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$74+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Jan 23 — Jan 301
Fri 1/23
Fri 1/30
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 December 24, 2025.

This American Airlines deal was found by Cheapflights users on 12/22. 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.
Mon 12/293:25 pmEYW - BOS
Nonstop3h 34mAmerican Airlines
Mon 1/510:44 amBOS - EYW
Nonstop4h 11mAmerican Airlines
Deal found 12/22$217
This United Airlines deal was found by Cheapflights users on 12/22. 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.
Mon 12/291:25 pmEYW - BOS
1 stop5h 23mUnited Airlines
Tue 12/306:01 amBOS - EYW
1 stop9h 11mUnited Airlines
Deal found 12/22$297
This Delta deal was found by Cheapflights users on 12/22. 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 12/296:20 pmEYW - BOS
1 stop6h 47mDelta
Mon 1/55:35 amBOS - EYW
1 stop8h 13mDelta
Deal found 12/22$318
This American Airlines deal was found by Cheapflights users on 12/23. 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 12/253:25 pmEYW - BOS
Nonstop3h 34mAmerican Airlines
Tue 12/3010:44 amBOS - EYW
Nonstop4h 11mAmerican Airlines
Deal found 12/23$347
This United Airlines deal was found by Cheapflights users on 12/22. 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.
Mon 12/291:25 pmEYW - BOS
2 stops9h 23mUnited Airlines
Mon 1/59:30 amBOS - EYW
1 stop6h 59mUnited Airlines
Deal found 12/22$352
This American Airlines deal was found by Cheapflights users on 12/22. 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.
Mon 12/293:25 pmEYW - BOS
Nonstop3h 34mAmerican Airlines
Tue 12/307:00 amBOS - EYW
1 stop8h 33mAmerican Airlines
Deal found 12/22$398
This United Airlines deal was found by Cheapflights users on 12/23. 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 12/2512:22 pmEYW - BOS
1 stop9h 22mUnited Airlines
Tue 12/305:20 amBOS - EYW
1 stop6h 21mUnited Airlines
Deal found 12/23$399
This United Airlines deal was found by Cheapflights users on 12/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:22 pmEYW - BDL
1 stop9h 13mUnited Airlines
Thu 1/16:00 amBDL - EYW
1 stop5h 41mUnited Airlines
Deal found 12/21$489

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 December 24, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$162
(Priceline)

One-way from

$74
(JetBlue)

Popular in

September

Cheapest in

November

Average price

$410

Good one-way deal

$268 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. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a one-way flight from Key West to Massachusetts.
Search Deals

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 December 24, 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

Mon 1/19

1:00 pm-4:36 pm

Nonstop3h 36m

Boston Logan Intl

Mon 1/26

8:09 am-12:05 pm

Nonstop3h 56m

$162

Key WestHartford

EYW - BDL

EYWBDL

Key West

Thu 1/29

10:06 am-11:56 pm

2 stops13h 50m

Hartford Bradley Intl

Sun 2/1

2:55 pm-9:09 am

1 stop18h 14m

$184

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 1/30

11:04 am-5:48 pm

1 stop6h 44m

Hartford Bradley Intl

Wed 2/4

8:05 am-9:06 am

1 stop25h 01m

$189

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 1/7

6:05 pm-11:49 pm

1 stop5h 44m

Boston Logan Intl

Sun 1/11

9:30 am-4:22 pm

1 stop6h 52m

$197

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 1/7

2:30 pm-1:19 am

2 stops10h 49m

Boston Logan Intl

Sun 1/11

11:06 am-12:26 pm

1 stop25h 20m

$207

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 1/30

2:25 pm-7:06 pm

2 stops28h 41m

Hartford Bradley Intl

Wed 2/4

8:05 am-9:06 am

1 stop25h 01m

$215

Key WestHartford

EYW - BDL

EYWBDL

Key West

Thu 1/29

12:51 pm-10:31 pm

2 stops9h 40m

Hartford Bradley Intl

Wed 2/4

8:05 am-9:06 am

1 stop25h 01m

$232

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 1/6

7:45 pm-12:59 am

1 stop5h 14m

Boston Logan Intl

Sat 1/10

8:15 am-12:32 pm

Nonstop4h 17m

$257

Key WestWorcester

EYW - ORH

EYWORH

Key West

Thu 1/29

5:24 pm-1:53 pm

1 stop20h 29m

Worcester

Sun 2/1

2:18 pm-1:16 pm

1 stop22h 58m

$272

Key WestWorcester

EYW - ORH

EYWORH

Key West

Thu 1/29

5:24 pm-1:53 pm

1 stop20h 29m

Worcester

Sat 1/31

2:23 pm-1:16 pm

1 stop22h 53m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 44 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 December 24, 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 43% versus a flight at noon.

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 December 24, 2025.

The most flights from EYW to USMA are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 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 December 24, 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
11,054 reviews

Overall

7.2

Crew

8.0

Boarding

7.5

Food

6.5

Entertainment

6.9

Comfort

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
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Overall

7.2

Crew

8.0

Boarding

7.5

Food

6.5

Entertainment

6.9

Comfort

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
2,898 reviews
American Airlines
7.2
Good
11,054 reviews

Overall

7.2

Crew

8.0

Boarding

7.5

Food

6.5

Entertainment

6.9

Comfort

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 3h 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 $138 and JetBlue from $138 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 (76%), TAP AIR PORTUGAL (74%) or Qatar Airways (63%) 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 $307 for a flight from Key West to Massachusetts. The cheapest flight overall is $185 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $196.

  • 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 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 December 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$347FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$277Average$456FlexibilityNo cancel feeOn-time62%

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