HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$142+ Cheap flights from Massachusetts to Key West (EYW)

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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Key West with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Massachusetts to Key West

Keep the following information in mind while searching for Massachusetts to Key West flight deals. Data was last updated July 3, 2025.

Round-trip from

$249
(Kiwi.com)

One-way from

$142
(Delta)

Popular in

April

Cheapest in

September

Average price

$416

Good round-trip deal

$312 or less

Good one-way deal

$193 or less
From Massachusetts to Key West
Search Deals
One-way flight from Massachusetts to Key West
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Key West.
Search Deals
Price to beat on a one-way flight from Massachusetts to Key West.
Search Deals

Find flight deals from Massachusetts to Key West

Cheapest flights from Massachusetts to Key West
Explore the most affordable flight options available from Massachusetts to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/146:00 amBDL - EYW
1 stop27h 22mBreeze Airways
Thu 7/2410:02 amEYW - BDL
2 stops7h 07mBreeze Airways
Deal found 6/30$249
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/237:00 amBOS - EYW
1 stop6h 09mAmerican Airlines
Sat 8/3012:50 pmEYW - BOS
1 stop6h 36mAmerican Airlines
Deal found 7/1$257
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Wed 8/203:37 pmBOS - EYW
3 stops24h 09mMultiple Airlines
Sun 8/244:36 pmEYW - BOS
1 stop15h 34mMultiple Airlines
Deal found 7/2$281
This American Airlines deal was found by Cheapflights users on 7/3. 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 10/145:40 amBDL - EYW
1 stop5h 12mAmerican Airlines
Sat 10/185:47 pmEYW - BDL
1 stop5h 03mAmerican Airlines
Deal found 7/3$283
This United Airlines deal was found by Cheapflights users on 6/30. 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.
Mon 8/117:00 amBOS - EYW
1 stop6h 26mUnited Airlines
Tue 8/122:22 pmEYW - BOS
1 stop6h 32mUnited Airlines
Deal found 6/30$287
This American Airlines deal was found by Cheapflights users on 7/1. 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 9/166:00 amALB - EYW
1 stop5h 49mAmerican Airlines
Sat 9/2011:25 amEYW - ALB
2 stops10h 34mAmerican Airlines
Deal found 7/1$288
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Mon 11/33:25 pmORH - EYW
1 stop22h 19mAmerican Airlines
Sat 11/84:00 pmEYW - ORH
2 stops22h 53mAmerican Airlines
Deal found 6/30$302
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/309:05 amBOS - EYW
1 stop8h 27mDelta
Tue 8/511:48 amEYW - BOS
1 stop7h 49mDelta
Deal found 6/30$302
This Delta deal was found by Cheapflights users on 7/1. 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.
Tue 7/292:16 pmBDL - EYW
1 stop5h 33mDelta
Tue 8/57:00 amEYW - BDL
1 stop6h 21mDelta
Deal found 7/1$306
This Delta deal was found by Cheapflights users on 7/1. 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.
Tue 7/295:45 amALB - EYW
2 stops11h 27mDelta
Sat 9/67:00 amEYW - ALB
1 stop6h 16mDelta
Deal found 7/1$311
This Mytrip deal was found by Cheapflights users on 7/3. 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.
Fri 11/78:52 amBOS - EYW
2 stops24h 09mAllegiant Air
Wed 11/1210:01 amEYW - BOS
2 stops24h 42mAllegiant Air
Deal found 7/3$385
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Tue 8/266:45 amBDL - EYW
2 stops26h 37mMultiple Airlines
Fri 8/2910:33 amEYW - BDL
1 stop11h 05mMultiple Airlines
Deal found 7/2$410

Cheapflights Fare Finder

Customize your flight search to find flights from Massachusetts to Key West 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 July 3, 2025.
Use the filters below to find and compare flights from Massachusetts to Key West that are best for you.

Fly from

Massachusetts

Fly to

Key West

Route

Depart

Return

Price

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Mon 7/14

6:00 am-9:22 am

1 stop27h 22m

Key West

Thu 7/24

10:02 am-5:09 pm

2 stops7h 07m

$249

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 8/23

7:00 am-1:09 pm

1 stop6h 09m

Key West

Sat 8/30

12:50 pm-7:26 pm

1 stop6h 36m

$257

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Wed 8/20

3:37 pm-3:46 pm

3 stops24h 09m

Key West

Sun 8/24

4:36 pm-8:10 am

1 stop15h 34m

$281

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Tue 8/12

6:00 am-1:05 pm

1 stop7h 05m

Key West

Tue 8/19

7:00 am-1:36 pm

1 stop6h 36m

$283

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Mon 8/11

7:00 am-1:26 pm

1 stop6h 26m

Key West

Tue 8/12

2:22 pm-8:54 pm

1 stop6h 32m

$287

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Tue 9/16

6:00 am-11:49 am

1 stop5h 49m

Key West

Sat 9/20

11:25 am-9:59 pm

2 stops10h 34m

$288

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Tue 8/12

5:50 am-12:58 pm

1 stop7h 08m

Key West

Tue 8/19

11:26 am-10:41 pm

2 stops11h 15m

$288

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Wed 7/30

5:35 am-10:51 am

1 stop5h 16m

Key West

Wed 8/6

6:27 pm-1:39 am

1 stop7h 12m

$302

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Mon 11/3

3:25 pm-1:44 pm

1 stop22h 19m

Key West

Sat 11/8

4:00 pm-2:53 pm

2 stops22h 53m

$302

AlbanyKey West

ALB - EYW

ALBEYW

Albany Intl

Tue 7/29

5:45 am-5:12 pm

2 stops11h 27m

Key West

Sat 9/6

7:00 am-1:16 pm

1 stop6h 16m

$311

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from Massachusetts to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Massachusetts 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 Massachusetts to Key West

