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Key West

$99+ Cheap flights from Boston to Key West (BOS - EYW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
May 27 — Jun 31
Wed 5/27
Wed 6/3
1 adult, Economy
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Find cheap flights from Boston to Key West with Cheapflights

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Cheapflights Tip: The best prices from Boston Logan Intl to Key West are usually found in September or October, booked 83 days in advance, depart on a Monday or Sunday and return on a Wednesday

Cheap flight deals from Boston to Key West

Cheapest flights from Boston to Key West
Explore the most affordable flight options available from Boston to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.

This American Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1310:12 am
BOS
-
EYW
1 stop8h 35m
American Airlines
Sat 7/187:29 pm
EYW
-
BOS
1 stop5h 07m
American Airlines
Deal found 4/25$327
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/177:00 am
BOS
-
EYW
1 stop28h 27m
Multiple Airlines
Fri 5/2212:07 pm
EYW
-
BOS
2 stops11h 47m
Multiple Airlines
Deal found 4/25$331
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:00 am
BOS
-
EYW
1 stop28h 25m
Multiple Airlines
Thu 5/2812:05 pm
EYW
-
BOS
1 stop9h 37m
Multiple Airlines
Deal found 4/23$332
This American Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:00 am
BOS
-
EYW
1 stop7h 27m
American Airlines
Fri 5/225:37 pm
EYW
-
BOS
1 stop6h 12m
American Airlines
Deal found 4/24$333
This Kiwi.com deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:07 am
BOS
-
EYW
1 stop25h 18m
Multiple Airlines
Mon 5/1112:07 pm
EYW
-
BOS
1 stop21h 05m
Multiple Airlines
Deal found 4/22$334
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/181:45 pm
BOS
-
EYW
1 stop5h 25m
American Airlines
Mon 6/227:29 pm
EYW
-
BOS
1 stop5h 11m
American Airlines
Deal found 4/22$337
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2510:52 am
BOS
-
EYW
2 stops8h 18m
American Airlines
Fri 5/295:37 pm
EYW
-
BOS
1 stop6h 12m
American Airlines
Deal found 4/26$338
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/39:06 am
BOS
-
EYW
1 stop25h 05m
Multiple Airlines
Sun 5/1012:05 pm
EYW
-
BOS
2 stops20h 39m
Multiple Airlines
Deal found 4/23$339
This Kiwi.com deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:00 am
BOS
-
EYW
1 stop28h 25m
Multiple Airlines
Fri 5/292:51 pm
EYW
-
BOS
2 stops16h 58m
Multiple Airlines
Deal found 4/25$340
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/238:15 pm
BOS
-
EYW
2 stops14h 38m
Delta
Thu 5/286:19 pm
EYW
-
BOS
1 stop7h 09m
Delta
Deal found 4/24$341
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:12 am
BOS
-
EYW
1 stop8h 35m
American Airlines
Wed 7/221:38 pm
EYW
-
BOS
2 stops8h 51m
American Airlines
Deal found 4/22$342

Find flight deals from Boston to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$327
(American Airlines)

One-way from

$99
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$601

Good round-trip deal

$462 or less

Good one-way deal

$233 or less
Provider with most accurate pricing for Boston Logan Intl-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Key West flights.
Search Deals
From Boston Logan Intl to Key West
Search Deals
One-way flight from Boston Logan Intl to Key West
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Key West.
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Key West.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 27, 2026.
Use the filters below to find and compare flights from Boston to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Fri 5/1

2:00 pm-7:40 pm

1 stop5h 40m

Key West

Tue 5/5

6:23 pm-1:15 am

1 stop6h 52m

$337

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Fri 5/8

7:30 am-3:07 pm

1 stop7h 37m

Key West

Wed 5/13

2:49 pm-10:14 pm

1 stop7h 25m

$340

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Fri 5/1

6:00 am-12:40 pm

1 stop6h 40m

Key West

Wed 5/6

6:23 pm-7:22 am

2 stops12h 59m

$410

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Wed 5/13

9:10 am-5:23 pm

1 stop8h 13m

Key West

Mon 5/18

7:30 am-1:49 pm

1 stop6h 19m

$413

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Thu 4/30

2:00 pm-7:40 pm

1 stop5h 40m

Key West

Tue 5/5

6:23 pm-7:29 am

2 stops13h 06m

$481

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 5/11

7:30 am-3:07 pm

1 stop7h 37m

Key West

Fri 5/15

2:49 pm-10:14 pm

1 stop7h 25m

$498

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Thu 4/30

2:00 pm-7:40 pm

1 stop5h 40m

Key West

Sat 5/2

1:22 pm-5:45 pm

1 stop28h 23m

$501

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sun 5/3

5:45 am-3:07 pm

2 stops9h 22m

Key West

Wed 5/6

4:05 pm-12:59 am

1 stop8h 54m

$513

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sun 5/3

5:45 am-3:07 pm

2 stops9h 22m

Key West

Thu 5/7

4:05 pm-12:59 am

1 stop8h 54m

$522

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 5/9

5:45 am-3:07 pm

2 stops9h 22m

Key West

Sat 5/16

2:49 pm-7:53 am

1 stop17h 04m

$616

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

Compare providers for flights from Boston to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Boston to Key West in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Super.comPrice Accuracy-Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Boston-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Boston-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Boston-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Boston-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Boston-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Boston to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Boston to Key West

