$149 Cheap Flights from Boston (BOS) to Key West (EYW)

View $149 flight on Sat, Dec 6, 2025Opens in a new window

Popular airlines from Logan International Airport (BOS) to Key West Intl. Airport (EYW)

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Cheap Flights from Boston to Key West (BOS-EYW)

Prices were available within the past 7 days and start at $149 for one-way flights and $297 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Thu, Dec 11 - Fri, Dec 19
BOS
Boston
EYW
Key West
$297 Roundtrip, just found
$297
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Dec 11 from Boston to Key West, returning Fri, Dec 19, priced at $297 just found
American Airlines
Sat, Dec 6 - Sat, Dec 13
BOS
Boston
EYW
Key West
$297 Roundtrip, found 7 hours ago
$297
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Dec 6 from Boston to Key West, returning Sat, Dec 13, priced at $297 found 7 hours ago
American Airlines
Sun, Feb 8 - Sat, Feb 14
BOS
Boston
EYW
Key West
$307 Roundtrip, found 1 hour ago
$307
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, Feb 8 from Boston to Key West, returning Sat, Feb 14, priced at $307 found 1 hour ago
United
Sun, Feb 8 - Sat, Feb 14
BOS
Boston
EYW
Key West
$310 Roundtrip, found 1 hour ago
$310
Roundtrip
found 1 hour ago
Select United flight, departing Sun, Feb 8 from Boston to Key West, returning Sat, Feb 14, priced at $310 found 1 hour ago
JetBlue Airways
Sat, Jan 24 - Wed, Jan 28
BOS
Boston
EYW
Key West
$312 Roundtrip, found 18 hours ago
$312
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Sat, Jan 24 from Boston to Key West, returning Wed, Jan 28, priced at $312 found 18 hours ago
United
Tue, Feb 3 - Sat, Feb 7
BOS
Boston
EYW
Key West
$315 Roundtrip, found 4 days ago
$315
Roundtrip
found 4 days ago
Select United flight, departing Tue, Feb 3 from Boston to Key West, returning Sat, Feb 7, priced at $315 found 4 days ago
Delta
Wed, Sep 3 - Sun, Sep 7
BOS
Boston
EYW
Key West
$317 Roundtrip, just found
$317
Roundtrip
just found
Select Delta flight, departing Wed, Sep 3 from Boston to Key West, returning Sun, Sep 7, priced at $317 just found
United
Mon, Jul 14 - Fri, Jul 18
BOS
Boston
EYW
Key West
$317 Roundtrip, just found
$317
Roundtrip
just found
Select United flight, departing Mon, Jul 14 from Boston to Key West, returning Fri, Jul 18, priced at $317 just found
JetBlue Airways
Tue, Jan 27 - Thu, Jan 29
BOS
Boston
EYW
Key West
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jan 27 from Boston to Key West, returning Thu, Jan 29, priced at $317 found 2 days ago
Breeze Airways
Sat, Aug 23 - Fri, Sep 5
PSM
Portsmouth
EYW
Key West
$464 Roundtrip, found 21 hours ago
$464
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Sat, Aug 23 from Portsmouth to Key West, returning Fri, Sep 5, priced at $464 found 21 hours ago

Find the cheapest month to fly from Boston (BOS) to Key West (EYW)

October is typically the cheapest month to fly

From $186 - $382 per traveler.

Graph displaying average flight prices per month

Flights from Boston (BOS) to Key West (EYW)
Origin airport
Logan Intl.
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, United
Roundtrip price
$297
Distance
1374 mi

Boston to Key West Flights

The cheapest times to fly from Boston to Key West

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Boston to Key West are during the month of December. You can find some of the cheapest flights from Boston to Key West with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Boston to Key West

Sunday is one of the best days to book for cheap flights from Boston to Key West: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Boston to Key West

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Boston to Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $149 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Boston to Key West flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Boston to Key West airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW) cost?
Discover the latest flight deals from BOS to EYW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from BOS to EYW?
The cheapest flights from BOS to EYW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW)?
Fly nonstop from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW) on a JetBlue Airways flight.
What is the cheapest airline that flies from BOS to EYW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from BOS to EYW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW)?
On average, you can choose from 6 direct flights each week from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW). For more flexibility, consider flights with layovers. Just enter your dates on Expedia and then set the filters to include one stop or more.
What are the most popular departure times for flights from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW)?
More travelers fly between BOS and EYW at 8 AM than at any other time of day. Looking to skip the crowds? Pick a flight outside the busiest times and it's possible you'll save on your fare as well.
What day of the week has the most flights from BOS to EYW?
Jet off on a Saturday if you're looking for the largest selection of flights from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW).
What is the earliest flight from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW)?
The earliest flight taking off from Logan Intl. Airport (BOS) is at around 8:50AM UTC-5. Hop on this flight and you'll land at Key West Intl. Airport (EYW) at approximately 12:41PM UTC-5. The entire trip takes 3h 51m.
How long does it take to fly from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW)?
Flights from BOS to EYW have an average travel time of 3 hours and 51 minutes. The total distance between these two airports is 1,400 mi.
What is the best time to fly from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW)?
Choose a flight from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW) that takes off before 3 PM to reduce the likelihood of delays and cancellations. Later departures are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Key West from Logan Intl. Airport (BOS)?
If you've booked a direct flight from Logan Intl. Airport (BOS) to Key West, Key West Intl. Airport (EYW) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW) last-minute?
Booking your ticket from BOS to EYW right before your journey is usually more expensive. But if there's some wiggle room with your itinerary, you could land a cheap last-minute fare.
Is it cheaper to book a BOS to EYW flight and hotel package?
Booking a BOS to EYW flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Select from our extensive range of hotels and then add car rentals, activities and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Logan Intl. Airport (BOS) to Key West Intl. Airport (EYW)?
If you reserved your BOS to EYW flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal if you want more information.

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*Available to One Key members.