What is the cheapest month to book a flight from Massachusetts to Key West?

Currently, August is the cheapest month in which you can book a flight from Massachusetts to Key West (average of $328). Flying from Massachusetts to Key West in March is currently the most expensive (average of $492). 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 MA to EYW?

Find hourly flight availability from Massachusetts to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

When flying from Massachusetts to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated July 3, 2025.
Read through reviews of airlines operating flights from Massachusetts to Key West, such as Breeze Airways, Alaska Airlines, and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
183 reviews

Boarding

8.3

Food

6.8

Crew

8.8

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
183 reviews
Breeze Airways
8.1
Very good
183 reviews

Boarding

8.3

Food

6.8

Crew

8.8

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Alaska Airlines
8.0
Very good
10,000 reviews
Breeze Airways
8.1
Very good
183 reviews

Boarding

8.3

Food

6.8

Crew

8.8

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,982 reviews
Breeze Airways
8.1
Very good
183 reviews

Boarding

8.3

Food

6.8

Crew

8.8

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,861 reviews
Breeze Airways
8.1
Very good
183 reviews

Boarding

8.3

Food

6.8

Crew

8.8

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
183 reviews

Boarding

8.3

Food

6.8

Crew

8.8

Comfort

8.2

Entertainment

6.6

Overall

8.1

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Key West. 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 into for flights to Key West from Massachusetts?

    If you book a flight to Key West from Massachusetts, you will be flying to 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 Massachusetts to Key West one-way?

    $142 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and Breeze Airways, with prices starting from $159 and $211, respectively.

  • What are the most popular routes from Massachusetts to Key West?

    While some choose either Hartford Bradley Intl - Key West or Albany Intl - Key West, Boston Logan Intl - Key West is the most popular route from Massachusetts to Key West.

  • What are the cheapest flights from Massachusetts to Key West?

    The cheapest flight price from Massachusetts to Key West is $158. On average you can expect to pay $463. The most popular route, (Boston Logan Intl - Key West), can usually be booked for $257.

  • Can I find deals for flights from Massachusetts to Key West that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Key West.

  • Can I find deals for business class flights from Massachusetts to Key West?

    Yes. Cheapflights offers flight deals from Massachusetts to Key West 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 Massachusetts to Key West?

    Currently, August is the cheapest month in which you can book a flight from Massachusetts to Key West (average of $328). Flying from Massachusetts to Key West in March is currently the most expensive (average of $492). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Massachusetts to Key West

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Miami flights
LaGuardia to Fort Lauderdale flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
Newark to Miami flights
LaGuardia to Miami flights
Dallas/Fort Worth to Orlando flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Orlando flights
Atlanta to Miami flights
LaGuardia to Orlando flights
Los Angeles to Orlando flights
John F Kennedy Intl to Tampa flights
Los Angeles to Miami flights
Dulles Intl to Miami flights
Baltimore to Miami flights
Boston to Orlando flights
Reagan-National to Miami flights
Philadelphia to Orlando flights
Baltimore to Fort Lauderdale flights
Dallas/Fort Worth to Miami flights
John F Kennedy Intl to West Palm Beach flights
O'Hare Intl to Miami flights
O'Hare Intl to Orlando flights
Newark to Tampa flights
Los Angeles to Fort Lauderdale flights
Philadelphia to Miami flights
O'Hare Intl to Fort Lauderdale flights
Hobby to Orlando flights
Atlanta to Fort Lauderdale flights
LaGuardia to Tampa flights
Dallas/Fort Worth to Fort Lauderdale flights
Dulles Intl to Orlando flights
Philadelphia to Fort Lauderdale flights
Baltimore to Orlando flights
Dulles Intl to Fort Lauderdale flights
Boston to Fort Lauderdale flights
O'Hare Intl to Tampa flights
Detroit to Orlando flights
Denver to Orlando flights
Boston to Miami flights
Raleigh to Orlando flights
Boston to Tampa flights
Hartford to Orlando flights
San Francisco to Miami flights
Seattle to Orlando flights
Minneapolis to Orlando flights
Newark to West Palm Beach flights
Dulles Intl to Tampa flights
Hobby to Miami flights

Top 5 airlines flying from Massachusetts to Key West

Discover the top 5 airlines that operate flights from Massachusetts to Key West. 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$102FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$145Average$376FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$214Average$528FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$350FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$261Average$413FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.