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Florida Keys

$37+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$62
(Kiwi.com)

One-way from

$37
(FlightHub)

Popular in

April

Cheapest in

September

Average price

$281
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. 10% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/20. 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.
Mon 3/104:00 pmBOS - MIA
Nonstop3h 40mSpirit Airlines
Sat 3/155:30 amMIA - BOS
Nonstop3h 22mSpirit Airlines
Deal found 2/20$62
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/84:00 pmBOS - MIA
Nonstop3h 40mMultiple Airlines
Thu 3/207:05 amMIA - BOS
Nonstop3h 28mMultiple Airlines
Deal found 2/20$66
This Frontier deal was found by Cheapflights users on 2/20. 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.
Thu 3/611:33 amBOS - MIA
Nonstop3h 42mFrontier
Thu 3/207:05 amMIA - BOS
Nonstop3h 28mFrontier
Deal found 2/20$78
This CheapOair deal was found by Cheapflights users on 2/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/211:40 amBDL - MIA
Nonstop3h 23mFrontier
Thu 3/63:12 pmMIA - BDL
Nonstop3h 10mFrontier
Deal found 2/19$81
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/104:55 pmBOS - MIA
Nonstop3h 47mDelta
Tue 3/187:20 pmMIA - BOS
Nonstop3h 24mDelta
Deal found 2/20$137
This JetBlue deal was found by Cheapflights users on 2/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/106:59 pmBOS - MIA
Nonstop3h 35mJetBlue
Wed 3/196:00 amMIA - BOS
Nonstop3h 10mJetBlue
Deal found 2/20$138
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/107:30 amBDL - MIA
1 stop7h 31mMultiple Airlines
Tue 4/88:59 amMIA - BDL
2 stops24h 41mMultiple Airlines
Deal found 2/19$157
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/184:30 pmBOS - MIA
1 stop6h 20mSouthwest
Tue 3/257:05 amMIA - BOS
2 stops10h 05mSouthwest
Deal found 2/20$162
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1011:36 amBDL - MIA
2 stops33h 04mSpirit Airlines
Tue 4/88:59 amMIA - BDL
2 stops24h 41mSpirit Airlines
Deal found 2/19$167
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Fri 5/27:16 amBDL - MIA
Nonstop3h 13mAmerican Airlines
Mon 5/58:06 pmMIA - BDL
Nonstop3h 08mAmerican Airlines
Deal found 2/20$179
This American Airlines deal was found by Cheapflights users on 2/18. 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.
Mon 3/32:15 pmORH - MIA
1 stop22h 28mAmerican Airlines
Wed 3/58:41 amMIA - ORH
1 stop5h 02mAmerican Airlines
Deal found 2/18$180
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/112:45 pmBOS - MIA
2 stops7h 41mUnited Airlines
Sat 3/87:00 amMIA - BOS
1 stop7h 34mUnited Airlines
Deal found 2/20$191

Find flights from Massachusetts to Florida Keys within your budget

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 February 20, 2025.

Fly from

Massachusetts

Fly to

Florida Keys

Route

Depart

Return

Price

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Mon 3/10

4:00 pm-7:40 pm

Nonstop3h 40m

Miami

Wed 3/19

9:45 am-1:11 pm

Nonstop3h 26m

$62

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sat 3/8

4:00 pm-7:40 pm

Nonstop3h 40m

Miami

Tue 3/11

7:05 am-10:33 am

Nonstop3h 28m

$66

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Thu 3/6

11:33 am-3:15 pm

Nonstop3h 42m

Miami

Thu 3/20

7:05 am-10:33 am

Nonstop3h 28m

$78

HartfordMiami

BDL - MIA

BDLMIA

Hartford Bradley Intl

Sun 3/2

11:40 am-3:03 pm

Nonstop3h 23m

Miami

Thu 3/6

3:12 pm-6:22 pm

Nonstop3h 10m

$81

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Mon 3/10

4:55 pm-8:42 pm

Nonstop3h 47m

Miami

Tue 3/18

7:20 pm-10:44 pm

Nonstop3h 24m

$137

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Mon 3/10

6:59 pm-10:34 pm

Nonstop3h 35m

Miami

Wed 3/19

6:00 am-9:10 am

Nonstop3h 10m

$138

HartfordMiami

BDL - MIA

BDLMIA

Hartford Bradley Intl

Fri 3/21

10:45 am-3:34 pm

2 stops28h 49m

Miami

Tue 3/25

10:17 am-9:50 am

2 stops23h 33m

$149

HartfordMiami

BDL - MIA

BDLMIA

Hartford Bradley Intl

Fri 3/21

7:30 am-3:34 pm

1 stop8h 04m

Miami

Tue 3/25

10:17 am-1:29 pm

1 stop27h 12m

$155

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Tue 3/18

4:30 pm-10:50 pm

1 stop6h 20m

Miami

Tue 3/25

7:05 am-5:10 pm

2 stops10h 05m

$162

HartfordMiami

BDL - MIA

BDLMIA

Hartford Bradley Intl

Fri 5/2

7:16 am-10:29 am

Nonstop3h 13m

Miami

Sun 5/4

9:00 pm-11:59 pm

Nonstop2h 59m

$179

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Massachusetts to Florida Keys

Get recent, data-driven insights about flights from Massachusetts to Florida Keys including ideal travel times, pricing trends, and more.

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 $510). 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 February 20, 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.

Rainfall in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Florida Keys ranges from 1.6 - 9.9 inches per month. September is typically the wettest month, when rainfall can reach 9.9 in. January is typically the driest time to visit Florida Keys when rainfall is around 1.6 in.

Temperature in Florida Keys by month

Plan your trip to Florida Keys by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Florida Keys, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 68.0 F).

Reviews of airlines servicing Florida Keys

Get insights into the airlines that provide service to Florida Keys. 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 Florida Keys. Reviews last updated February 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines and Delta from Massachusetts to Florida Keys to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Qatar Airways
7.4
Good
3,609 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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.

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $37. However, be on the lookout for offers from Frontier and American Airlines, 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 $510). 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

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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 4 airlines flying from Massachusetts to Florida Keys

Discover the top 4 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$210Average$556FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$348FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$233Average$380FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$256Average$405FlexibilityNo cancel feeOn-time71%
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