HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$54+ Cheap flights from Florida Keys 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Florida Keys 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.

Find flight deals from Florida Keys to Massachusetts

Cheapest flights from Florida Keys to Massachusetts
Explore the most affordable flight options available from Florida Keys to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This CheapOair deal was found by Cheapflights users on 11/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2310:24 amMIA - BDL
Nonstop3h 05mFrontier
Tue 11/255:42 pmBDL - MIA
Nonstop3h 22mFrontier
Deal found 11/12$60
This CheapOair deal was found by Cheapflights users on 11/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2310:24 amMIA - BDL
Nonstop3h 05mFrontier
Sun 11/302:24 pmBDL - MIA
Nonstop3h 22mFrontier
Deal found 11/12$70
This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/133:38 pmMIA - BDL
Nonstop3h 06mFrontier
Mon 11/177:36 pmBDL - MIA
Nonstop3h 16mFrontier
Deal found 11/11$99
This Frontier deal was found by Cheapflights users on 11/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2310:24 amMIA - BDL
Nonstop3h 05mFrontier
Thu 11/2710:54 amBDL - MIA
1 stop12h 46mFrontier
Deal found 11/11$102
This Priceline deal was found by Cheapflights users on 11/10. 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 11/133:38 pmMIA - BDL
Nonstop3h 06mFrontier
Sun 11/232:24 pmBDL - MIA
Nonstop3h 22mFrontier
Deal found 11/10$113
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/2712:28 pmMIA - BOS
1 stop8h 21mMultiple Airlines
Tue 12/212:44 pmBOS - MIA
1 stop23h 58mMultiple Airlines
Deal found 11/12$115
This Trip.com deal was found by Cheapflights users on 11/12. 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.
Fri 11/143:35 pmMIA - BDL
Nonstop3h 06mFrontier
Sun 12/2112:05 pmBDL - MIA
1 stop12h 42mFrontier
Deal found 11/12$117
This Priceline deal was found by Cheapflights users on 11/13. 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.
Fri 12/267:05 pmMIA - BOS
1 stop6h 09mMultiple Airlines
Sun 2/15:14 pmBOS - MIA
Nonstop3h 42mMultiple Airlines
Deal found 11/13$121
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Wed 12/175:58 pmMIA - BOS
1 stop16h 10mMultiple Airlines
Thu 1/16:00 amBOS - MIA
1 stop7h 06mMultiple Airlines
Deal found 11/11$122
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Mon 12/2210:19 pmMIA - BOS
1 stop11h 23mFrontier
Tue 1/66:00 amBOS - MIA
1 stop18h 46mFrontier
Deal found 11/11$123
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/2210:19 pmMIA - BOS
1 stop11h 23mFrontier
Tue 12/3010:37 amBOS - MIA
1 stop8h 53mFrontier
Deal found 11/12$125
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/205:30 amMIA - BOS
1 stop19h 44mFrontier
Thu 1/110:47 amBOS - MIA
1 stop9h 26mFrontier
Deal found 11/12$127

Cheap flight deals from Florida Keys to Massachusetts

Keep the following information in mind while searching for Florida Keys to Massachusetts flight deals. Data was last updated November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$60
(CheapOair)

One-way from

$54
(Kiwi.com)

Popular in

September

Cheapest in

June

Average price

$356
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 Florida Keys to Massachusetts
Search Deals
One-way flight from Florida Keys to Massachusetts
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Florida Keys 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 November 13, 2025.
Use the filters below to find and compare flights from Florida Keys to Massachusetts that are best for you.

