HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$70+ 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 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Feb 3 — Feb 101
Tue 2/3
Tue 2/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Key West to Massachusetts 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 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 January 4, 2026.

This Breeze Airways deal was found by Cheapflights users on 1/2. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/231:06 pmEYW - BDL
1 stop25h 59mBreeze Airways
Sun 1/253:00 pmBDL - EYW
1 stop18h 09mBreeze Airways
Deal found 1/2$173
This United Airlines deal was found by Cheapflights users on 1/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/296:05 pmEYW - BOS
1 stop5h 44mUnited Airlines
Tue 2/39:30 amBOS - EYW
1 stop6h 52mUnited Airlines
Deal found 1/2$197
This Mytrip deal was found by Cheapflights users on 1/3. 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.
Mon 1/262:25 pmEYW - BOS
1 stop9h 32mSpirit Airlines
Thu 1/295:34 amBOS - EYW
1 stop6h 22mSpirit Airlines
Deal found 1/3$198
This Breeze Airways deal was found by Cheapflights users on 1/4. 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.
Sat 1/3110:49 amEYW - BDL
1 stop27h 26mBreeze Airways
Sun 2/83:00 pmBDL - EYW
1 stop18h 09mBreeze Airways
Deal found 1/4$204
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/1510:06 amEYW - BOS
1 stop13h 13mMultiple Airlines
Sat 1/173:43 pmBOS - EYW
1 stop17h 43mMultiple Airlines
Deal found 1/2$206
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2210:06 amEYW - BOS
1 stop13h 13mMultiple Airlines
Mon 1/265:34 amBOS - EYW
1 stop7h 56mMultiple Airlines
Deal found 1/2$208
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2910:06 amEYW - BOS
1 stop13h 13mMultiple Airlines
Mon 2/25:34 amBOS - EYW
1 stop7h 56mMultiple Airlines
Deal found 1/2$211
This United Airlines deal was found by Cheapflights users on 1/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/216:05 pmEYW - BOS
1 stop5h 44mUnited Airlines
Mon 1/269:30 amBOS - EYW
1 stop6h 52mUnited Airlines
Deal found 1/2$217
This Priceline deal was found by Cheapflights users on 1/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/171:00 pmEYW - BOS
Nonstop3h 36mJetBlue
Wed 1/218:09 amBOS - EYW
Nonstop3h 56mJetBlue
Deal found 1/2$218
This United Airlines deal was found by Cheapflights users on 1/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/222:25 pmEYW - BOS
2 stops9h 24mUnited Airlines
Mon 1/269:30 amBOS - EYW
1 stop6h 52mUnited Airlines
Deal found 1/2$222
This JetBlue deal was found by Cheapflights users on 1/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/221:00 pmEYW - BOS
Nonstop3h 36mJetBlue
Mon 1/268:09 amBOS - EYW
Nonstop3h 56mJetBlue
Deal found 1/3$223
This Kiwi.com deal was found by Cheapflights users on 1/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/2210:06 amEYW - BOS
1 stop13h 13mMultiple Airlines
Tue 1/276:00 amBOS - EYW
2 stops28h 09mMultiple Airlines
Deal found 1/2$224

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 January 4, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$173
(Breeze Airways)

One-way from

$70
(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.
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. 6% potential increase in price ($27 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 January 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 January 4, 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

