Cheap Flights from Madison to Key West (MSN to EYW)

Discover more affordable routes and cheaper dates from Madison to Key West (MSN to EYW) within a date range.

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US$551

6:08pm - 8:15am
Wed Sep 3rd 2025

13h 7m
Madison (MSN) → Key West (EYW)

1 Stop

Wed Sep 3rd 2025 BREEZE · MX 807 Depart at 6:08pm from Madison (MSN) Fly for 3h 0m Arrive at 10:08pm in Orlando (MCO)

Layover in Orlando for 8h 52m

Thu Sep 4th 2025 BREEZE · MX 159 Depart at 7:00am from Orlando (MCO) Fly for 1h 15m Arrive at 8:15am in Key West (EYW)
US$551

6:25pm - 9:22am
Sat Jun 28th 2025

13h 57m
Madison (MSN) → Key West (EYW)

1 Stop

Sat Jun 28th 2025 BREEZE · MX 131 Depart at 6:25pm from Madison (MSN) Fly for 2h 51m Arrive at 10:16pm in Tampa (TPA)

Layover in Tampa for 9h 59m

Sun Jun 29th 2025 BREEZE · MX 160 Depart at 8:15am from Tampa (TPA) Fly for 1h 7m Arrive at 9:22am in Key West (EYW)
US$551

6:25pm - 9:22am
Sat Jul 5th 2025

13h 57m
Madison (MSN) → Key West (EYW)

1 Stop

Sat Jul 5th 2025 BREEZE · MX 131 Depart at 6:25pm from Madison (MSN) Fly for 2h 51m Arrive at 10:16pm in Tampa (TPA)

Layover in Tampa for 9h 59m

Sun Jul 6th 2025 BREEZE · MX 160 Depart at 8:15am from Tampa (TPA) Fly for 1h 7m Arrive at 9:22am in Key West (EYW)
US$571

6:08pm - 8:15am
Sat Oct 4th 2025

13h 7m
Madison (MSN) → Key West (EYW)

1 Stop

Sat Oct 4th 2025 BREEZE · MX 807 Depart at 6:08pm from Madison (MSN) Fly for 3h 0m Arrive at 10:08pm in Orlando (MCO)

Layover in Orlando for 8h 52m

Sun Oct 5th 2025 BREEZE · MX 159 Depart at 7:00am from Orlando (MCO) Fly for 1h 15m Arrive at 8:15am in Key West (EYW)
US$591

6:25pm - 9:22am
Wed Jul 16th 2025

13h 57m
Madison (MSN) → Key West (EYW)

1 Stop

Wed Jul 16th 2025 BREEZE · MX 131 Depart at 6:25pm from Madison (MSN) Fly for 2h 51m Arrive at 10:16pm in Tampa (TPA)

Layover in Tampa for 9h 59m

Thu Jul 17th 2025 BREEZE · MX 160 Depart at 8:15am from Tampa (TPA) Fly for 1h 7m Arrive at 9:22am in Key West (EYW)
US$591

6:25pm - 9:22am
Wed Jul 30th 2025

13h 57m
Madison (MSN) → Key West (EYW)

1 Stop

Wed Jul 30th 2025 BREEZE · MX 131 Depart at 6:25pm from Madison (MSN) Fly for 2h 51m Arrive at 10:16pm in Tampa (TPA)

Layover in Tampa for 9h 59m

Thu Jul 31st 2025 BREEZE · MX 160 Depart at 8:15am from Tampa (TPA) Fly for 1h 7m Arrive at 9:22am in Key West (EYW)
US$610

6:25pm - 9:22am
Wed Aug 6th 2025

13h 57m
Madison (MSN) → Key West (EYW)

1 Stop

Wed Aug 6th 2025 BREEZE · MX 131 Depart at 6:25pm from Madison (MSN) Fly for 2h 51m Arrive at 10:16pm in Tampa (TPA)

Layover in Tampa for 9h 59m

Thu Aug 7th 2025 BREEZE · MX 160 Depart at 8:15am from Tampa (TPA) Fly for 1h 7m Arrive at 9:22am in Key West (EYW)
US$630

6:25pm - 9:22am
Wed Jul 23rd 2025

13h 57m
Madison (MSN) → Key West (EYW)

1 Stop

Wed Jul 23rd 2025 BREEZE · MX 131 Depart at 6:25pm from Madison (MSN) Fly for 2h 51m Arrive at 10:16pm in Tampa (TPA)

Layover in Tampa for 9h 59m

Thu Jul 24th 2025 BREEZE · MX 160 Depart at 8:15am from Tampa (TPA) Fly for 1h 7m Arrive at 9:22am in Key West (EYW)
US$709