Fly from

Florida Keys

Fly to

Massachusetts

Route

Depart

Return

Price

MiamiHartford

MIA - BDL

MIABDL

Miami

Sun 11/23

10:24 am-1:29 pm

Nonstop3h 05m

Hartford Bradley Intl

Tue 11/25

5:42 pm-9:04 pm

Nonstop3h 22m

$60

MiamiHartford

MIA - BDL

MIABDL

Miami

Thu 1/29

5:30 am-11:16 am

1 stop5h 46m

Hartford Bradley Intl

Sun 2/1

12:11 pm-12:47 am

1 stop12h 36m

$124

MiamiBoston

MIA - BOS

MIABOS

Miami

Fri 12/5

6:53 am-10:15 am

Nonstop3h 22m

Boston Logan Intl

Sun 12/7

7:59 pm-11:37 pm

Nonstop3h 38m

$137

MiamiBoston

MIA - BOS

MIABOS

Miami

Sun 12/14

6:53 am-10:15 am

Nonstop3h 22m

Boston Logan Intl

Mon 12/15

7:59 pm-11:37 pm

Nonstop3h 38m

$137

MiamiBoston

MIA - BOS

MIABOS

Miami

Fri 12/5

6:53 am-10:15 am

Nonstop3h 22m

Boston Logan Intl

Mon 12/8

3:20 pm-7:02 pm

Nonstop3h 42m

$137

MiamiBoston

MIA - BOS

MIABOS

Miami

Thu 12/4

7:59 pm-11:25 pm

Nonstop3h 26m

Boston Logan Intl

Sun 12/7

7:59 pm-11:37 pm

Nonstop3h 38m

$137

MiamiBoston

MIA - BOS

MIABOS

Miami

Sat 12/6

7:59 pm-11:25 pm

Nonstop3h 26m

Boston Logan Intl

Sun 12/7

7:59 pm-11:37 pm

Nonstop3h 38m

$137

MiamiBoston

MIA - BOS

MIABOS

Miami

Wed 12/3

6:53 am-10:15 am

Nonstop3h 22m

Boston Logan Intl

Wed 12/3

5:13 pm-12:46 am

1 stop7h 33m

$147

MiamiBoston

MIA - BOS

MIABOS

Miami

Thu 11/27

6:55 am-10:18 am

Nonstop3h 23m

Boston Logan Intl

Wed 12/3

7:59 pm-11:37 pm

Nonstop3h 38m

$148

MiamiHartford

MIA - BDL

MIABDL

Miami

Mon 12/22

12:20 pm-3:29 pm

Nonstop3h 09m

Hartford Bradley Intl

Sun 1/4

12:05 pm-12:47 am

1 stop12h 42m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Florida Keys to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Florida Keys 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 Florida Keys to Massachusetts

What is the cheapest month to book a flight from Florida Keys to Massachusetts?

Currently, November is the cheapest month in which you can book a flight from Florida Keys to Massachusetts (average of $170). Flying from Florida Keys to Massachusetts in February is currently the most expensive (average of $331). 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 EOA to MA?

Find hourly flight availability from Florida Keys 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 November 13, 2025.

When flying from Florida Keys to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 45% versus a flight at noon.

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 November 13, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and JetBlue from Florida Keys to Massachusetts. 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.
Delta
7.9
Good
8,007 reviews

Food

7.3

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,051 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
JetBlue
7.2
Good
2,907 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Spirit Airlines
6.3
Okay
8,138 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Frontier
5.8
Fair
3,109 reviews
Delta
7.9
Good
8,007 reviews

Food

7.3

Overall

7.9

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Florida Keys to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Florida Keys to Massachusetts?

    For as low as $60, Frontier can have you in Massachusetts from Florida Keys in 3h 05m. There are 1195 mi between Florida Keys and Massachusetts. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Florida Keys to Massachusetts one-way?

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $68. Delta flights start at $79 while deals on Southwest start at $79 one-way.

  • Can I find deals for flights from Florida Keys to Massachusetts that include hotel bookings?

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

  • How can I find direct flights from Florida Keys to Massachusetts?

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

  • Can I find deals for business class flights from Florida Keys to Massachusetts?

    Yes. Cheapflights offers flight deals from Florida Keys 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 Florida Keys to Massachusetts?

    Currently, November is the cheapest month in which you can book a flight from Florida Keys to Massachusetts (average of $170). Flying from Florida Keys to Massachusetts in February is currently the most expensive (average of $331). 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 Florida Keys to Massachusetts

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

Top 2 airlines flying from Florida Keys to Massachusetts

Discover the top 2 airlines that operate flights from Florida Keys 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$226Average$346FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$251Average$496FlexibilityNo 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.