price includes taxes and charges.From $514, select.
Key West.$591 per passenger.Departing Wed, 11 Nov, returning Sat, 14 Nov.Return flight with United.Outbound indirect flight with United, departs from Madison on Wed, 11 Nov, arriving in Key West International.Inbound indirect flight with United, departs from Key West International on Sat, 14 Nov, arriving in Madison.Price includes taxes and charges.From $591, select.
Key West.$685 per passenger.Departing Fri, 31 Jul, returning Mon, 3 Aug.Return flight with United.Outbound indirect flight with United, departs from Madison on Fri, 31 Jul, arriving in Key West International.Inbound indirect flight with United, departs from Key West International on Mon, 3 Aug, arriving in Madison.Price includes taxes and charges.From $685, select.
Key West.$1,222 per passenger.Departing Thu, 8 Oct, returning Sun, 11 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Madison on Thu, 8 Oct, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Sun, 11 Oct, arriving in Madison.Price includes taxes and charges.From $1,222, select.
Key West.$1,621 per passenger.Departing Sat, 16 Jan, returning Sat, 23 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Madison on Sat, 16 Jan, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Sat, 23 Jan, arriving in Madison.Price includes taxes and charges.From $1,621, select.
Key West.$1,797 per passenger.Departing Fri, 25 Dec, returning Sat, 2 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Madison on Fri, 25 Dec, arriving in Key West International.Inbound indirect flight with Delta, departs from Key West International on Sat, 2 Jan, arriving in Madison.Price includes taxes and charges.From $1,797, select.

Find the cheapest month to fly from Madison to Key West International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Madison to Key West International flights are currently cheapest in September.
Jul
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Aug
from $479
Sep
from $459
Oct
from $1,222
Nov
from $591
Dec
from $460
Jan
from $1,621
Feb
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Mar
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Apr
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May
from $514
Jun
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Madison to Key West International: Alternative routes

Compare routes from Madison to Key West below. You may find an airport to fly into that's cheaper, faster, or easier than Key West International.

Key West International

5km from central Key West
ClosestCheapest
from $459
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Madison to Key West: Flight information

The things to know before you go.
Cheapest flight found$459
Cheapest month to flySeptember

Finding cheap flights from Madison to Key West International: Frequently asked questions

The best price we found for a return flight from Madison to Key West International is $459. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Madison to Key West International. But we found flights with one or more stops from $459.
As of July 2026, there are no flights flying from Madison to Key West International.
The cheapest month to fly from Madison to Key West International is usually September.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Madison Airport to Key West International Airport on Tuesday, 22 September 2026.
No airlines currently offer direct flights between Madison Airport and Key West International Airport. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Key West International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Key West is around 40 days in advance, so don’t leave your flight to the last minute.

Currently, Delta offers the cheapest flight tickets to Key West International.

Travelling from Madison Airport (MSN) to Key West International Airport (EYW): what you need to know

  • Get to the airport on time so you don't miss your MSN to EYW flight. Be there at least two hours ahead for international flights and an hour early for domestic departures to prevent a last-minute sprint to your gate.

  • You'll likely experience longer queues in popular months such as August. Arriving up to four hours ahead of international flights and two hours for domestic departures is a wise move.

  • If you want to explore another city along the way, simply uncheck 'Direct flights only' when searching for your ticket from Madison Airport to Key West International Airport. These are the most popular stopovers between MSN and EYW:

    • Chicago O'Hare International Airport

    • Atlanta Hartsfield-Jackson Airport

    • Charlotte Douglas Airport

How to find the cheapest flights from Madison Airport (MSN) to Key West International Airport (EYW)

  • $511 is currently the lowest price for a one-way Madison Airport to Key West International Airport flight. A return flight starts from $459. These prices may change depending on availability and demand.

  • It's a good idea to book ahead of time if you're looking for cheap tickets from MSN to EYW. That's because airlines change prices based on demand, which tends to increase closer to departure.

  • If you're willing to be flexible with your travel dates, use the 'Whole month' search tool. It'll find the lowest price in every month when searching for a flight from Madison Airport to Key West International Airport.

  • You don't need to check back in every day to see if fares have dropped when you set up a Price Alert. We'll send you an update as soon as the price changes on cheap flights from MSN to EYW.

  • Choose your preferred arrival and departure times, number of stops and airlines with the filters. Alternatively, sort your results by 'Cheapest' to get the best deals on flights from Madison Airport to Key West International Airport.

Handy information about Madison Airport (MSN)

  • MSN's address is 4000 International Lane.

  • Of all flights leaving Madison Airport, 75% land on schedule at their destination.

  • Central Madison to Madison Airport is approximately 13 kilometres. Depending on traffic, it'll take you about 20 minutes to get there if you're catching a taxi, ride-sharing or driving.

  • The journey on public transport takes roughly 40 minutes.

  • Get your holiday off to a hassle-free start by staying near MSN. Whether you're catching an early flight from Madison Airport to Key West International Airport or want to avoid feeling rushed, these stays are perfect:

Arriving at Key West International Airport (EYW)

Getting from Key West International Airport (EYW) to central Key West

  • The street address for EYW is 3491 South Roosevelt Boulevard.

  • From Key West International Airport, Key West is approximately 5 kilometres away. It takes around 10 minutes to reach the centre by car.

  • Getting there by public transport takes roughly 20 minutes.

When to fly to Key West International Airport (EYW)

  • April is the busiest month for flights from Madison Airport to Key West International Airport. To avoid the crowds, go to Key West in September.

  • The warmest month in Key West is August, with temperatures ranging between 26ºC (79ºF) and 30ºC (86ºF). Book your flights from Madison Airport to Key West International Airport in this month if this is the kind of weather you like.

  • January sees average temperatures of between 18ºC (64ºF) and 23ºC (73ºF). Look for cheap tickets from MSN to EYW around that time if you like cooler conditions.

Explore more of the United States

  • Miami is just one of the many cities in the United States waiting to be explored after you've seen Key West. Around 209 kilometres away to the north-east, its top attractions include Beach, Ocean Drive and Port of Miami.

  • Tampa is another sought-after destination in the United States and is around 386 kilometres north of Key West. No trip is complete without dropping by Busch Gardens Tampa, The Florida Aquarium and ZooTampa at Lowry Park.

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Prices shown on this page are estimated lowest prices only. Found in the last 12 days.