6:25pm - 9:22am
Wed Jun 18th 2025

13h 57m
Madison (MSN) → Key West (EYW)

1 Stop

Wed Jun 18th 2025 BREEZE · MX 131 Depart at 6:25pm from Madison (MSN) Fly for 2h 51m Arrive at 10:16pm in Tampa (TPA)

Layover in Tampa for 9h 59m

Thu Jun 19th 2025 BREEZE · MX 160 Depart at 8:15am from Tampa (TPA) Fly for 1h 7m Arrive at 9:22am in Key West (EYW)
US$1064

3:55pm - 2:00pm
Tue May 27th 2025

21h 5m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 4409 Depart at 3:55pm from Madison (MSN) Fly for 1h 10m Arrive at 5:05pm in Chicago (ORD)

Layover in Chicago for 1h 10m

Tue May 27th 2025 United Airlines · UA 2075 Depart at 6:15pm from Chicago (ORD) Fly for 2h 51m Arrive at 10:06pm in Tampa (TPA)

Layover in Tampa for 14h 39m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1064

3:09pm - 2:00pm
Tue May 27th 2025

21h 51m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 1784 Depart at 3:09pm from Madison (MSN) Fly for 2h 31m Arrive at 4:40pm in Denver (DEN)

Layover in Denver for 1h 25m

Tue May 27th 2025 United Airlines · UA 314 Depart at 6:05pm from Denver (DEN) Fly for 3h 38m Arrive at 11:43pm in Tampa (TPA)

Layover in Tampa for 13h 2m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1064

2:35pm - 2:00pm
Tue May 27th 2025

22h 25m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 3504 Depart at 2:35pm from Madison (MSN) Fly for 1h 10m Arrive at 3:45pm in Chicago (ORD)

Layover in Chicago for 2h 30m

Tue May 27th 2025 United Airlines · UA 2075 Depart at 6:15pm from Chicago (ORD) Fly for 2h 51m Arrive at 10:06pm in Tampa (TPA)

Layover in Tampa for 14h 39m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1064

10:55am - 2:00pm
Tue May 27th 2025

26h 5m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 3634 Depart at 10:55am from Madison (MSN) Fly for 1h 10m Arrive at 12:05pm in Chicago (ORD)

Layover in Chicago for 0h 45m

Tue May 27th 2025 United Airlines · UA 1484 Depart at 12:50pm from Chicago (ORD) Fly for 2h 50m Arrive at 4:40pm in Tampa (TPA)

Layover in Tampa for 20h 5m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1086

3:09pm - 6:05pm
Tue May 27th 2025

25h 56m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 1784 Depart at 3:09pm from Madison (MSN) Fly for 2h 31m Arrive at 4:40pm in Denver (DEN)

Layover in Denver for 1h 1m

Tue May 27th 2025 United Airlines · UA 1374 Depart at 5:41pm from Denver (DEN) Fly for 4h 5m Arrive at 11:46pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 17h 14m

Wed May 28th 2025 United Airlines · UA 3094 Depart at 5:00pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:05pm in Key West (EYW)
US$1123

8:20am - 2:00pm
Tue May 27th 2025

28h 40m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 3672 Depart at 8:20am from Madison (MSN) Fly for 1h 10m Arrive at 9:30am in Chicago (ORD)

Layover in Chicago for 1h 42m

Tue May 27th 2025 United Airlines · UA 1834 Depart at 11:12am from Chicago (ORD) Fly for 2h 50m Arrive at 3:02pm in Tampa (TPA)

Layover in Tampa for 21h 43m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1123

8:20am - 2:00pm
Tue May 27th 2025

28h 40m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 3672 Depart at 8:20am from Madison (MSN) Fly for 1h 10m Arrive at 9:30am in Chicago (ORD)

Layover in Chicago for 3h 20m

Tue May 27th 2025 United Airlines · UA 1484 Depart at 12:50pm from Chicago (ORD) Fly for 2h 50m Arrive at 4:40pm in Tampa (TPA)

Layover in Tampa for 20h 5m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1134

7:05am - 12:53pm
Thu Jun 19th 2025

28h 48m
Madison (MSN) → Key West (EYW)

1 Stop

Thu Jun 19th 2025 United Airlines · UA 3664 Depart at 7:05am from Madison (MSN) Fly for 2h 20m Arrive at 10:25am in New York (EWR)

