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 $245 One Way, $341 Round Trip

Prices starting at $341 for return flights and $245 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, Aug 15 - Thu, Aug 20
MSN
Madison
EYW
Key West
$341 Roundtrip, found 13 hours ago
$341
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Aug 15 from Madison to Key West, returning Thu, Aug 20, priced at $341 found 13 hours ago
Thu, Jan 7 - Mon, Jan 11
MSN
Madison
EYW
Key West
$349 Roundtrip, found 2 days ago
$349
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Jan 7 from Madison to Key West, returning Mon, Jan 11, priced at $349 found 2 days ago
Sat, Aug 15 - Thu, Aug 20
MSN
Madison
EYW
Key West
$388 Roundtrip, found 13 hours ago
$388
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Aug 15 from Madison to Key West, returning Thu, Aug 20, priced at $388 found 13 hours ago
Fri, Apr 17 - Fri, Apr 24
MSN
Madison
EYW
Key West
$390 Roundtrip, found 1 day ago
$390
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Apr 17 from Madison to Key West, returning Fri, Apr 24, priced at $390 found 1 day ago
Thu, Jan 7 - Mon, Jan 11
MSN
Madison
EYW
Key West
$391 Roundtrip, found 2 days ago
$391
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Jan 7 from Madison to Key West, returning Mon, Jan 11, priced at $391 found 2 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
The price is $513 total per night from Apr 20 to Apr 21
$513 total
per night
Apr 20 - Apr 21
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 ...
9.4/10 Exceptional! (1,012 reviews)
Room was very spacious and clean!

Reviewed on Mar 30, 2026

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
The price is $343 total per night from May 3 to May 4
$343 total
per night
May 3 - May 4
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! (1,323 reviews)
Great choice for families with kids.

Reviewed on Apr 1, 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
The price is $310 total per night from Apr 19 to Apr 20
$310 total
per night
Apr 19 - Apr 20
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 ...
8.2/10 Very Good! (1,008 reviews)
Yes

Reviewed on Mar 31, 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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
The price is $347 total per night from May 3 to May 4
$347 total
per night
May 3 - May 4
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 ...
8.2/10 Very Good! (2,023 reviews)
We loved our stay here, absolutely loved it!!! Beautiful property, great pool temp and atmosphere, good food and drinks on site and most of the staff was super friendly and over the top accommodating, we will be back!!! Thank you Blue Flamingo

Reviewed on Apr 2, 2026

Blue Flamingo Resort Key West
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
The price is $368 total per night from Apr 28 to Apr 29
$368 total
per night
Apr 28 - Apr 29
Book a stay at this beach hotel in Key West. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the pool and the restaurant ...
8.8/10 Excellent! (1,805 reviews)
Fun, clean and relaxing

Reviewed on Mar 31, 2026

Margaritaville Beach House Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
The price is $367 total per night from Apr 13 to Apr 14
$367 total
per night
Apr 13 - Apr 14
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! (2,106 reviews)
The private beach is not what was expected, but adequate for children to play.

Reviewed on Apr 1, 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
The price is $310 total per night from Apr 19 to Apr 20
$310 total
per night
Apr 19 - Apr 20
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 ...
8.2/10 Very Good! (1,008 reviews)
Yes

Reviewed on Mar 31, 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
The price is $343 total per night from May 3 to May 4
$343 total
per night
May 3 - May 4
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! (1,323 reviews)
Great choice for families with kids.

Reviewed on Apr 1, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
The price is $445 total per night from Apr 5 to Apr 6
$445 total
per night
Apr 5 - Apr 6
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! (1,000 reviews)
It was great overall

Reviewed on Mar 30, 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
The price is $338 total per night from Apr 26 to Apr 27
$338 total
per night
Apr 26 - Apr 27
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! (1,298 reviews)
My husband and I had a great time. The staff was friendly, this is a great location for the price. The Tipsy Rooster was fantastic, the drinks and music were perfect. We will be back

Reviewed on Apr 1, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
The price is $271 total per night from Apr 6 to Apr 7
$271 total
per night
Apr 6 - Apr 7
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)
Very nice location.

Reviewed on Apr 1, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
The price is $302 total per night from Apr 5 to Apr 6
$302 total
per night
Apr 5 - Apr 6
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 ...
9.4/10 Exceptional! (1,016 reviews)
Very accommodating. Very friendly. Excellent facilities, breakfast, pool. Will definitely stay again!!

Reviewed on Apr 1, 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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Book a stay at this beach hotel in Key West. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Popular attractions Duval Street and Smathers Beach ...
8.4/10 Very Good! (999 reviews)

Families like: Outdoor pool, babysitting, close to beach, bicycle rentals

Travelers say...
Great visit

Reviewed on Feb 27, 2026

Get rates
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
The price is $347 total per night from May 3 to May 4
$347 total
per night
May 3 - May 4
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 ...
8.2/10 Very Good! (2,023 reviews)

Families like: Outdoor pools, miniature golf, game room, bicycle rentals

Travelers say...
We loved our stay here, absolutely loved it!!! Beautiful property, great pool temp and atmosphere, good food and drinks on site and most of the staff was super friendly and over the top accommodating, we will be back!!! Thank you Blue Flamingo

Reviewed on Apr 2, 2026

Blue Flamingo Resort Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
The price is $313 total per night from Apr 29 to Apr 30
$313 total
per night
Apr 29 - Apr 30
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 ...
9/10 Wonderful! (1,848 reviews)
Amazing location, the room and property were spotless. Staff were very friendly. Would stay here again!

Reviewed on Apr 2, 2026

Oceans Edge Key West Resort, Hotel & 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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