Fri 1/23

1:06 pm-3:05 pm

1 stop25h 59m

Hartford Bradley Intl

Sun 1/25

3:00 pm-9:09 am

1 stop18h 09m

$173

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/29

6:05 pm-11:49 pm

1 stop5h 44m

Boston Logan Intl

Mon 2/2

9:30 am-4:22 pm

1 stop6h 52m

$197

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/29

6:05 pm-11:49 pm

1 stop5h 44m

Boston Logan Intl

Tue 2/3

9:30 am-4:22 pm

1 stop6h 52m

$197

Key WestHartford

EYW - BDL

EYWBDL

Key West

Sat 1/31

10:49 am-2:15 pm

1 stop27h 26m

Hartford Bradley Intl

Sun 2/8

3:00 pm-9:09 am

1 stop18h 09m

$204

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/22

2:25 pm-11:49 pm

2 stops9h 24m

Boston Logan Intl

Mon 1/26

9:30 am-4:22 pm

1 stop6h 52m

$222

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/22

1:00 pm-4:36 pm

Nonstop3h 36m

Boston Logan Intl

Mon 1/26

8:09 am-12:05 pm

Nonstop3h 56m

$223

Key WestBoston

EYW - BOS

EYWBOS

Key West

Thu 1/29

10:06 am-11:19 pm

1 stop13h 13m

Boston Logan Intl

Mon 2/2

5:23 pm-10:09 am

2 stops40h 46m

$228

Key WestHartford

EYW - BDL

EYWBDL

Key West

Wed 1/28

4:06 pm-4:03 pm

2 stops23h 57m

Hartford Bradley Intl

Sat 1/31

8:01 pm-9:26 am

1 stop13h 25m

$233

Key WestBoston

EYW - BOS

EYWBOS

Key West

Wed 1/21

10:49 am-11:57 pm

2 stops13h 08m

Boston Logan Intl

Mon 1/26

5:34 am-1:30 pm

1 stop7h 56m

$235

Key WestBoston

EYW - BOS

EYWBOS

Key West

Sat 1/17

6:05 pm-11:49 pm

1 stop5h 44m

Boston Logan Intl

Wed 1/21

9:30 am-4:22 pm

1 stop6h 52m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

Showing 1-10 of 32 results
1
2
3
4

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 January 4, 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.

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 January 4, 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
11,078 reviews

Food

6.4

Overall

7.2

Crew

8.0

Entertainment

6.9

Comfort

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
11,078 reviews
American Airlines
7.2
Good
11,078 reviews

Food

6.4

Overall

7.2

Crew

8.0

Entertainment

6.9

Comfort

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
2,900 reviews
American Airlines
7.2
Good
11,078 reviews

Food

6.4

Overall

7.2

Crew

8.0

Entertainment

6.9

Comfort

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 5h 44m. 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 $223.

  • 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.

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 Key West to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to John F Kennedy Intl flights
Fort Lauderdale to John F Kennedy Intl flights
Miami to John F Kennedy Intl flights
Fort Lauderdale to Newark flights
Fort Lauderdale to Las Vegas flights
Fort Lauderdale to LaGuardia flights
Miami to LaGuardia flights
Orlando to Las Vegas flights
Tampa to John F Kennedy Intl flights
Miami to Newark flights
Fort Lauderdale to Sky Harbor Intl flights
Tampa to LaGuardia flights
Miami to Sky Harbor Intl flights
Orlando to Newark flights
West Palm Beach to Newark flights
Orlando to LaGuardia flights
Miami to Denver flights
Orlando to Los Angeles flights
West Palm Beach to John F Kennedy Intl flights
Tampa to Newark flights
Orlando to Denver flights
Miami to Las Vegas flights
Orlando to Seattle flights
Tampa to Las Vegas flights
Orlando to Sky Harbor Intl flights
Fort Lauderdale to Denver flights
Tampa to Seattle flights
Miami to Los Angeles flights
Jacksonville to John F Kennedy Intl flights
Tampa to Atlanta flights
Tampa to Sky Harbor Intl flights
Tampa to Denver flights
Fort Lauderdale to Atlanta flights
Tampa to Dulles Intl flights
Fort Lauderdale to Los Angeles flights
Orlando to Dallas/Fort Worth flights
Orlando to Dulles Intl flights
Orlando to Reagan-National flights
Miami to Atlanta flights
Fort Lauderdale to Dallas/Fort Worth flights
Tampa to Los Angeles flights
Jacksonville to Newark flights
West Palm Beach to Sky Harbor Intl flights
Miami to Dallas/Fort Worth flights
Tampa to Boston flights
West Palm Beach to LaGuardia flights
Tampa to Dallas/Fort Worth flights
Jacksonville to LaGuardia flights
Miami to Dulles Intl flights
Fort Lauderdale to Seattle flights

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 January 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$346FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$277Average$447FlexibilityNo cancel feeOn-time62%

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.