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Cheap flights from Madison to Key West from $219

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Key West departing on 4/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
9:18 am - 6:19 pm
MSN
-
EYW
8h 01m
1 stop
American Airlines Logo
6:49 pm - 11:38 pm
EYW
-
MSN
5h 49m
1 stop
$303American Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
11:33 am - 10:58 pm
MSN
-
EYW
10h 25m
2 stops
American Airlines Logo
6:49 pm - 11:38 pm
EYW
-
MSN
5h 49m
1 stop
$308American Airlines
Tue, Apr 7 - Tue, Apr 14
American Airlines Logo
7:00 am - 5:02 pm
MSN
-
EYW
9h 02m
1 stop
American Airlines Logo
2:12 pm - 9:14 pm
EYW
-
MSN
8h 02m
1 stop
$309American Airlines
Fri, Apr 24 - Thu, Apr 30
American Airlines Logo
2:18 pm - 10:36 pm
MSN
-
EYW
7h 18m
2 stops
American Airlines Logo
11:56 am - 4:28 pm
EYW
-
MSN
5h 32m
1 stop
$314American Airlines
Fri, Apr 24 - Thu, Apr 30
Breeze Airways Logo
6:36 pm - 9:06 am
MSN
-
EYW
13h 30m
1 stop
Breeze Airways Logo
1:01 pm - 9:08 am
EYW
-
MSN
21h 07m
1 stop
$320Breeze Airways
Sat, Apr 11 - Tue, Apr 14
Delta Logo
11:26 am - 7:41 pm
MSN
-
EYW
7h 15m
1 stop
Delta Logo
6:00 pm - 10:35 pm
EYW
-
MSN
5h 35m
1 stop
$323Delta
Sat, Apr 11 - Wed, Sep 16
Delta Logo
7:00 am - 7:41 pm
MSN
-
EYW
11h 41m
2 stops
Delta Logo
6:00 pm - 10:35 pm
EYW
-
MSN
5h 35m
1 stop
$328Delta
Sat, Apr 11 - Wed, Sep 16
Multiple Airlines Logo
6:36 pm - 3:00 pm
MSN
-
EYW
19h 24m
1 stop
Multiple Airlines Logo
9:53 am - 8:25 am
EYW
-
MSN
47h 32m
2 stops
$330Multiple Airlines
Sat, Apr 11 - Sat, Sep 12
American Airlines Logo
2:18 pm - 10:36 pm
MSN
-
EYW
7h 18m
2 stops
American Airlines Logo
4:20 pm - 11:54 pm
EYW
-
MSN
8h 34m
1 stop
$331American Airlines
Sat, May 16 - Wed, May 20
American Airlines Logo
11:35 am - 10:58 pm
MSN
-
EYW
10h 23m
2 stops
American Airlines Logo
3:00 pm - 9:27 pm
EYW
-
MSN
7h 27m
2 stops
$333American Airlines
Sat, Apr 11 - Tue, Sep 15

American Airlines flights from Madison to Key West

Our best American Airlines deals on Madison to Key West flight tickets
American Airlines
Apr 7
MSN9:56 amMadison Truax Field
7h 23m
1 stop
EYW6:19 pmKey West
Apr 14
EYW6:49 pmKey West
5h 49m
1 stop
MSN11:38 pmMadison Truax Field
$303
American Airlines
Apr 7
MSN9:56 amMadison Truax Field
7h 23m
1 stop
EYW6:19 pmKey West
Apr 14
EYW6:45 amKey West
8h 46m
2 stops
MSN2:31 pmMadison Truax Field
$308
American Airlines
Apr 24
MSN7:00 amMadison Truax Field
9h 02m
1 stop
EYW5:02 pmKey West
Apr 30
EYW2:12 pmKey West
8h 02m
1 stop
MSN9:14 pmMadison Truax Field
$309

United Airlines flights from Madison to Key West

Our best United Airlines deals on Madison to Key West flight tickets
United Airlines
Apr 7
MSN6:30 amMadison Truax Field
7h 21m
1 stop
EYW2:51 pmKey West
Apr 14
EYW3:52 pmKey West
6h 29m
1 stop
MSN9:21 pmMadison Truax Field
$334
United Airlines
Apr 7
MSN5:00 amMadison Truax Field
9h 57m
2 stops
EYW3:57 pmKey West
Apr 14
EYW3:52 pmKey West
6h 29m
1 stop
MSN9:21 pmMadison Truax Field
$340
United Airlines
Aug 15
MSN2:45 pmMadison Truax Field
6h 26m
1 stop
EYW10:11 pmKey West
Aug 22
EYW4:05 pmKey West
6h 00m
1 stop
MSN9:05 pmMadison Truax Field
$383

