HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$150+ 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 3/19. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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.

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

Cheap flight deals from Madison to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$244
(American Airlines)

One-way from

$150
(American Airlines)

Popular in

May

Cheapest in

August

Average price

$448
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. 8% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/20. 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 4/1411:07 amMSN - EYW
1 stop6h 48mAmerican Airlines
Wed 4/231:39 pmEYW - MSN
2 stops8h 22mAmerican Airlines
Deal found 2/20$244
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 3/72:19 pmMSN - EYW
1 stop5h 44mUnited Airlines
Tue 3/113:59 pmEYW - MSN
1 stop7h 31mUnited Airlines
Deal found 2/20$320
This Delta deal was found by Cheapflights users on 2/20. 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 3/410:58 amMSN - EYW
2 stops8h 13mDelta
Tue 3/117:00 amEYW - MSN
2 stops10h 35mDelta
Deal found 2/20$463

Find flights from Madison to Key West within your budget

Customize your flight search to find flights from Madison to Key West 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 February 20, 2025.

Fly from

Madison

Fly to

Key West

Route

Depart

Return

Price

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Mon 4/14

11:07 am-6:55 pm

1 stop6h 48m

Key West

Wed 4/23

1:39 pm-9:01 pm

2 stops8h 22m

$244

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 3/7

2:19 pm-9:03 pm

1 stop5h 44m

Key West

Tue 3/11

3:59 pm-10:30 pm

1 stop7h 31m

$320

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Tue 3/4

10:58 am-8:11 pm

2 stops8h 13m

Key West

Tue 3/11

7:00 am-4:35 pm

2 stops10h 35m

$463

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 3/19

6:00 am-6:59 pm

2 stops11h 59m

$150

MadisonKey West

MSN - EYW

MSNEYW

Madison Truax Field

Thu 3/27

6:15 am-3:03 pm

1 stop7h 48m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust 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.

Travel insights for flights from Madison to Key West

Get recent, data-driven insights about flights from Madison to Key West including ideal travel times, pricing trends, and more.

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 February 14, 2025.

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 $510). 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

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

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

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated February 20, 2025.
Read reviews from past customers who have flown Delta, United Airlines and American 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.
Delta
8.0
Very good
8,220 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20

2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Delta
8.0
Very good
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20

2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

United Airlines
7.4
Good
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20

2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,220 reviews

Comfort

8.0

Overall

8.0

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Reviews

1 / 20

2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

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?

    According to our current data, American Airlines ($244), United Airlines ($320), and Delta ($463) offers the cheapest pricing from Madison to Key West. You may be able to fly from Madison to Key West for 43% 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 $510). 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

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.
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
Minneapolis to Orlando flights
O'Hare Intl to Orlando flights
Minneapolis to Fort Myers flights
Minneapolis to Tampa flights
Minneapolis to Fort Lauderdale flights
Minneapolis to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to West Palm Beach flights
Milwaukee to Orlando flights
Minneapolis to Sarasota flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Key West flights
O'Hare Intl to Pensacola flights
Milwaukee to Fort Myers flights
Minneapolis to West Palm Beach flights
O'Hare Intl to Panama City flights
Milwaukee to Fort Lauderdale flights
Milwaukee to Miami flights
Appleton to Orlando flights
Minneapolis to Valparaiso flights
Minneapolis to St Petersburg flights
Milwaukee to Tampa flights
Minneapolis to Pensacola flights
Minneapolis to Jacksonville flights
Appleton to Fort Myers flights
Appleton to Orlando Sanford Intl flights
Appleton to Tampa flights
Minneapolis to Key West flights
Madison to Fort Myers flights
Minneapolis to Panama City flights
Appleton to St Petersburg flights
Madison to Orlando flights
O'Hare Intl to Valparaiso flights
Appleton to Sarasota flights
Milwaukee to Sarasota flights
O'Hare Intl to Daytona Beach flights
Appleton to Fort Lauderdale flights
Madison to Miami flights
Green Bay to Tampa flights
Appleton to Miami flights
Madison to Fort Lauderdale flights
Minneapolis to Daytona Beach flights
Milwaukee to Pensacola flights
Milwaukee to West Palm Beach flights
Madison to Tampa flights
Appleton to Key West flights

Top 3 airlines flying from Madison to Key West

Discover the top 3 airlines that operate flights from Madison to Key West. 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$238Average$597FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$249Average$406FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$288Average$498FlexibilityNo cancel feeOn-time69%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.