HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$90+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
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 November 2, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$204
(Kiwi.com)

One-way from

$90
(Priceline)

Popular in

April

Cheapest in

September

Average price

$366

Good round-trip deal

$331 or less

Good one-way deal

$173 or less
Provider with most accurate pricing for Boston Logan Intl-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Key West flights.
Search Deals
From Massachusetts to Key West
Search Deals
One-way flight from Massachusetts to Key West
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($96 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 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 November 2, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Sun 11/161:36 pmBDL - EYW
1 stop18h 39mMultiple Airlines
Thu 11/208:55 amEYW - BDL
1 stop10h 37mMultiple Airlines
Deal found 10/31$204
This American Airlines deal was found by Cheapflights users on 10/31. 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 12/163:34 pmORH - EYW
1 stop22h 17mAmerican Airlines
Wed 12/244:03 pmEYW - ORH
2 stops21h 08mAmerican Airlines
Deal found 10/31$237
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/38:05 amBDL - EYW
1 stop24h 10mMultiple Airlines
Sun 12/78:55 amEYW - BDL
1 stop28h 17mMultiple Airlines
Deal found 11/1$240
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/208:04 pmALB - EYW
1 stop25h 33mAllegiant Air
Tue 12/3010:32 pmEYW - ALB
1 stop11h 42mAllegiant Air
Deal found 11/1$242
This American Airlines deal was found by Cheapflights users on 10/31. 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 11/153:27 pmORH - EYW
1 stop20h 40mAmerican Airlines
Wed 11/195:09 pmEYW - ORH
1 stop21h 42mAmerican Airlines
Deal found 10/31$242
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Mon 12/88:55 amEYW - BDL
2 stops13h 48mBreeze Airways
Deal found 11/1$245
This Orbitz deal was found by Cheapflights users on 11/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/115:45 amBOS - EYW
1 stop5h 35mSpirit Airlines
Sun 12/1412:20 pmEYW - BOS
1 stop11h 36mSpirit Airlines
Deal found 11/2$250
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 11/1511:43 amBOS - EYW
2 stops22h 36mMultiple Airlines
Sat 11/222:24 pmEYW - BOS
1 stop9h 29mMultiple Airlines
Deal found 10/31$251
This United Airlines deal was found by Cheapflights users on 10/31. 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 11/196:02 amBOS - EYW
1 stop8h 02mUnited Airlines
Tue 11/252:45 pmEYW - BOS
1 stop7h 57mUnited Airlines
Deal found 10/31$252
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/111:04 pmBOS - EYW
2 stops35h 03mMultiple Airlines
Sat 12/62:30 pmEYW - BOS
1 stop9h 26mMultiple Airlines
Deal found 10/31$253
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Sat 12/68:11 pmBOS - EYW
1 stop12h 04mMultiple Airlines
Wed 12/104:31 pmEYW - BOS
2 stops31h 25mMultiple Airlines
Deal found 10/30$254
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:05 amBDL - EYW
1 stop24h 10mBreeze Airways
Mon 11/179:57 amEYW - BDL
2 stops26h 16mBreeze Airways
Deal found 11/1$255

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 November 2, 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

