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Cheap flights from Key West to Madison from $209

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Key West to Madison departing on 6/4. 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
0 bags

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Find the cheapest flights from Key West to Madison

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:19 pm - 10:44 pm
EYW
-
MSN
5h 25m
1 stop
Delta Logo
5:48 am - 1:28 pm
MSN
-
EYW
6h 40m
1 stop
$323Delta
Wed, Jun 3 - Wed, Jun 10
Delta Logo
6:19 pm - 10:44 pm
EYW
-
MSN
5h 25m
1 stop
Delta Logo
9:30 am - 7:53 pm
MSN
-
EYW
9h 23m
2 stops
$328Delta
Wed, Jun 3 - Wed, Jun 10
American Airlines Logo
1:39 pm - 12:09 am
EYW
-
MSN
11h 30m
2 stops
American Airlines Logo
7:18 am - 6:49 pm
MSN
-
EYW
10h 31m
2 stops
$333American Airlines
Wed, Jun 3 - Wed, Jun 10
Delta Logo
2:03 pm - 8:49 pm
EYW
-
MSN
7h 46m
2 stops
Delta Logo
9:30 am - 7:53 pm
MSN
-
EYW
9h 23m
2 stops
$371Delta
Wed, Jun 3 - Wed, Jun 10
American Airlines Logo
7:29 pm - 11:59 pm
EYW
-
MSN
5h 30m
1 stop
American Airlines Logo
6:01 am - 1:41 pm
MSN
-
EYW
6h 40m
1 stop
$444American Airlines
Thu, Jun 4 - Sun, Jun 7
American Airlines Logo
4:44 pm - 11:59 pm
EYW
-
MSN
8h 15m
1 stop
American Airlines Logo
7:00 am - 7:10 pm
MSN
-
EYW
11h 10m
2 stops
$449American Airlines
Thu, Jun 4 - Sun, Jun 7
American Airlines Logo
11:28 am - 9:20 pm
EYW
-
MSN
10h 52m
2 stops
American Airlines Logo
7:00 am - 7:10 pm
MSN
-
EYW
11h 10m
2 stops
$455American Airlines
Thu, Jun 4 - Sun, Jun 7
American Airlines Logo
4:20 pm - 11:54 pm
EYW
-
MSN
8h 34m
1 stop
American Airlines Logo
7:10 am - 5:02 pm
MSN
-
EYW
8h 52m
1 stop
$481American Airlines
Thu, May 7 - Sun, May 10
American Airlines Logo
3:58 pm - 11:54 pm
EYW
-
MSN
8h 56m
2 stops
American Airlines Logo
7:10 am - 5:02 pm
MSN
-
EYW
8h 52m
1 stop
$486American Airlines
Thu, May 7 - Sun, May 10
American Airlines Logo
3:58 pm - 11:54 pm
EYW
-
MSN
8h 56m
2 stops
American Airlines Logo
7:10 am - 4:30 pm
MSN
-
EYW
8h 20m
2 stops
$491American Airlines
Thu, May 7 - Sun, May 10

United Airlines flights from Key West to Madison

Our best United Airlines deals on Key West to Madison flight tickets
United Airlines
May 23
EYW2:26 pmKey West
9h 16m
2 stops
MSN10:42 pmMadison Truax Field
May 26
MSN8:10 amMadison Truax Field
5h 57m
1 stop
EYW3:07 pmKey West
$687
United Airlines
May 23
EYW2:26 pmKey West
9h 16m
2 stops
MSN10:42 pmMadison Truax Field
May 26
MSN8:10 amMadison Truax Field
28h 20m
2 stops
EYW1:30 pmKey West
$834
United Airlines
May 23
EYW2:26 pmKey West
7h 13m
1 stop
MSN8:39 pmMadison Truax Field
May 26
MSN8:10 amMadison Truax Field
5h 57m
1 stop
EYW3:07 pmKey West
$906

