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$134+ 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 9/3. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$221
(Trip.com)

One-way from

$142
(Delta)

Popular in

December

Cheapest in

September

Average price

$349

Good round-trip deal

$277 or less

Good one-way deal

$384 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. 14% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Key West to Massachusetts.
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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 May 1, 2025.

This Trip.com deal was found by Cheapflights users on 4/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/32:45 pmEYW - BOS
1 stop9h 58mMultiple Airlines
Mon 7/76:00 amBOS - EYW
1 stop8h 00mMultiple Airlines
Deal found 4/30$221
This Mytrip deal was found by Cheapflights users on 4/29. 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 5/224:06 pmEYW - BOS
1 stop16h 04mAllegiant Air
Wed 5/2811:00 amBOS - EYW
1 stop28h 16mAllegiant Air
Deal found 4/29$237
This American Airlines deal was found by Cheapflights users on 4/30. 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 9/237:21 pmEYW - BOS
1 stop5h 14mAmerican Airlines
Tue 10/77:41 amBOS - EYW
1 stop5h 19mAmerican Airlines
Deal found 4/30$247
This Delta deal was found by Cheapflights users on 4/29. 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.
Fri 5/96:25 pmEYW - BDL
1 stop5h 34mDelta
Mon 5/122:59 pmBDL - EYW
1 stop5h 08mDelta
Deal found 4/29$379
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/95:24 pmEYW - BDL
1 stop5h 19mAmerican Airlines
Mon 5/125:06 amBDL - EYW
2 stops9h 31mAmerican Airlines
Deal found 4/29$384
This United Airlines deal was found by Cheapflights users on 4/30. 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 5/62:18 pmEYW - BOS
1 stop8h 09mUnited Airlines
Sat 5/107:00 amBOS - EYW
1 stop6h 34mUnited Airlines
Deal found 4/30$393
This JetBlue deal was found by Cheapflights users on 4/29. 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.
Sun 5/252:45 pmEYW - BOS
1 stop8h 21mJetBlue
Thu 5/296:10 amBOS - EYW
1 stop7h 50mJetBlue
Deal found 4/29$499
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/98:45 amEYW - BDL
3 stops15h 14mUnited Airlines
Mon 5/126:00 amBDL - EYW
2 stops12h 05mUnited Airlines
Deal found 4/29$505

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 May 1, 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 7/3

2:45 pm-12:43 am

1 stop9h 58m

Boston Logan Intl

Mon 7/7

6:00 am-2:00 pm

1 stop8h 00m

$221

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 5/22

4:06 pm-8:10 am

1 stop16h 04m

Boston Logan Intl

Wed 5/28

11:00 am-3:16 pm

1 stop28h 16m

$237

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 9/23

7:21 pm-12:35 am

1 stop5h 14m

Boston Logan Intl

Tue 10/7

7:41 am-1:00 pm

1 stop5h 19m

$247

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 5/15

8:45 am-11:59 pm

2 stops15h 14m

Boston Logan Intl

Mon 5/19

6:00 am-6:05 pm

2 stops12h 05m

$402

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sun 5/25

2:45 pm-11:06 pm

1 stop8h 21m

Boston Logan Intl

Thu 5/29

6:10 am-2:00 pm

1 stop7h 50m

$499

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 9/3

1:27 pm-6:31 pm

1 stop5h 04m

$134

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 6/17

8:45 am-10:53 pm

1 stop14h 08m

$139

Key WestHartford

EYW - BDL

EYWBDL

Key West

Wed 8/6

6:27 pm-11:46 pm

1 stop5h 19m

$142

Key WestHartford

EYW - BDL

EYWBDL

Key West

Wed 8/6

1:52 pm-11:35 pm

2 stops9h 43m

$147

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 6/17

2:12 pm-11:59 pm

2 stops9h 47m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 16 results
1
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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 $310). 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 May 1, 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 May 1, 2025.
See what other customers who have flown with Alaska Airlines, Delta and United Airlines 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.
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Allegiant Air
7.3
Good
734 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Entertainment

7.1

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $142 on Delta. Other airlines that offer cheap prices include American Airlines from $147 and Allegiant Air from $171 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 American Airlines (66%), Republic Airways (66%) or JetBlue (64%) 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 $737 for a flight from Key West to Massachusetts. The cheapest flight overall is $277 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 July is currently the most expensive (average of $310). 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$371FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$516FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$246Average$332FlexibilityNo cancel feeOn-time71%

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