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Madison

$115+ Cheap flights from Florida Keys to Madison (MSN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Florida Keys to Madison

Keep the following information in mind while searching for Florida Keys to Madison flight deals. Data was last updated May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$294
(Delta)

One-way from

$115
(Frontier)

Popular in

February

Cheapest in

April

Average price

$507
Provider with most accurate pricing for Key West-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Key West-Madison Truax Field flights.
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From Florida Keys to Madison Truax Field
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One-way flight from Florida Keys to Madison Truax Field
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Highest demand for flights based on searches. 8% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Find flight deals from Florida Keys to Madison

Cheapest flights from Florida Keys to Madison
Explore the most affordable flight options available from Florida Keys to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Delta deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/156:27 pmEYW - MSN
1 stop5h 07mDelta
Wed 8/1311:11 amMSN - EYW
1 stop7h 35mDelta
Deal found 4/30$294
This American Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/36:00 amMIA - MSN
1 stop5h 49mAmerican Airlines
Sat 6/76:25 amMSN - MIA
1 stop6h 55mAmerican Airlines
Deal found 4/30$307
This United Airlines deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/164:16 pmMIA - MSN
1 stop7h 07mUnited Airlines
Sat 10/183:00 pmMSN - MIA
1 stop7h 44mUnited Airlines
Deal found 4/29$334
This United Airlines deal was found by Cheapflights users on 4/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/146:45 pmEYW - MSN
2 stops17h 58mUnited Airlines
Wed 8/132:35 pmMSN - EYW
2 stops16h 25mUnited Airlines
Deal found 4/30$364
This American Airlines deal was found by Cheapflights users on 5/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/25:24 pmEYW - MSN
1 stop7h 21mAmerican Airlines
Mon 6/166:25 amMSN - EYW
1 stop6h 23mAmerican Airlines
Deal found 5/1$376
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/108:10 amMIA - MSN
1 stop5h 20mDelta
Sat 5/105:49 pmMSN - MIA
1 stop4h 57mDelta
Deal found 4/29$677

Cheapflights Fare Finder

Customize your flight search to find flights from Florida Keys 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, Cheapflights users made 2,558,603 searches. Data last updated May 1, 2025.
Use the filters below to find and compare flights from Florida Keys to Madison that are best for you.

Fly from

Florida Keys

Fly to

Madison

Route

Depart

Return

Price

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 7/15

6:27 pm-10:34 pm

1 stop5h 07m

Madison Truax Field

Wed 8/13

11:11 am-7:46 pm

1 stop7h 35m

$294

MiamiMadison

MIA - MSN

MIAMSN

Miami

Tue 6/3

6:00 am-10:49 am

1 stop5h 49m

Madison Truax Field

Sat 6/7

6:25 am-2:20 pm

1 stop6h 55m

$307

Key WestMadison

EYW - MSN

EYWMSN

Key West

Mon 7/14

6:45 pm-11:43 am

2 stops17h 58m

Madison Truax Field

Wed 8/13

2:35 pm-8:00 am

2 stops16h 25m

$364

Key WestMadison

EYW - MSN

EYWMSN

Key West

Mon 6/2

5:24 pm-11:45 pm

1 stop7h 21m

Madison Truax Field

Mon 6/16

6:25 am-1:48 pm

1 stop6h 23m

$376

MiamiMadison

MIA - MSN

MIAMSN

Miami

Tue 6/3

6:00 am-1:54 pm

2 stops8h 54m

Madison Truax Field

Sat 6/7

8:20 am-10:45 pm

2 stops13h 25m

$397

MiamiMadison

MIA - MSN

MIAMSN

Miami

Wed 5/14

5:35 am-10:19 am

1 stop5h 44m

Madison Truax Field

Sun 5/18

6:00 am-1:43 pm

1 stop6h 43m

$464

MiamiMadison

MIA - MSN

MIAMSN

Miami

Sun 5/4

6:00 am-7:06 pm

1 stop14h 06m

$115

MiamiMadison

MIA - MSN

MIAMSN

Miami

Thu 7/3

6:30 pm-11:13 am

2 stops17h 43m

$158

MiamiMadison

MIA - MSN

MIAMSN

Miami

Tue 5/27

10:45 pm-10:49 am

2 stops13h 04m

$232

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 6/20

2:07 pm-8:01 am

1 stop18h 54m

$278

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 14 results
1
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Best time to book a flight from Florida Keys to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Florida Keys with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Florida Keys to Madison

Rainfall in Madison by month

Plan your trip to Madison by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Madison ranges from 1.2 - 4.5 inches per month. June is typically the wettest month, when rainfall can reach 4.5 in. January is typically the driest time to visit Madison when rainfall is around 1.2 in.

Temperature in Madison by month

Plan your trip to Madison by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Madison, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madison. Reviews last updated May 1, 2025.
Peruse reviews from past customers who have flown with Breeze Airways, Delta and United Airlines from Florida Keys to Madison to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Overall

8.1

Entertainment

6.6

Crew

8.8

Comfort

8.2

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Overall

8.1

Entertainment

6.6

Crew

8.8

Comfort

8.2

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,934 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Overall

8.1

Entertainment

6.6

Crew

8.8

Comfort

8.2

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,696 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Overall

8.1

Entertainment

6.6

Crew

8.8

Comfort

8.2

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Overall

8.1

Entertainment

6.6

Crew

8.8

Comfort

8.2

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Frontier
6.0
Okay
3,287 reviews
Breeze Airways
8.1
Very good
160 reviews

Boarding

8.3

Overall

8.1

Entertainment

6.6

Crew

8.8

Comfort

8.2

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Madison from Florida Keys?

    For a flight from Florida Keys to Madison, you will be flying into Truax Field. Madison Truax Field (MSN) is just 5.4 mi from the center of the city.

  • What are the cheapest airlines to fly from Florida Keys to Madison one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $115. Delta flights start at $158 while deals on American Airlines start at $232 one-way.

  • Can I find deals for flights from Florida Keys to Madison that include hotel bookings?

    Yes. In addition to deals on Florida Keys to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Florida Keys to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida Keys to Madison.

  • Can I find deals for business class flights from Florida Keys to Madison?

    Yes. Cheapflights offers flight deals from Florida Keys to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Florida Keys to Madison?

    Currently, January is the cheapest month in which you can book a flight from Florida Keys to Madison (average of $338). Flying from Florida Keys to Madison in June is currently the most expensive (average of $423). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Florida Keys?

Book flights to Florida Keys if you plan to visit one of these locations
Portage
Middleton
Baraboo

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Alternative routes for Florida Keys to Madison

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Florida Keys to Madison

Discover the top airline that operate flights from Florida Keys to Madison. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$222Average$398FlexibilityNo cancel feeOn-time71%

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