Cheap flights from MSN to EYW (Dane County Regional to Key West Intl.)

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Cheap Flights from MSN to EYW starting at $339 One Way, $427 Round Trip

Prices starting at $427 for return flights and $339 for one-way flights to Key West Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 1 - Sat, May 8
MSN
Madison
EYW
Key West
$427 Roundtrip, found 5 days ago
$427
Roundtrip
found 5 days ago
Select United flight, departing Sat, May 1 from Madison to Key West, returning Sat, May 8, priced at $427 found 5 days ago
Sat, May 1 - Sat, May 8
MSN
Madison
EYW
Key West
$471 Roundtrip, found 5 days ago
$471
Roundtrip
found 5 days ago
Select United flight, departing Sat, May 1 from Madison to Key West, returning Sat, May 8, priced at $471 found 5 days ago
Thu, Apr 15 - Wed, Apr 21
MSN
Madison
EYW
Key West
$483 Roundtrip, found 5 days ago
$483
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Apr 15 from Madison to Key West, returning Wed, Apr 21, priced at $483 found 5 days ago
Thu, Apr 15 - Wed, Apr 21
MSN
Madison
EYW
Key West
$495 Roundtrip, found 5 days ago
$495
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Apr 15 from Madison to Key West, returning Wed, Apr 21, priced at $495 found 5 days ago
Tue, Mar 2 - Sat, Mar 13
MSN
Madison
EYW
Key West
$500 Roundtrip, found 6 days ago
$500
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Mar 2 from Madison to Key West, returning Sat, Mar 13, priced at $500 found 6 days ago

Hotel Ideas near Key West Intl.

Airport Hotels near Key West Intl.

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
$227 nightly
The price is $256 total per night from Oct 26 to Oct 27
$256 total
Oct 26 - Oct 27
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, free parking, and a snack bar/deli. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Hyatt Vacation Club at Windward Pointe, Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$181 nightly
The price is $204 total per night from Oct 13 to Oct 14
$204 total
Oct 13 - Oct 14
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,549 reviews)
"We loved the property. Rented a golf cart, bikes, and booked a sunset cruise from our hotel. Don't expect beautiful beaches in key West. Though we loved coast guard state Park beach. You can walk from the airport to the hotel it's that close Would definitely come back to this hotel"

Reviewed on Oct 8, 2026

Hampton Inn Key West FL
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$157 nightly
The price is $177 total per night from Oct 27 to Oct 28
$177 total
Oct 27 - Oct 28
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,111 reviews)
"Don’t use this hotel their unethical & have horrible customer service. They refused to be helpful when I was in a terrible situation. Book another hotel"

Reviewed on Oct 7, 2026

DoubleTree Resort by Hilton Grand Key - Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Key West

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$265 nightly
The price is $298 total per night from Oct 12 to Oct 13
$298 total
Oct 12 - Oct 13
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), a free airport shuttle, and room service. Our guests praise the pool and the restaurant ...
Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$168 nightly
The price is $189 total per night from Oct 11 to Oct 12
$189 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Blue Flamingo Resort Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
$195 nightly
The price is $219 total per night from Oct 27 to Oct 28
$219 total
Oct 27 - Oct 28
Total with taxes and fees
Book a stay at this beach hotel in Key West. Enjoy free WiFi, 2 restaurants, and a private beach. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (2,592 reviews)
"Front desk people act like you bother them"

Reviewed on Oct 8, 2026

Beachside Resort & Residences
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Key West Hotels With Airport Transportation

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
$157 nightly
The price is $177 total per night from Oct 27 to Oct 28
$177 total
Oct 27 - Oct 28
Total with taxes and fees
Book a stay at this business-friendly resort in Key West. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,111 reviews)
"Don’t use this hotel their unethical & have horrible customer service. They refused to be helpful when I was in a terrible situation. Book another hotel"

Reviewed on Oct 7, 2026

DoubleTree Resort by Hilton Grand Key - Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
$181 nightly
The price is $204 total per night from Oct 13 to Oct 14
$204 total
Oct 13 - Oct 14
Total with taxes and fees
Book a stay at this business-friendly hotel in Key West. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
9/10 Wonderful! (1,549 reviews)
"We loved the property. Rented a golf cart, bikes, and booked a sunset cruise from our hotel. Don't expect beautiful beaches in key West. Though we loved coast guard state Park beach. You can walk from the airport to the hotel it's that close Would definitely come back to this hotel"

Reviewed on Oct 8, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$171 nightly
The price is $193 total per night from Oct 12 to Oct 13
$193 total
Oct 12 - Oct 13
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free WiFi, in-room massages, and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. ...
9/10 Wonderful! (1,002 reviews)
"We will definitely stay again. Everyone was extremely pleasant and very accommodating. We enjoyed it."

