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Massachusetts

$95+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap 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 February 12, 2026.

This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:25 pm
EYW
-
BOS
1 stop9h 19m
Spirit Airlines
Mon 3/95:27 am
BOS
-
EYW
1 stop8h 03m
Spirit Airlines
Deal found 2/10$185
This American Airlines deal was found by Cheapflights users on 2/10. 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.
Fri 4/172:01 pm
EYW
-
ORH
2 stops24h 13m
American Airlines
Sat 4/252:39 pm
ORH
-
EYW
2 stops20h 45m
American Airlines
Deal found 2/10$207
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Tue 3/106:28 pm
EYW
-
BOS
1 stop5h 29m
United Airlines
Tue 3/176:00 am
BOS
-
EYW
1 stop7h 23m
United Airlines
Deal found 2/10$207
This Expedia deal was found by Cheapflights users on 2/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:48 pm
EYW
-
BOS
Nonstop3h 36m
Multiple Airlines
Thu 3/55:27 am
BOS
-
EYW
1 stop8h 03m
Multiple Airlines
Deal found 2/9$218
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:15 pm
EYW
-
BOS
1 stop11h 44m
Spirit Airlines
Sat 4/257:55 pm
BOS
-
EYW
1 stop15h 22m
Spirit Airlines
Deal found 2/10$219
This Breeze Airways deal was found by Cheapflights users on 2/10. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:04 am
EYW
-
BDL
1 stop6h 04m
Breeze Airways
Mon 3/91:11 pm
BDL
-
EYW
2 stops23h 10m
Breeze Airways
Deal found 2/10$222
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/269:46 am
EYW
-
BDL
1 stop24h 02m
Multiple Airlines
Mon 3/21:11 pm
BDL
-
EYW
2 stops23h 10m
Multiple Airlines
Deal found 2/11$223
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/101:01 pm
EYW
-
BOS
2 stops28h 14m
Multiple Airlines
Tue 3/175:49 pm
BOS
-
EYW
1 stop17h 41m
Multiple Airlines
Deal found 2/10$232
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:15 pm
EYW
-
BOS
1 stop11h 44m
Spirit Airlines
Fri 4/245:40 am
BOS
-
EYW
1 stop7h 50m
Spirit Airlines
Deal found 2/10$235
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/129:46 am
EYW
-
BOS
1 stop12h 15m
Multiple Airlines
Tue 3/175:49 pm
BOS
-
EYW
1 stop17h 41m
Multiple Airlines
Deal found 2/10$239
This United Airlines deal was found by Cheapflights users on 2/10. 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.
Thu 3/57:00 am
EYW
-
BOS
2 stops10h 19m
United Airlines
Mon 3/910:30 am
BOS
-
EYW
1 stop7h 15m
United Airlines
Deal found 2/10$242
This United Airlines deal was found by Cheapflights users on 2/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:35 pm
EYW
-
BOS
1 stop5h 22m
United Airlines
Mon 3/27:45 am
BOS
-
EYW
1 stop7h 15m
United Airlines
Deal found 2/11$247

Find 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 February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$185
(Priceline)

One-way from

$95
(Cheapflightsfares)

Popular in

September

Cheapest in

November

Average price

$376

Good one-way deal

$154 or less
Provider with most accurate pricing for Key West-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Boston Logan Intl flights.
Search Deals
From Key West to Massachusetts
Search Deals
One-way flight from Key West to Massachusetts
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals
Price to beat on a one-way flight from Key West to Massachusetts.
Search Deals

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 February 12, 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 WestWorcester

EYW - ORH

EYWORH

Key West

Fri 4/17

2:01 pm-2:14 pm

2 stops24h 13m

Worcester

Sat 4/25

2:39 pm-11:24 am

2 stops20h 45m

$207

Key WestBoston

EYW - BOS

EYWBOS

Key West

Tue 3/10

6:28 pm-11:57 pm

1 stop5h 29m

Boston Logan Intl

Tue 3/17

6:00 am-1:23 pm

1 stop7h 23m

$207

Key WestBoston

EYW - BOS

EYWBOS

Key West

Mon 3/2

12:48 pm-4:24 pm

Nonstop3h 36m

Boston Logan Intl

Thu 3/5

5:27 am-1:30 pm

1 stop8h 03m

$218

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 4/16

12:15 pm-11:59 pm

1 stop11h 44m

Boston Logan Intl

Sat 4/25

7:55 pm-11:17 am

1 stop15h 22m

$219

Key WestHartford

EYW - BDL

EYWBDL

Key West

Fri 3/6

11:04 am-5:08 pm

1 stop6h 04m

Hartford Bradley Intl

Mon 3/9

1:11 pm-12:21 pm

2 stops23h 10m

$222

Key WestHartford

EYW - BDL

EYWBDL

Key West

Thu 2/26

9:46 am-9:48 am

1 stop24h 02m

Hartford Bradley Intl

Mon 3/2

1:11 pm-12:21 pm

2 stops23h 10m

$223

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 3/5

7:00 am-5:19 pm

2 stops10h 19m

Boston Logan Intl

Mon 3/9

10:30 am-5:45 pm

1 stop7h 15m

$242

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 4/17

2:25 pm-11:59 pm

1 stop9h 34m

Boston Logan Intl

Sat 4/25

7:55 pm-11:17 am

1 stop15h 22m

$247

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 2/26

6:35 pm-11:57 pm

1 stop5h 22m

Boston Logan Intl

Mon 3/2

7:45 am-3:00 pm

1 stop7h 15m

$247

Key WestBoston

EYW - BOS

EYWBOS

Key West

Fri 4/17

2:25 pm-11:59 pm

1 stop9h 34m

Boston Logan Intl

Fri 4/24

5:40 am-1:30 pm

1 stop7h 50m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 39 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 $321). 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 February 12, 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 February 12, 2026.

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).

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 February 12, 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
11,271 reviews

Comfort

7.2

Entertainment

6.9

Overall

7.2

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,271 reviews
American Airlines
7.2
Good
11,271 reviews

Comfort

7.2

Entertainment

6.9

Overall

7.2

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
JetBlue
7.2
Good
2,895 reviews
American Airlines
7.2
Good
11,271 reviews

Comfort

7.2

Entertainment

6.9

Overall

7.2

Food

6.4

Boarding

7.5

Crew

8.0

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 29m. 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 $109 on JetBlue. Other airlines that offer cheap prices include American Airlines from $128 and United Airlines 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 (73%), American Airlines (71%) or Republic Airways (71%) 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 $231 for a flight from Key West to Massachusetts. The cheapest flight overall is $108 while the most popular route, (Key West - Boston Logan Intl) is currently priced at $185.

  • 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 $321). 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 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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$351FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$251Average$442FlexibilityNo cancel feeOn-time62%

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