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$276+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — EYW
Jul 30 — Aug 61
From?
To?
Tue 7/30
Tue 8/6
1 adult, Economy
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The best prices from Madison Truax Field to Key West are usually found in December or August, booked 23 days in advance, depart on a Wednesday or Sunday and return on a Tuesday

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 July 25, 2024.

Popular in

March

Cheapest in

December

Round-trip from

$278
(American Airlines)

One-way from

$276
(American Airlines)
High demand for flights, 39% potential price rise
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Best time to find cheap flights, 35% potential price drop
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From Madison Truax Field to Key West
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One-way flight from Madison Truax Field to Key West
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What is the cheapest day to fly round-trip from Madison to Key West?

Flying to your destination on a Wednesday 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 24 days before your planned departure. Booking around this time can save you about 130% 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 $543.

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 December, with the cheapest ticket starting at $245.

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 18% on your trip compared to booking a flight in the morning.

Cheap Madison to Key West flights in July & August 2024

Find cheap flight options from Madison to Key West specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on July 25, 2024.
These are some of the best deals we've found on flights to Key West in 2024 at this time. If these deals don't appeal to you, be sure to come back soon for more options.
This Delta deal was found by Cheapflights users on 7/25. 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 8/241:53 pmMSN - EYW
1 stop4h 45mDelta
Fri 8/306:03 pmEYW - MSN
1 stop6h 00mDelta
Deal found 7/25$293
This Delta deal was found by Cheapflights users on 7/25. 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 8/246:03 amMSN - EYW
2 stops10h 05mDelta
Fri 8/306:03 pmEYW - MSN
1 stop6h 00mDelta
Deal found 7/25$298
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Fri 8/95:30 amMSN - EYW
1 stop7h 55mAmerican Airlines
Tue 8/132:47 pmEYW - MSN
1 stop8h 28mAmerican Airlines
Deal found 7/25$328
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Fri 8/95:30 amMSN - EYW
1 stop7h 55mAmerican Airlines
Tue 8/132:47 pmEYW - MSN
2 stops9h 43mAmerican Airlines
Deal found 7/25$333
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Sat 8/246:30 amMSN - EYW
2 stops31h 15mUnited Airlines
Fri 8/303:30 pmEYW - MSN
2 stops30h 50mUnited Airlines
Deal found 7/25$411
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Sat 8/245:30 amMSN - EYW
2 stops9h 56mAmerican Airlines
Fri 8/3011:30 amEYW - MSN
2 stops10h 30mAmerican Airlines
Deal found 7/25$425
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Fri 8/95:30 amMSN - EYW
2 stops12h 28mAmerican Airlines
Tue 8/132:47 pmEYW - MSN
2 stops9h 43mAmerican Airlines
Deal found 7/25$469
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Sat 8/246:30 amMSN - EYW
3 stops25h 45mUnited Airlines
Fri 8/303:30 pmEYW - MSN
2 stops30h 50mUnited Airlines
Deal found 7/25$491
This United Airlines deal was found by Cheapflights users on 7/25. 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 8/91:15 pmMSN - EYW
2 stops20h 20mUnited Airlines
Tue 8/133:20 pmEYW - MSN
3 stops32h 09mUnited Airlines
Deal found 7/25$724

Madison to Key West 2024 flight deals

Discover exclusive flight deals for travel between Madison and Key West in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
These are some of the best deals we've found on flights to Key West in 2024 at this time. If these deals don't appeal to you, be sure to come back soon for more options.
This Delta deal was found by Cheapflights users on 7/25. 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 8/241:53 pmMSN - EYW
1 stop4h 45mDelta
Fri 8/306:03 pmEYW - MSN
1 stop6h 00mDelta
Deal found 7/25$293
This Delta deal was found by Cheapflights users on 7/25. 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 8/246:03 amMSN - EYW
2 stops10h 05mDelta
Fri 8/306:03 pmEYW - MSN
1 stop6h 00mDelta
Deal found 7/25$298
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Fri 8/95:30 amMSN - EYW
1 stop7h 55mAmerican Airlines
Tue 8/132:47 pmEYW - MSN
1 stop8h 28mAmerican Airlines
Deal found 7/25$328
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Fri 8/95:30 amMSN - EYW
1 stop7h 55mAmerican Airlines
Tue 8/132:47 pmEYW - MSN
2 stops9h 43mAmerican Airlines
Deal found 7/25$333
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Sat 8/246:30 amMSN - EYW
2 stops31h 15mUnited Airlines
Fri 8/303:30 pmEYW - MSN
2 stops30h 50mUnited Airlines
Deal found 7/25$411
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Fri 12/610:45 amMSN - EYW
1 stop8h 24mAmerican Airlines
Fri 12/135:23 pmEYW - MSN
1 stop5h 01mAmerican Airlines
Deal found 7/25$415
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Fri 12/610:45 amMSN - EYW
1 stop8h 24mAmerican Airlines
Fri 12/1312:09 pmEYW - MSN
2 stops10h 15mAmerican Airlines
Deal found 7/25$420
This American Airlines deal was found by Cheapflights users on 7/25. 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.
Sat 8/245:30 amMSN - EYW
2 stops9h 56mAmerican Airlines
Fri 8/3011:30 amEYW - MSN
2 stops10h 30mAmerican Airlines
Deal found 7/25$425
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Sat 11/306:30 amMSN - EYW
1 stop7h 31mUnited Airlines
Sat 12/74:05 pmEYW - MSN
1 stop5h 44mUnited Airlines
Deal found 7/25$443

