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Cheap flights from Key West to Madison from $146

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 3/17. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
2:12 pm - 9:14 pm
EYW
-
MSN
8h 02m
1 stop
American Airlines Logo
6:45 am - 3:40 pm
MSN
-
EYW
7h 55m
1 stop
$306American Airlines
Wed, May 6 - Sun, May 10
American Airlines Logo
2:12 pm - 10:54 pm
EYW
-
MSN
9h 42m
1 stop
American Airlines Logo
10:19 am - 6:16 pm
MSN
-
EYW
6h 57m
1 stop
$309American Airlines
Fri, May 1 - Mon, May 4
American Airlines Logo
6:45 am - 2:31 pm
EYW
-
MSN
8h 46m
2 stops
American Airlines Logo
6:45 am - 3:40 pm
MSN
-
EYW
7h 55m
1 stop
$311American Airlines
Wed, May 6 - Sun, May 10
American Airlines Logo
2:12 pm - 10:54 pm
EYW
-
MSN
9h 42m
1 stop
American Airlines Logo
11:44 am - 10:36 pm
MSN
-
EYW
9h 52m
2 stops
$314American Airlines
Fri, May 1 - Mon, May 4
Breeze Airways Logo
1:01 pm - 9:08 am
EYW
-
MSN
21h 07m
1 stop
Breeze Airways Logo
6:36 pm - 9:06 am
MSN
-
EYW
13h 30m
1 stop
$352Breeze Airways
Tue, Apr 21 - Wed, Apr 22
American Airlines Logo
6:46 pm - 11:38 pm
EYW
-
MSN
5h 52m
1 stop
American Airlines Logo
9:18 am - 6:16 pm
MSN
-
EYW
7h 58m
1 stop
$359American Airlines
Fri, Apr 17 - Sat, Apr 18
American Airlines Logo
6:45 am - 2:31 pm
EYW
-
MSN
8h 46m
2 stops
American Airlines Logo
5:30 am - 4:30 pm
MSN
-
EYW
10h 00m
2 stops
$431American Airlines
Wed, May 6 - Sun, May 10
American Airlines Logo
11:24 am - 7:54 pm
EYW
-
MSN
9h 30m
2 stops
American Airlines Logo
1:05 pm - 10:36 pm
MSN
-
EYW
8h 31m
2 stops
$433American Airlines
Fri, Apr 17 - Sat, Apr 18
American Airlines Logo
3:58 pm - 11:55 pm
EYW
-
MSN
8h 57m
2 stops
American Airlines Logo
6:00 am - 4:30 pm
MSN
-
EYW
9h 30m
2 stops
$434American Airlines
Fri, May 1 - Mon, May 4
American Airlines Logo
4:20 pm - 11:55 pm
EYW
-
MSN
8h 35m
1 stop
American Airlines Logo
2:18 pm - 10:36 pm
MSN
-
EYW
7h 18m
2 stops
$442American Airlines
Thu, Apr 16 - Fri, Apr 17

American Airlines flights from Key West to Madison

Our best American Airlines deals on Key West to Madison flight tickets
American Airlines
May 6
EYW2:12 pmKey West
8h 02m
1 stop
MSN9:14 pmMadison Truax Field
May 10
MSN6:45 amMadison Truax Field
7h 55m
1 stop
EYW3:40 pmKey West
$306
American Airlines
May 1
EYW2:12 pmKey West
9h 42m
1 stop
MSN10:54 pmMadison Truax Field
May 4
MSN10:19 amMadison Truax Field
6h 57m
1 stop
EYW6:16 pmKey West
$309
American Airlines
May 6
EYW6:45 amKey West
8h 46m
2 stops
MSN2:31 pmMadison Truax Field
May 10
MSN6:45 amMadison Truax Field
7h 55m
1 stop
EYW3:40 pmKey West
$311

United Airlines flights from Key West to Madison

Our best United Airlines deals on Key West to Madison flight tickets
United Airlines
Apr 22
EYW2:35 pmKey West
6h 58m
1 stop
MSN8:33 pmMadison Truax Field
Apr 25
MSN5:00 amMadison Truax Field
5h 24m
1 stop
EYW11:24 amKey West
$475
United Airlines
Apr 22
EYW2:35 pmKey West
6h 58m
1 stop
MSN8:33 pmMadison Truax Field
Apr 25
MSN6:30 amMadison Truax Field
10h 09m
2 stops
EYW5:39 pmKey West
$480
United Airlines
Apr 22
EYW4:38 pmKey West
18h 33m
2 stops
MSN10:11 amMadison Truax Field
Apr 25
MSN6:30 amMadison Truax Field
7h 21m
1 stop
EYW2:51 pmKey West
$495

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 March 10, 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

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 5/6

2:12 pm-9:14 pm

1 stop8h 02m

Madison Truax Field

Sun 5/10

6:45 am-3:40 pm

1 stop7h 55m

$306

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 5/1

2:12 pm-10:54 pm

1 stop9h 42m

Madison Truax Field

Mon 5/4

10:19 am-6:16 pm

1 stop6h 57m

$309

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 5/6

6:45 am-2:31 pm

2 stops8h 46m

Madison Truax Field

Sun 5/10

6:45 am-3:40 pm

1 stop7h 55m

$311

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 5/1

2:12 pm-10:54 pm

1 stop9h 42m

Madison Truax Field

Mon 5/4

11:44 am-10:36 pm

2 stops9h 52m

$314

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 4/21

1:01 pm-9:08 am

1 stop21h 07m

Madison Truax Field

Wed 4/22

6:36 pm-9:06 am

1 stop13h 30m

$352
Quickest round-trip

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 4/17

6:46 pm-11:38 pm

1 stop5h 52m

Madison Truax Field

Sat 4/18

9:18 am-6:16 pm

1 stop7h 58m

$359

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 5/6

6:45 am-2:31 pm

2 stops8h 46m

Madison Truax Field

Sun 5/10

5:30 am-4:30 pm

2 stops10h 00m

$431

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 4/17

11:24 am-7:54 pm

2 stops9h 30m

Madison Truax Field

Sat 4/18

1:05 pm-10:36 pm

2 stops8h 31m

$433

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 5/1

3:58 pm-11:55 pm

2 stops8h 57m

Madison Truax Field

Mon 5/4

6:00 am-4:30 pm

2 stops9h 30m

$434

Key WestMadison

EYW - MSN

EYWMSN

Key West

Thu 4/16

4:20 pm-11:55 pm

1 stop8h 35m

Madison Truax Field

Fri 4/17

2:18 pm-10:36 pm

2 stops7h 18m

$442

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 13% 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

11h 03m

Direct flights

None
The fastest flight from Key West to Madison takes 11h 03m
There are no direct flights from Key West to Madison. There are no popular flight routes from Key West to Madison.
Search flight deals

  • 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 11h 03m.

  • 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
Fitchburg
Middleton
Sun Prairie
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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