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Florida Keys

$67+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — EYW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$125
(CheapOair)

One-way from

$67
(FlightHub)

Popular in

April

Cheapest in

September

Average price

$247
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. 2% potential increase in price ($5 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 July 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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 9/106:13 pmBOS - MIA
Nonstop3h 37mAmerican Airlines
Mon 9/159:40 pmMIA - BOS
Nonstop3h 19mAmerican Airlines
Deal found 7/29$122
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Sat 8/233:25 pmBOS - MIA
Nonstop3h 41mSpirit Airlines
Thu 8/2811:09 amMIA - BOS
Nonstop3h 21mSpirit Airlines
Deal found 7/29$125
This Delta deal was found by Cheapflights users on 7/28. 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.
Tue 11/119:15 amBOS - MIA
1 stop8h 03mDelta
Wed 11/1211:15 amMIA - BOS
Nonstop3h 24mDelta
Deal found 7/28$127
This FlightHub deal was found by Cheapflights users on 7/30. 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.
Thu 10/3011:25 amBOS - MIA
Nonstop3h 36mFrontier
Sun 11/27:05 amMIA - BOS
Nonstop3h 25mFrontier
Deal found 7/30$135
This Frontier deal was found by Cheapflights users on 7/31. 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 10/2312:59 pmBDL - MIA
Nonstop3h 16mFrontier
Sun 10/269:05 amMIA - BDL
Nonstop3h 06mFrontier
Deal found 7/31$141
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 9/105:43 amBDL - MIA
Nonstop3h 13mAmerican Airlines
Sat 9/137:48 pmMIA - BDL
Nonstop3h 12mAmerican Airlines
Deal found 7/29$159
This FlightHub deal was found by Cheapflights users on 7/31. 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.
Fri 10/241:00 pmBDL - MIA
1 stop23h 13mSpirit Airlines
Mon 10/276:00 amMIA - BDL
1 stop5h 55mSpirit Airlines
Deal found 7/31$165
This Mytrip deal was found by Cheapflights users on 7/30. 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 9/811:00 amALB - MIA
1 stop6h 33mMultiple Airlines
Thu 9/117:01 pmMIA - ALB
1 stop15h 09mMultiple Airlines
Deal found 7/30$168
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Sat 8/3012:45 pmBOS - EYW
1 stop6h 22mAmerican Airlines
Fri 9/56:17 pmEYW - BOS
1 stop5h 27mAmerican Airlines
Deal found 7/31$170
This Southwest deal was found by Cheapflights users on 7/28. 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.
Sun 8/313:50 pmBDL - MIA
1 stop5h 10mSouthwest
Fri 9/56:05 amMIA - BDL
1 stop6h 00mSouthwest
Deal found 7/28$178
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Wed 8/275:27 pmALB - MIA
1 stop5h 32mAmerican Airlines
Wed 9/35:35 pmMIA - ALB
1 stop6h 24mAmerican Airlines
Deal found 7/30$182
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 9/226:00 amBDL - EYW
1 stop27h 07mBreeze Airways
Thu 9/258:55 amEYW - BDL
2 stops14h 09mBreeze Airways
Deal found 7/28$205

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 July 31, 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

Wed 9/10

6:13 pm-9:50 pm

Nonstop3h 37m

Miami

Mon 9/15

9:40 pm-12:59 am

Nonstop3h 19m

$122

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sat 8/23

3:25 pm-7:06 pm

Nonstop3h 41m

Miami

Thu 8/28

11:09 am-2:30 pm

Nonstop3h 21m

$125

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 9/24

7:10 am-10:43 am

Nonstop3h 33m

Miami

Sat 9/27

11:38 am-2:59 pm

Nonstop3h 21m

$127

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Thu 10/9

11:25 am-3:01 pm

Nonstop3h 36m

Miami

Thu 10/16

7:05 am-10:30 am

Nonstop3h 25m

$136

HartfordMiami

BDL - MIA

BDLMIA

Hartford Bradley Intl

Thu 10/23

12:59 pm-4:15 pm

Nonstop3h 16m

Miami

Sun 10/26

9:05 am-12:11 pm

Nonstop3h 06m

$141

HartfordMiami

BDL - MIA

BDLMIA

Hartford Bradley Intl

Wed 9/10

5:43 am-8:56 am

Nonstop3h 13m

Miami

Sat 9/13

7:48 pm-11:00 pm

Nonstop3h 12m

$159

HartfordMiami

BDL - MIA

BDLMIA

Hartford Bradley Intl

Fri 10/24

1:00 pm-12:13 pm

1 stop23h 13m

Miami

Mon 10/27

6:00 am-11:55 am

1 stop5h 55m

$165

AlbanyMiami

ALB - MIA

ALBMIA

Albany Intl

Mon 9/8

11:00 am-5:33 pm

1 stop6h 33m

Miami

Thu 9/11

7:01 pm-10:10 am

1 stop15h 09m

$168

BostonKey West

BOS - EYW

BOSEYW

Boston Logan Intl

Sat 8/30

12:45 pm-7:07 pm

1 stop6h 22m

Key West

Fri 9/5

6:17 pm-11:44 pm

1 stop5h 27m

$170

HartfordMiami

BDL - MIA

BDLMIA

Hartford Bradley Intl

Sun 8/31

3:50 pm-9:00 pm

1 stop5h 10m

Miami

Fri 9/5

6:05 am-12:05 pm

1 stop6h 00m

$178

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 $492). 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 July 31, 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.

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 July 31, 2025.
See what other customers who have flown with Southwest, Delta, and Breeze Airways from Massachusetts to Florida Keys have to say. 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.
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Breeze Airways
8.0
Very good
191 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $67. However, be on the lookout for offers from Delta 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 $492). 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 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$102FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$145Average$376FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$211Average$526FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$344FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$266Average$413FlexibilityNo cancel feeOn-time71%

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