What are the cheapest airlines flying from Madison to Key West round-trip?

According to our current data, American Airlines ($214), Delta ($319), and United Airlines ($451) offers the cheapest pricing from Madison to Key West. You may be able to fly from Madison to Key West for 51% less than the average price by searching for these airlines.

What is the cheapest day to fly from Madison to Key West?

Travelers seeking maximum savings on their Madison to Key West flight should consider departing on Saturday at noon when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the most popular airlines that fly from Madison to Key West?

The most popular airlines flying from Madison to Key West are American Airlines, Delta and United Airlines. Something to consider prior to booking your flight.

What is the cheapest day to fly round-trip from Madison to Key West?

Flying to your destination on a Friday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Key West. Check prices with Cheapflights to find a great deal for your trip.

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

To save on the cost of your flight from Madison to Key West, book at least 61 days before your planned departure. Booking around this time can save you about 56% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $270 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $376.

What is the cheapest month to fly from Madison to Key West?

Flights from Madison to Key West lean towards being more expensive in March. Prices are generally better when you fly from Madison to Key West in August, with the cheapest ticket starting at $208.

What is the cheapest time of day to fly from MSN to EYW?

A simple way to save on the total cost of your ticket is to fly from Madison to Key West at noon. If you’re flexible enough to do this you can expect to save up to 30% on your trip compared to booking a flight in the morning.

Most accurate provider : When it comes to deals on Madison-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Key West flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Madison-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Can I find deals for flights from Madison to Key West that include hotel bookings?

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

How can I find direct flights from Madison to Key West?

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

Can I find deals for business class flights from Madison to Key West?

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

$105+ Flights from Madison to Key West

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Find cheap flights from Madison to Key West with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Madison Truax Field to Key West are usually found in August or April, booked 77 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Cheap flight deals from Madison to Key West

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$214 (American Airlines)
One-way from	$105 (American Airlines)
Popular in	March
Cheapest in	August
Average price	$683

Provider with most accurate pricing for Madison Truax Field-Key West flight deals.

Search Deals

Provider most trusted by Cheapflights users for Madison Truax Field-Key West flights.

Search Deals

From Madison Truax Field to Key West

Search Deals

One-way flight from Madison Truax Field to Key West

Search Deals

Highest demand for flights based on searches. 12% potential increase in price ($60 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 5% potential price decrease ($22 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in March 2025

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Find flight deals from Madison to Key West

Cheapest flights from Madison to Key West
Explore the most affordable flight options available from Madison to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

Fri 7/47:20 amMSN - EYW

1 stop5h 43mAmerican Airlines

Tue 7/81:25 pmEYW - MSN

2 stops11h 37mAmerican Airlines

Deal found 3/24

$214

Sun 4/275:45 amMSN - EYW

1 stop4h 45mDelta

Fri 5/21:35 pmEYW - MSN

1 stop9h 22mDelta

Deal found 3/25

$349

Mon 4/146:30 amMSN - EYW

1 stop7h 34mUnited Airlines

Tue 4/228:45 amEYW - MSN

2 stops28h 32mUnited Airlines

Deal found 3/23

$381

Best flights from Madison to Key West
Discover carefully curated flight deals from Madison to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 26, 2025.

Fri 7/46:25 amMSN - EYW

1 stop8h 42mAmerican Airlines

Tue 7/81:25 pmEYW - MSN

2 stops11h 37mAmerican Airlines

Deal found 3/25

$214

Mon 4/285:45 amMSN - EYW

1 stop4h 45mDelta

Tue 5/61:35 pmEYW - MSN

1 stop9h 22mDelta

Deal found 3/25

$319

Fri 7/46:30 amMSN - EYW

3 stops24h 30mUnited Airlines

Tue 7/88:45 amEYW - MSN

2 stops27h 58mUnited Airlines

Deal found 3/25

$451

Last-minute flights from Madison to Key West
Discover last-minute flight deals from Madison to Key West. Data last updated March 26, 2025 and is based on user searches.

Tue 4/16:15 amMSN - EYW

1 stop9h 21mAmerican Airlines

Wed 4/93:56 pmEYW - MSN

2 stops8h 48mAmerican Airlines

Deal found 3/25

$340

Tue 4/15:45 amMSN - EYW

1 stop4h 50mDelta

Wed 4/97:00 amEYW - MSN

1 stop4h 44mDelta

Deal found 3/25

$395

Wed 4/235:50 amMSN - EYW

1 stop8h 28mAmerican Airlines

Wed 4/304:56 pmEYW - MSN

1 stop6h 48mAmerican Airlines

Deal found 3/25

$264

Sun 4/276:30 amMSN - EYW

2 stops10h 35mUnited Airlines

Fri 5/28:45 amEYW - MSN

2 stops30h 35mUnited Airlines

Deal found 3/25

$501

Mon 4/285:45 amMSN - EYW

1 stop4h 45mDelta

Tue 5/61:35 pmEYW - MSN

1 stop9h 22mDelta

Deal found 3/25

$319

One-way flights from Madison to Key West
Search for one-way flight options from Madison to Key West. Find affordable one-way fares based on user searches. Data last updated March 26, 2025.

