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 $340 One Way, $452 Round Trip

Prices starting at $452 for return flights and $340 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, Oct 31 - Wed, Nov 4
MSN
Madison
EYW
Key West
$452 Roundtrip, found 1 day ago
$452
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 31 from Madison to Key West, returning Wed, Nov 4, priced at $452 found 1 day ago
Thu, Nov 12 - Tue, Nov 17
MSN
Madison
EYW
Key West
$463 Roundtrip, found 1 day ago
$463
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Nov 12 from Madison to Key West, returning Tue, Nov 17, priced at $463 found 1 day ago
Sat, Jan 2 - Wed, Jan 6
MSN
Madison
EYW
Key West
$464 Roundtrip, found 1 day ago
$464
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jan 2 from Madison to Key West, returning Wed, Jan 6, priced at $464 found 1 day ago
Fri, Feb 19 - Fri, Feb 26
MSN
Madison
EYW
Key West
$475 Roundtrip, found 13 hours ago
$475
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Fri, Feb 19 from Madison to Key West, returning Fri, Feb 26, priced at $475 found 13 hours ago
Sat, Oct 31 - Wed, Nov 4
MSN
Madison
EYW
Key West
$478 Roundtrip, found 1 day ago
$478
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 31 from Madison to Key West, returning Wed, Nov 4, priced at $478 found 1 day 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
$207 nightly
The price is $233 total per night from Sep 22 to Sep 23
$233 total
Sep 22 - Sep 23
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
$139 nightly
The price is $156 total per night from Sep 20 to Sep 21
$156 total
Sep 20 - Sep 21
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! (1,489 reviews)
"Cancelled reservation"

Reviewed on Sep 6, 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
$140 nightly
The price is $157 total per night from Sep 15 to Sep 16
$157 total
Sep 15 - Sep 16
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 ...
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
$210 nightly
The price is $237 total per night from Sep 13 to Sep 14
$237 total
Sep 13 - Sep 14
Total with taxes and fees
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Southernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
$188 nightly
The price is $212 total per night from Sep 20 to Sep 21
$212 total
Sep 20 - Sep 21
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. ...
Beachside Resort & Residences
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
$234 nightly
The price is $263 total per night from Sep 20 to Sep 21
$263 total
Sep 20 - Sep 21
Total with taxes and fees
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 ...
Margaritaville Beach House 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.

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
$140 nightly
The price is $157 total per night from Sep 15 to Sep 16
$157 total
Sep 15 - Sep 16
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 ...
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
$139 nightly
The price is $156 total per night from Sep 20 to Sep 21
$156 total
Sep 20 - Sep 21
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! (1,489 reviews)
"Cancelled reservation"

Reviewed on Sep 6, 2026

Hampton Inn Key West FL
Eden House

Eden House

4 out of 5
1015 Fleming St Key West FL
$142 nightly
The price is $160 total per night from Sep 8 to Sep 9
$160 total
Sep 8 - Sep 9
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! (1,004 reviews)
"Loved the key west aesthetic that managed to feel like you were staying in a home vs a hotel. The outdoor pool was very clean and the bar drinks were good. Huge bonus that they let you use the pool and hot tub 24 hours a day. We needed a cell phone delivered and the staff was super helpful and on ..."

Reviewed on Sep 7, 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
$155 nightly
The price is $174 total per night from Sep 8 to Sep 9
$174 total
Sep 8 - Sep 9
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! (1,377 reviews)
"It was small and old fashioned, but it had an old Florida vibe that we loved. Everything we needed was there. The staff were very helpful."

Reviewed on Sep 5, 2026

Southwinds Motel
Seashell Motel

Seashell Motel

1.5 out of 5
718 South Street Key West FL
$87 nightly
The price is $98 total per night from Sep 9 to Sep 10
$98 total
Sep 9 - Sep 10
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! (1,003 reviews)
"Perfect"

Reviewed on Sep 6, 2026

Seashell Motel
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
$119 nightly
The price is $131 total per night from Sep 8 to Sep 9
$131 total
Sep 8 - Sep 9
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 ...
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
$210 nightly
The price is $237 total per night from Sep 13 to Sep 14
$237 total
Sep 13 - Sep 14
Total with taxes and fees
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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
$160 nightly
The price is $180 total per night from Sep 8 to Sep 9
$180 total
Sep 8 - Sep 9
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 ...
8.6/10 Excellent! (2,658 reviews)

Families like: Outdoor pools, playground, miniature golf, game room

Travelers say...
"Beautiful resort, something to do for everybody."

Reviewed on Sep 6, 2026

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
$167 nightly
The price is $188 total per night from Sep 16 to Sep 17
$188 total
Sep 16 - Sep 17
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 ...
9/10 Wonderful! (1,825 reviews)
"We stayed 3 nights at this resort while on a roadtrip. Lovely place in close proximity to Key West. Great restaurant with an amazing waiter Nina! She was so kind and absolutely made our day! Resort staff were friendly and helpful, rooms were very clean. Would overall recommend this resort to anyone ..."

Reviewed on Sep 7, 2026

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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