Flights to Key West
23 cities in 2 countries. In each country, prices we can stand behind come first, then the cheapest.
Departure cities with a recent price: 23
Recent prices: 38
Fares Aviasales flagged as unusually low
No fares flagged as unusually low in the last two days.
When these trips depart
Every price counted here was found on or after 13 Oct.
Return
November 2026: 2 cities with a price listed here, from $583
Albany · 4 Nov – 9 Nov · found yesterday · See prices for these dates
December 2026: 6 cities with a price listed here, from $178
Tampa · 31 Dec – 2 Jan 2027 · found 3 days ago · See prices for these dates
January 2027: 2 cities with a price listed here, from $256
Philadelphia · 5 Jan 2027 – 8 Jan 2027 · found 5 days ago · See prices for these dates
February 2027: 1 city with a price listed here, from $441
Boston · 12 Feb 2027 – 18 Feb 2027 · found yesterday · See prices for these dates
March 2027: 2 cities with a price listed here, from $774
Minneapolis · 18 Mar 2027 – 21 Mar 2027 · found 2 days ago · See prices for these dates
One-way
October 2026: 8 cities with a price listed here, from $41
Tampa · 28 Oct · found yesterday · Open this trip
December 2026: 3 cities with a price listed here, from $132
Boston · 6 Dec · found 5 days ago · Open this trip
May 2027: 1 city with a price listed here, from $281
Atlanta · 22 May 2027 · found 5 days ago · Open this trip
August 2027: 1 city with a price listed here, from C$457 (US$323)
Toronto · 10 Aug 2027 · found 6 days ago · Open this trip
Everywhere, by country
1 traveler · Economy
| City | From | Trip | Dates | Airports | Stops | Airline | Found | |
|---|---|---|---|---|---|---|---|---|
| United States | ||||||||
| Tampa | $41 | one-way | 28 Oct | PIE → EYW | nonstop | Allegiant Air | found yesterday | Open this trip |
| Orlando | $52 | one-way | 25 Oct | SFB → EYW | nonstop | Allegiant Air | found 4 days ago | Open this trip |
| Louisville | $113 | one-way | 25 Oct | SDF → EYW | 1 stop | Breeze Airways | found 4 days ago | Open this trip |
| Boston | $132 | one-way | 6 Dec | BOS → EYW | 1 stop | Allegiant Air | found 5 days ago | Open this trip |
| Philadelphia | $147 | one-way | 31 Dec | PHL → EYW | 1 stop | Frontier Airlines | found 3 days ago | Open this trip |
| El Paso | $265 | one-way | 30 Dec | ELP → EYW | 2 stops | Frontier Airlines | found 3 days ago | Open this trip |
| Atlanta | $281 | one-way | 22 May 2027 | ATL → EYW | 2 stops | jetBlue | found 5 days ago | Open this trip |
| New Bern | $302 | one-way | 26 Oct | EWN → EYW | 2 stops | Breeze Airways | found 3 days ago | Open this trip |
| Fort Lauderdale | $303 | one-way | 26 Oct | FLL → EYW | stops unknown | Breeze Airways | found 3 days ago | Open this trip |
| Hilton Head | $401 | one-way | 28 Oct | HHH → EYW | 1 stop | American Airlines | found yesterday | Open this trip |
| Greensboro | $417 | one-way | 28 Oct | GSO → EYW | 1 stop | American Airlines | found yesterday | Open this trip |
| Boston | $441 | return | 12 Feb 2027 – 18 Feb 2027 | BOS → EYW | out 2 stops, back 1 stop | Allegiant Air | found yesterday | See prices for these dates |
| State College | $478 | one-way | 28 Oct | SCE → EYW | 1 stop | American Airlines | found yesterday | Open this trip |
| Albany | $583 | return | 4 Nov – 9 Nov | ALB → EYW | out 2 stops, back 2 stops | jetBlue | found yesterday | See prices for these dates |
| Parkersburg | $762 | return | 26 Dec – 30 Dec | PKB → EYW | out 2 stops, back 3 stops | Contour Airlines | found yesterday | See prices for these dates |
| New York | $788 | return | 27 Dec – 3 Jan 2027 | JFK → EYW | out 1 stop, back 1 stop | jetBlue | found yesterday | See prices for these dates |
| Newburgh | $821 | return | 27 Dec – 3 Jan 2027 | SWF → EYW | out 1 stop, back 2 stops | Breeze Airways | found yesterday | See prices for these dates |
| San Jose | $845 | return | 9 Nov – 16 Nov | SJC → EYW | out 1 stop, back 1 stop | American Airlines | found yesterday | See prices for these dates |
| Tampa | $178 | return | 31 Dec – 2 Jan 2027 | PIE → EYW | out nonstop, back nonstop | Allegiant Air | found 3 days ago | See prices for these dates |
| Minneapolis | $774 | return | 18 Mar 2027 – 21 Mar 2027 | MSP → EYW | out 1 stop, back 1 stop | American Airlines | found 2 days ago | See prices for these dates |
| Grand Island | $793 | return | 6 Mar 2027 – 3 Apr 2027 | GRI → EYW | out 2 stops, back 2 stops | American Airlines | found 3 days ago | See prices for these dates |
| Cincinnati | $234 | return | 6 Dec – 10 Dec | CVG → EYW | out 1 stop, back 1 stop | Frontier Airlines | found 5 days ago | See prices for these dates |
| Philadelphia | $256 | return | 5 Jan 2027 – 8 Jan 2027 | PHL → EYW | out 1 stop, back 1 stop | Frontier Airlines | found 5 days ago | See prices for these dates |
| Baltimore | $285 | return | 23 Jan 2027 – 30 Jan 2027 | BWI → EYW | out 2 stops, back 2 stops | Frontier Airlines | found 5 days ago | See prices for these dates |
| Gulfport | $324 | return | 11 Dec – 13 Dec | GPT → EYW | out 1 stop, back 1 stop | Breeze Airways | found 5 days ago | See prices for these dates |
| Canada | ||||||||
| Toronto | C$457 (US$323) | one-way | 10 Aug 2027 | YYZ → EYW | 1 stop | American Airlines | found 6 days ago | Open this trip |
Prices are what travelers' searches on Aviasales found in the last 7 days: the price the seller showed on Aviasales; bags may cost extra. Canadian dollars at the Bank of Canada rate of 2026-10-16, US dollars in brackets. Fares change, so check today's price before you book. How our prices work