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$93+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
feb. 7 — feb. 141
sáb. 2/7
sáb. 2/14
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 enero 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$183
(Kiwi.com)

One-way from

$93
(Kiwi.com)

Popular in

September

Cheapest in

November

Average price

$492

Good one-way deal

$268 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. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 enero 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
vie. 1/239:49 amEYW - BDL
2 stops13h 04mBreeze Airways
dom. 1/253:00 pmBDL - EYW
1 stop18h 09mBreeze Airways
Deal found 1/6$183
This United Airlines deal was found by Cheapflights users on 1/7. 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. 2/56:05 pmEYW - BOS
1 stop5h 44mUnited Airlines
mar. 2/109:30 amBOS - EYW
1 stop6h 52mUnited Airlines
Deal found 1/7$197
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
mié. 1/2110:49 amEYW - BOS
2 stops13h 08mMultiple Airlines
sáb. 1/243:43 pmBOS - EYW
1 stop17h 43mMultiple Airlines
Deal found 1/7$199
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
lun. 2/22:25 pmEYW - BOS
1 stop9h 32mMultiple Airlines
sáb. 2/73:43 pmBOS - EYW
1 stop17h 23mMultiple Airlines
Deal found 1/7$203
This Expedia deal was found by Cheapflights users on 1/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 1/211:00 pmEYW - BOS
Nonstop3h 36mJetBlue
sáb. 1/248:09 amBOS - EYW
Nonstop3h 56mJetBlue
Deal found 1/7$208
This Kiwi.com deal was found by Cheapflights users on 1/8. 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.
vie. 2/131:06 pmEYW - BOS
1 stop22h 44mMultiple Airlines
mié. 2/186:10 pmBOS - EYW
1 stop19h 20mMultiple Airlines
Deal found 1/8$214
This Expedia deal was found by Cheapflights users on 1/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 1/2212:51 pmEYW - BOS
1 stop11h 06mMultiple Airlines
lun. 1/268:09 amBOS - EYW
Nonstop3h 56mMultiple Airlines
Deal found 1/7$216
This United Airlines deal was found by Cheapflights users on 1/7. 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. 1/222:25 pmEYW - BOS
1 stop7h 27mUnited Airlines
lun. 1/266:00 amBOS - EYW
1 stop9h 17mUnited Airlines
Deal found 1/7$217
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
mié. 1/2110:49 amEYW - BDL
2 stops37h 07mMultiple Airlines
dom. 1/258:31 pmBDL - EYW
1 stop15h 55mMultiple Airlines
Deal found 1/6$221
This United Airlines deal was found by Cheapflights users on 1/7. 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.
mar. 2/36:05 pmEYW - BOS
1 stop5h 44mUnited Airlines
lun. 2/95:45 amBOS - EYW
2 stops9h 32mUnited Airlines
Deal found 1/7$230
This Kiwi.com deal was found by Cheapflights users on 1/7. 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.
mié. 1/284:06 pmEYW - BDL
2 stops23h 57mMultiple Airlines
sáb. 1/318:01 pmBDL - EYW
1 stop13h 25mMultiple Airlines
Deal found 1/7$233
This American Airlines deal was found by Cheapflights users on 1/7. 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. 1/212:44 pmEYW - BOS
1 stop7h 45mAmerican Airlines
sáb. 1/248:15 amBOS - EYW
Nonstop4h 17mAmerican Airlines
Deal found 1/7$237

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 enero 8, 2026.
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 WestHartford

EYW - BDL

EYWBDL

Key West

vie. 1/23

9:49 am-10:53 pm

2 stops13h 04m

Hartford Bradley Intl

dom. 1/25

3:00 pm-9:09 am

1 stop18h 09m

$183

Key WestBoston

EYW - BOS

EYWBOS

Key West

jue. 2/5

6:05 pm-11:49 pm

1 stop5h 44m

Boston Logan Intl

mar. 2/10

9:30 am-4:22 pm

1 stop6h 52m

$197

Key WestBoston

EYW - BOS

EYWBOS

Key West

jue. 2/19

7:00 am-2:30 pm

1 stop7h 30m

Boston Logan Intl

mar. 2/24

6:00 am-1:15 pm

1 stop7h 15m

$197

Key WestBoston

EYW - BOS

EYWBOS

Key West

mié. 1/21

1:00 pm-4:36 pm

Nonstop3h 36m

Boston Logan Intl

sáb. 1/24

8:09 am-12:05 pm

Nonstop3h 56m

$208

Key WestBoston

EYW - BOS

EYWBOS

Key West

vie. 2/13

1:06 pm-11:50 am

1 stop22h 44m

Boston Logan Intl

mié. 2/18

6:10 pm-1:30 pm

1 stop19h 20m

$214

Key WestBoston

EYW - BOS

EYWBOS

Key West

jue. 1/22

12:51 pm-11:57 pm

1 stop11h 06m

Boston Logan Intl

lun. 1/26

8:09 am-12:05 pm

Nonstop3h 56m

$216

Key WestBoston

EYW - BOS

EYWBOS

Key West

mar. 2/3

6:06 pm-1:04 am

1 stop6h 58m

Boston Logan Intl

lun. 2/9

6:00 am-12:48 pm

1 stop6h 48m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

jue. 1/22

2:25 pm-9:52 pm

1 stop7h 27m

Boston Logan Intl

lun. 1/26

6:00 am-3:17 pm

1 stop9h 17m

$217

Key WestHartford

EYW - BDL

EYWBDL

Key West

mié. 1/21

10:49 am-11:56 pm

2 stops37h 07m

Hartford Bradley Intl

dom. 1/25

8:31 pm-12:26 pm

1 stop15h 55m

$221

Key WestBoston

EYW - BOS

EYWBOS

Key West

mar. 2/3

6:05 pm-11:49 pm

1 stop5h 44m

Boston Logan Intl

lun. 2/9

5:45 am-3:17 pm

2 stops9h 32m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 45 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, November is the cheapest month in which you can book a flight from Key West to Massachusetts (average of $170). Flying from Key West to Massachusetts in May is currently the most expensive (average of $320). 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 enero 8, 2026.

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.

Weekly flight availability from Key West to Massachusetts

Explore weekly flight availability from Key West to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated enero 8, 2026.

The most flights from EYW to USMA are scheduled on a Thursday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

How much does it cost to fly round-trip from Key West to Massachusetts?

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 enero 8, 2026.
See what other customers who have flown with 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.
American Airlines
7.2
Good
11,095 reviews

Entertainment

6.9

Food

6.4

Comfort

7.2

Crew

8.0

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,095 reviews
American Airlines
7.2
Good
11,095 reviews

Entertainment

6.9

Food

6.4

Comfort

7.2

Crew

8.0

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
JetBlue
7.2
Good
2,893 reviews
American Airlines
7.2
Good
11,095 reviews

Entertainment

6.9

Food

6.4

Comfort

7.2

Crew

8.0

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 36m. 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 $128 on American Airlines. Other airlines that offer cheap prices include JetBlue from $138 and Delta from $148 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 (85%), TAP AIR PORTUGAL (84%) or Qatar Airways (42%) 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 $289 for a flight from Key West to Massachusetts. The cheapest flight overall is $146 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $197.

  • 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, November is the cheapest month in which you can book a flight from Key West to Massachusetts (average of $170). Flying from Key West to Massachusetts in May is currently the most expensive (average of $320). 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.

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Top 2 airlines flying from Key West to Massachusetts

Discover the top 2 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 enero 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$346FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$277Average$442FlexibilityNo cancel feeOn-time62%

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