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$104+ Cheap flights from Key West (EYW) to Massachusetts

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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheap flight deals from Key West to Massachusetts

Keep the following information in mind while searching for Key West to Massachusetts flight deals. Data was last updated October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$217
(JetBlue)

One-way from

$104
(Kiwi.com)

Popular in

September

Cheapest in

June

Average price

$353

Good round-trip deal

$332 or less

Good one-way deal

$203 or less
Provider with most accurate pricing for Key West-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Key West-Boston Logan Intl flights.
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From Key West to Massachusetts
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One-way flight from Key West to Massachusetts
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Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Key West to Massachusetts.
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Price to beat on a one-way flight from Key West to Massachusetts.
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Find flight deals from Key West to Massachusetts

Cheapest flights from Key West to Massachusetts
Explore the most affordable flight options available from Key West to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This JetBlue deal was found by Cheapflights users on 10/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:45 pmEYW - BOS
Nonstop3h 30mJetBlue
Mon 11/38:00 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 10/12$217
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Thu 10/303:23 pmEYW - BOS
1 stop17h 05mMultiple Airlines
Tue 11/46:16 amBOS - EYW
2 stops26h 55mMultiple Airlines
Deal found 10/12$222
This JetBlue deal was found by Cheapflights users on 10/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3012:45 pmEYW - BOS
Nonstop3h 30mJetBlue
Sun 11/28:00 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 10/13$227
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Thu 11/69:36 pmEYW - BOS
1 stop10h 52mMultiple Airlines
Mon 11/1012:20 pmBOS - EYW
2 stops22h 45mMultiple Airlines
Deal found 10/12$231
This JetBlue deal was found by Cheapflights users on 10/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3112:45 pmEYW - BOS
Nonstop3h 30mJetBlue
Sun 11/28:00 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 10/13$237
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:17 pmEYW - BOS
1 stop6h 56mDelta
Mon 11/1012:10 pmBOS - EYW
1 stop7h 43mDelta
Deal found 10/13$247
This Kiwi.com deal was found by Cheapflights users on 10/11. 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.
Thu 10/303:23 pmEYW - BOS
1 stop17h 05mMultiple Airlines
Sun 11/28:40 amBOS - EYW
2 stops23h 35mMultiple Airlines
Deal found 10/11$253
This Priceline deal was found by Cheapflights users on 10/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:04 pmEYW - BOS
Nonstop3h 52mJetBlue
Sun 10/268:00 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 10/12$257
This Priceline deal was found by Cheapflights users on 10/11. 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.
Wed 11/2612:49 pmEYW - BOS
Nonstop3h 31mJetBlue
Sat 11/298:00 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 10/11$270
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/156:17 pmEYW - BOS
1 stop6h 56mDelta
Tue 10/285:40 amBOS - EYW
1 stop7h 22mDelta
Deal found 10/13$277
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 10/243:39 pmEYW - BOS
1 stop18h 32mMultiple Airlines
Tue 10/283:00 pmBOS - EYW
2 stops19h 07mMultiple Airlines
Deal found 10/11$283
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1710:47 amEYW - BDL
1 stop11h 59mMultiple Airlines
Sun 12/218:39 pmBDL - EYW
1 stop15h 51mMultiple Airlines
Deal found 10/13$294

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Massachusetts 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 October 14, 2025.
Use the filters below to find and compare flights from Key West to Massachusetts that are best for you.

