Key West

$86+ 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
Aug 27 — Sep 31
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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 August 22, 2025.

Round-trip from

$209
(American Airlines)

One-way from

$86
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$350

Good round-trip deal

$332 or less

Good one-way deal

$158 or less
From Massachusetts to Key West
One-way flight from Massachusetts to Key West
Highest demand for flights based on searches. 16% potential increase in price ($86 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Average for round-trip flights in August 2025
Price to beat on a round-trip flight from Massachusetts to Key West.
Price to beat on a one-way flight from Massachusetts to Key West.

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 August 22, 2025.

This American Airlines deal was found by Cheapflights users on 8/20. 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 12/136:00 amBOS - EYW
1 stop5h 42mAmerican Airlines
Fri 12/197:35 pmEYW - BOS
1 stop4h 59mAmerican Airlines
Deal found 8/20$209
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:30 amBOS - EYW
1 stop6h 39mAmerican Airlines
Thu 12/113:55 pmEYW - BOS
1 stop5h 00mAmerican Airlines
Deal found 8/21$214
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/611:14 amBOS - EYW
1 stop5h 24mAmerican Airlines
Sat 9/137:31 pmEYW - BOS
1 stop5h 28mAmerican Airlines
Deal found 8/20$215
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1411:05 amBOS - EYW
2 stops8h 17mAmerican Airlines
Sat 10/1811:22 amEYW - BOS
1 stop4h 50mAmerican Airlines
Deal found 8/21$219
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Fri 12/127:52 amBOS - EYW
1 stop5h 21mAmerican Airlines
Mon 12/155:19 pmEYW - BOS
1 stop5h 08mAmerican Airlines
Deal found 8/20$223
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/59:45 amBOS - EYW
1 stop8h 06mAmerican Airlines
Tue 11/118:00 pmEYW - BOS
1 stop4h 46mAmerican Airlines
Deal found 8/21$225
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Fri 9/129:17 amBOS - EYW
2 stops9h 42mAmerican Airlines
Mon 9/157:31 pmEYW - BOS
1 stop5h 28mAmerican Airlines
Deal found 8/20$228
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:45 pmBOS - EYW
1 stop6h 21mDelta
Tue 11/46:17 pmEYW - BOS
1 stop6h 56mDelta
Deal found 8/21$229
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/129:17 amBOS - EYW
2 stops9h 42mAmerican Airlines
Tue 9/1611:25 amEYW - BOS
2 stops9h 00mAmerican Airlines
Deal found 8/19$234
This Delta deal was found by Cheapflights users on 8/20. 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.
Sat 9/61:35 pmBOS - EYW
1 stop6h 37mDelta
Tue 9/96:20 pmEYW - BOS
1 stop7h 01mDelta
Deal found 8/20$239
This American Airlines deal was found by Cheapflights users on 8/19. 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 11/11:42 pmALB - EYW
1 stop8h 14mAmerican Airlines
Wed 11/57:31 amEYW - ALB
1 stop5h 15mAmerican Airlines
Deal found 8/19$283
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:25 amBDL - EYW
1 stop5h 46mAmerican Airlines
Sat 10/114:57 pmEYW - BDL
1 stop6h 04mAmerican Airlines
Deal found 8/21$283

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 August 22, 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

Tue 10/28

7:30 am-1:52 pm

1 stop6h 22m

Key West

Sat 11/1

7:52 pm-12:34 am

1 stop4h 42m

$214

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Wed 10/15

6:00 am-1:52 pm

1 stop7h 52m

Key West

Sat 10/18

7:52 pm-12:34 am

1 stop4h 42m

$214

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Fri 9/26

1:05 pm-6:59 pm

1 stop5h 54m

Key West

Tue 9/30

7:31 pm-12:59 am

1 stop5h 28m

$214

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Tue 10/7

7:30 am-1:52 pm

1 stop6h 22m

Key West

Fri 10/10

7:52 pm-12:34 am

1 stop4h 42m

$214

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Fri 10/3

1:05 pm-6:59 pm

1 stop5h 54m

Key West

Tue 10/7

2:14 pm-7:55 pm

1 stop5h 41m

$214

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 10/25

6:00 am-12:10 pm

1 stop6h 10m

Key West

Thu 10/30

5:47 pm-11:30 pm

1 stop5h 43m

$214

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 11/8

1:13 pm-9:49 pm

1 stop8h 36m

Key West

Wed 11/12

7:31 am-12:33 pm

1 stop5h 02m

$214

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Wed 11/5

9:45 am-5:51 pm

1 stop8h 06m

Key West

Sun 11/9

8:06 am-3:38 pm

1 stop7h 32m

$214

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Tue 10/14

7:10 am-12:58 pm

1 stop5h 48m

Key West

Sat 10/18

7:52 pm-12:34 am

1 stop4h 42m

$214

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 11/10

1:23 pm-9:48 pm

1 stop8h 25m

Key West

Tue 11/11

8:00 pm-12:46 am

1 stop4h 46m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 49 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 $492). 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 August 22, 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 6h 22m. American Airlines provides one of the quickest options available for as low as $214. The distance from Massachusetts to Key West is about 1374 mi.

  • What are the most popular routes 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 $148. On average you can expect to pay $296. The most popular route, (Boston Logan Intl - Key West), can usually be booked for $217.

  • 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 $492). 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

See prices for flight routes from nearby airports that may be better suited for you.

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 August 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$102FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$145Average$379FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$213Average$526FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$344FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$262Average$412FlexibilityNo cancel feeOn-time71%

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