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$86+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
ago. 26 — sep. 21
mar. 8/26
mar. 9/2
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 agosto 21, 2025.

Round-trip from

$171
(American Airlines)

One-way from

$86
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$343
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. 17% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 agosto 21, 2025.

This American Airlines deal was found by Cheapflights users on 8/20. 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.
mar. 9/237:31 pmEYW - BOS
1 stop5h 28mAmerican Airlines
mar. 10/77:10 amBOS - EYW
1 stop5h 48mAmerican Airlines
Deal found 8/20$171
This American Airlines deal was found by Cheapflights users on 8/20. 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.
mié. 9/107:31 pmEYW - BOS
1 stop5h 28mAmerican Airlines
sáb. 9/139:15 amBOS - EYW
2 stops9h 44mAmerican Airlines
Deal found 8/20$196
This American Airlines deal was found by Cheapflights users on 8/20. 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.
vie. 10/107:52 pmEYW - BOS
1 stop4h 42mAmerican Airlines
dom. 10/196:00 amBOS - EYW
1 stop7h 52mAmerican Airlines
Deal found 8/20$214
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/222:14 pmEYW - BOS
1 stop7h 35mAmerican Airlines
sáb. 10/255:30 amBOS - EYW
1 stop5h 22mAmerican Airlines
Deal found 8/21$225
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/255:10 pmEYW - BOS
1 stop6h 24mAmerican Airlines
mié. 10/2912:52 pmBOS - EYW
1 stop6h 30mAmerican Airlines
Deal found 8/21$244
This American Airlines deal was found by Cheapflights users on 8/20. 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.
vie. 11/215:09 pmEYW - BOS
1 stop5h 10mAmerican Airlines
mar. 11/257:00 amBOS - EYW
1 stop6h 55mAmerican Airlines
Deal found 8/20$247
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/176:17 pmEYW - BDL
1 stop5h 12mDelta
lun. 10/202:12 pmBDL - EYW
1 stop5h 54mDelta
Deal found 8/21$393
This American Airlines deal was found by Cheapflights users on 8/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1711:22 amEYW - BDL
2 stops9h 03mAmerican Airlines
dom. 10/198:22 amBDL - EYW
1 stop8h 05mAmerican Airlines
Deal found 8/21$398
This United Airlines deal was found by Cheapflights users on 8/19. 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.
jue. 9/43:50 pmEYW - BDL
2 stops31h 54mUnited Airlines
lun. 9/87:54 pmBDL - EYW
2 stops18h 07mUnited Airlines
Deal found 8/19$583
This Gotogate deal was found by Cheapflights users on 8/21. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1711:11 amEYW - BDL
3 stops30h 56mBreeze Airways
dom. 10/1912:55 pmBDL - EYW
2 stops19h 20mBreeze Airways
Deal found 8/21$696
This United Airlines deal was found by Cheapflights users on 8/21. 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.
vie. 10/173:12 pmEYW - BDL
2 stops18h 25mUnited Airlines
lun. 10/206:00 amBDL - EYW
2 stops8h 29mUnited Airlines
Deal found 8/21$803
This Delta deal was found by Cheapflights users on 8/20. 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.
lun. 8/256:20 pmEYW - BDL
1 stop5h 10mDelta
jue. 8/286:00 amBDL - EYW
1 stop7h 05mDelta
Deal found 8/20$809

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 agosto 21, 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

mar. 12/9

8:10 am-4:40 pm

1 stop8h 30m

Boston Logan Intl

mar. 12/16

8:08 am-1:46 pm

1 stop5h 38m

$171

Key WestBoston

EYW - BOS

EYWBOS

Key West

mar. 9/23

7:31 pm-12:59 am

1 stop5h 28m

Boston Logan Intl

mar. 10/7

7:10 am-12:58 pm

1 stop5h 48m

$171

Key WestBoston

EYW - BOS

EYWBOS

Key West

vie. 10/31

5:47 pm-11:30 pm

1 stop5h 43m

Boston Logan Intl

dom. 11/2

7:00 am-1:55 pm

1 stop6h 55m

$171

Key WestBoston

EYW - BOS

EYWBOS

Key West

sáb. 10/18

11:22 am-4:12 pm

1 stop4h 50m

Boston Logan Intl

mié. 10/22

12:52 pm-7:22 pm

1 stop6h 30m

$171

Key WestBoston

EYW - BOS

EYWBOS

Key West

jue. 9/11

1:59 pm-8:14 pm

1 stop6h 15m

Boston Logan Intl

dom. 9/14

7:36 am-1:29 pm

1 stop5h 53m

$191

Key WestBoston

EYW - BOS

EYWBOS

Key West

mié. 9/10

7:31 pm-12:59 am

1 stop5h 28m

Boston Logan Intl

sáb. 9/13

9:15 am-6:59 pm

2 stops9h 44m

$196

Key WestHartford

EYW - BDL

EYWBDL

Key West

vie. 10/17

6:17 pm-11:29 pm

1 stop5h 12m

Hartford Bradley Intl

lun. 10/20

2:12 pm-8:06 pm

1 stop5h 54m

$393

Key WestHartford

EYW - BDL

EYWBDL

Key West

vie. 10/17

5:47 pm-10:52 pm

1 stop5h 05m

Hartford Bradley Intl

dom. 10/19

8:22 am-4:27 pm

1 stop8h 05m

$393

Key WestHartford

EYW - BDL

EYWBDL

Key West

jue. 9/4

3:50 pm-11:44 pm

2 stops31h 54m

Hartford Bradley Intl

lun. 9/8

7:54 pm-2:01 pm

2 stops18h 07m

$583

Key WestHartford

EYW - BDL

EYWBDL

Key West

vie. 10/17

11:11 am-6:07 pm

3 stops30h 56m

Hartford Bradley Intl

dom. 10/19

12:55 pm-8:15 am

2 stops19h 20m

$696

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 27 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 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 agosto 21, 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 agosto 21, 2025.
See what other customers who have flown with Delta, 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.
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
JetBlue
7.2
Good
2,916 reviews
Delta
8.0
Very good
7,981 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

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 5h 12m. Key West and Massachusetts are separated by a distance of 1308 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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.

  • 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 agosto 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$357FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$502FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$258Average$340FlexibilityNo cancel feeOn-time71%

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