When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 23 days in advance, which can save you up to 39% on flights from Massachusetts to Key West compared to booking the week you need them. Waiting 23 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $415. For sooner than that we have options available in the next 3 days from $516.
Flights from Massachusetts to Key West lean towards being more expensive in April. Prices are generally better when you fly from Massachusetts to Key West in August, with the cheapest ticket starting at $209.
When flying from Massachusetts to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$227 - $481
Route
Depart
Return
Price
Albany IntlKey West
ALB - EYW
ALBEYW
Albany Intl
Tue 8/6
2 stops7h 35m
Key West
Fri 8/9
1 stop5h 55m
Hartford Bradley IntlKey West
BDL - EYW
BDLEYW
Hartford Bradley Intl
Mon 8/12
1 stop6h 25m
Key West
Fri 8/16
1 stop7h 33m
Boston Logan IntlKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Tue 7/9
1 stop5h 20m
Key West
Tue 7/16
1 stop8h 28m
Boston Logan IntlKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Wed 7/10
1 stop5h 45m
Key West
Wed 7/17
1 stop6h 16m
Albany IntlKey West
ALB - EYW
ALBEYW
Albany Intl
Tue 7/30
2 stops11h 23m
Key West
Wed 8/7
1 stop5h 55m
Albany IntlKey West
ALB - EYW
ALBEYW
Albany Intl
Tue 7/30
2 stops11h 23m
Key West
Wed 8/7
2 stops10h 25m
Boston Logan IntlKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Sun 9/8
1 stop8h 09m
Key West
Fri 9/13
1 stop5h 38m
Boston Logan IntlKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Sun 9/8
2 stops20h 52m
Key West
Fri 9/13
3 stops19h 30m
Boston Logan IntlKey West
BOS - EYW
BOSEYW
Boston Logan Intl
Sun 10/27
Nonstop4h 18m
Key West
Thu 10/31
1 stop7h 59m
No data available for this route at this time. Please check back soon.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Comfort
Entertainment
Food
Boarding
Crew
Overall
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
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