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$89+ 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$237
(Delta)

One-way from

$89
(Travelocity)

Popular in

December

Cheapest in

September

Average price

$373

Good one-way deal

$173 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. 15% potential increase in price ($73 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 June 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 June 12, 2025.

This Delta deal was found by Cheapflights users on 6/10. 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.
Tue 9/236:00 pmEYW - BOS
1 stop7h 00mDelta
Tue 10/77:00 amBOS - EYW
1 stop6h 08mDelta
Deal found 6/10$237
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/2312:00 pmEYW - BOS
2 stops9h 46mAmerican Airlines
Tue 10/71:14 pmBOS - EYW
1 stop5h 53mAmerican Airlines
Deal found 6/11$242
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/104:20 pmEYW - BOS
1 stop15h 51mMultiple Airlines
Sun 7/1310:08 amBOS - EYW
2 stops30h 28mMultiple Airlines
Deal found 6/11$307
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Fri 6/272:07 pmEYW - BDL
1 stop10h 12mBreeze Airways
Sun 6/298:05 amBDL - EYW
2 stops29h 12mBreeze Airways
Deal found 6/10$307
This Delta deal was found by Cheapflights users on 6/10. 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 7/196:27 pmEYW - BDL
1 stop5h 21mDelta
Tue 7/226:00 amBDL - EYW
1 stop7h 08mDelta
Deal found 6/10$311
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/204:20 pmEYW - BOS
1 stop15h 51mAllegiant Air
Sun 8/311:31 amBOS - EYW
2 stops27h 45mAllegiant Air
Deal found 6/11$339
This American Airlines deal was found by Cheapflights users on 6/12. 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 8/155:02 pmEYW - BDL
1 stop5h 45mAmerican Airlines
Wed 8/205:30 amBDL - EYW
2 stops7h 42mAmerican Airlines
Deal found 6/12$343
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 7/186:45 pmEYW - BOS
2 stops18h 58mUnited Airlines
Tue 7/226:05 amBOS - EYW
2 stops12h 00mUnited Airlines
Deal found 6/11$363
This Mytrip deal was found by Cheapflights users on 6/10. 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 6/2710:12 amEYW - BDL
2 stops22h 49mMultiple Airlines
Sun 6/298:50 amBDL - EYW
2 stops31h 48mMultiple Airlines
Deal found 6/10$410
This United Airlines deal was found by Cheapflights users on 6/10. 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 6/172:12 pmEYW - BDL
2 stops9h 24mUnited Airlines
Tue 6/246:00 amBDL - EYW
2 stops12h 05mUnited Airlines
Deal found 6/10$415

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 June 12, 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

6:00 pm-1:00 am

1 stop7h 00m

Boston Logan Intl

Tue 10/7

7:00 am-1:08 pm

1 stop6h 08m

$237

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 9/23

12:00 pm-9:46 pm

2 stops9h 46m

Boston Logan Intl

Tue 10/7

1:14 pm-7:07 pm

1 stop5h 53m

$242

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 7/10

4:20 pm-8:11 am

1 stop15h 51m

Boston Logan Intl

Sun 7/13

10:08 am-4:36 pm

2 stops30h 28m

$307

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 6/27

2:07 pm-12:19 am

1 stop10h 12m

Hartford Bradley Intl

Sun 6/29

8:05 am-1:17 pm

2 stops29h 12m

$307

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sat 7/19

6:27 pm-11:48 pm

1 stop5h 21m

Hartford Bradley Intl

Tue 7/22

6:00 am-1:08 pm

1 stop7h 08m

$311

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sun 7/20

4:20 pm-8:11 am

1 stop15h 51m

Boston Logan Intl

Sun 8/3

11:31 am-3:16 pm

2 stops27h 45m

$339

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 8/15

5:02 pm-10:47 pm

1 stop5h 45m

Hartford Bradley Intl

Wed 8/20

5:30 am-1:12 pm

2 stops7h 42m

$343

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 7/18

6:45 pm-1:43 pm

2 stops18h 58m

Boston Logan Intl

Tue 7/22

6:05 am-6:05 pm

2 stops12h 00m

$363

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 6/27

10:12 am-9:01 am

2 stops22h 49m

Hartford Bradley Intl

Sun 6/29

8:50 am-4:38 pm

2 stops31h 48m

$410

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sat 7/19

6:45 pm-11:59 pm

2 stops29h 14m

Hartford Bradley Intl

Tue 7/22

6:00 am-8:00 am

3 stops26h 00m

$485

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 22 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, 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 June 12, 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 June 12, 2025.
See what other customers who have flown with Breeze Airways, Alaska Airlines and Delta 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.
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

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
178 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

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!
Alaska Airlines
8.0
Very good
10,000 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

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
7,950 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

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
8,790 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

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!
JetBlue
7.3
Good
2,925 reviews
Breeze Airways
8.1
Very good
178 reviews

Food

6.7

Boarding

8.3

Entertainment

6.6

Overall

8.1

Comfort

8.2

Crew

8.8

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 $89 on Breeze Airways. Other airlines that offer cheap prices include American Airlines from $119 and Allegiant Air from $134 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 (71%), TAP AIR PORTUGAL (71%) or Qatar Airways (36%) 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 $259 for a flight from Key West to Massachusetts. The cheapest flight overall is $158 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $237.

  • 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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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$357FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$520FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$246Average$337FlexibilityNo cancel feeOn-time71%

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