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Key West

$78+ Cheap flights from Massachusetts to Key West (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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap flight deals from Massachusetts to Key West

Cheapest flights from Massachusetts to Key West
Explore the most affordable flight options available from Massachusetts to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/108:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Wed 12/1710:47 amEYW - BDL
1 stop11h 59mBreeze Airways
Deal found 12/4$191
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/138:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Wed 12/1710:47 amEYW - BDL
1 stop11h 59mBreeze Airways
Deal found 12/4$201
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/108:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Fri 12/128:55 amEYW - BDL
2 stops13h 48mBreeze Airways
Deal found 12/4$204
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/108:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Thu 12/1110:59 amEYW - BDL
1 stop25h 46mBreeze Airways
Deal found 12/4$208
This Breeze Airways deal was found by Cheapflights users on 12/2. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/108:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Mon 12/158:55 amEYW - BDL
2 stops13h 48mBreeze Airways
Deal found 12/2$217
This Mytrip deal was found by Cheapflights users on 12/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:20 pmALB - EYW
2 stops15h 00mMultiple Airlines
Thu 1/810:27 pmEYW - ALB
1 stop10h 20mMultiple Airlines
Deal found 12/2$218
This American Airlines deal was found by Cheapflights users on 12/2. 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 12/221:45 pmORH - EYW
2 stops27h 24mAmerican Airlines
Sat 12/275:10 pmEYW - ORH
1 stop20h 07mAmerican Airlines
Deal found 12/2$222
This American Airlines deal was found by Cheapflights users on 12/3. 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.
Sun 12/211:45 pmORH - EYW
2 stops26h 12mAmerican Airlines
Sun 12/284:03 pmEYW - ORH
2 stops21h 14mAmerican Airlines
Deal found 12/3$227
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/138:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Mon 12/158:55 amEYW - BDL
2 stops13h 48mBreeze Airways
Deal found 12/4$229
This American Airlines deal was found by Cheapflights users on 12/2. 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.
Wed 12/173:30 pmORH - EYW
1 stop22h 17mAmerican Airlines
Sun 12/215:10 pmEYW - ORH
1 stop20h 07mAmerican Airlines
Deal found 12/2$232
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/108:05 amBDL - EYW
1 stop24h 10mMultiple Airlines
Wed 12/174:31 pmEYW - BDL
2 stops30h 31mMultiple Airlines
Deal found 12/4$239
This United Airlines deal was found by Cheapflights users on 12/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:45 amALB - EYW
1 stop5h 56mUnited Airlines
Thu 1/86:05 pmEYW - ALB
1 stop5h 36mUnited Airlines
Deal found 12/2$244

Find flight deals from Massachusetts to Key West

Keep the following information in mind while searching for Massachusetts to Key West flight deals. Data was last updated December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$197
(Kiwi.com)

One-way from

$78
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$409

Good round-trip deal

$339 or less

Good one-way deal

$191 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 Massachusetts to Key West
Search Deals
One-way flight from Massachusetts to Key West
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($93 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Key West.
Search Deals
Price to beat on a one-way flight from Massachusetts to Key West.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts 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 December 4, 2025.
Use the filters below to find and compare flights from Massachusetts to Key West that are best for you.

Fly from

Massachusetts

Fly to

Key West

Route

Depart

Return

Price

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Thu 1/22

9:31 am-11:15 am

2 stops25h 44m

Key West

Sun 1/25

10:27 pm-8:47 am

1 stop10h 20m

$216

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Tue 1/6

5:40 am-12:48 pm

1 stop7h 08m

Key West

Wed 1/14

7:10 am-1:24 pm

1 stop6h 14m

$219

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Thu 1/8

1:40 pm-9:47 pm

1 stop8h 07m

Key West

Mon 1/12

5:24 pm-10:34 pm

1 stop5h 10m

$219

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 1/10

10:07 am-4:22 pm

1 stop6h 15m

Key West

Wed 1/14

6:05 pm-11:44 pm

1 stop5h 39m

$219

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Sat 1/31

1:40 pm-9:47 pm

1 stop8h 07m

Key West

Tue 2/3

7:08 am-12:55 pm

1 stop5h 47m

$219

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 2/28

6:00 am-11:22 am

1 stop5h 22m

Key West

Wed 3/4

3:20 pm-10:42 pm

1 stop7h 22m

$219

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Mon 12/22

1:45 pm-5:09 pm

2 stops27h 24m

Key West

Sat 12/27

5:10 pm-1:17 pm

1 stop20h 07m

$222

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sun 12/21

1:45 pm-3:57 pm

2 stops26h 12m

Key West

Sun 12/28

4:03 pm-1:17 pm

2 stops21h 14m

$227

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Wed 1/21

8:05 am-9:26 am

1 stop25h 21m

Key West

Sun 1/25

10:27 pm-10:13 pm

2 stops23h 46m

$229

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Tue 3/3

5:35 am-12:45 pm

1 stop7h 10m

Key West

Wed 3/18

6:25 pm-11:59 pm

1 stop5h 34m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Massachusetts 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 Massachusetts to Key West

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

Currently, May is the cheapest month in which you can book a flight from Massachusetts to Key West (average of $179). Flying from Massachusetts to Key West in March is currently the most expensive (average of $300). 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 MA to EYW?

Find hourly flight availability from Massachusetts 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 December 4, 2025.

When flying from Massachusetts to Key West, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 64% versus a flight in the evening.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts 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 airport do you fly into for flights to Key West from Massachusetts?

    If you book a flight to Key West from Massachusetts, you will be flying to Key West, which is the city’s only airport. Key West (EYW) is located 2.6 mi from the center of Key West.

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

    A quick flight from Massachusetts to Key West can take about 7h 08m. Allegiant Air provides one of the quickest options available for as low as $219. The distance from Massachusetts to Key West is about 1335 mi. This flight may include one or multiple stops.

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

    $113 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $119 and $138, respectively.

  • What are the most popular routes from Massachusetts to Key West?

    While some choose either Hartford Bradley Intl - Key West or Albany Intl - Key West, Boston Logan Intl - Key West is the most popular route from Massachusetts to Key West.

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

    The cheapest flight price from Massachusetts to Key West is $115. On average you can expect to pay $308. The most popular route, (Boston Logan Intl - Key West), can usually be booked for $187.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts 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 Massachusetts to Key West?

    Currently, May is the cheapest month in which you can book a flight from Massachusetts to Key West (average of $179). Flying from Massachusetts to Key West in March is currently the most expensive (average of $300). 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.

See more FAQs

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Top 5 airlines flying from Massachusetts to Key West

Discover the top 5 airlines that operate flights from Massachusetts 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$112FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$135Average$376FlexibilityNo cancel feeOn-time69%
DeltaCheapest$178Average$391FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$240Average$525FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$250Average$411FlexibilityNo cancel feeOn-time71%

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