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Key West

$84+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$173
(Breeze Airways)

One-way from

$84
(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 13, 2025.

This Breeze Airways deal was found by Cheapflights users on 11/10. 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
Wed 12/1710:47 amEYW - BDL
1 stop11h 59mBreeze Airways
Deal found 11/10$173
This Breeze Airways deal was found by Cheapflights users on 11/10. 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
Wed 12/1710:47 amEYW - BDL
1 stop11h 59mBreeze Airways
Deal found 11/10$183
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 11/10$187
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/142:03 pmBDL - EYW
1 stop18h 12mMultiple Airlines
Wed 12/1710:47 amEYW - BDL
1 stop11h 59mMultiple Airlines
Deal found 11/10$189
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/142:03 pmBDL - EYW
1 stop18h 12mMultiple Airlines
Thu 12/188:55 amEYW - BDL
1 stop10h 22mMultiple Airlines
Deal found 11/10$199
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 12/142:01 pmBDL - EYW
2 stops18h 14mBreeze Airways
Wed 12/1710:47 amEYW - BDL
1 stop11h 59mBreeze Airways
Deal found 11/10$212
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/156:00 amBDL - EYW
1 stop9h 04mMultiple Airlines
Wed 12/1710:47 amEYW - BDL
1 stop11h 59mMultiple Airlines
Deal found 11/12$224
This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Fri 12/121:19 pmBDL - EYW
2 stops24h 11mMultiple Airlines
Wed 12/1710:47 amEYW - BDL
1 stop11h 59mMultiple Airlines
Deal found 11/10$233
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 11/228:05 amBDL - EYW
1 stop24h 10mMultiple Airlines
Thu 11/278:55 amEYW - BDL
1 stop10h 37mMultiple Airlines
Deal found 11/10$238
This Breeze Airways deal was found by Cheapflights users on 11/13. 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.
Thu 11/131:33 pmBDL - EYW
1 stop20h 58mBreeze Airways
Thu 11/2010:59 amEYW - BDL
1 stop25h 46mBreeze Airways
Deal found 11/13$240
This Mytrip deal was found by Cheapflights users on 11/13. 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.
Thu 12/119:59 amALB - EYW
1 stop5h 45mMultiple Airlines
Thu 12/1810:32 pmEYW - ALB
2 stops17h 01mMultiple Airlines
Deal found 11/13$245
This Delta deal was found by Cheapflights users on 11/10. 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.
Sun 12/75:40 amBOS - EYW
1 stop6h 03mDelta
Sat 12/136:10 pmEYW - BOS
1 stop7h 17mDelta
Deal found 11/10$259

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 13, 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

Wed 12/10

8:05 am-8:15 am

1 stop24h 10m

Key West

Wed 12/17

10:47 am-10:46 pm

1 stop11h 59m

$173

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 12/13

8:05 am-8:15 am

1 stop24h 10m

Key West

Wed 12/17

10:47 am-10:46 pm

1 stop11h 59m

$187

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sun 12/14

2:03 pm-8:15 am

1 stop18h 12m

Key West

Thu 12/18

8:55 am-11:02 pm

2 stops14h 07m

$206

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

$230

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Thu 1/29

3:00 pm-9:09 am

1 stop18h 09m

Key West

Thu 2/5

11:01 am-10:04 pm

1 stop11h 03m

$236

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Fri 2/6

1:11 pm-10:09 am

2 stops20h 58m

Key West

Sun 2/8

9:46 am-11:56 pm

2 stops14h 10m

$240

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Wed 2/25

8:05 am-9:06 am

1 stop25h 01m

Key West

Mon 3/2

1:06 pm-4:20 pm

1 stop27h 14m

$240

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Wed 2/4

8:05 am-9:06 am

1 stop25h 01m

Key West

Sun 2/8

9:46 am-11:56 pm

2 stops14h 10m

$248

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Wed 12/10

12:10 pm-8:06 pm

1 stop7h 56m

Key West

Sat 12/13

6:10 pm-1:27 am

1 stop7h 17m

$259

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Thu 3/5

2:04 pm-12:26 pm

2 stops22h 22m

Key West

Mon 3/9

1:06 pm-4:20 pm

1 stop27h 14m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 48 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 $306). 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 13, 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 03m. Breeze Airways provides one of the quickest options available for as low as $291. The distance from Massachusetts to Key West is about 1374 mi. This flight may include one or multiple stops.

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

    $85 is the cheapest one-way deal found within the past few days, from Breeze Airways. You may also be able to find cheap deals on JetBlue and Allegiant Air, with prices starting from $96 and $180, 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 $116. On average you can expect to pay $297. The most popular route, (Boston Logan Intl - Key West), can usually be booked for $184.

  • 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 $306). 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 13, 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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