Reviewed on Oct 8, 2026

Eden House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Key West Hotels

Southwinds Motel

Southwinds Motel

2 out of 5
1321 Simonton Street Key West FL
$173 nightly
The price is $195 total per night from Oct 12 to Oct 13
$195 total
Oct 12 - Oct 13
Total with taxes and fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,390 reviews)
"Close to a lot of places I wanted to see. The ice cream and doughnuts bar was awesome! The was really comfortable."

Reviewed on Oct 8, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$122 nightly
The price is $137 total per night from Oct 13 to Oct 14
$137 total
Oct 13 - Oct 14
Total with taxes and fees
Stay at this hostel in Key West. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (1,007 reviews)
"The air conditioning in our room kept kicking off in the middle of the night, so we woke up several times hot. No vending machines, pool is very small. Parking is good and the lot is gravel. Fairy quiet and in a great walking area. We were able to walk about 15 minutes to an electric car ..."

Reviewed on Oct 8, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$190 nightly
The price is $211 total per night from Oct 14 to Oct 15
$211 total
Oct 14 - Oct 15
Total with taxes and fees
Stay at this B&B in Key West. Enjoy parking (surcharge), daily housekeeping, and a garden. Our guests praise the breakfast and the pool in our reviews. Popular ...
9.6/10 Exceptional! (1,111 reviews)
"Fun place to stay!! Very nice staff."

Reviewed on Oct 7, 2026

Duval House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Key West

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$211 nightly
The price is $238 total per night from Oct 11 to Oct 12
$238 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this spa hotel in Key West. Enjoy 3 outdoor pools, a full-service spa, and 2 poolside bars. Our guests praise the pool and the helpful staff in ...
8.6/10 Excellent! (3,629 reviews)
"Extremely small rooms. As a VIP, the upgrade was the same of a regular room. Beach was covered in sargassum and it smelled badly."

Reviewed on Oct 8, 2026

Southernmost Beach Resort and Guesthouses
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
$168 nightly
The price is $189 total per night from Oct 11 to Oct 12
$189 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this family-friendly hotel in Key West. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Blue Flamingo Resort Key West
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$171 nightly
The price is $192 total per night from Oct 15 to Oct 16
$192 total
Oct 15 - Oct 16
Total with taxes and fees
Book a stay at this luxury hotel in Key West. Enjoy free WiFi, 6 outdoor pools, and a marina. Our guests praise the pool and the restaurant in our reviews. Popular ...
Hilton Key West Resort & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

MSN to EYW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
MSN Address & GPS
Address:
4000 International Lane
Madison WI, 53704-3120
United States
IATA Code:
MSN
Longitude:
-89.346497
Latitude:
43.136377
Time Zone:
America/Chicago
EYW Address & GPS
Address:
3491 South Roosevelt Boulevard
Key West FL, 33040-5260
United States
IATA Code:
EYW
Longitude:
-81.75501
Latitude:
24.553574
Time Zone:
America/New_York

Frequently asked questions

Are there non-stop flights from Truax Field to Key West Intl. Airport?
You'll have to change planes if you're wanting to fly from Truax Field to Key West Intl. Airport (EYW). Numerous companies service this route with just one stopover, including American Airlines, Delta Air Lines and United Airlines.
What is the shortest flight from Truax Field to EYW?
Jetting from Truax Field to Key West Intl. Airport will take you at least 5 hours and 3 minutes. Enjoy a tipple and watch a flick or two — it's the ideal opportunity to just relax.
How many hours flight from Dane County Regional Airport (MSN) to EYW?
The flight from MSN to EYW will take about 5 hours and 6 minutes. A few movies, a gripping novel and a decent snooze will help make time zip by.
What airlines have the most flights from Truax Field to Key West Intl. Airport?
You won't find any airlines that fly direct between MSN and Key West Intl. Airport (EYW). Plan ahead and book a multi-stop or one-stop plane ticket.

Map To Nearby Hotels

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.

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