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Tue 12/16

3:34 pm-2:54 pm

2 stops23h 20m

Key West

Wed 12/24

4:03 pm-1:11 pm

2 stops21h 08m

$242

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Sat 11/15

3:27 pm-12:07 pm

1 stop20h 40m

Key West

Wed 11/19

5:09 pm-2:51 pm

1 stop21h 42m

$242

WorcesterKey West

ORH - EYW

ORHEYW

Worcester

Wed 12/17

3:30 pm-12:08 pm

2 stops20h 38m

Key West

Wed 12/24

4:03 pm-1:11 pm

2 stops21h 08m

$242

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Wed 2/4

8:05 am-9:06 am

1 stop25h 01m

Key West

Sun 2/8

9:46 am-11:56 pm

2 stops14h 10m

$255

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Wed 12/3

8:05 am-8:15 am

1 stop24h 10m

Key West

Mon 12/8

11:11 am-5:26 pm

1 stop6h 15m

$256

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Wed 11/12

10:15 am-5:23 pm

1 stop7h 08m

Key West

Wed 11/19

7:40 am-3:36 pm

1 stop7h 56m

$257

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Tue 12/9

8:00 am-2:07 pm

1 stop6h 07m

Key West

Sat 12/13

6:10 pm-1:27 am

1 stop7h 17m

$262

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Tue 1/27

6:00 am-3:17 pm

2 stops9h 17m

Key West

Thu 2/5

2:25 pm-11:44 pm

2 stops9h 19m

$269

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Wed 2/25

2:20 pm-7:44 pm

1 stop5h 24m

Key West

Tue 3/3

7:00 am-1:18 pm

1 stop6h 18m

$269

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 12/6

2:12 pm-8:06 pm

1 stop5h 54m

Key West

Tue 12/9

6:10 pm-11:47 pm

1 stop5h 37m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/31

Showing 1-10 of 50 results
1
2
3
...
5

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, September is the cheapest month in which you can book a flight from Massachusetts to Key West (average of $179). Flying from Massachusetts to Key West in March is currently the most expensive (average of $311). 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 November 2, 2025.

When flying from Massachusetts to Key West, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 65% versus a flight in the evening.

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.

  • How long is the flight from Massachusetts to Key West?

    A quick flight from Massachusetts to Key West can take about 7h 08m. American Airlines provides one of the quickest options available for as low as $257. The distance from Massachusetts to Key West is about 1374 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Massachusetts to Key West one-way?

    $96 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Breeze Airways and American Airlines, with prices starting from $139 and $154, 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 $113. On average you can expect to pay $290. The most popular route, (Boston Logan Intl - Key West), can usually be booked for $191.

  • 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, September is the cheapest month in which you can book a flight from Massachusetts to Key West (average of $179). Flying from Massachusetts to Key West in March is currently the most expensive (average of $311). 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 Fort Lauderdale flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
Newark to Miami flights
John F Kennedy Intl to Orlando flights
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
John F Kennedy Intl to West Palm Beach flights
Newark to Orlando flights
LaGuardia to Orlando flights
Newark to West Palm Beach flights
LaGuardia to Tampa flights
Dulles Intl to Miami flights
John F Kennedy Intl to Tampa flights
Philadelphia to Orlando flights
Dallas/Fort Worth to Orlando flights
Newark to Tampa flights
Boston to Miami flights
Reagan-National to Miami flights
Boston to Orlando flights
Boston to Fort Lauderdale flights
O'Hare Intl to Orlando flights
LaGuardia to West Palm Beach flights
O'Hare Intl to Miami flights
Boston to Tampa flights
Reagan-National to Orlando flights
Los Angeles to Orlando flights
Baltimore to Fort Lauderdale flights
Los Angeles to Miami flights
Dallas/Fort Worth to Miami flights
O'Hare Intl to Tampa flights
Dulles Intl to Orlando flights
Los Angeles to Fort Lauderdale flights
O'Hare Intl to Fort Lauderdale flights
Baltimore to Orlando flights
Minneapolis to Orlando flights
Baltimore to Miami flights
Dallas/Fort Worth to Fort Lauderdale flights
Providence to Orlando flights
Philadelphia to Fort Lauderdale flights
Denver to Orlando flights
Cleveland to Orlando flights
Dulles Intl to Fort Lauderdale flights
Newark to Fort Myers flights
Hartford to Orlando flights
John F Kennedy Intl to Fort Myers flights
Boston to West Palm Beach flights
Seattle to Orlando flights
O'Hare Intl to Fort Myers flights
Atlanta to Fort Lauderdale 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 November 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$102FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$135Average$375FlexibilityNo cancel feeOn-time69%
DeltaCheapest$178Average$352FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$222Average$526FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$252Average$411FlexibilityNo 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.