Fly from

Key West

Fly to

Massachusetts

Route

Depart

Return

Price

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 10/30

12:45 pm-4:15 pm

Nonstop3h 30m

Boston Logan Intl

Mon 11/3

8:00 am-11:53 am

Nonstop3h 53m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 11/6

12:45 pm-4:15 pm

Nonstop3h 30m

Boston Logan Intl

Mon 11/10

8:00 am-11:53 am

Nonstop3h 53m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 12/6

12:47 pm-4:17 pm

Nonstop3h 30m

Boston Logan Intl

Sat 12/13

8:02 am-11:55 am

Nonstop3h 53m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 10/30

6:17 pm-1:13 am

1 stop6h 56m

Boston Logan Intl

Tue 11/4

12:10 pm-8:06 pm

1 stop7h 56m

$227

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 10/30

12:45 pm-4:15 pm

Nonstop3h 30m

Boston Logan Intl

Sun 11/2

8:00 am-11:53 am

Nonstop3h 53m

$227

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 10/24

3:12 pm-10:57 pm

1 stop7h 45m

Boston Logan Intl

Tue 10/28

6:00 am-1:52 pm

1 stop7h 52m

$237

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 11/6

7:40 am-3:49 pm

1 stop8h 09m

Boston Logan Intl

Mon 11/10

5:40 am-2:03 pm

1 stop8h 23m

$237

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 10/31

12:45 pm-4:15 pm

Nonstop3h 30m

Boston Logan Intl

Sun 11/2

8:00 am-11:53 am

Nonstop3h 53m

$237

Key WestHartford

EYW - BDL

EYWBDL

Key West

Wed 12/17

10:47 am-10:46 pm

1 stop11h 59m

Hartford Bradley Intl

Sun 12/21

8:39 pm-12:30 pm

1 stop15h 51m

$294

Key WestHartford

EYW - BDL

EYWBDL

Key West

Wed 12/17

10:47 am-10:46 pm

1 stop11h 59m

Hartford Bradley Intl

Sun 12/21

2:06 pm-12:30 pm

2 stops22h 24m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/11

Showing 1-10 of 34 results
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Best time to book a flight from Key West to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Key West 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 Key West to Massachusetts

What is the cheapest month to book a flight from Key West to Massachusetts?

Currently, November is the cheapest month in which you can book a flight from Key West to Massachusetts (average of $170). Flying from Key West to Massachusetts in February is currently the most expensive (average of $331). 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 EYW to MA?

Find hourly flight availability from Key West to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 14, 2025.

When flying from Key West to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 48% versus a flight at noon.

How much does it cost to fly round-trip from Key West to Massachusetts?

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated October 14, 2025.
See what other customers who have flown with Delta, American Airlines, and JetBlue from Key West to Massachusetts have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,973 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
8.0
Very good
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,043 reviews
Delta
8.0
Very good
7,973 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
JetBlue
7.2
Good
2,904 reviews
Delta
8.0
Very good
7,973 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Key West to Massachusetts. 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 from for flights from Key West to Massachusetts?

    If you book a flight to Massachusetts from Key West, you will be flying from 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 Key West to Massachusetts?

    Departing from Key West to Massachusetts will take you 3h 30m. Key West and Massachusetts are separated by a distance of 1374 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    One-way options have recently been found by users for as low as $119 on United Airlines. Other airlines that offer cheap prices include Delta from $129 and JetBlue from $129 one-way.

  • What are the most popular routes from Key West to Massachusetts?

    The most popular flight routes from Key West to Massachusetts are Key West - Boston Logan Intl, Key West - Hartford Bradley Intl and Key West - Worcester.

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

    On average you can expect to pay $278 for a flight from Key West to Massachusetts. The cheapest flight overall is $149 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $215.

  • Can I find deals for flights from Key West to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Key West to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Massachusetts.

  • Can I find deals for business class flights from Key West to Massachusetts?

    Yes. Cheapflights offers flight deals from Key West to Massachusetts 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 Key West to Massachusetts?

    Currently, November is the cheapest month in which you can book a flight from Key West to Massachusetts (average of $170). Flying from Key West to Massachusetts in February is currently the most expensive (average of $331). 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 Key West to Massachusetts

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Top 3 airlines flying from Key West to Massachusetts

Discover the top 3 airlines that operate flights from Key West to Massachusetts. 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$399FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$226Average$346FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$236Average$502FlexibilityNo cancel feeOn-time62%

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