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$105+ Cheap flights from Key West to Madison (EYW - 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — MSN
Jan 19 — Jan 261
Sun 1/19
Sun 1/26
1 adult, Economy
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Cheap flight deals from Key West to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Madison (MSN). 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 January 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$404
(United Airlines)

One-way from

$105
(American Airlines)

Popular in

March

Cheapest in

February

Average price

$328
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 Key West to Madison Truax Field
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One-way flight from Key West to Madison Truax Field
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High demand for flights, 13% potential price rise
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Best time to find cheap flights, 9% potential price drop
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Average for round-trip flights in January 2025
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Find flight deals from Key West to Madison

Cheapest flights from Key West to Madison
Explore the most affordable flight options available from Key West to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 14, 2025.

This United Airlines deal was found by Cheapflights users on 1/13. 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.
Tue 1/2810:55 amEYW - MSN
2 stops13h 48mUnited Airlines
Sat 2/13:53 pmMSN - EYW
2 stops26h 02mUnited Airlines
Deal found 1/13$404
This American Airlines deal was found by Cheapflights users on 1/13. 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 1/281:06 pmEYW - MSN
1 stop5h 43mAmerican Airlines
Sat 2/15:45 amMSN - EYW
2 stops12h 22mAmerican Airlines
Deal found 1/13$540

Find flights from Key West to Madison within your budget

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, Cheapflights users made 2,558,603 searches. Data last updated January 14, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 1/28

10:55 am-11:43 pm

2 stops13h 48m

Madison Truax Field

Sat 2/1

3:53 pm-6:55 pm

2 stops26h 02m

$404

Key WestMadison

EYW - MSN

EYWMSN

Key West

Tue 1/28

1:06 pm-5:49 pm

1 stop5h 43m

Madison Truax Field

Sat 2/1

5:45 am-7:07 pm

2 stops12h 22m

$540

Key WestMadison

EYW - MSN

EYWMSN

Key West

Wed 2/5

8:09 am-3:46 pm

1 stop8h 37m

$105

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 1/31

7:40 pm-11:54 am

2 stops17h 14m

$222

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 1/31

6:16 pm-10:49 pm

1 stop5h 33m

$259

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 1/31

10:23 am-9:08 am

3 stops23h 45m

$323

Key WestMadison

EYW - MSN

EYWMSN

Key West

Fri 2/14

11:20 am-8:30 pm

3 stops34h 10m

$850

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Compare providers for flights from Key West to Madison

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

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

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

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 January 14, 2025.
Alaska Airlines
8.0
Very good
9,672 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 10

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
9,672 reviews
Alaska Airlines
8.0
Very good
9,672 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 10

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
8,508 reviews
Alaska Airlines
8.0
Very good
9,672 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 10

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
8,961 reviews
Alaska Airlines
8.0
Very good
9,672 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 10

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
9,672 reviews

Food

7.1

Comfort

7.9

Entertainment

7.1

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 10

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

Find useful and relevant information for your journey from Key West to Madison. 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 Key West to Madison round-trip?

    Cheapflights users have booked flights from Key West to Madison round-trip from $404. Another airline that can offer you cheap pricing is American Airlines. You may be able to fly from Key West to Madison for 2% less than the average price by searching for these airlines.

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

    One-way options have recently been found by users for as low as $105 on American Airlines. Other airlines that offer cheap prices include United Airlines from $222 and Delta from $259 one-way.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Key West 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 Key West to Madison?

    Currently, January is the cheapest month in which you can book a flight from Key West to Madison (average of $338). Flying from Key West 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 Key West?

Book flights to Key West if you plan to visit one of these locations
Portage
Middleton
Baraboo

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Alternative routes for Key West to Madison

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Top airline flying from Key West to Madison

Discover the top airline that operate flights from Key West 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 January 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$398FlexibilityNo cancel feeOn-time71%
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