One-way flights to Key West from Madison

Search for one-way flight options from Madison to Key West. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,752,877 searches. Data last updated July 25, 2024.
Take a look at some of the best available options we've come across on one-way flights from Madison to Key West. Users in need of a round-trip flight from Madison to Key West instead should update the search form at the top of page.
This American Airlines deal was found by Cheapflights users on 7/23. 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.
Fri 11/110:35 amMSN - EYW
1 stop5h 18mAmerican Airlines
Deal found 7/23$276
This American Airlines deal was found by Cheapflights users on 7/23. 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.
Fri 11/16:38 amMSN - EYW
2 stops9h 15mAmerican Airlines
Deal found 7/23$281
This Delta deal was found by Cheapflights users on 7/24. 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.
Mon 12/3011:24 amMSN - EYW
1 stop7h 07mDelta
Deal found 7/24$379
This Delta deal was found by Cheapflights users on 7/24. 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.
Mon 12/307:00 amMSN - EYW
2 stops11h 31mDelta
Deal found 7/24$384
This United deal was found by Cheapflights users on 7/24. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/306:20 amMSN - EYW
3 stops24h 55mUnited Airlines
Deal found 7/24$400

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 2,752,877 searches. Data last updated July 25, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$278 - $450

Route

Depart

Return

Price

Madison Truax FieldKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 11/1

1 stop5h 18m

Key West

Fri 11/8

1 stop5h 49m

$278

Madison Truax FieldKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 11/1

2 stops9h 15m

Key West

Fri 11/8

1 stop5h 49m

$283

Madison Truax FieldKey West

MSN - EYW

MSNEYW

Madison Truax Field

Fri 11/1

2 stops9h 15m

Key West

Fri 11/8

2 stops6h 57m

$288

Madison Truax FieldKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 8/24

1 stop4h 45m

Key West

Fri 8/30

1 stop6h 00m

$303

Madison Truax FieldKey West

MSN - EYW

MSNEYW

Madison Truax Field

Sat 8/24

2 stops10h 05m

Key West

Fri 8/30

1 stop6h 00m

$308

Madison Truax FieldKey West

MSN - EYW

MSNEYW

Madison Truax Field

Mon 11/11

2 stops8h 05m

Key West

Sat 11/16

2 stops8h 42m

$313

Madison Truax FieldKey West

MSN - EYW

MSNEYW

Madison Truax Field

Mon 11/11

1 stop8h 26m

Key West

Sat 11/16

1 stop5h 02m

$328

Madison Truax FieldKey West

MSN - EYW

MSNEYW

Madison Truax Field

Wed 10/2

3 stops34h 50m

Key West

Mon 10/7

2 stops30h 50m

$416

Madison Truax FieldKey West

MSN - EYW

MSNEYW

Madison Truax Field

Mon 12/9

1 stop7h 01m

Key West

Fri 12/13

2 stops28h 44m

$450

Flights are sorted by cheapest first

Deals found on 7/23

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 July 25, 2024.
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 23 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

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

Use this chart to determine the cheapest time to fly round-trip from Madison to Key West. Price data was last updated on July 21, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Madison to Key West flight should consider departing on Wednesday mornings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

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.

Temperature and rainfall in Key West by month

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

EYW

Temperature

69.8 - 84.2 °F

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 July 25, 2024.
Read reviews from past customers who have flown American Airlines, United Airlines and Delta 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
9,630 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

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
9,630 reviews
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

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
10,000 reviews
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

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
7.3
Good
10,000 reviews
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Food

7.4

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

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.

  • Can I find flights from Madison to Key West for under $300 on Cheapflights?

    Yes, there are multiple flights from Madison to Key West for under $300. The cheapest flight booked recently is on American Airlines for just $278, but on average you can expect to pay $401.

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

    According to our current data, American Airlines ($278), Delta ($303), and United Airlines ($416) offers the cheapest pricing from Madison to Key West. You may be able to fly from Madison to Key West for 42% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Madison to Key West one-way?

    The cheapest airlines for a one-way flight from Madison to Key West are American Airlines ($276), Delta ($379), and United Airlines ($400).

  • What does MSN to EYW mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Madison Truax Field Airport to Key West Airport flight would often be abbreviated as a MSN to EYW flight.

  • Can I find deals for flights from Madison to Key West that include extra baggage allowance?

    The amount of baggage you can bring on your Madison to Key West flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Madison to Key West with specific airlines?

    Yes, Cheapflights allows you to browse and filter Madison to Key West flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by 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.

  • Can I find deals for flights from Madison to Key West that allow pets onboard?

    Many airlines flying from Madison to Key West offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Madison to Key West?

    Yes, you can often find last-minute deals on Madison to Key West flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Madison to Key West flight deals updated?

    The Madison to Key West flight deals you see on this page were last updated on 7/25.

  • 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 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 $344). Flying from Madison to Key West in March is currently the most expensive (average of $499). 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

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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 2,752,877 searches. Data last updated July 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$243Average$438FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$245Average$462FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$319Average$558FlexibilityNo cancel feeOn-time69%
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Search flights from Madison to Key West by cabin class

Find flights from Madison to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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