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$99+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Massachusetts to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

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 20, 2024.

This JetBlue deal was found by Cheapflights users on 11/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/98:00 amBOS - EYW
Nonstop3h 55mJetBlue
Fri 12/1312:50 pmEYW - BOS
Nonstop3h 26mJetBlue
Deal found 11/20$207
This Delta deal was found by Cheapflights users on 11/20. 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.
Mon 12/95:25 amBOS - EYW
1 stop7h 59mDelta
Fri 12/136:30 pmEYW - BOS
1 stop6h 42mDelta
Deal found 11/20$216
This American Airlines deal was found by Cheapflights users on 11/19. 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 12/131:50 pmBDL - EYW
1 stop5h 04mAmerican Airlines
Tue 12/173:55 pmEYW - BDL
1 stop7h 46mAmerican Airlines
Deal found 11/19$243
This American Airlines deal was found by Cheapflights users on 11/18. 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 12/149:00 amBOS - EYW
Nonstop4h 10mAmerican Airlines
Wed 12/188:05 amEYW - BOS
1 stop5h 28mAmerican Airlines
Deal found 11/18$249
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/175:45 amBOS - EYW
2 stops9h 16mUnited Airlines
Sat 12/214:19 pmEYW - BOS
1 stop8h 35mUnited Airlines
Deal found 11/19$251
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/308:30 pmBOS - EYW
1 stop13h 11mMultiple Airlines
Sun 1/55:56 pmEYW - BOS
1 stop16h 02mMultiple Airlines
Deal found 11/20$270
This American Airlines deal was found by Cheapflights users on 11/18. 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 12/42:37 pmORH - EYW
2 stops25h 59mAmerican Airlines
Sun 12/81:44 pmEYW - ORH
2 stops24h 10mAmerican Airlines
Deal found 11/18$337
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/52:24 pmBDL - EYW
1 stop6h 06mDelta
Tue 12/107:25 amEYW - BDL
1 stop6h 00mDelta
Deal found 11/19$378
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/136:10 amBDL - EYW
1 stop8h 51mUnited Airlines
Sun 12/157:40 pmEYW - BDL
2 stops28h 19mUnited Airlines
Deal found 11/20$389
This United Airlines deal was found by Cheapflights users on 11/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/196:00 amALB - EYW
2 stops12h 55mUnited Airlines
Thu 12/262:22 pmEYW - ALB
1 stop5h 41mUnited Airlines
Deal found 11/19$405
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 12/196:10 amALB - EYW
1 stop7h 46mAmerican Airlines
Thu 12/265:05 pmEYW - ALB
1 stop6h 29mAmerican Airlines
Deal found 11/19$408
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/166:05 amALB - EYW
1 stop5h 32mDelta
Fri 12/206:02 pmEYW - ALB
1 stop5h 51mDelta
Deal found 11/19$498

Find flights from Massachusetts to Key West within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sun 1/19

7:40 pm-9:15 am

1 stop13h 35m

Key West

Fri 1/24

10:00 am-7:19 pm

1 stop9h 19m

$198

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 12/9

8:00 am-11:55 am

Nonstop3h 55m

Key West

Fri 12/13

12:50 pm-4:16 pm

Nonstop3h 26m

$207

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 12/9

5:25 am-1:24 pm

1 stop7h 59m

Key West

Fri 12/13

6:30 pm-1:12 am

1 stop6h 42m

$216

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 1/25

2:19 pm-8:11 pm

1 stop5h 52m

Key West

Tue 1/28

6:20 pm-11:56 pm

1 stop5h 36m

$218

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 1/25

6:00 am-4:37 pm

2 stops10h 37m

Key West

Tue 1/28

8:09 am-1:58 pm

1 stop5h 49m

$223

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sun 1/12

6:00 am-12:47 pm

1 stop6h 47m

Key West

Sat 1/18

1:50 pm-9:36 pm

1 stop7h 46m

$244

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 1/25

6:00 am-2:20 pm

1 stop8h 20m

Key West

Sat 2/1

3:05 pm-12:27 am

1 stop9h 22m

$245

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 2/8

9:00 am-1:07 pm

Nonstop4h 07m

Key West

Sat 2/15

1:15 pm-4:51 pm

Nonstop3h 36m

$248

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Sat 2/22

11:40 am-4:40 pm

1 stop5h 00m

Key West

Thu 2/27

4:16 pm-12:14 am

1 stop7h 58m

$268

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Sat 1/4

6:20 am-1:53 pm

1 stop7h 33m

Key West

Sat 1/11

1:45 pm-7:10 pm

1 stop5h 25m

$293

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 29 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.

Travel insights for flights from Massachusetts to Key West

Get recent, data-driven insights about flights from Massachusetts to Key West including ideal travel times, pricing trends, and more.

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 November 20, 2024.

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.

Rainfall in Key West by month

Plan your trip to Key West by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

Plan your trip to Key West by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated November 20, 2024.
See what other customers who have flown with JetBlue, Delta and United Airlines from Massachusetts to Key West have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,756 reviews
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

JetBlue
7.5
Good
3,394 reviews
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
9,171 reviews
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,756 reviews

Comfort

7.9

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Reviews

1 / 10

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

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

    $99 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Delta and United Airlines, with prices starting from $108 and $118, 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 American Airlines (100%), Republic Airways (100%) or JetBlue (96%) 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 $90. On average you can expect to pay $277. 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 $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.

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Top 4 airlines flying from Massachusetts to Key West

Discover the top 4 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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$238Average$392FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$241Average$575FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$253Average$423FlexibilityNo cancel feeOn-time69%
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