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$70+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
Apr 29 — May 61
Tue 4/29
Tue 5/6
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 April 24, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$106
(Cheapflightsfares)

One-way from

$70
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$557
Provider with most accurate pricing for Key West-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Key West-Boston Logan Intl flights.
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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. 14% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/23. 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.
Thu 5/82:21 pmMIA - BOS
Nonstop3h 25mSpirit Airlines
Sun 5/119:46 amBOS - MIA
Nonstop3h 30mSpirit Airlines
Deal found 4/23$106
This Delta deal was found by Cheapflights users on 4/23. 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 7/18:27 pmMIA - BOS
Nonstop3h 32mDelta
Tue 7/153:45 pmBOS - MIA
Nonstop3h 44mDelta
Deal found 4/23$159
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Wed 5/2811:11 amMIA - BOS
Nonstop3h 28mJetBlue
Sun 6/17:42 pmBOS - MIA
Nonstop3h 31mJetBlue
Deal found 4/23$163
This American Airlines deal was found by Cheapflights users on 4/23. 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 6/28:25 amMIA - BOS
Nonstop3h 20mAmerican Airlines
Fri 6/65:15 amBOS - MIA
Nonstop3h 29mAmerican Airlines
Deal found 4/23$176
This Southwest deal was found by Cheapflights users on 4/23. 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.
Wed 5/215:05 pmMIA - BOS
1 stop5h 20mSouthwest
Wed 5/283:00 pmBOS - MIA
1 stop6h 55mSouthwest
Deal found 4/23$183
This Orbitz deal was found by Cheapflights users on 4/21. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/127:58 pmMIA - BDL
1 stop12h 12mSpirit Airlines
Sun 9/149:15 amBDL - MIA
1 stop9h 38mSpirit Airlines
Deal found 4/21$192
This American Airlines deal was found by Cheapflights users on 4/23. 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 6/48:06 pmMIA - BDL
Nonstop3h 07mAmerican Airlines
Wed 6/115:37 amBDL - MIA
Nonstop3h 13mAmerican Airlines
Deal found 4/23$195
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Tue 5/208:30 amMIA - ALB
1 stop7h 27mAmerican Airlines
Thu 5/2212:16 pmALB - MIA
1 stop6h 47mAmerican Airlines
Deal found 4/23$197
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Fri 5/1610:14 amMIA - BOS
1 stop7h 07mUnited Airlines
Mon 5/198:05 amBOS - MIA
1 stop8h 11mUnited Airlines
Deal found 4/23$209
This Delta deal was found by Cheapflights users on 4/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/85:35 amMIA - BDL
1 stop5h 03mDelta
Sun 5/117:08 pmBDL - MIA
1 stop5h 29mDelta
Deal found 4/21$217
This Delta deal was found by Cheapflights users on 4/23. 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.
Thu 5/155:59 pmMIA - ALB
1 stop6h 02mDelta
Mon 5/196:55 pmALB - MIA
1 stop5h 42mDelta
Deal found 4/23$217
This Southwest deal was found by Cheapflights users on 4/21. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/86:10 pmMIA - BDL
1 stop4h 50mSouthwest
Mon 5/126:10 amBDL - MIA
2 stops8h 35mSouthwest
Deal found 4/21$222

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 April 24, 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

MiamiBoston

MIA - BOS

MIABOS

Miami

Thu 5/8

2:21 pm-5:46 pm

Nonstop3h 25m

Boston Logan Intl

Sun 5/11

9:46 am-1:16 pm

Nonstop3h 30m

$106

MiamiBoston

MIA - BOS

MIABOS

Miami

Tue 7/1

8:27 pm-11:59 pm

Nonstop3h 32m

Boston Logan Intl

Tue 7/15

3:45 pm-7:29 pm

Nonstop3h 44m

$159

MiamiBoston

MIA - BOS

MIABOS

Miami

Wed 5/28

11:11 am-2:39 pm

Nonstop3h 28m

Boston Logan Intl

Sun 6/1

7:42 pm-11:13 pm

Nonstop3h 31m

$163

MiamiBoston

MIA - BOS

MIABOS

Miami

Mon 6/2

8:25 am-11:45 am

Nonstop3h 20m

Boston Logan Intl

Fri 6/6

5:15 am-8:44 am

Nonstop3h 29m

$176

MiamiBoston

MIA - BOS

MIABOS

Miami

Wed 5/21

5:05 pm-10:25 pm

1 stop5h 20m

Boston Logan Intl

Wed 5/28

3:00 pm-9:55 pm

1 stop6h 55m

$183

MiamiHartford

MIA - BDL

MIABDL

Miami

Fri 9/12

7:58 pm-8:10 am

1 stop12h 12m

Hartford Bradley Intl

Sun 9/14

9:15 am-6:53 pm

1 stop9h 38m

$192

MiamiHartford

MIA - BDL

MIABDL

Miami

Wed 6/4

8:06 pm-11:13 pm

Nonstop3h 07m

Hartford Bradley Intl

Wed 6/11

5:37 am-8:50 am

Nonstop3h 13m

$195

MiamiAlbany

MIA - ALB

MIAALB

Miami

Tue 5/20

8:30 am-3:57 pm

1 stop7h 27m

Albany Intl

Thu 5/22

12:16 pm-7:03 pm

1 stop6h 47m

$197

MiamiBoston

MIA - BOS

MIABOS

Miami

Fri 5/16

10:14 am-5:21 pm

1 stop7h 07m

Boston Logan Intl

Mon 5/19

8:05 am-4:16 pm

1 stop8h 11m

$209

MiamiHartford

MIA - BDL

MIABDL

Miami

Thu 5/8

5:35 am-10:38 am

1 stop5h 03m

Hartford Bradley Intl

Sun 5/11

7:08 pm-12:37 am

1 stop5h 29m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 April 24, 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.

Rainfall in Massachusetts by month

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

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

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

If weather is an important factor for your trip to Massachusetts, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 April 24, 2025.
To help decide which airline to fly from Florida Keys to Massachusetts, see what other customers have to say about Alaska Airlines, Southwest and Delta. 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.
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,685 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Crew

8.5

Food

7.1

Boarding

8.2

Entertainment

7.1

Overall

8.0

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

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

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $70. Southwest flights start at $90 while deals on American Airlines start at $98 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

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$216Average$371FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$236Average$516FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$246Average$327FlexibilityNo cancel feeOn-time71%

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