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated March 10, 2026.
Use the filters below to find and compare flights from Madison to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 4/7

9:18 am-6:19 pm

1 stop8h 01m

Key West

Tue 4/14

6:49 pm-11:38 pm

1 stop5h 49m

$303

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 4/7

11:33 am-10:58 pm

2 stops10h 25m

Key West

Tue 4/14

6:49 pm-11:38 pm

1 stop5h 49m

$308

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 4/24

7:00 am-5:02 pm

1 stop9h 02m

Key West

Thu 4/30

2:12 pm-9:14 pm

1 stop8h 02m

$309
Quickest round-trip

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 4/24

2:18 pm-10:36 pm

2 stops7h 18m

Key West

Thu 4/30

11:56 am-4:28 pm

1 stop5h 32m

$314

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/11

6:36 pm-9:06 am

1 stop13h 30m

Key West

Tue 4/14

1:01 pm-9:08 am

1 stop21h 07m

$320

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/11

11:26 am-7:41 pm

1 stop7h 15m

Key West

Wed 9/16

6:00 pm-10:35 pm

1 stop5h 35m

$323

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/11

7:00 am-7:41 pm

2 stops11h 41m

Key West

Wed 9/16

6:00 pm-10:35 pm

1 stop5h 35m

$328

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/11

6:36 pm-3:00 pm

1 stop19h 24m

Key West

Sat 9/12

9:53 am-8:25 am

2 stops47h 32m

$330

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 5/16

2:18 pm-10:36 pm

2 stops7h 18m

Key West

Wed 5/20

4:20 pm-11:54 pm

1 stop8h 34m

$331

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 4/11

11:35 am-10:58 pm

2 stops10h 23m

Key West

Tue 9/15

3:00 pm-9:27 pm

2 stops7h 27m

$333

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to Key West from

How to get the cheapest flight ticket from Madison to Key West

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Madison and Key West?

What is the cheapest month to fly to Key West?

In general, July is the cheapest month to fly from Madison to Key West. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $301. If you are unable to visit Key West during the month of July, then departing from Madison during the month August is also very affordable. Most momondo users find prices during this month for around $333.

How far in advance should I book a flight to Key West?

You are more likely to see cheaper flights to Key West from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Key West for around $419 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Key West from Madison for as low as $315 on momondo.

Can stopping save me money on Madison to Key West flights?

You could potentially save up to 14% on your flight if you consider stops on a Madison to Key West flight.

When to book flights from Madison to Key West

Are you open to changing your travel dates? Check out the ideal times to fly from Madison to Key West according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Madison to Key West (MSN to EYW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Key West

Fastest flight time

5h 21m

Direct flights

None
The fastest flight from Madison to Key West takes 5h 21m
There are no direct flights from Madison to Key West. There are no popular flight routes from Madison to Key West.
Search flight deals

  • How far is Madison Truax Field to Key West by plane?

    There are 1349.4 mi between Madison Truax Field and Key West. In terms of flight time, this usually takes a little over 5h 21m.

  • When did momondo last update prices for flights from Madison Truax Field Airport to Key West Airport?

    Prices for flights from Madison Truax Field Airport to Key West Airport are updated daily.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Key West Airport?

  • How old do you have to be to fly from Madison Truax Field Airport to Key West Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Madison Truax Field Airport to Key West Airport.

  • What documentation or ID do you need to fly to Key West Airport?

    The travel and health documents you'll need for your trip to Key West Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Key West Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Madison to Key West?

Best airlines flying from Madison to Key West

Compare and see reviews for airlines that fly from Madison to Key West with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $267Free CancellationRating
7.9
8,276 reviews
Search Delta flights
American AirlinesPriceFrom $268Free CancellationRating
7.1
11,413 reviews
Search American Airlines flights
United AirlinesPriceFrom $313Free CancellationRating
7.4
9,409 reviews
Search United Airlines flights

Traveling to a place near Key West?

Book flights to Key West if you plan to visit one of these locations
Big Pine Key
Little Torch Key

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Key West?

It is quick and easy to find Madison to Key West flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Key West that suits you.

Can I find flights from Madison to Key West with flexible booking policies on momondo?

momondo does allow users to show only those flights to Key West from Madison which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Madison to Key West?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Madison to Key West.

I’m not ready to book a flight from Madison to Key West right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Madison to Key West flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Key West trip

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