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Florida Keys

$50+ Cheap flights from Massachusetts to Florida Keys

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 10/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Oct 22 — Oct 291
Wed 10/22
Wed 10/29
1 adult, Economy
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Cheap flight deals from Massachusetts to Florida Keys

Keep the following information in mind while searching for Massachusetts to Florida Keys flight deals. Data was last updated September 22, 2025.

Round-trip from

$97
(Cheapflightsfares)

One-way from

$50
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$194
From Massachusetts to Florida Keys
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One-way flight from Massachusetts to Florida Keys
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Highest demand for flights based on searches. 1% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 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 Massachusetts to Florida Keys

Cheapest flights from Massachusetts to Florida Keys
Explore the most affordable flight options available from Massachusetts to Florida Keys. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 22, 2025.

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.
Sun 12/712:20 pmBOS - MIA
Nonstop3h 32mSpirit Airlines
Sun 12/148:00 amMIA - BOS
Nonstop3h 25mSpirit Airlines
Deal found 9/20$97
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.
Mon 10/64:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
Fri 10/1712:40 pmMIA - BOS
Nonstop3h 16mSpirit Airlines
Deal found 9/20$98
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.
Sat 10/42:18 pmBOS - MIA
Nonstop3h 32mMultiple Airlines
Sat 10/111:55 pmMIA - BOS
1 stop17h 41mMultiple Airlines
Deal found 9/20$99
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1611:44 amBOS - MIA
Nonstop3h 36mFrontier
Sun 10/197:24 amMIA - BOS
Nonstop3h 25mFrontier
Deal found 9/20$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.
Mon 10/204:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
Fri 10/2412:40 pmMIA - BOS
Nonstop3h 16mSpirit Airlines
Deal found 9/20$104
This Mytrip deal was found by Cheapflights users on 9/22. 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 10/2311:44 amBOS - MIA
Nonstop3h 36mFrontier
Sun 10/267:24 amMIA - BOS
Nonstop3h 25mFrontier
Deal found 9/22$105
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.
Sat 9/272:18 pmBOS - MIA
Nonstop3h 32mSpirit Airlines
Sat 10/49:56 amMIA - BOS
Nonstop3h 27mSpirit Airlines
Deal found 9/20$106
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/174:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
Fri 10/2412:40 pmMIA - BOS
Nonstop3h 16mSpirit Airlines
Deal found 9/21$107
This Kiwi.com deal was found by Cheapflights users on 9/22. 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 11/911:18 amBOS - MIA
Nonstop3h 32mSpirit Airlines
Thu 11/137:00 amMIA - BOS
Nonstop3h 23mSpirit Airlines
Deal found 9/22$109
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/177:49 pmBDL - MIA
Nonstop3h 16mFrontier
Mon 10/203:48 pmMIA - BDL
Nonstop3h 06mFrontier
Deal found 9/20$119
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.
Fri 10/177:49 pmBDL - MIA
Nonstop3h 16mFrontier
Sun 10/194:30 pmMIA - BDL
Nonstop3h 06mFrontier
Deal found 9/21$121
This Frontier deal was found by Cheapflights users on 9/22. 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.
Thu 11/67:39 pmBDL - MIA
Nonstop3h 16mFrontier
Thu 11/133:38 pmMIA - BDL
Nonstop3h 06mFrontier
Deal found 9/22$129

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Florida Keys 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 September 22, 2025.
Use the filters below to find and compare flights from Massachusetts to Florida Keys that are best for you.

Fly from

Massachusetts

Fly to

Florida Keys

Route

Depart

Return

Price

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Thu 10/23

4:26 pm-8:00 pm

Nonstop3h 34m

Miami

Sat 10/25

7:35 pm-11:00 pm

Nonstop3h 25m

$137

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sat 11/8

6:22 pm-12:29 am

1 stop6h 07m

Miami

Tue 11/11

6:55 am-10:19 am

Nonstop3h 24m

$147

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sat 10/4

7:10 am-10:43 am

Nonstop3h 33m

Miami

Sat 10/11

12:43 pm-4:05 pm

Nonstop3h 22m

$147

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Mon 10/6

9:59 am-4:57 pm

1 stop6h 58m

Miami

Wed 10/15

12:05 pm-3:26 pm

Nonstop3h 21m

$157

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Thu 10/23

4:26 pm-8:00 pm

Nonstop3h 34m

Miami

Mon 11/3

5:25 pm-11:49 pm

1 stop6h 24m

$157

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sat 12/6

4:15 pm-7:56 pm

Nonstop3h 41m

Miami

Wed 12/10

7:00 am-10:19 am

Nonstop3h 19m

$159

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 12/3

4:10 pm-7:51 pm

Nonstop3h 41m

Miami

Tue 12/9

7:00 am-10:19 am

Nonstop3h 19m

$159

AlbanyMiami

ALB - MIA

ALBMIA

Albany Intl

Sun 10/19

5:50 am-11:55 am

1 stop6h 05m

Miami

Tue 10/28

7:55 am-12:30 pm

1 stop4h 35m

$167

AlbanyMiami

ALB - MIA

ALBMIA

Albany Intl

Mon 10/27

5:50 pm-10:35 pm

1 stop4h 45m

Miami

Wed 10/29

11:45 am-7:30 pm

1 stop7h 45m

$167

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sat 10/4

5:05 pm-11:10 pm

1 stop6h 05m

Miami

Mon 10/6

7:35 pm-11:00 pm

Nonstop3h 25m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/20

Showing 1-10 of 60 results
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Best time to book a flight from Massachusetts to Florida Keys

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

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

Currently, August is the cheapest month in which you can book a flight from Massachusetts to Florida Keys (average of $328). Flying from Massachusetts to Florida Keys in March is currently the most expensive (average of $489). 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 EOA?

Find hourly flight availability from Massachusetts to Florida Keys. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 22, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Florida Keys. 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 Massachusetts to Florida Keys?

    There are many flights that can get you from Massachusetts to Florida Keys in 3h 34m. Fly via Delta, Southwest, or JetBlue to get the fastest option. There are 1259 mi between Massachusetts and Florida Keys. Both multi-stop and nonstop flights can be found to your destination and back.

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

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $74. However, be on the lookout for offers from American Airlines and Southwest, as they are both options that can get you from Massachusetts to Florida Keys for a low price.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Massachusetts to Florida Keys (average of $328). Flying from Massachusetts to Florida Keys in March is currently the most expensive (average of $489). 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 Massachusetts to Florida Keys

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Massachusetts to Florida Keys

Discover the top 5 airlines that operate flights from Massachusetts to Florida Keys. 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 September 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$102FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$135Average$378FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$370FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$217Average$527FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$250Average$409FlexibilityNo cancel feeOn-time71%

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