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$184+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$317
(American Airlines)

One-way from

$184
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$551

Good round-trip deal

$277 or less

Good one-way deal

$509 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. 15% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This JetBlue deal was found by Cheapflights users on 4/16. 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.
Tue 10/211:00 pmEYW - BOS
Nonstop3h 32mJetBlue
Sat 10/258:15 amBOS - EYW
Nonstop3h 35mJetBlue
Deal found 4/16$297
This American Airlines deal was found by Cheapflights users on 4/17. 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 9/235:22 pmEYW - BOS
1 stop7h 13mAmerican Airlines
Tue 10/75:43 amBOS - EYW
1 stop5h 14mAmerican Airlines
Deal found 4/17$317
This Delta deal was found by Cheapflights users on 4/16. 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 5/17:00 amEYW - BOS
1 stop5h 34mDelta
Mon 5/56:00 amBOS - EYW
1 stop6h 55mDelta
Deal found 4/16$347
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Tue 6/108:45 amEYW - BOS
2 stops28h 43mUnited Airlines
Thu 6/129:30 amBOS - EYW
2 stops22h 30mUnited Airlines
Deal found 4/17$373
This Mytrip deal was found by Cheapflights users on 4/16. 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.
Fri 6/135:28 pmEYW - BOS
2 stops14h 46mMultiple Airlines
Thu 6/196:00 amBOS - EYW
3 stops34h 38mMultiple Airlines
Deal found 4/16$418
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/215:10 pmEYW - BOS
2 stops18h 26mAllegiant Air
Wed 4/239:41 amBOS - EYW
2 stops22h 32mAllegiant Air
Deal found 4/15$492
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/185:23 pmEYW - BDL
1 stop5h 03mAmerican Airlines
Tue 5/205:44 amBDL - EYW
1 stop7h 07mAmerican Airlines
Deal found 4/17$615
This Mytrip deal was found by Cheapflights users on 4/17. 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.
Sun 5/185:35 pmEYW - BDL
2 stops28h 58mMultiple Airlines
Tue 5/207:15 amBDL - EYW
2 stops32h 41mMultiple Airlines
Deal found 4/17$635

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 April 17, 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

Tue 9/23

5:22 pm-12:35 am

1 stop7h 13m

Boston Logan Intl

Tue 10/7

5:43 am-10:57 am

1 stop5h 14m

$317

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 5/1

7:00 am-12:34 pm

1 stop5h 34m

Boston Logan Intl

Mon 5/5

6:00 am-12:55 pm

1 stop6h 55m

$347

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 6/10

8:45 am-1:28 pm

2 stops28h 43m

Boston Logan Intl

Thu 6/12

9:30 am-8:00 am

2 stops22h 30m

$373

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 6/13

5:28 pm-8:14 am

2 stops14h 46m

Boston Logan Intl

Thu 6/19

6:00 am-4:38 pm

3 stops34h 38m

$418

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sun 5/18

5:23 pm-10:26 pm

1 stop5h 03m

Hartford Bradley Intl

Tue 5/20

5:44 am-12:51 pm

1 stop7h 07m

$615

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sun 6/15

8:45 am-4:20 pm

1 stop7h 35m

Boston Logan Intl

Fri 6/20

11:05 am-6:05 pm

1 stop7h 00m

$618

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sun 5/18

5:35 pm-10:33 pm

2 stops28h 58m

Hartford Bradley Intl

Tue 5/20

7:15 am-3:56 pm

2 stops32h 41m

$635

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 5/2

6:15 pm-11:44 pm

1 stop5h 29m

$184

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 7/11

6:45 pm-4:29 pm

2 stops21h 44m

$188

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 10/14

1:00 pm-4:32 pm

Nonstop3h 32m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 16 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 April 17, 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 April 17, 2025.
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,926 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Crew

8.5

Entertainment

7.1

Overall

8.0

Comfort

7.9

Food

7.1

Boarding

8.2

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 $184 on American Airlines. Other airlines that offer cheap prices include United Airlines from $188 and Allegiant Air from $192 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 (66%), Republic Airways (66%) or JetBlue (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 $701 for a flight from Key West to Massachusetts. The cheapest flight overall is $277 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $253.

  • 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

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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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$371FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$520FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$246Average$327FlexibilityNo cancel feeOn-time71%

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