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$120+ 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 7/31. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$257
(American Airlines)

One-way from

$120
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$366

Good one-way deal

$158 or less
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. 16% potential increase in price ($78 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 July 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 July 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/237:31 pmEYW - BOS
1 stop5h 28mAmerican Airlines
Tue 10/75:13 amBOS - EYW
1 stop5h 39mAmerican Airlines
Deal found 7/1$257
This Delta deal was found by Cheapflights users on 7/2. 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.
Sat 8/306:20 pmEYW - BOS
1 stop7h 00mDelta
Fri 9/51:35 pmBOS - EYW
1 stop6h 37mDelta
Deal found 7/2$287
This Delta deal was found by Cheapflights users on 7/3. 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.
Fri 8/152:00 pmEYW - BDL
1 stop8h 21mDelta
Wed 8/202:31 pmBDL - EYW
1 stop5h 41mDelta
Deal found 7/3$338
This American Airlines deal was found by Cheapflights users on 7/3. 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.
Fri 8/151:29 pmEYW - BDL
2 stops10h 07mAmerican Airlines
Wed 8/205:30 amBDL - EYW
1 stop6h 10mAmerican Airlines
Deal found 7/3$343
This Mytrip deal was found by Cheapflights users on 7/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1610:02 amEYW - BOS
3 stops22h 35mMultiple Airlines
Sun 7/206:15 amBOS - EYW
1 stop6h 52mMultiple Airlines
Deal found 7/1$456
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Sat 8/22:08 pmEYW - BOS
1 stop8h 23mUnited Airlines
Tue 8/125:30 amBOS - EYW
2 stops31h 42mUnited Airlines
Deal found 7/3$541
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Wed 7/162:12 pmEYW - BDL
2 stops9h 47mUnited Airlines
Sun 7/206:10 amBDL - EYW
2 stops31h 02mUnited Airlines
Deal found 7/1$662

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 July 3, 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

7:31 pm-12:59 am

1 stop5h 28m

Boston Logan Intl

Tue 10/7

5:13 am-10:52 am

1 stop5h 39m

$257

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 8/30

6:20 pm-1:20 am

1 stop7h 00m

Boston Logan Intl

Fri 9/5

1:35 pm-8:12 pm

1 stop6h 37m

$287

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 8/15

2:00 pm-10:21 pm

1 stop8h 21m

Hartford Bradley Intl

Wed 8/20

8:00 am-1:05 pm

1 stop5h 05m

$338

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 8/15

11:26 am-10:40 pm

2 stops11h 14m

Hartford Bradley Intl

Wed 8/20

9:15 am-4:46 pm

1 stop7h 31m

$343

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 7/16

10:02 am-8:37 am

3 stops22h 35m

Boston Logan Intl

Sun 7/20

6:15 am-1:07 pm

1 stop6h 52m

$456

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 8/2

2:08 pm-10:31 pm

1 stop8h 23m

Boston Logan Intl

Tue 8/12

5:30 am-1:12 pm

2 stops31h 42m

$541

Key WestHartford

EYW - BDL

EYWBDL

Key West

Wed 7/16

2:12 pm-11:59 pm

2 stops9h 47m

Hartford Bradley Intl

Sun 7/20

6:10 am-1:12 pm

2 stops31h 02m

$662

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 7/31

4:20 pm-8:11 am

1 stop15h 51m

$120

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 8/12

2:22 pm-8:54 pm

1 stop6h 32m

$129

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 8/8

10:02 am-5:41 pm

2 stops7h 39m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 16 results
1
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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, 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 June is currently the most expensive (average of $306). 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 July 3, 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.

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 July 3, 2025.
See what other customers who have flown with Breeze Airways, Delta, and United Airlines 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.
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
183 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,970 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,845 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Allegiant Air
7.2
Good
709 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Boarding

8.3

Entertainment

6.6

Overall

8.1

Crew

8.8

Food

6.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 $120 on Allegiant Air. Other airlines that offer cheap prices include United Airlines from $129 and Breeze Airways from $143 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 - Hartford Bradley Intl, Key West - Boston Logan Intl and Key West - Worcester.

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

    On average you can expect to pay $193 for a flight from Key West to Massachusetts. The cheapest flight overall is $121 while the most popular route, (Key West - Hartford Bradley Intl) is currently priced at $338.

  • 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 June is currently the most expensive (average of $306). 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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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$357FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$520FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$241Average$339FlexibilityNo cancel feeOn-time71%

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