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$90+ 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 2/13. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$233
(United Airlines)

One-way from

$90
(Kiwi.com)

Popular in

September

Cheapest in

November

Average price

$476

Good round-trip deal

$388 or less

Good one-way deal

$225 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. 6% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 15, 2026.

This Breeze Airways deal was found by Cheapflights users on 1/14. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2311:04 am
EYW
-
BDL
1 stop6h 44m
Breeze Airways
Sun 1/253:00 pm
BDL
-
EYW
1 stop18h 09m
Breeze Airways
Deal found 1/14$201
This United Airlines deal was found by Cheapflights users on 1/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/122:15 pm
EYW
-
BOS
1 stop7h 36m
United Airlines
Mon 2/1610:30 am
BOS
-
EYW
1 stop7h 14m
United Airlines
Deal found 1/14$234
This United Airlines deal was found by Cheapflights users on 1/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/296:05 pm
EYW
-
BOS
1 stop5h 44m
United Airlines
Mon 2/29:30 am
BOS
-
EYW
1 stop6h 52m
United Airlines
Deal found 1/14$237
This Expedia deal was found by Cheapflights users on 1/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2912:51 pm
EYW
-
BOS
1 stop11h 06m
Multiple Airlines
Mon 2/28:09 am
BOS
-
EYW
Nonstop3h 56m
Multiple Airlines
Deal found 1/14$250
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/91:06 pm
EYW
-
BDL
1 stop22h 18m
Multiple Airlines
Wed 2/1810:19 am
BDL
-
EYW
1 stop29h 00m
Multiple Airlines
Deal found 1/15$263
This United Airlines deal was found by Cheapflights users on 1/15. 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.
Thu 1/222:25 pm
EYW
-
BOS
1 stop7h 27m
United Airlines
Thu 1/296:00 am
BOS
-
EYW
1 stop9h 17m
United Airlines
Deal found 1/15$267
This Expedia deal was found by Cheapflights users on 1/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1912:25 pm
EYW
-
BOS
1 stop11h 34m
Spirit Airlines
Sun 3/225:40 am
BOS
-
EYW
1 stop5h 50m
Spirit Airlines
Deal found 1/15$269
This United Airlines deal was found by Cheapflights users on 1/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/56:05 pm
EYW
-
BOS
1 stop5h 44m
United Airlines
Mon 2/96:00 am
BOS
-
EYW
1 stop9h 17m
United Airlines
Deal found 1/14$277
This American Airlines deal was found by Cheapflights users on 1/15. 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 2/104:37 pm
EYW
-
BDL
2 stops7h 07m
American Airlines
Wed 2/255:10 pm
BDL
-
EYW
1 stop5h 12m
American Airlines
Deal found 1/15$291
This American Airlines deal was found by Cheapflights users on 1/15. 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 2/106:06 am
EYW
-
BDL
2 stops8h 43m
American Airlines
Mon 2/237:44 am
BDL
-
EYW
1 stop8h 13m
American Airlines
Deal found 1/15$294
This Delta deal was found by Cheapflights users on 1/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/226:06 pm
EYW
-
BOS
1 stop6h 58m
Delta
Tue 1/276:00 am
BOS
-
EYW
1 stop6h 48m
Delta
Deal found 1/14$297
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/710:49 am
EYW
-
BDL
2 stops37h 07m
Multiple Airlines
Wed 2/1810:19 am
BDL
-
EYW
1 stop29h 00m
Multiple Airlines
Deal found 1/15$308

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 January 15, 2026.
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 2/12

2:15 pm-9:51 pm

1 stop7h 36m

Boston Logan Intl

Mon 2/16

10:30 am-5:44 pm

1 stop7h 14m

$234

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/29

6:05 pm-11:49 pm

1 stop5h 44m

Boston Logan Intl

Mon 2/2

9:30 am-4:22 pm

1 stop6h 52m

$237

Key WestHartford

EYW - BDL

EYWBDL

Key West

Mon 2/9

1:06 pm-11:24 am

1 stop22h 18m

Hartford Bradley Intl

Wed 2/18

10:19 am-3:19 pm

1 stop29h 00m

$263

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 3/19

12:25 pm-11:59 pm

1 stop11h 34m

Boston Logan Intl

Sun 3/22

5:40 am-11:30 am

1 stop5h 50m

$269

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 2/5

2:25 pm-11:49 pm

2 stops9h 24m

Boston Logan Intl

Mon 2/9

6:00 am-3:17 pm

1 stop9h 17m

$282

Key WestHartford

EYW - BDL

EYWBDL

Key West

Tue 2/10

6:06 am-2:49 pm

2 stops8h 43m

Hartford Bradley Intl

Wed 2/18

5:10 pm-10:22 pm

1 stop5h 12m

$291

Key WestHartford

EYW - BDL

EYWBDL

Key West

Tue 2/10

6:06 am-2:49 pm

2 stops8h 43m

Hartford Bradley Intl

Mon 2/23

7:44 am-3:57 pm

1 stop8h 13m

$294

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 2/13

5:19 pm-11:59 pm

1 stop6h 40m

Boston Logan Intl

Mon 2/16

6:00 am-1:48 pm

1 stop7h 48m

$307

Key WestHartford

EYW - BDL

EYWBDL

Key West

Tue 2/10

6:05 pm-11:44 pm

1 stop5h 39m

Hartford Bradley Intl

Wed 2/18

10:30 am-4:07 pm

1 stop5h 37m

$311

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sat 2/7

6:05 pm-11:44 pm

1 stop5h 39m

Hartford Bradley Intl

Wed 2/18

10:30 am-4:07 pm

1 stop5h 37m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 43 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 May is currently the most expensive (average of $320). 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 January 15, 2026.

When flying from Key West to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Key West to Massachusetts

Explore weekly flight availability from Key West to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 15, 2026.

The most flights from EYW to USMA are scheduled on a Thursday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 January 15, 2026.
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
11,132 reviews

Comfort

7.2

Overall

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,132 reviews
American Airlines
7.2
Good
11,132 reviews

Comfort

7.2

Overall

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
JetBlue
7.2
Good
2,887 reviews
American Airlines
7.2
Good
11,132 reviews

Comfort

7.2

Overall

7.2

Entertainment

6.9

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 36m. 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 $128 on American Airlines. Other airlines that offer cheap prices include United Airlines from $148 and Delta from $148 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 (85%), TAP AIR PORTUGAL (84%) or Qatar Airways (42%) 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 $317 for a flight from Key West to Massachusetts. The cheapest flight overall is $173 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $234.

  • 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 May is currently the most expensive (average of $320). 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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Alternative routes for Key West to Massachusetts

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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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$346FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$277Average$442FlexibilityNo cancel feeOn-time62%

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