Layover in New York for 23h 12m

Fri Jun 20th 2025 United Airlines · UA 1822 Depart at 9:37am from New York (EWR) Fly for 3h 16m Arrive at 12:53pm in Key West (EYW)
US$1134

6:35am - 12:41pm
Sun Jun 29th 2025

29h 6m
Madison (MSN) → Key West (EYW)

1 Stop

Sun Jun 29th 2025 United Airlines · UA 3587 Depart at 6:35am from Madison (MSN) Fly for 2h 22m Arrive at 9:57am in New York (EWR)

Layover in New York for 23h 32m

Mon Jun 30th 2025 United Airlines · UA 1822 Depart at 9:29am from New York (EWR) Fly for 3h 12m Arrive at 12:41pm in Key West (EYW)
US$1134

6:30am - 12:41pm
Thu Jul 3rd 2025

29h 11m
Madison (MSN) → Key West (EYW)

1 Stop

Thu Jul 3rd 2025 United Airlines · UA 3587 Depart at 6:30am from Madison (MSN) Fly for 2h 22m Arrive at 9:52am in New York (EWR)

Layover in New York for 23h 37m

Fri Jul 4th 2025 United Airlines · UA 1822 Depart at 9:29am from New York (EWR) Fly for 3h 12m Arrive at 12:41pm in Key West (EYW)
US$1134

6:30am - 12:41pm
Fri Jul 4th 2025

29h 11m
Madison (MSN) → Key West (EYW)

1 Stop

Fri Jul 4th 2025 United Airlines · UA 3587 Depart at 6:30am from Madison (MSN) Fly for 2h 22m Arrive at 9:52am in New York (EWR)

Layover in New York for 23h 37m

Sat Jul 5th 2025 United Airlines · UA 1822 Depart at 9:29am from New York (EWR) Fly for 3h 12m Arrive at 12:41pm in Key West (EYW)
US$1373

8:20am - 6:05pm
Tue May 27th 2025

8h 45m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 3672 Depart at 8:20am from Madison (MSN) Fly for 1h 10m Arrive at 9:30am in Chicago (ORD)

Layover in Chicago for 1h 5m

Tue May 27th 2025 United Airlines · UA 1775 Depart at 10:35am from Chicago (ORD) Fly for 3h 18m Arrive at 2:53pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 7m

Tue May 27th 2025 United Airlines · UA 3094 Depart at 5:00pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:05pm in Key West (EYW)
US$1474

5:23pm - 2:00pm
Tue May 27th 2025

19h 37m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 4603 Depart at 5:23pm from Madison (MSN) Fly for 1h 5m Arrive at 6:28pm in Chicago (ORD)

Layover in Chicago for 13h 2m

Wed May 28th 2025 United Airlines · UA 2326 Depart at 7:30am from Chicago (ORD) Fly for 2h 51m Arrive at 11:21am in Tampa (TPA)

Layover in Tampa for 1h 24m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1474

3:55pm - 2:00pm
Tue May 27th 2025

21h 5m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 4409 Depart at 3:55pm from Madison (MSN) Fly for 1h 10m Arrive at 5:05pm in Chicago (ORD)

Layover in Chicago for 14h 25m

Wed May 28th 2025 United Airlines · UA 2326 Depart at 7:30am from Chicago (ORD) Fly for 2h 51m Arrive at 11:21am in Tampa (TPA)

Layover in Tampa for 1h 24m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1474

2:35pm - 2:00pm
Tue May 27th 2025

22h 25m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 3504 Depart at 2:35pm from Madison (MSN) Fly for 1h 10m Arrive at 3:45pm in Chicago (ORD)

Layover in Chicago for 15h 45m

Wed May 28th 2025 United Airlines · UA 2326 Depart at 7:30am from Chicago (ORD) Fly for 2h 51m Arrive at 11:21am in Tampa (TPA)

Layover in Tampa for 1h 24m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1474

5:23pm - 6:05pm
Tue May 27th 2025

23h 42m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 4603 Depart at 5:23pm from Madison (MSN) Fly for 1h 5m Arrive at 6:28pm in Chicago (ORD)

Layover in Chicago for 16h 7m

Wed May 28th 2025 United Airlines · UA 1775 Depart at 10:35am from Chicago (ORD) Fly for 3h 18m Arrive at 2:53pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 7m

Wed May 28th 2025 United Airlines · UA 3094 Depart at 5:00pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:05pm in Key West (EYW)
US$1474

3:55pm - 6:05pm
Tue May 27th 2025

25h 10m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 4409 Depart at 3:55pm from Madison (MSN) Fly for 1h 10m Arrive at 5:05pm in Chicago (ORD)

