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Key West

$89+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Feb 6 — Feb 131
Fri 2/6
Fri 2/13
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 January 7, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$170
(American Airlines)

One-way from

$89
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$381

Good round-trip deal

$340 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. 16% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 7, 2026.

This Breeze Airways deal was found by Cheapflights users on 1/5. 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.
Sun 1/183:00 pmBDL - EYW
1 stop18h 09mBreeze Airways
Thu 1/2211:06 amEYW - BDL
1 stop10h 58mBreeze Airways
Deal found 1/5$157
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/103:59 pmBDL - EYW
1 stop17h 27mBreeze Airways
Thu 1/1510:06 amEYW - BDL
2 stops13h 50mBreeze Airways
Deal found 1/6$164
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/219:00 pmBDL - EYW
1 stop12h 06mMultiple Airlines
Thu 2/269:46 amEYW - BDL
1 stop24h 02mMultiple Airlines
Deal found 1/6$174
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/318:01 pmBDL - EYW
1 stop13h 25mMultiple Airlines
Fri 2/131:06 pmEYW - BDL
1 stop21h 58mMultiple Airlines
Deal found 1/5$175
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/18:31 pmBDL - EYW
1 stop15h 55mMultiple Airlines
Fri 2/131:06 pmEYW - BDL
1 stop21h 58mMultiple Airlines
Deal found 1/5$178
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/48:05 amBDL - EYW
1 stop25h 01mBreeze Airways
Thu 2/1211:01 amEYW - BDL
1 stop11h 03mBreeze Airways
Deal found 1/5$179
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/318:01 pmBDL - EYW
1 stop13h 25mMultiple Airlines
Thu 2/124:21 pmEYW - BDL
1 stop25h 08mMultiple Airlines
Deal found 1/5$185
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/318:01 pmBDL - EYW
1 stop13h 25mMultiple Airlines
Mon 2/91:06 pmEYW - BDL
1 stop22h 18mMultiple Airlines
Deal found 1/5$186
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/18:31 pmBDL - EYW
1 stop15h 55mMultiple Airlines
Thu 2/124:21 pmEYW - BDL
1 stop25h 08mMultiple Airlines
Deal found 1/5$188
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/18:31 pmBDL - EYW
1 stop15h 55mMultiple Airlines
Mon 2/91:06 pmEYW - BDL
1 stop22h 18mMultiple Airlines
Deal found 1/5$189
This Priceline deal was found by Cheapflights users on 1/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:34 amBOS - EYW
1 stop6h 22mSpirit Airlines
Thu 2/122:25 pmEYW - BOS
1 stop9h 19mSpirit Airlines
Deal found 1/6$203
This JetBlue deal was found by Cheapflights users on 1/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/28:09 amBOS - EYW
Nonstop3h 56mJetBlue
Thu 2/51:00 pmEYW - BOS
Nonstop3h 36mJetBlue
Deal found 1/7$204

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 January 7, 2026.
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

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Fri 2/6

2:18 pm-10:53 am

2 stops20h 35m

Key West

Mon 2/9

4:37 pm-1:53 pm

2 stops21h 16m

$208

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 1/26

6:00 am-1:03 pm

1 stop7h 03m

Key West

Wed 2/4

2:25 pm-11:49 pm

2 stops9h 24m

$212

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Tue 2/3

1:30 pm-7:40 pm

1 stop6h 10m

Key West

Wed 2/11

6:06 pm-1:04 am

1 stop6h 58m

$217

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 2/9

6:00 am-3:17 pm

1 stop9h 17m

Key West

Wed 2/11

2:25 pm-9:52 pm

1 stop7h 27m

$217

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 3/7

3:59 pm-8:06 am

1 stop16h 07m

Key West

Wed 3/11

11:51 am-4:56 pm

2 stops29h 05m

$225

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sun 2/22

10:30 am-5:44 pm

1 stop7h 14m

Key West

Thu 2/26

2:15 pm-11:57 pm

2 stops9h 42m

$234

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Wed 2/4

9:45 am-4:22 pm

1 stop6h 37m

Key West

Wed 2/11

2:25 pm-9:52 pm

1 stop7h 27m

$235

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Mon 2/23

1:11 pm-12:21 pm

2 stops23h 10m

Key West

Fri 2/27

9:49 am-10:53 pm

2 stops13h 04m

$238

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Mon 1/19

2:18 pm-10:57 am

2 stops20h 39m

Key West

Fri 1/23

5:24 pm-1:58 pm

1 stop20h 34m

$242

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 2/23

6:00 am-12:45 pm

1 stop6h 45m

Key West

Thu 2/26

5:56 pm-1:09 am

1 stop7h 13m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

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 $163). Flying from Massachusetts to Key West in March is currently the most expensive (average of $297). 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 January 7, 2026.

When flying from Massachusetts 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.

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 6h 10m. American Airlines provides one of the quickest options available for as low as $217. 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?

    $103 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on American Airlines and JetBlue, with prices starting from $119 and $128, 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 most reliable airlines from Massachusetts to Key West?

    No one likes to see their flight delayed. When booking a flight from Massachusetts to Key West consider choosing JetBlue (75%), TAP AIR PORTUGAL (73%) or American Airlines (47%) as they are the most reliable in getting you off to your destination on time.

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

    The cheapest flight price from Massachusetts to Key West is $96. On average you can expect to pay $320. The most popular route, (Boston Logan Intl - Key West), can usually be booked for $178.

  • 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 $163). Flying from Massachusetts to Key West in March is currently the most expensive (average of $297). 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 January 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$83Average$182FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$135Average$389FlexibilityNo cancel feeOn-time69%
DeltaCheapest$206Average$407FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$247Average$412FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$273Average$528FlexibilityNo cancel feeOn-time62%

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