$249 Cheap flight deals from Madison (JAN) to Key West (EYW)
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This Weekend's Flight Deals from Madison to Key West
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
JAN
Evers Intl.
EYW
Key West Intl.
$295 Roundtrip, found 3 hours ago
$295
Roundtrip
found 3 hours ago
Airfares from $249 One Way, $269 Round Trip from Madison to Key West
Prices starting at $269 for return flights and $249 for one-way flights to Key West were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
JAN
Jackson
EYW
Key West
$269 Roundtrip, found 3 hours ago
$269
Roundtrip
found 3 hours ago
JAN
Jackson
EYW
Key West
$270 Roundtrip, found 3 days ago
$270
Roundtrip
found 3 days ago
JAN
Jackson
EYW
Key West
$274 Roundtrip, found 3 hours ago
$274
Roundtrip
found 3 hours ago
JAN
Jackson
EYW
Key West
$276 Roundtrip, found 3 days ago
$276
Roundtrip
found 3 days ago
JAN
Jackson
EYW
Key West
$277 Roundtrip, found 4 days ago
$277
Roundtrip
found 4 days ago
Key West economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Blue Flamingo Resort Key West
8/10 Very Good! (1,693 reviews)
Feb 22 - Feb 26
4 night stay
Jackson (JAN) to Key West (EYW)
Delta • Non-stop roundtrip • Coach
Price was $1,580, price is now $1,175 per person
$1,175
per person
found 20 hours ago
The Blue Flamingo is an amazing a GEM in Key West, the location and property are simply fabulous, every employee always with a smile, cant mention all but will state Mr. Jose (Ambassador), Leidy, Irina, Skiff, David and all Waiters and Bartenders go over and beyond to make your stay memorable, Lobby and Reception, housekeepers, pool boys, all friendly and helpful. We will be back many times!
Reviewed on Nov 25, 2025
2.5-star property
The Key West Hotel
9.2/10 Wonderful! (505 reviews)
Feb 19 - Feb 22
3 night stay
Jackson (JAN) to Key West (EYW)
Delta • Non-stop • Coach
Key West (EYW) to Jackson (JAN)
American Airlines • Non-stop • Coach
Price was $5,312, price is now $3,722 per person
$3,722
per person
found 22 hours ago
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025
4.0-star property
Southernmost Beach Resort and Guesthouses
8.6/10 Excellent! (2,844 reviews)
Feb 19 - Feb 22
3 night stay
Jackson (JAN) to Key West (EYW)
Delta • Non-stop • Coach
Key West (EYW) to Jackson (JAN)
American Airlines • Non-stop • Coach
Price was $3,222, price is now $2,487 per person
$2,487
per person
found 22 hours ago
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.
Reviewed on Nov 1, 2025
Key West first class flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Ibis Bay Beach Resort
8.2/10 Very Good! (2,000 reviews)
Mar 8 - Mar 12
4 night stay
Jackson (JAN) to Key West (EYW)
Delta • Non-stop • FirstClass
Key West (EYW) to Jackson (JAN)
American Airlines • Non-stop • FirstClass
Price was $2,040, price is now $1,695 per person
$1,695
per person
just found
Room was very small. Window shade wouldn't block the light beaming in my window all night. Not that big of a deal though, i wasn't there for the room. The beach was pretty much rock, so that wasn't great. The facilities offer plenty for you. Bar, restaurant, boat rentals. Tours. My favorite was probably be the hammocks a plenty
Reviewed on Jul 15, 2025
2.5-star property
The Key West Hotel
9.2/10 Wonderful! (505 reviews)
Mar 8 - Mar 12
4 night stay
Jackson (JAN) to Key West (EYW)
Delta • Non-stop • FirstClass
Key West (EYW) to Jackson (JAN)
American Airlines • Non-stop • FirstClass
Price was $3,372, price is now $2,241 per person
$2,241
per person
just found
Gorgeous property right on Duval Street but hidden from the noise and bustle. Convenient to everything you want to do and see. Wonderfully helpful and friendly staff.
Reviewed on Jan 5, 2025
4.0-star property
Oceans Edge Key West Resort, Hotel & Marina
9/10 Wonderful! (1,736 reviews)
Mar 8 - Mar 12
4 night stay
Jackson (JAN) to Key West (EYW)
Delta • Non-stop • FirstClass
Key West (EYW) to Jackson (JAN)
American Airlines • Non-stop • FirstClass
Price was $2,147, price is now $1,706 per person
$1,706
per person
just found
We LOVED the setting and the surrounding area! Absolutely beautiful!
Be aware the hotel IS in the airport landing zone. If you like to watch/hear commercial planes you'll be very happy.
Ask for a room on the top floor only - so you can (1) look over the marina AND (2) so you won't hear people moving chairs on their balcony above you.
The max/min air conditioning is centrally controlled. If you want it colder than 67, you will not be able to. Not sure what the max heat was.
Be extra vigilant about putting a thick towel on the floor to soak up any water that gets past the shower door. It WILL happen! Please do not slip on the wet tile floor!
Be aware that if you want/need a later checkout, they will charge you an additional $50/hour past their usual checkout time of 11am.
Be prepared for onsite meal expenses. They are very good, but they ARE on the pricy side.
Our particular room smelled strongly of smoke on arrival. I'm nearly POSITIVE we asked for a nonsmoking room as we both have underlying medical problems that preclude exposre to smoke. Perhaps call ahead to ENSURE you get a nonsmoking on arrival. The entire hotel was booked so we did not have any other choice.
Reviewed on Dec 28, 2025
More About Flying To Key West from Madison
Route Information for Flights from Madison to Key West
Origin Airport IATA Code | JAN |
|---|---|
Destination Airport IATA Code | EYW |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Madison to Key West
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.