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$85+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
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 November 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$197
(United Airlines)

One-way from

$85
(Kiwi.com)

Popular in

September

Cheapest in

June

Average price

$343

Good one-way deal

$163 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. 4% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/88:55 amEYW - BOS
1 stop25h 06mMultiple Airlines
Wed 12/108:11 pmBOS - EYW
1 stop12h 04mMultiple Airlines
Deal found 11/21$212
This Priceline deal was found by Cheapflights users on 11/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/132:30 pmEYW - BOS
1 stop9h 26mSpirit Airlines
Wed 12/315:45 amBOS - EYW
1 stop7h 45mSpirit Airlines
Deal found 11/20$217
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:55 amEYW - BDL
2 stops14h 07mBreeze Airways
Mon 12/86:00 amBDL - EYW
1 stop29h 05mBreeze Airways
Deal found 11/19$230
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Fri 12/55:09 pmEYW - ORH
1 stop22h 03mAmerican Airlines
Tue 12/93:34 pmORH - EYW
1 stop22h 17mAmerican Airlines
Deal found 11/20$232
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:55 amEYW - BDL
1 stop27h 29mMultiple Airlines
Mon 12/86:00 amBDL - EYW
1 stop29h 05mMultiple Airlines
Deal found 11/19$234
This Delta deal was found by Cheapflights users on 11/18. 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.
Thu 12/412:38 pmEYW - BOS
1 stop6h 55mDelta
Sat 12/612:10 pmBOS - EYW
1 stop7h 56mDelta
Deal found 11/18$237
This Priceline deal was found by Cheapflights users on 11/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/412:47 pmEYW - BOS
Nonstop3h 30mJetBlue
Mon 12/88:02 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 11/19$242
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/132:30 pmEYW - BOS
2 stops19h 52mMultiple Airlines
Wed 12/315:45 amBOS - EYW
1 stop7h 45mMultiple Airlines
Deal found 11/20$243
This Kiwi.com deal was found by Cheapflights users on 11/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/610:47 amEYW - BDL
2 stops36h 15mBreeze Airways
Wed 12/108:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Deal found 11/21$249
This American Airlines deal was found by Cheapflights users on 11/20. 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.
Sat 12/134:53 pmEYW - BOS
1 stop5h 51mAmerican Airlines
Wed 12/3110:44 amBOS - EYW
Nonstop4h 11mAmerican Airlines
Deal found 11/20$252
This JetBlue deal was found by Cheapflights users on 11/18. 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 12/412:47 pmEYW - BOS
Nonstop3h 30mJetBlue
Sat 12/68:02 amBOS - EYW
Nonstop3h 53mJetBlue
Deal found 11/18$257
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 12/511:11 amEYW - BDL
1 stop6h 15mBreeze Airways
Tue 12/97:05 amBDL - EYW
2 stops27h 02mBreeze Airways
Deal found 11/18$262

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 November 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

Mon 12/8

8:55 am-10:01 am

1 stop25h 06m

Boston Logan Intl

Wed 12/10

8:11 pm-8:15 am

1 stop12h 04m

$212

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 3/4

7:10 am-2:15 pm

1 stop7h 05m

Boston Logan Intl

Tue 3/10

1:55 pm-7:44 pm

1 stop5h 49m

$217

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 12/13

2:30 pm-11:56 pm

1 stop9h 26m

Boston Logan Intl

Wed 12/31

5:45 am-1:30 pm

1 stop7h 45m

$217

Key WestHartford

EYW - BDL

EYWBDL

Key West

Thu 12/4

8:55 am-11:02 pm

2 stops14h 07m

Hartford Bradley Intl

Mon 12/8

6:00 am-11:05 am

1 stop29h 05m

$230

Key WestWorcester

EYW - ORH

EYWORH

Key West

Fri 12/5

5:09 pm-3:12 pm

1 stop22h 03m

Worcester

Tue 12/9

3:34 pm-1:51 pm

1 stop22h 17m

$232

Key WestHartford

EYW - BDL

EYWBDL

Key West

Thu 12/4

8:55 am-12:24 pm

1 stop27h 29m

Hartford Bradley Intl

Mon 12/8

6:00 am-11:05 am

1 stop29h 05m

$234

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 12/4

12:38 pm-7:33 pm

1 stop6h 55m

Boston Logan Intl

Sat 12/6

12:10 pm-8:06 pm

1 stop7h 56m

$237

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sat 12/6

10:47 am-11:02 pm

2 stops36h 15m

Hartford Bradley Intl

Wed 12/10

8:05 am-8:15 am

1 stop24h 10m

$249

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 12/13

4:53 pm-10:44 pm

1 stop5h 51m

Boston Logan Intl

Wed 12/31

10:44 am-2:55 pm

Nonstop4h 11m

$252

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 12/9

11:45 am-11:56 pm

2 stops36h 11m

Boston Logan Intl

Thu 12/11

11:08 am-8:15 am

1 stop21h 07m

$276

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 38 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 February is currently the most expensive (average of $331). 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 November 21, 2025.

When flying from Key West to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 45% versus a flight at noon.

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 November 21, 2025.

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

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 November 21, 2025.
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
11,047 reviews

Overall

7.2

Entertainment

6.9

Comfort

7.2

Food

6.4

Crew

8.0

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
11,047 reviews
American Airlines
7.2
Good
11,047 reviews

Overall

7.2

Entertainment

6.9

Comfort

7.2

Food

6.4

Crew

8.0

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
2,902 reviews
American Airlines
7.2
Good
11,047 reviews

Overall

7.2

Entertainment

6.9

Comfort

7.2

Food

6.4

Crew

8.0

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 7h 05m. 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 $96 on Breeze Airways. Other airlines that offer cheap prices include Delta from $119 and American Airlines from $215 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 (54%), Qatar Airways (52%) or TAP AIR PORTUGAL (52%) 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 $253 for a flight from Key West to Massachusetts. The cheapest flight overall is $118 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $181.

  • 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 February is currently the most expensive (average of $331). 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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Alternative routes for Key West to Massachusetts

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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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$226Average$346FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$251Average$496FlexibilityNo cancel feeOn-time62%

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