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$54+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 November 13, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$89
(Frontier)

One-way from

$54
(Expedia)

Popular in

November

Cheapest in

September

Average price

$287
Provider with most accurate pricing for Boston Logan Intl-Miami flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Miami flights.
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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. 9% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 13, 2025.

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.
Fri 11/147:36 pmBDL - MIA
Nonstop3h 16mFrontier
Sun 11/2310:24 amMIA - BDL
Nonstop3h 05mFrontier
Deal found 11/11$89
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2710:54 amBDL - MIA
1 stop12h 46mFrontier
Fri 12/1912:20 pmMIA - BDL
Nonstop3h 09mFrontier
Deal found 11/12$92
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.
Mon 11/177:36 pmBDL - MIA
Nonstop3h 16mFrontier
Sun 11/2310:24 amMIA - BDL
Nonstop3h 05mFrontier
Deal found 11/11$94
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.
Fri 12/1211:59 amBDL - MIA
1 stop12h 47mFrontier
Fri 12/1912:20 pmMIA - BDL
Nonstop3h 09mFrontier
Deal found 11/12$95
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.
Sun 11/302:24 pmBDL - MIA
Nonstop3h 22mFrontier
Fri 12/1912:20 pmMIA - BDL
Nonstop3h 09mFrontier
Deal found 11/12$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.
Mon 11/177:36 pmBDL - MIA
Nonstop3h 16mFrontier
Tue 11/251:52 pmMIA - BDL
Nonstop3h 05mFrontier
Deal found 11/11$103
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/232:24 pmBDL - MIA
Nonstop3h 22mFrontier
Tue 11/251:52 pmMIA - BDL
Nonstop3h 05mFrontier
Deal found 11/13$108
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 11/302:24 pmBDL - MIA
Nonstop3h 22mFrontier
Sun 12/75:30 amMIA - BDL
1 stop6h 00mFrontier
Deal found 11/12$109
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.
Fri 12/194:30 pmBDL - MIA
Nonstop3h 28mFrontier
Mon 12/225:05 amMIA - BDL
1 stop28h 03mFrontier
Deal found 11/12$112
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:39 pmBDL - MIA
Nonstop3h 16mFrontier
Sun 11/2310:24 amMIA - BDL
Nonstop3h 05mFrontier
Deal found 11/11$113
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/152:07 pmBDL - MIA
2 stops10h 39mFrontier
Fri 12/1912:20 pmMIA - BDL
Nonstop3h 09mFrontier
Deal found 11/10$119
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.
Sun 12/710:22 amBOS - MIA
1 stop6h 52mMultiple Airlines
Sat 12/136:05 amMIA - BOS
1 stop28h 17mMultiple Airlines
Deal found 11/11$127

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 November 13, 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

Mon 12/8

7:59 pm-11:37 pm

Nonstop3h 38m

Miami

Thu 12/18

8:05 am-3:41 pm

1 stop7h 36m

$147

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sat 12/6

5:00 pm-11:23 pm

1 stop6h 23m

Miami

Thu 12/11

6:53 am-10:15 am

Nonstop3h 22m

$147

AlbanyMiami

ALB - MIA

ALBMIA

Albany Intl

Wed 2/4

3:40 pm-9:00 pm

1 stop5h 20m

Miami

Thu 2/5

6:30 am-1:50 pm

1 stop7h 20m

$159

AlbanyMiami

ALB - MIA

ALBMIA

Albany Intl

Tue 2/3

8:55 am-4:10 pm

1 stop7h 15m

Miami

Mon 2/9

6:05 pm-11:00 pm

1 stop4h 55m

$159

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Tue 12/2

7:59 pm-11:37 pm

Nonstop3h 38m

Miami

Thu 12/4

6:00 am-11:15 am

1 stop5h 15m

$162

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Wed 12/10

8:05 am-8:15 am

1 stop24h 10m

Key West

Wed 12/17

10:47 am-10:46 pm

1 stop11h 59m

$173

AlbanyMiami

ALB - MIA

ALBMIA

Albany Intl

Tue 12/9

8:30 am-4:10 pm

1 stop7h 40m

Miami

Tue 12/16

1:30 pm-7:15 pm

1 stop5h 45m

$177

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Tue 12/2

5:13 pm-12:46 am

1 stop7h 33m

Miami

Mon 12/8

6:53 am-10:15 am

Nonstop3h 22m

$177

HartfordKey West

BDL - EYW

BDLEYW

Hartford Bradley Intl

Sat 12/13

8:05 am-8:15 am

1 stop24h 10m

Key West

Wed 12/17

10:47 am-10:46 pm

1 stop11h 59m

$187

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sun 12/7

12:00 pm-6:50 pm

1 stop6h 50m

Miami

Sat 12/13

7:00 am-2:27 pm

1 stop7h 27m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

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, May is the cheapest month in which you can book a flight from Massachusetts to Florida Keys (average of $179). Flying from Massachusetts to Florida Keys in March is currently the most expensive (average of $306). 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 November 13, 2025.

A simple way to save on the total cost of your ticket is to fly from Massachusetts to Florida Keys at noon. If you’re flexible enough to do this you can expect to save up to 65% on your trip compared to booking a flight in the evening.

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 38m. Fly via Delta, Southwest, or Breeze Airways 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 $79. However, be on the lookout for offers from Southwest and Frontier, 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, May is the cheapest month in which you can book a flight from Massachusetts to Florida Keys (average of $179). Flying from Massachusetts to Florida Keys in March is currently the most expensive (average of $306). 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 November 13, 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%

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