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Key West

$90+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Dec 23 — Dec 301
Tue 12/23
Tue 12/30
1 adult, Economy
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Cheap 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 November 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$207
(American Airlines)

One-way from

$90
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$394

Good round-trip deal

$331 or less

Good one-way deal

$173 or less
Provider with most accurate pricing for Boston Logan Intl-Key West flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Key West flights.
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From Massachusetts to Key West
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One-way flight from Massachusetts to Key West
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Highest demand for flights based on searches. 18% potential increase in price ($93 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Massachusetts to Key West.
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Price to beat on a one-way flight from Massachusetts to Key West.
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Find 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 November 23, 2025.

This Breeze Airways deal was found by Cheapflights users on 11/22. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/126:00 amBDL - EYW
1 stop28h 07mBreeze Airways
Mon 12/158:55 amEYW - BDL
2 stops9h 01mBreeze Airways
Deal found 11/22$221
This American Airlines deal was found by Cheapflights users on 11/22. 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.
Sun 12/73:34 pmORH - EYW
1 stop20h 38mAmerican Airlines
Thu 12/115:09 pmEYW - ORH
1 stop21h 56mAmerican Airlines
Deal found 11/22$232
This Kiwi.com deal was found by Cheapflights users on 11/23. 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.
Mon 12/86:00 amBDL - EYW
1 stop29h 05mBreeze Airways
Fri 12/128:55 amEYW - BDL
2 stops13h 48mBreeze Airways
Deal found 11/23$235
This Kiwi.com deal was found by Cheapflights users on 11/21. 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 12/79:59 amALB - EYW
1 stop5h 45mMultiple Airlines
Fri 12/129:57 amEYW - ALB
1 stop9h 07mMultiple Airlines
Deal found 11/21$238
This Kiwi.com deal was found by Cheapflights users on 11/21. 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 12/149:59 amALB - EYW
1 stop5h 45mMultiple Airlines
Fri 12/199:57 amEYW - ALB
1 stop9h 36mMultiple Airlines
Deal found 11/21$240
This Kiwi.com deal was found by Cheapflights users on 11/22. 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.
Sun 12/149:59 amALB - EYW
1 stop5h 45mAllegiant Air
Thu 12/1810:32 pmEYW - ALB
1 stop21h 01mAllegiant Air
Deal found 11/22$256
This Mytrip deal was found by Cheapflights users on 11/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/149:59 amALB - EYW
1 stop5h 45mMultiple Airlines
Thu 12/1812:20 pmEYW - ALB
2 stops22h 45mMultiple Airlines
Deal found 11/22$258
This Kiwi.com deal was found by Cheapflights users on 11/21. 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.
Thu 12/119:59 amALB - EYW
1 stop5h 45mMultiple Airlines
Mon 12/158:55 amEYW - ALB
2 stops48h 16mMultiple Airlines
Deal found 11/21$260
This Kiwi.com deal was found by Cheapflights users on 11/21. 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 12/149:59 amALB - EYW
1 stop5h 45mAllegiant Air
Fri 12/197:03 pmEYW - ALB
1 stop24h 11mAllegiant Air
Deal found 11/21$264
This Kiwi.com deal was found by Cheapflights users on 11/21. 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 12/72:03 pmBDL - EYW
1 stop18h 12mMultiple Airlines
Sat 12/132:30 pmEYW - BDL
2 stops21h 00mMultiple Airlines
Deal found 11/21$264
This Kiwi.com deal was found by Cheapflights users on 11/22. 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.
Thu 12/49:00 amBOS - EYW
1 stop28h 39mMultiple Airlines
Tue 12/911:45 amEYW - BOS
2 stops36h 11mMultiple Airlines
Deal found 11/22$266
This United Airlines deal was found by Cheapflights users on 11/21. 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.
Sat 11/296:02 amBOS - EYW
1 stop8h 02mUnited Airlines
Fri 12/52:47 pmEYW - BOS
2 stops8h 54mUnited Airlines
Deal found 11/21$268

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 November 23, 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

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Fri 12/12

6:00 am-10:07 am

1 stop28h 07m

Key West

Mon 12/15

8:55 am-5:56 pm

2 stops9h 01m

$221

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Fri 2/6

1:11 pm-10:09 am

2 stops20h 58m

Key West

Mon 2/9

1:06 pm-11:16 pm

2 stops10h 10m

$226

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sun 12/7

3:34 pm-12:12 pm

1 stop20h 38m

Key West

Thu 12/11

5:09 pm-3:05 pm

1 stop21h 56m

$232

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Mon 12/8

6:00 am-11:05 am

1 stop29h 05m

Key West

Fri 12/12

8:55 am-10:43 pm

2 stops13h 48m

$235

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Fri 1/2

6:00 am-7:07 am

1 stop25h 07m

Key West

Fri 1/9

9:49 am-10:53 pm

2 stops13h 04m

$242

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Thu 12/11

9:59 am-3:44 pm

1 stop5h 45m

Key West

Mon 12/15

8:55 am-9:11 am

2 stops48h 16m

$260

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Thu 2/5

9:36 am-12:26 pm

1 stop26h 50m

Key West

Sun 2/8

10:27 pm-8:47 am

1 stop10h 20m

$262

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

$269

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Sat 1/3

5:19 pm-10:44 pm

1 stop5h 25m

Key West

Tue 1/13

7:08 am-12:55 pm

1 stop5h 47m

$269

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Fri 1/9

11:22 am-7:40 pm

1 stop8h 18m

Key West

Wed 1/14

7:10 am-1:33 pm

1 stop6h 23m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/21

Showing 1-10 of 43 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 November 23, 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 65% 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. Breeze Airways provides one of the quickest options available for as low as $269. 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?

    $96 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Breeze Airways and United Airlines, with prices starting from $104 and $106, respectively.

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

    While some choose either Albany Intl - Key West or Hartford Bradley 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 $116. On average you can expect to pay $297. 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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Alternative routes for Massachusetts to Key West

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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 November 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$102FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$135Average$375FlexibilityNo cancel feeOn-time69%
DeltaCheapest$178Average$352FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$222Average$526FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$252Average$411FlexibilityNo cancel feeOn-time71%

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