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$86+ 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 12/21. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
janv. 1 — janv. 81
jeu. 1/1
jeu. 1/8
1 adult, Economy
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Cheap 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 décembre 2, 2025.

This Kissandfly.com deal was found by Cheapflights users on 12/1. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 12/712:45 pmEYW - BOS
Nonstop3h 30mJetBlue
lun. 12/158:02 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 12/1$164
This Expedia deal was found by Cheapflights users on 11/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/3012:20 pmEYW - BOS
1 stop11h 37mSpirit Airlines
mar. 1/65:45 amBOS - EYW
1 stop5h 35mSpirit Airlines
Deal found 11/30$223
This Kiwi.com deal was found by Cheapflights users on 11/30. 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.
ven. 12/261:10 pmEYW - BDL
2 stops9h 33mBreeze Airways
sam. 1/38:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Deal found 11/30$238
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
ven. 12/191:10 pmEYW - BOS
1 stop20h 51mMultiple Airlines
lun. 12/2212:29 pmBOS - EYW
2 stops22h 51mMultiple Airlines
Deal found 12/1$256
This Kiwi.com deal was found by Cheapflights users on 11/30. 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.
lun. 12/158:55 amEYW - BOS
1 stop10h 11mMultiple Airlines
ven. 12/198:18 amBOS - EYW
2 stops29h 12mMultiple Airlines
Deal found 11/30$264
This Delta deal was found by Cheapflights users on 11/29. 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.
jeu. 12/117:40 amEYW - BOS
1 stop8h 01mDelta
lun. 12/156:45 amBOS - EYW
1 stop7h 22mDelta
Deal found 11/29$267
This United Airlines deal was found by Cheapflights users on 12/1. 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.
ven. 12/265:10 pmEYW - BDL
1 stop6h 48mUnited Airlines
sam. 1/36:00 amBDL - EYW
1 stop5h 41mUnited Airlines
Deal found 12/1$269
This Kiwi.com deal was found by Cheapflights users on 11/30. 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.
mar. 12/3012:20 pmEYW - BOS
2 stops21h 48mMultiple Airlines
mar. 1/611:55 amBOS - EYW
1 stop25h 35mMultiple Airlines
Deal found 11/30$273
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
ven. 12/191:10 pmEYW - BOS
1 stop20h 51mMultiple Airlines
dim. 12/2110:56 amBOS - EYW
1 stop25h 34mMultiple Airlines
Deal found 12/1$294
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
sam. 12/202:30 pmEYW - BOS
1 stop9h 27mSpirit Airlines
lun. 12/2212:29 pmBOS - EYW
2 stops22h 51mSpirit Airlines
Deal found 12/1$300
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
dim. 12/79:59 amEYW - BOS
1 stop23h 07mMultiple Airlines
lun. 12/158:28 amBOS - EYW
2 stops26h 37mMultiple Airlines
Deal found 12/1$305
This Priceline deal was found by Cheapflights users on 12/1. 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.
sam. 12/202:30 pmEYW - BOS
1 stop9h 27mSpirit Airlines
mar. 12/235:45 amBOS - EYW
1 stop5h 35mSpirit Airlines
Deal found 12/1$315

Find 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 décembre 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$217
(Delta)

One-way from

$86
(Kiwi.com)

Popular in

September

Cheapest in

June

Average price

$475

Good round-trip deal

$440 or less

Good one-way deal

$201 or less
Provider with most accurate pricing for Key West-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Boston Logan Intl flights.
Search Deals
From Key West to Massachusetts
Search Deals
One-way flight from Key West to Massachusetts
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Key West to Massachusetts.
Search Deals
Price to beat on a one-way flight from Key West to Massachusetts.
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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 décembre 2, 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

mer. 3/4

7:10 am-2:15 pm

1 stop7h 05m

Boston Logan Intl

mar. 3/10

12:40 pm-7:41 pm

1 stop7h 01m

$217

Key WestHartford

EYW - BDL

EYWBDL

Key West

jeu. 1/22

6:06 pm-11:55 pm

1 stop5h 49m

Hartford Bradley Intl

lun. 1/26

11:22 am-7:40 pm

1 stop8h 18m

$219

Key WestHartford

EYW - BDL

EYWBDL

Key West

ven. 12/26

1:10 pm-10:43 pm

2 stops9h 33m

Hartford Bradley Intl

sam. 1/3

8:05 am-8:15 am

1 stop24h 10m

$238

Key WestBoston

EYW - BOS

EYWBOS

Key West

mer. 3/18

12:25 pm-12:07 am

1 stop11h 42m

Boston Logan Intl

mer. 3/25

5:04 pm-11:30 am

1 stop18h 26m

$269

Key WestHartford

EYW - BDL

EYWBDL

Key West

ven. 12/26

5:10 pm-11:58 pm

1 stop6h 48m

Hartford Bradley Intl

sam. 1/3

6:00 am-11:41 am

1 stop5h 41m

$269

Key WestWorcester

EYW - ORH

EYWORH

Key West

ven. 1/23

7:10 am-3:36 pm

2 stops8h 26m

Worcester

mar. 1/27

4:16 pm-12:48 pm

1 stop20h 32m

$276

Key WestWorcester

EYW - ORH

EYWORH

Key West

ven. 1/23

5:24 pm-1:58 pm

1 stop20h 34m

Worcester

mar. 1/27

2:18 pm-7:10 pm

2 stops28h 52m

$282

Key WestBoston

EYW - BOS

EYWBOS

Key West

mar. 3/17

7:35 am-4:18 pm

1 stop8h 43m

Boston Logan Intl

lun. 3/23

11:10 am-7:41 pm

1 stop8h 31m

$288

Key WestBoston

EYW - BOS

EYWBOS

Key West

jeu. 3/19

7:35 am-4:18 pm

1 stop8h 43m

Boston Logan Intl

mar. 3/24

11:10 am-5:28 pm

1 stop6h 18m

$288

Key WestBoston

EYW - BOS

EYWBOS

Key West

ven. 12/19

1:10 pm-10:01 am

1 stop20h 51m

Boston Logan Intl

lun. 12/22

11:55 am-11:20 am

1 stop23h 25m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/1

Showing 1-10 of 45 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 décembre 2, 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 45% versus a flight at noon.

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 décembre 2, 2025.
See what other customers who have flown with 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.
American Airlines
7.2
Good
11,042 reviews

Crew

8.0

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,042 reviews
American Airlines
7.2
Good
11,042 reviews

Crew

8.0

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
JetBlue
7.2
Good
2,904 reviews
American Airlines
7.2
Good
11,042 reviews

Crew

8.0

Entertainment

6.9

Boarding

7.5

Comfort

7.2

Food

6.5

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 7h 05m. 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 $108 on Delta. Other airlines that offer cheap prices include United Airlines from $118 and American Airlines from $128 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 most reliable airlines from Key West to Massachusetts?

    Consider JetBlue (54%), Qatar Airways (52%) or TAP AIR PORTUGAL (52%) when booking your flight. These represent the most reliable airlines when flying from Key West to Massachusetts.

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

    On average you can expect to pay $417 for a flight from Key West to Massachusetts. The cheapest flight overall is $177 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $164.

  • 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

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Key West to Massachusetts

Discover the top 2 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 décembre 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$344FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$251Average$474FlexibilityNo cancel feeOn-time62%

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