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Cheap flights from Key West to Madison from $326

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Key West to Madison departing on 7/29. 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

Find the cheapest flights from Key West to Madison

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
7:33 pm - 11:42 pm
EYW
-
MSN
5h 09m
1 stop
American Airlines Logo
7:47 am - 4:18 pm
MSN
-
EYW
7h 31m
1 stop
$326American Airlines
Wed, Jul 29 - Fri, Aug 7
American Airlines Logo
7:33 pm - 11:42 pm
EYW
-
MSN
5h 09m
1 stop
American Airlines Logo
7:47 am - 4:18 pm
MSN
-
EYW
7h 31m
1 stop
$386American Airlines
Wed, Jul 29 - Fri, Aug 7
American Airlines Logo
1:01 pm - 11:19 pm
EYW
-
MSN
11h 18m
2 stops
American Airlines Logo
7:47 am - 4:18 pm
MSN
-
EYW
7h 31m
1 stop
$448American Airlines
Wed, Jul 29 - Fri, Aug 7
American Airlines Logo
1:01 pm - 11:19 pm
EYW
-
MSN
11h 18m
2 stops
American Airlines Logo
7:47 am - 4:18 pm
MSN
-
EYW
7h 31m
1 stop
$509American Airlines
Wed, Jul 29 - Fri, Aug 7
American Airlines Logo
1:47 pm - 11:42 pm
EYW
-
MSN
10h 55m
2 stops
American Airlines Logo
5:00 am - 4:18 pm
MSN
-
EYW
10h 18m
2 stops
$702American Airlines
Wed, Jul 29 - Fri, Aug 7
United Airlines Logo
2:20 pm - 1:42 pm
EYW
-
MSN
24h 22m
2 stops
United Airlines Logo
8:10 am - 1:29 pm
MSN
-
EYW
28h 19m
2 stops
$926United Airlines
Tue, Sep 1 - Sat, Sep 5
United Airlines Logo
2:20 pm - 8:53 pm
EYW
-
MSN
31h 33m
2 stops
United Airlines Logo
3:55 pm - 1:29 pm
MSN
-
EYW
20h 34m
2 stops
$936United Airlines
Tue, Sep 1 - Sat, Sep 5
United Airlines Logo
2:20 pm - 6:56 pm
EYW
-
MSN
29h 36m
3 stops
United Airlines Logo
5:48 pm - 1:29 pm
MSN
-
EYW
18h 41m
2 stops
$968United Airlines
Tue, Sep 1 - Sat, Sep 5
United Airlines Logo
2:20 pm - 6:56 pm
EYW
-
MSN
29h 36m
3 stops
United Airlines Logo
3:55 pm - 1:29 pm
MSN
-
EYW
20h 34m
2 stops
$978United Airlines
Tue, Sep 1 - Sat, Sep 5
United Airlines Logo
2:20 pm - 8:15 pm
EYW
-
MSN
6h 55m
1 stop
United Airlines Logo
3:55 pm - 1:29 pm
MSN
-
EYW
20h 34m
2 stops
$991United Airlines
Tue, Sep 1 - Sat, Sep 5

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American Airlines flights from Key West to Madison

Our best American Airlines deals on Key West to Madison flight tickets
American Airlines
Jul 29
EYW7:33 pmKey West
5h 09m
1 stop
MSN11:42 pmMadison Truax Field
Aug 7
MSN7:47 amMadison Truax Field
7h 31m
1 stop
EYW4:18 pmKey West
$326
American Airlines
Jul 29
EYW7:33 pmKey West
5h 09m
1 stop
MSN11:42 pmMadison Truax Field
Aug 7
MSN7:47 amMadison Truax Field
7h 31m
1 stop
EYW4:18 pmKey West
$386
American Airlines
Jul 29
EYW1:01 pmKey West
11h 18m
2 stops
MSN11:19 pmMadison Truax Field
Aug 7
MSN7:47 amMadison Truax Field
7h 31m
1 stop
EYW4:18 pmKey West
$448

United Airlines flights from Key West to Madison

Our best United Airlines deals on Key West to Madison flight tickets
United Airlines
Sep 1
EYW2:20 pmKey West
24h 22m
2 stops
MSN1:42 pmMadison Truax Field
Sep 5
MSN8:10 amMadison Truax Field
28h 19m
2 stops
EYW1:29 pmKey West
$926
United Airlines
Sep 1
EYW2:20 pmKey West
31h 33m
2 stops
MSN8:53 pmMadison Truax Field
Sep 5
MSN3:55 pmMadison Truax Field
20h 34m
2 stops
EYW1:29 pmKey West
$936
United Airlines
Sep 1
EYW2:20 pmKey West
29h 36m
3 stops
MSN6:56 pmMadison Truax Field
Sep 5
MSN5:48 pmMadison Truax Field
18h 41m
2 stops
EYW1:29 pmKey West
$968

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 June 20, 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 7/29

7:33 pm-11:42 pm

1 stop5h 09m

Madison Truax Field

Fri 8/7

7:47 am-4:18 pm

1 stop7h 31m

$326

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 7/29

7:33 pm-11:42 pm

1 stop5h 09m

Madison Truax Field

Fri 8/7

7:47 am-4:18 pm

1 stop7h 31m

$386

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 7/29

1:01 pm-11:19 pm

2 stops11h 18m

Madison Truax Field

Fri 8/7

7:47 am-4:18 pm

1 stop7h 31m

$448

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 7/29

1:01 pm-11:19 pm

2 stops11h 18m

Madison Truax Field

Fri 8/7

7:47 am-4:18 pm

1 stop7h 31m

$509

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 7/29

1:47 pm-11:42 pm

2 stops10h 55m

Madison Truax Field

Fri 8/7

5:00 am-4:18 pm

2 stops10h 18m

$702

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 9/1

2:20 pm-1:42 pm

2 stops24h 22m

Madison Truax Field

Sat 9/5

8:10 am-1:29 pm

2 stops28h 19m

$926

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 9/1

2:20 pm-8:53 pm

2 stops31h 33m

Madison Truax Field

Sat 9/5

3:55 pm-1:29 pm

2 stops20h 34m

$936

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 9/1

2:20 pm-6:56 pm

3 stops29h 36m

Madison Truax Field

Sat 9/5

5:48 pm-1:29 pm

2 stops18h 41m

$968

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 9/1

2:20 pm-6:56 pm

3 stops29h 36m

Madison Truax Field

Sat 9/5

3:55 pm-1:29 pm

2 stops20h 34m

$978

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 9/1

2:20 pm-8:15 pm

1 stop6h 55m

Madison Truax Field

Sat 9/5

3:55 pm-1:29 pm

2 stops20h 34m

$991

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 29% 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

8h 12m

Direct flights

None
The fastest flight from Key West to Madison takes 8h 12m
There are no direct flights from Key West to Madison. There are no popular flight routes from Key West to Madison.
Search flight deals

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 8h 12m.

  • 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
Middleton
Fitchburg
Sun Prairie
Portage
Windsor
Evansville
Cambridge
Oxford

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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