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$126+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$272
(Mytrip)

One-way from

$126
(Mytrip)

Popular in

April

Cheapest in

September

Average price

$387

Good one-way deal

$498 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
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($42 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 March 2025
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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 March 28, 2025.

This Mytrip deal was found by Cheapflights users on 3/27. 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.
Thu 4/104:24 pmEYW - BOS
1 stop16h 12mMultiple Airlines
Mon 4/142:12 pmBOS - EYW
2 stops23h 32mMultiple Airlines
Deal found 3/27$277
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Thu 4/104:24 pmEYW - BOS
1 stop16h 12mAllegiant Air
Mon 4/149:26 amBOS - EYW
1 stop28h 18mAllegiant Air
Deal found 3/27$295
This American Airlines deal was found by Cheapflights users on 3/27. 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 5/1312:50 pmEYW - BOS
1 stop6h 20mAmerican Airlines
Mon 5/267:49 amBOS - EYW
1 stop6h 48mAmerican Airlines
Deal found 3/27$317
This United Airlines deal was found by Cheapflights users on 3/27. 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 4/244:04 pmEYW - BOS
1 stop8h 54mUnited Airlines
Mon 4/286:00 amBOS - EYW
1 stop7h 04mUnited Airlines
Deal found 3/27$322
This JetBlue deal was found by Cheapflights users on 3/27. 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 4/101:04 pmEYW - BOS
Nonstop3h 39mJetBlue
Mon 4/148:20 amBOS - EYW
Nonstop3h 49mJetBlue
Deal found 3/27$383
This United deal was found by Cheapflights users on 3/27. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/138:45 amEYW - BDL
2 stops29h 20mUnited Airlines
Tue 6/36:00 amBDL - EYW
2 stops12h 05mUnited Airlines
Deal found 3/27$392
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Sun 4/136:15 pmEYW - BDL
1 stop5h 43mAmerican Airlines
Tue 6/35:44 amBDL - EYW
1 stop7h 07mAmerican Airlines
Deal found 3/27$404
This Delta deal was found by Cheapflights users on 3/27. 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 5/157:00 amEYW - BOS
2 stops9h 59mDelta
Sun 5/188:00 amBOS - EYW
2 stops12h 07mDelta
Deal found 3/27$1,026

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 March 28, 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 4/10

4:24 pm-8:36 am

1 stop16h 12m

Boston Logan Intl

Mon 4/14

2:12 pm-1:44 pm

2 stops23h 32m

$277

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 4/10

4:24 pm-8:36 am

1 stop16h 12m

Boston Logan Intl

Mon 4/14

9:26 am-1:44 pm

1 stop28h 18m

$295

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 5/13

12:50 pm-7:10 pm

1 stop6h 20m

Boston Logan Intl

Mon 5/26

7:49 am-2:37 pm

1 stop6h 48m

$317

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 4/24

4:04 pm-12:58 am

1 stop8h 54m

Boston Logan Intl

Mon 4/28

6:00 am-1:04 pm

1 stop7h 04m

$322

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 4/10

1:04 pm-4:43 pm

Nonstop3h 39m

Boston Logan Intl

Mon 4/14

8:20 am-12:09 pm

Nonstop3h 49m

$383

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sun 4/13

8:45 am-2:05 pm

2 stops29h 20m

Hartford Bradley Intl

Tue 6/3

6:00 am-6:05 pm

2 stops12h 05m

$392

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sun 4/13

6:15 pm-11:58 pm

1 stop5h 43m

Hartford Bradley Intl

Tue 6/3

5:44 am-12:51 pm

1 stop7h 07m

$404

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 4/29

7:00 am-12:40 pm

1 stop5h 40m

Boston Logan Intl

Thu 5/1

1:45 pm-8:30 pm

1 stop6h 45m

$619

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 5/15

4:06 pm-8:10 am

1 stop16h 04m

$126

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 5/16

8:45 am-11:29 pm

1 stop14h 44m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 18 results
1
2

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, January is the cheapest month in which you can book a flight from Key West to Massachusetts (average of $218). Flying from Key West to Massachusetts in July is currently the most expensive (average of $311). 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 March 28, 2025.

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.

Rainfall in Massachusetts by month

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

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

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

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 March 28, 2025.
See what other customers who have flown with Alaska Airlines, Delta and United Airlines from Key West to Massachusetts have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,798 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,603 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,923 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Allegiant Air
7.3
Good
731 reviews
Alaska Airlines
8.0
Very good
9,798 reviews

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.

  • 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 $126 on Allegiant Air. Other airlines that offer cheap prices include American Airlines from $159 and United Airlines from $179 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 American Airlines (65%), Republic Airways (65%) or TAP AIR PORTUGAL (64%) 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 $648 for a flight from Key West to Massachusetts. The cheapest flight overall is $259 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $225.

  • 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, January is the cheapest month in which you can book a flight from Key West to Massachusetts (average of $218). Flying from Key West to Massachusetts in July is currently the most expensive (average of $311). 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 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$371FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$216Average$538FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$246Average$327FlexibilityNo cancel feeOn-time71%
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