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$107+ 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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$227
(Delta)

One-way from

$107
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$300

Good one-way deal

$125 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 ($77 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 September 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 September 11, 2025.

This Priceline deal was found by Cheapflights users on 9/9. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/91:04 pmEYW - BOS
Nonstop3h 52mJetBlue
Mon 10/138:10 amBOS - EYW
Nonstop3h 59mJetBlue
Deal found 9/9$207
This JetBlue deal was found by Cheapflights users on 9/9. 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 10/161:04 pmEYW - BOS
Nonstop3h 52mJetBlue
Sun 10/268:00 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 9/9$217
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/153:12 pmEYW - BOS
1 stop7h 44mUnited Airlines
Tue 10/286:00 amBOS - EYW
1 stop7h 52mUnited Airlines
Deal found 9/9$222
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:40 amEYW - BOS
1 stop8h 09mDelta
Tue 10/289:05 amBOS - EYW
1 stop8h 16mDelta
Deal found 9/11$227
This United Airlines deal was found by Cheapflights users on 9/9. 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 11/13:00 pmEYW - BOS
2 stops8h 42mUnited Airlines
Mon 11/36:00 amBOS - EYW
1 stop8h 04mUnited Airlines
Deal found 9/9$228
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1511:22 amEYW - BOS
2 stops8h 13mAmerican Airlines
Tue 10/285:30 amBOS - EYW
1 stop7h 25mAmerican Airlines
Deal found 9/10$232
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1511:22 amEYW - BOS
2 stops8h 13mAmerican Airlines
Tue 10/219:17 amBOS - EYW
2 stops7h 59mAmerican Airlines
Deal found 9/10$237
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/77:30 amBOS - EYW
1 stop6h 22mAmerican Airlines
Deal found 9/9$247
This JetBlue deal was found by Cheapflights users on 9/9. 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.
Fri 10/171:04 pmEYW - BOS
Nonstop3h 52mJetBlue
Mon 10/278:00 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 9/9$251
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/13:45 pmEYW - BOS
1 stop7h 59mAmerican Airlines
Wed 10/86:00 amBOS - EYW
1 stop6h 58mAmerican Airlines
Deal found 9/10$264
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Wed 9/173:50 pmEYW - BOS
1 stop7h 32mUnited Airlines
Wed 9/249:05 amBOS - EYW
1 stop5h 50mUnited Airlines
Deal found 9/10$267
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Thu 10/98:55 amEYW - BDL
2 stops14h 11mBreeze Airways
Mon 10/136:00 amBDL - EYW
1 stop29h 05mBreeze Airways
Deal found 9/9$305

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 September 11, 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 10/16

1:04 pm-4:56 pm

Nonstop3h 52m

Boston Logan Intl

Mon 10/20

8:10 am-12:09 pm

Nonstop3h 59m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 10/16

1:04 pm-4:56 pm

Nonstop3h 52m

Boston Logan Intl

Sun 10/19

8:10 am-12:09 pm

Nonstop3h 59m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 10/15

3:12 pm-10:56 pm

1 stop7h 44m

Boston Logan Intl

Tue 10/28

6:00 am-1:52 pm

1 stop7h 52m

$222

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 10/15

6:17 pm-1:13 am

1 stop6h 56m

Boston Logan Intl

Wed 10/29

5:40 am-11:27 am

1 stop5h 47m

$227

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 10/15

5:47 pm-11:30 pm

1 stop5h 43m

Boston Logan Intl

Tue 10/21

7:30 am-1:52 pm

1 stop6h 22m

$227

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 10/21

3:12 pm-10:56 pm

1 stop7h 44m

Boston Logan Intl

Tue 10/28

7:30 am-1:52 pm

1 stop6h 22m

$227

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 10/15

7:40 am-3:49 pm

1 stop8h 09m

Boston Logan Intl

Tue 10/28

9:05 am-5:21 pm

1 stop8h 16m

$227

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 10/15

7:52 pm-12:34 am

1 stop4h 42m

Boston Logan Intl

Tue 10/28

6:00 am-12:55 pm

2 stops6h 55m

$232

Key WestHartford

EYW - BDL

EYWBDL

Key West

Thu 10/9

8:55 am-11:06 pm

2 stops14h 11m

Hartford Bradley Intl

Mon 10/13

6:00 am-11:05 am

1 stop29h 05m

$305

Key WestWorcester

EYW - ORH

EYWORH

Key West

Fri 10/17

1:25 pm-3:39 pm

2 stops26h 14m

Worcester

Tue 10/28

4:55 pm-1:52 pm

1 stop20h 57m

$312

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 48 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 September 11, 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 September 11, 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
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

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
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

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
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

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
2,913 reviews
Delta
8.0
Very good
7,960 reviews

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Boarding

8.2

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 3h 52m. Key West and Massachusetts are separated by a distance of 1374 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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 $114 on JetBlue. Other airlines that offer cheap prices include American Airlines from $144 and Breeze Airways from $149 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 cheapest flights from Key West to Massachusetts?

    On average you can expect to pay $131 for a flight from Key West to Massachusetts. The cheapest flight overall is $125 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $207.

  • 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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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$399FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$502FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$258Average$341FlexibilityNo cancel feeOn-time71%

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