Layover in Chicago for 17h 30m

Wed May 28th 2025 United Airlines · UA 1775 Depart at 10:35am from Chicago (ORD) Fly for 3h 18m Arrive at 2:53pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 7m

Wed May 28th 2025 United Airlines · UA 3094 Depart at 5:00pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:05pm in Key West (EYW)
US$1474

10:55am - 2:00pm
Tue May 27th 2025

26h 5m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 3634 Depart at 10:55am from Madison (MSN) Fly for 1h 10m Arrive at 12:05pm in Chicago (ORD)

Layover in Chicago for 19h 25m

Wed May 28th 2025 United Airlines · UA 2326 Depart at 7:30am from Chicago (ORD) Fly for 2h 51m Arrive at 11:21am in Tampa (TPA)

Layover in Tampa for 1h 24m

Wed May 28th 2025 United Airlines · UA 3136 Depart at 12:45pm from Tampa (TPA) Fly for 1h 15m Arrive at 2:00pm in Key West (EYW)
US$1474

2:35pm - 6:05pm
Tue May 27th 2025

26h 30m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 3504 Depart at 2:35pm from Madison (MSN) Fly for 1h 10m Arrive at 3:45pm in Chicago (ORD)

Layover in Chicago for 18h 50m

Wed May 28th 2025 United Airlines · UA 1775 Depart at 10:35am from Chicago (ORD) Fly for 3h 18m Arrive at 2:53pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 7m

Wed May 28th 2025 United Airlines · UA 3094 Depart at 5:00pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:05pm in Key West (EYW)
US$1584

5:23pm - 6:05pm
Tue May 27th 2025

23h 42m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 4603 Depart at 5:23pm from Madison (MSN) Fly for 1h 5m Arrive at 6:28pm in Chicago (ORD)

Layover in Chicago for 12h 32m

Wed May 28th 2025 United Airlines · UA 1421 Depart at 7:00am from Chicago (ORD) Fly for 3h 13m Arrive at 11:13am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 5h 47m

Wed May 28th 2025 United Airlines · UA 3094 Depart at 5:00pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:05pm in Key West (EYW)
US$1584

3:55pm - 6:05pm
Tue May 27th 2025

25h 10m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 4409 Depart at 3:55pm from Madison (MSN) Fly for 1h 10m Arrive at 5:05pm in Chicago (ORD)

Layover in Chicago for 13h 55m

Wed May 28th 2025 United Airlines · UA 1421 Depart at 7:00am from Chicago (ORD) Fly for 3h 13m Arrive at 11:13am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 5h 47m

Wed May 28th 2025 United Airlines · UA 3094 Depart at 5:00pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:05pm in Key West (EYW)
US$1584

2:35pm - 6:05pm
Tue May 27th 2025

26h 30m
Madison (MSN) → Key West (EYW)

2 Stops

Tue May 27th 2025 United Airlines · UA 3504 Depart at 2:35pm from Madison (MSN) Fly for 1h 10m Arrive at 3:45pm in Chicago (ORD)

Layover in Chicago for 15h 15m

Wed May 28th 2025 United Airlines · UA 1421 Depart at 7:00am from Chicago (ORD) Fly for 3h 13m Arrive at 11:13am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 5h 47m

Wed May 28th 2025 United Airlines · UA 3094 Depart at 5:00pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:05pm in Key West (EYW)
US$1689

6:39am - 12:53pm
Sun Jun 1st 2025

29h 14m
Madison (MSN) → Key West (EYW)

1 Stop

Sun Jun 1st 2025 United Airlines · UA 3664 Depart at 6:39am from Madison (MSN) Fly for 2h 20m Arrive at 9:59am in New York (EWR)

Layover in New York for 23h 38m

Mon Jun 2nd 2025 United Airlines · UA 1822 Depart at 9:37am from New York (EWR) Fly for 3h 16m Arrive at 12:53pm in Key West (EYW)

Sarah Belizaire

@sarahbb1

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John Ford

@eyupitsjohn

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Roaming Sonaa

@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality. It's designed for remote workers, backpackers, and people living abroad.

Read Sonaa's 7 Amazing Skyscanner Alternatives for Booking Travel

ANDY TRAVELS

@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Read Josh's Ultimate Guide To Find Cheap One Way Flights

Wesley Mergard

@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Read Wesley's My Best Cheap Flight Hacks (Why Pay More?)

Cheap Flights from Madison to Key West (MSN to EYW)

Sarah Belizaire

John Ford

Roaming Sonaa

ANDY TRAVELS

Travel With Bender

Wesley Mergard

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