Flights from Boston to Key West
Pick a departure date to see flights and seller prices
We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.
Best fares from Boston to Key West
Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date
Where to connect
Options with one connection, fastest first
- fastest, via Tampa
- 7h 33m
- two tickets, via Orlando
- $78
- connection options
- 5
- straight-line distance
- 1,374 mi (2,211 km)
fastest
Via Tampa
7h 33m
with the connection
Boston to Tampa
flight 3h 29m
Connection of about 3h
Arrival: St. Petersburg-Clearwater International, Tampa International. Departure to Key West: St. Petersburg-Clearwater International, Tampa International.
Tampa to Key West
flight 1h 4m
two ticketsfrom $249
Via Miami
7h 39m
with the connection
Boston to Miami
flight 3h 36m
Connection of about 3h
Arrival: Fort Lauderdale-Hollywood International, Miami International. Departure to Key West: Miami International.
Miami to Key West
flight 1h 3m
two ticketsfrom $200
Via Orlando
7h 45m
with the connection
Boston to Orlando
flight 3h 25m
Connection of about 3h
Arrival: Orlando International, Orlando Sanford International. Departure to Key West: Orlando International, Orlando Sanford International.
Orlando to Key West
flight 1h 20m
two ticketsfrom $78
Via Philadelphia
8h 1m
with the connection
two ticketsfrom $636
Via Washington
8h 2m
with the connection
Boston to Washington
flight 1h 46m
Connection of about 3h
Arrival: Baltimore/Wash International Thurgood Marshall, Ronald Reagan National, Washington Dulles International. Departure to Key West: Ronald Reagan National, Washington Dulles International.
Washington to Key West
flight 3h 16m
two ticketsfrom $372
One ticket or two
How the options are calculated and what to keep in mind at the connection
Flight times come from the nonstop schedule (estimated from the distance where there is no schedule), with 3h allowed for the connection. The price of an option is the sum of the lowest known fares for each leg; their dates may not match, so treat it as a guide. The search shows tickets for your dates, including connections on a single ticket.
Nearest nonstop flights
The closest you can get without a connection
From Boston to cities closest to Key West
Boston to Miami
Miami: 130 mi (209 km) from Key West, flight 3h 36m
from $105
Boston to Fort Myers
Fort Myers: 144 mi (232 km) from Key West, flight 3h 39m
from $231
Boston to Tampa
Tampa: 238 mi (383 km) from Key West, flight 3h 29m
from $112
Boston to Orlando
Orlando: 276 mi (444 km) from Key West, flight 3h 25m
from $37
Boston to Jacksonville
Jacksonville: 399 mi (642 km) from Key West, flight 3h 6m
Boston to Cancun
Cancun: 399 mi (642 km) from Key West, flight 4h 45m
from $165
To Key West from cities closest to Boston
New York to Key West
New York: 190 mi (306 km) from Boston, flight 3h 47m
from $238
Philadelphia to Key West
Philadelphia: 270 mi (435 km) from Boston, flight 3h 22m
from $215
Washington to Key West
Washington: 394 mi (634 km) from Boston, flight 3h 16m
from $100
Chicago to Key West
Chicago: 849 mi (1,366 km) from Boston, flight 3h 29m
Orlando to Key West
Orlando: 1,116 mi (1,796 km) from Boston, flight 1h 20m
from $41
Tampa to Key West
Tampa: 1,183 mi (1,904 km) from Boston, flight 1h 4m
from $42
Frequently asked questions
Is there a nonstop flight from Boston to Key West?
There are no nonstop flights in the schedule. You will need a connection, the fastest is via Tampa.
What is the fastest way to fly from Boston to Key West?
Via Tampa: 3h 29m to the connection, 1h 4m after it, about 7h 33m in total with 3h for the connection.
How much does a flight from Boston to Key West with a connection cost?
Two nonstop tickets via Orlando from $78. This is the sum of the lowest known prices for each leg, and their dates may not match.
Which cities can you connect in between Boston and Key West?
Tampa (7h 33m total), Miami (7h 39m total), Orlando (7h 45m total), Philadelphia (8h 1m total) and Washington (8h 2m total).
How far is Key West from Boston?
1,374 mi (2,211 km) in a straight line between the cities.
How much time should I allow for the connection?
The options allow 3h. On a single ticket the carrier is responsible for the connection; on separate tickets you set the margin yourself, allowing time to collect and re-check your bags.