How far ahead should I book a flight from Boston to Key West?

Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from Boston to Key West. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Boston to Key West?

Currently, September is the cheapest month in which you can book a flight from Boston to Key West (average of $316). Flying from Boston to Key West in April is currently the most expensive (average of $601). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from BOS to EYW?

Find hourly flight availability from Boston to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 27, 2026.

When flying from Boston 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.

How much does it cost to fly round-trip from Boston to Key West?

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated April 27, 2026.
See what other customers who have flown with Delta,United Airlines, andJetBlue from Boston to Key West have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,462 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
8,462 reviews
Delta
7.9
Good
8,462 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
9,668 reviews
Delta
7.9
Good
8,462 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
JetBlue
7.2
Good
2,963 reviews
Delta
7.9
Good
8,462 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.1
Good
11,667 reviews
Delta
7.9
Good
8,462 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Spirit Airlines
6.3
Okay
8,633 reviews
Delta
7.9
Good
8,462 reviews

Crew

8.5

Food

7.2

Entertainment

7.8

Comfort

7.9

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Boston to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airports do I use to fly from Boston to Key West?

    If you book a flight from Boston to Key West, you will be flying from Logan Intl to Key West. Flights to Key West (EYW) from Boston Logan Intl (BOS) take 3h 38m for a nonstop flight. There is 1 flight from Logan Intl to Key West per day from 5 airlines.

  • How long is the flight from Boston to Key West?

    Airlines like Delta and United Airlines fly from Boston to Key West in about 5h 40m. The time it takes to get you to your destination can typically vary by up to 1h 57m. Boston and Key West are separated by a distance of 1374 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Boston to Key West round-trip?

    Currently priced at $123, Spirit Airlines will fly you from Boston to Key West and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and United Airlines - these airlines can fly you to your destination from $148 and $196, respectively. Spirit Airlines is 70% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Boston to Key West one-way?

    The cheapest airlines for a one-way flight from Boston to Key West are JetBlue ($100), United Airlines ($103), and Spirit Airlines ($107).

  • What are the most reliable airlines from Boston to Key West?

    No one likes to see their flight delayed. When booking a flight from Boston to Key West consider choosing JetBlue (79%), TAP AIR PORTUGAL (76%) or Envoy Air (75%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Key West?

    The cheapest flight price from Boston to Key West is $208. On average you can expect to pay $473. The most popular route, (Boston Logan Intl - Key West), can usually be booked for $235.

  • Where are the most common layover locations when flying from Boston to Key West?

    Flights departing from Boston and landing in Key West layover in Charlotte most frequently.

  • What are some popular things to do or see while on a layover in Charlotte?

    North Carolina Blumenthal Performing Arts Center, Mint Museum Uptown, and NASCAR Hall of Fame are currently the most popular points of interest in Charlotte at the moment. Those on a layover in Charlotte interested in visiting North Carolina Blumenthal Performing Arts Center, Mint Museum Uptown, or NASCAR Hall of Fame can do so by traveling 5.8 mi, 5.4 mi, and 5.7 mi, respectively from Charlotte Douglas. Travelers in need of a car in Charlotte can rent one for about $50 per day.

  • Where are the least popular layover locations for Boston to Key West flights?

    Boston to Key West flights have a layover in Miami the least frequently.

  • Can I find deals for flights from Boston to Key West that include hotel bookings?

    Yes. In addition to deals on Boston to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Key West.

  • Can I find deals for business class flights from Boston to Key West?

    Yes. Cheapflights offers flight deals from Boston to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Boston to Key West?

    Currently, September is the cheapest month in which you can book a flight from Boston to Key West (average of $316). Flying from Boston to Key West in April is currently the most expensive (average of $601). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Boston to Key West

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Top 5 airlines flying from Boston to Key West

Discover the top 5 airlines that operate flights from Boston to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$123Average$239FlexibilityNo cancel feeOn-time65%
DeltaCheapest$148Average$378FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$196Average$327FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$213Average$501FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$246Average$404FlexibilityNo cancel feeOn-time71%

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