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$50+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
oct. 22 — oct. 291
mié. 10/22
mié. 10/29
1 adult, Economy
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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 septiembre 22, 2025.

Round-trip from

$101
(Kiwi.com)

One-way from

$50
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$300
From Florida Keys to Massachusetts
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One-way flight from Florida Keys to Massachusetts
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Highest demand for flights based on searches. 15% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 septiembre 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
jue. 10/94:30 pmMIA - BDL
Nonstop3h 06mFrontier
dom. 10/128:31 pmBDL - MIA
Nonstop3h 13mFrontier
Deal found 9/21$101
This Priceline deal was found by Cheapflights users on 9/21. 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.
vie. 11/73:35 pmMIA - BDL
Nonstop3h 06mFrontier
lun. 11/107:36 pmBDL - MIA
Nonstop3h 16mFrontier
Deal found 9/21$102
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
sáb. 10/49:56 amMIA - BOS
Nonstop3h 27mSpirit Airlines
lun. 10/64:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
Deal found 9/20$106
This Cheapflightsfares deal was found by Cheapflights users on 9/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/2012:40 pmMIA - BOS
Nonstop3h 16mSpirit Airlines
lun. 10/274:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
Deal found 9/20$107
This Booking.com deal was found by Cheapflights users on 9/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/27:25 amMIA - BOS
1 stop24h 27mMultiple Airlines
sáb. 10/42:18 pmBOS - MIA
Nonstop3h 32mMultiple Airlines
Deal found 9/20$110
This Booking.com deal was found by Cheapflights users on 9/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/29:56 amMIA - BOS
Nonstop3h 27mSpirit Airlines
sáb. 10/42:18 pmBOS - MIA
Nonstop3h 32mSpirit Airlines
Deal found 9/20$111
This Frontier deal was found by Cheapflights users on 9/19. 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.
vie. 10/173:48 pmMIA - BDL
Nonstop3h 06mFrontier
dom. 10/198:31 pmBDL - MIA
Nonstop3h 13mFrontier
Deal found 9/19$119
This Frontier deal was found by Cheapflights users on 9/21. 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.
dom. 10/127:24 amMIA - BOS
Nonstop3h 25mFrontier
jue. 10/1611:44 amBOS - MIA
Nonstop3h 36mFrontier
Deal found 9/21$119
This Flightnetwork deal was found by Cheapflights users on 9/20. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/49:56 amMIA - BOS
Nonstop3h 27mMultiple Airlines
lun. 10/68:47 amBOS - MIA
1 stop12h 51mMultiple Airlines
Deal found 9/20$121
This Gotogate deal was found by Cheapflights users on 9/20. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/29:56 amMIA - BOS
Nonstop3h 27mSpirit Airlines
lun. 10/64:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
Deal found 9/20$122
This American Airlines deal was found by Cheapflights users on 9/21. 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.
mié. 11/510:41 amMIA - BOS
Nonstop3h 28mAmerican Airlines
mié. 11/122:59 pmBOS - MIA
Nonstop3h 42mAmerican Airlines
Deal found 9/21$126
This American Airlines deal was found by Cheapflights users on 9/20. 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.
jue. 11/67:42 pmMIA - BOS
Nonstop3h 23mAmerican Airlines
mar. 11/116:46 amBOS - MIA
Nonstop3h 45mAmerican Airlines
Deal found 9/20$127

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 septiembre 22, 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

vie. 11/7

3:35 pm-6:41 pm

Nonstop3h 06m

Hartford Bradley Intl

dom. 11/9

7:39 pm-10:55 pm

Nonstop3h 16m

$102

MiamiBoston

MIA - BOS

MIABOS

Miami

sáb. 10/18

3:33 pm-10:27 pm

1 stop6h 54m

Boston Logan Intl

sáb. 10/25

7:30 am-11:06 am

Nonstop3h 36m

$147

MiamiBoston

MIA - BOS

MIABOS

Miami

vie. 11/7

7:35 pm-11:00 pm

Nonstop3h 25m

Boston Logan Intl

lun. 11/10

9:59 am-4:10 pm

1 stop6h 11m

$147

MiamiBoston

MIA - BOS

MIABOS

Miami

mar. 11/4

6:00 am-12:35 pm

1 stop6h 35m

Boston Logan Intl

dom. 11/9

7:55 pm-11:32 pm

Nonstop3h 37m

$147

MiamiBoston

MIA - BOS

MIABOS

Miami

vie. 11/7

6:20 am-5:40 pm

1 stop11h 20m

Boston Logan Intl

lun. 11/10

6:50 am-4:30 pm

1 stop9h 40m

$156

MiamiBoston

MIA - BOS

MIABOS

Miami

mar. 10/21

11:45 am-10:10 pm

2 stops10h 25m

Boston Logan Intl

mar. 10/28

5:30 am-10:55 am

1 stop5h 25m

$156

MiamiBoston

MIA - BOS

MIABOS

Miami

mar. 11/4

7:35 pm-11:00 pm

Nonstop3h 25m

Boston Logan Intl

sáb. 11/8

6:22 pm-12:29 am

1 stop6h 07m

$157

MiamiBoston

MIA - BOS

MIABOS

Miami

vie. 12/5

7:00 am-10:19 am

Nonstop3h 19m

Boston Logan Intl

lun. 12/8

7:59 pm-11:36 pm

Nonstop3h 37m

$159

MiamiAlbany

MIA - ALB

MIAALB

Miami

jue. 10/16

6:25 am-12:20 pm

1 stop5h 55m

Albany Intl

dom. 10/19

5:50 am-11:55 am

1 stop6h 05m

$167

MiamiAlbany

MIA - ALB

MIAALB

Miami

jue. 10/23

6:25 am-12:20 pm

1 stop5h 55m

Albany Intl

dom. 10/26

5:20 am-10:40 am

1 stop5h 20m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/19

Showing 1-10 of 60 results
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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, January is the cheapest month in which you can book a flight from Florida Keys to Massachusetts (average of $218). Flying from Florida Keys to Massachusetts in July 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 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 septiembre 22, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Florida Keys to Massachusetts as you normally would.

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 septiembre 22, 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
8.0
Very good
7,974 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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
8.0
Very good
7,974 reviews
Delta
8.0
Very good
7,974 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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
10,000 reviews
Delta
8.0
Very good
7,974 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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
2,911 reviews
Delta
8.0
Very good
7,974 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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
8,031 reviews
Delta
8.0
Very good
7,974 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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
3,166 reviews
Delta
8.0
Very good
7,974 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.2

Overall

8.0

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 $102, Frontier can have you in Massachusetts from Florida Keys in 3h 06m. 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 $59. Southwest flights start at $71 while deals on Delta start at $74 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, January is the cheapest month in which you can book a flight from Florida Keys to Massachusetts (average of $218). Flying from Florida Keys to Massachusetts in July 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

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Alternative routes for Florida Keys to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Florida Keys to Massachusetts

Discover the top 3 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 septiembre 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$399FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$498FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$258Average$343FlexibilityNo cancel feeOn-time71%

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