Delta flights from Key West to Madison

Our best Delta deals on Key West to Madison flight tickets
Delta
Jun 3
EYW6:19 pmKey West
5h 25m
1 stop
MSN10:44 pmMadison Truax Field
Jun 10
MSN5:48 amMadison Truax Field
6h 40m
1 stop
EYW1:28 pmKey West
$323
Delta
Jun 3
EYW6:19 pmKey West
5h 25m
1 stop
MSN10:44 pmMadison Truax Field
Jun 10
MSN9:30 amMadison Truax Field
9h 23m
2 stops
EYW7:53 pmKey West
$328
Delta
Jun 3
EYW2:03 pmKey West
7h 46m
2 stops
MSN8:49 pmMadison Truax Field
Jun 10
MSN9:30 amMadison Truax Field
9h 23m
2 stops
EYW7:53 pmKey West
$371

momondo Fare Finder

 
Customize your flight search to find flights from Key West to Madison 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 April 28, 2026.
Use the filters below to find and compare flights from Key West to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 6/3

6:19 pm-10:44 pm

1 stop5h 25m

Madison Truax Field

Wed 6/10

5:48 am-1:28 pm

1 stop6h 40m

$323

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 6/3

6:19 pm-10:44 pm

1 stop5h 25m

Madison Truax Field

Wed 6/10

9:30 am-7:53 pm

2 stops9h 23m

$328

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 6/3

1:39 pm-12:09 am

2 stops11h 30m

Madison Truax Field

Wed 6/10

7:18 am-6:49 pm

2 stops10h 31m

$333

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 6/3

2:03 pm-8:49 pm

2 stops7h 46m

Madison Truax Field

Wed 6/10

9:30 am-7:53 pm

2 stops9h 23m

$371

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 6/4

7:29 pm-11:59 pm

1 stop5h 30m

Madison Truax Field

Sun 6/7

6:01 am-1:41 pm

1 stop6h 40m

$444

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 6/4

4:44 pm-11:59 pm

1 stop8h 15m

Madison Truax Field

Sun 6/7

7:00 am-7:10 pm

2 stops11h 10m

$449

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 6/4

11:28 am-9:20 pm

2 stops10h 52m

Madison Truax Field

Sun 6/7

7:00 am-7:10 pm

2 stops11h 10m

$455

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 5/7

4:20 pm-11:54 pm

1 stop8h 34m

Madison Truax Field

Sun 5/10

7:10 am-5:02 pm

1 stop8h 52m

$481

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 5/7

3:58 pm-11:54 pm

2 stops8h 56m

Madison Truax Field

Sun 5/10

7:10 am-5:02 pm

1 stop8h 52m

$486

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 5/7

3:58 pm-11:54 pm

2 stops8h 56m

Madison Truax Field

Sun 5/10

7:10 am-4:30 pm

2 stops8h 20m

$491

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 Madison from

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

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

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

You could potentially save up to 6% on your flight if you consider stops on a Key West to Madison flight.

When to book flights from Key West to Madison

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

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

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

Fastest flight time

5h 25m

Direct flights

None
The fastest flight from Key West to Madison takes 5h 25m
There are no direct flights from Key West to Madison. There are no popular flight routes from Key West to Madison.
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Frequently asked questions about flying from Key West to Madison

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

    A flight from Key West to Madison Truax Field will travel around 1349.4 mi. In terms of flight time, this usually takes a little over 5h 25m.

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

    Prices for flights from Key West Airport to Madison Truax Field Airport were last updated today.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Key West Airport to Madison Truax Field Airport.

  • What documentation or ID do you need to fly to Madison Truax Field Airport?

    The travel and health documents required for your trip to Madison Truax Field Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Madison Truax Field Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Wisconsin Dells
Baraboo
Sun Prairie
Middleton
Fitchburg
Portage
Windsor
Cambridge
Oxford
Evansville

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Key West to Madison. momondo saves you time and could save you money on your trip.

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

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

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

Once you have performed a search for Key West to Madison flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Madison from Key West. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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Thu 5/28
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