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Key West

$108+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$217
(JetBlue)

One-way from

$108
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$316

Good round-trip deal

$312 or less

Good one-way deal

$203 or less
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 ($92 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 September 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 September 17, 2025.

This JetBlue deal was found by Cheapflights users on 9/17. 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 10/138:10 amBOS - EYW
Nonstop3h 59mJetBlue
Thu 10/161:04 pmEYW - BOS
Nonstop3h 52mJetBlue
Deal found 9/17$217
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 10/286:00 amBOS - EYW
1 stop7h 52mUnited Airlines
Mon 11/33:00 pmEYW - BOS
1 stop7h 47mUnited Airlines
Deal found 9/15$222
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 12/65:52 amBOS - EYW
1 stop6h 13mAmerican Airlines
Wed 12/107:30 amEYW - BOS
1 stop7h 12mAmerican Airlines
Deal found 9/15$227
This Travelocity deal was found by Cheapflights users on 9/17. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:45 amBOS - EYW
1 stop7h 45mSpirit Airlines
Sun 12/72:25 pmEYW - BOS
1 stop10h 15mSpirit Airlines
Deal found 9/17$230
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/137:00 amBOS - EYW
1 stop5h 55mAmerican Airlines
Fri 10/1711:22 amEYW - BOS
2 stops8h 13mAmerican Airlines
Deal found 9/16$232
This Priceline deal was found by Cheapflights users on 9/16. 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.
Mon 10/138:10 amBOS - EYW
Nonstop3h 59mJetBlue
Fri 10/171:04 pmEYW - BOS
Nonstop3h 52mJetBlue
Deal found 9/16$234
This Orbitz deal was found by Cheapflights users on 9/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/95:45 amBOS - EYW
1 stop7h 45mSpirit Airlines
Sun 11/162:25 pmEYW - BOS
1 stop10h 15mSpirit Airlines
Deal found 9/16$235
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 10/44:24 pmORH - EYW
2 stops21h 05mAmerican Airlines
Sat 10/255:10 pmEYW - ORH
2 stops22h 40mAmerican Airlines
Deal found 9/15$237
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Tue 10/149:20 amBOS - EYW
2 stops7h 56mAmerican Airlines
Sat 10/1811:22 amEYW - BOS
2 stops8h 57mAmerican Airlines
Deal found 9/15$237
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/1511:00 amBOS - EYW
2 stops8h 22mAmerican Airlines
Wed 10/2211:22 amEYW - BOS
2 stops8h 13mAmerican Airlines
Deal found 9/15$242
This Travelocity deal was found by Cheapflights users on 9/14. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/45:45 amBOS - EYW
1 stop7h 45mSpirit Airlines
Mon 12/82:25 pmEYW - BOS
1 stop10h 15mSpirit Airlines
Deal found 9/14$245
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/75:21 amBOS - EYW
1 stop6h 44mAmerican Airlines
Sat 12/131:57 pmEYW - BOS
1 stop6h 59mAmerican Airlines
Deal found 9/14$247

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 September 17, 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

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 10/13

8:10 am-12:09 pm

Nonstop3h 59m

Key West

Thu 10/16

1:04 pm-4:56 pm

Nonstop3h 52m

$217

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Tue 9/30

5:35 am-10:55 am

1 stop5h 20m

Key West

Fri 10/3

6:10 pm-1:18 am

1 stop7h 08m

$227

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Tue 10/7

4:17 pm-12:58 pm

2 stops20h 41m

Key West

Tue 10/28

5:47 pm-3:50 pm

2 stops22h 03m

$237

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sat 10/4

4:24 pm-1:29 pm

2 stops21h 05m

Key West

Sat 10/25

5:10 pm-3:50 pm

2 stops22h 40m

$237

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sun 10/12

6:00 am-2:29 pm

1 stop8h 29m

Key West

Thu 10/16

3:12 pm-10:56 pm

1 stop7h 44m

$247

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 12/15

6:00 am-3:09 pm

1 stop9h 09m

Key West

Fri 12/19

3:09 pm-10:48 pm

1 stop7h 39m

$247

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Thu 12/11

8:00 am-1:51 pm

1 stop5h 51m

Key West

Sun 12/14

5:09 pm-10:40 pm

1 stop5h 31m

$247

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Fri 10/31

9:55 am-10:07 am

2 stops24h 12m

Key West

Fri 11/7

9:01 am-9:43 am

1 stop24h 42m

$249

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Mon 11/10

7:00 am-11:05 am

2 stops28h 05m

Key West

Fri 11/14

11:11 am-5:26 pm

1 stop6h 15m

$260

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 10/18

8:10 am-12:09 pm

Nonstop3h 59m

Key West

Fri 10/24

1:04 pm-4:56 pm

Nonstop3h 52m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 53 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, August is the cheapest month in which you can book a flight from Massachusetts to Key West (average of $328). Flying from Massachusetts to Key West in March is currently the most expensive (average of $491). 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 September 17, 2025.

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 3h 59m. JetBlue 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?

    $108 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 American Airlines, with prices starting from $114 and $175, 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 $123. On average you can expect to pay $344. The most popular route, (Boston Logan Intl - Key West), can usually be booked for $207.

  • 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, August is the cheapest month in which you can book a flight from Massachusetts to Key West (average of $328). Flying from Massachusetts to Key West in March is currently the most expensive (average of $491). 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$102FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$145Average$378FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$367FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$217Average$527FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$251Average$408FlexibilityNo cancel feeOn-time71%

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