Tue 4/225:35 amMSN - EYW

1 stop7h 23mAmerican Airlines

Deal found 3/25

$105

Sat 5/1010:45 amMSN - EYW

1 stop20h 18mMultiple Airlines

Deal found 3/25

$282

Tue 6/101:27 pmMSN - EYW

3 stops23h 14mAlaska Airlines

Deal found 3/25

$800

Cheapflights Fare Finder

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

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 7/4

6:25 am-4:07 pm

1 stop8h 42m

Key West

Tue 7/8

1:25 pm-12:02 am

2 stops11h 37m

$214

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Mon 4/28

5:45 am-11:30 am

1 stop4h 45m

Key West

Tue 5/6

1:35 pm-9:57 pm

1 stop9h 22m

$319

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 7/4

6:30 am-8:00 am

3 stops24h 30m

Key West

Tue 7/8

8:45 am-11:43 am

2 stops27h 58m

$451

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 4/22

5:35 am-1:58 pm

1 stop7h 23m

$105

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 5/10

10:45 am-8:03 am

1 stop20h 18m

$282

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 6/10

1:27 pm-1:41 pm

3 stops23h 14m

$800

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Compare providers for flights from Madison to Key West

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Key West in March.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Madison-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Key West flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Madison-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Madison to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Madison 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 Madison to Key West

How far ahead should I book a flight from Madison to Key West?

The price you pay for your flight from Madison to Key West may vary depending on when you book. For the best chance of a lower fare, look to book 75 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Madison to Key West?

Currently, August is the cheapest month in which you can book a flight from Madison to Key West (average of $328). Flying from Madison to Key West in March is currently the most expensive (average of $495). 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.

Rainfall in Key West by month

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

Reviews of airlines servicing Key West

Read reviews from past customers who have flown Alaska Airlines, Delta and United Airlines from Madison to Key West. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

9,789 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines

8.0

Very good

9,789 reviews

Alaska Airlines

8.0

Very good

9,789 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta

8.0

Very good

7,891 reviews

Alaska Airlines

8.0

Very good

9,789 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines

7.4

Good

8,608 reviews

Alaska Airlines

8.0

Very good

9,789 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines

7.2

Good

10,000 reviews

Alaska Airlines

8.0

Very good

9,789 reviews

Reviews

1 / 20

10.0

Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Related info for your journey

What are the cheapest airlines flying from Madison to Key West round-trip?
According to our current data, American Airlines ($214), Delta ($319), and United Airlines ($451) offers the cheapest pricing from Madison to Key West. You may be able to fly from Madison to Key West for 51% less than the average price by searching for these airlines.
Can I find deals for flights from Madison to Key West that include hotel bookings?
Yes. In addition to deals on Madison to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Madison to Key West?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Key West.
Can I find deals for business class flights from Madison to Key West?
Yes. Cheapflights offers flight deals from Madison to Key West 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 Madison to Key West?
Currently, August is the cheapest month in which you can book a flight from Madison to Key West (average of $328). Flying from Madison to Key West in March is currently the most expensive (average of $495). 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

Browse thousands of different options on Cheapflights for your next trip

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Other flights to Key West

Top 3 airlines flying from Madison to Key West

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$238	Average$572	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$240	Average$407	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$288	Average$498	FlexibilityNo cancel fee	On-time69%

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$105+ Cheap flights from Madison to Key West (MSN - EYW)

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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Madison to Key West with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Madison Truax Field to Key West are usually found in August or April, booked 77 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

Cheap flight deals from Madison to Key West

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Madison to Key West

Cheapest flights from Madison to Key WestExplore the most affordable flight options available from Madison to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

Explore the most affordable flight options available from Madison to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Madison to Key West that are best for you.

Compare providers for flights from Madison to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Key West in March.

Best time to book a flight from Madison to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Madison with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Madison to Key West

How far ahead should I book a flight from Madison to Key West?

Use this chart to determine the optimal time to book a round-trip flight from Madison to Key West. Price data was last updated on March 21, 2025.

What is the cheapest month to book a flight from Madison to Key West?

Rainfall in Key West by month

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

Temperature in Key West by month

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

Reviews of airlines servicing Key West

Read reviews from past customers who have flown Alaska Airlines, Delta and United Airlines from Madison to Key West. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

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

What are the cheapest airlines flying from Madison to Key West round-trip?

Can I find deals for flights from Madison to Key West that include hotel bookings?

How can I find direct flights from Madison to Key West?

Can I find deals for business class flights from Madison to Key West?

What is the cheapest month to book a flight from Madison to Key West?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Key West

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Madison to Key West

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Cheapest flights from Madison to Key West
Explore the most affordable flight options available from Madison to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 26, 2025.