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$64+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
feb. 7 — feb. 141
sáb. 2/7
sáb. 2/14
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 enero 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$80
(CheapOair)

One-way from

$64
(Southwest)

Popular in

September

Cheapest in

November

Average price

$492
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
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 enero 8, 2026.

This CheapOair deal was found by Cheapflights users on 1/8. 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.
vie. 2/612:55 pmMIA - BOS
Nonstop3h 23mSpirit Airlines
mar. 2/105:53 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/8$80
This Kiwi.com deal was found by Cheapflights users on 1/8. 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.
sáb. 1/2412:56 pmMIA - BOS
Nonstop3h 23mSpirit Airlines
sáb. 1/315:23 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/8$81
This Cheapflightsfares deal was found by Cheapflights users on 1/6. 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.
jue. 1/2212:56 pmMIA - BOS
Nonstop3h 23mSpirit Airlines
dom. 1/255:23 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/6$82
This Cheapflightsfares deal was found by Cheapflights users on 1/5. 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.
vie. 2/138:37 pmMIA - BOS
Nonstop3h 22mSpirit Airlines
mié. 2/185:50 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/5$85
This CheapOair deal was found by Cheapflights users on 1/5. 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.
vie. 2/278:37 pmMIA - BOS
Nonstop3h 22mSpirit Airlines
mar. 3/33:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
Deal found 1/5$86
This Priceline deal was found by Cheapflights users on 1/7. 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.
vie. 1/2312:56 pmMIA - BOS
Nonstop3h 23mSpirit Airlines
dom. 1/255:23 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/7$87
This Cheapflightsfares deal was found by Cheapflights users on 1/6. 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.
jue. 2/512:55 pmMIA - BOS
Nonstop3h 23mSpirit Airlines
dom. 2/85:53 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/6$88
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
mar. 5/191:34 pmMIA - BOS
Nonstop3h 24mSpirit Airlines
mié. 5/275:55 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/6$89
This CheapOair deal was found by Cheapflights users on 1/7. 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.
vie. 2/278:37 pmMIA - BOS
Nonstop3h 22mSpirit Airlines
lun. 3/25:50 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/7$90
This Kiwi.com deal was found by Cheapflights users on 1/8. 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.
sáb. 1/2412:56 pmMIA - BOS
Nonstop3h 23mSpirit Airlines
mié. 1/285:23 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/8$91
This Kiwi.com deal was found by Cheapflights users on 1/8. 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.
vie. 1/2312:56 pmMIA - BOS
Nonstop3h 23mSpirit Airlines
mar. 1/275:23 pmBOS - MIA
Nonstop3h 42mSpirit Airlines
Deal found 1/8$93
This CheapOair deal was found by Cheapflights users on 1/6. 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.
jue. 4/212:20 pmMIA - BDL
Nonstop3h 17mFrontier
lun. 4/64:37 pmBDL - MIA
Nonstop3h 37mFrontier
Deal found 1/6$104

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 enero 8, 2026.
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

MiamiAlbany

MIA - ALB

MIAALB

Miami

mié. 2/11

5:20 pm-10:10 pm

1 stop4h 50m

Albany Intl

mié. 2/25

9:00 am-4:10 pm

1 stop7h 10m

$127

MiamiAlbany

MIA - ALB

MIAALB

Miami

mié. 2/11

4:30 pm-10:05 pm

1 stop5h 35m

Albany Intl

lun. 2/23

12:45 pm-8:20 pm

1 stop7h 35m

$143

MiamiBoston

MIA - BOS

MIABOS

Miami

vie. 2/13

8:30 pm-11:59 pm

Nonstop3h 29m

Boston Logan Intl

mié. 2/18

11:00 am-6:54 pm

1 stop7h 54m

$147

MiamiBoston

MIA - BOS

MIABOS

Miami

sáb. 1/31

6:55 am-10:14 am

Nonstop3h 19m

Boston Logan Intl

lun. 2/2

7:59 pm-11:51 pm

Nonstop3h 52m

$167

MiamiAlbany

MIA - ALB

MIAALB

Miami

sáb. 1/31

7:50 am-1:30 pm

1 stop5h 40m

Albany Intl

jue. 2/5

12:45 pm-8:20 pm

1 stop7h 35m

$167

MiamiBoston

MIA - BOS

MIABOS

Miami

vie. 1/30

6:55 am-10:14 am

Nonstop3h 19m

Boston Logan Intl

vie. 1/30

8:15 pm-12:05 am

Nonstop3h 50m

$167

MiamiBoston

MIA - BOS

MIABOS

Miami

vie. 1/30

8:30 pm-11:59 pm

Nonstop3h 29m

Boston Logan Intl

dom. 2/1

7:59 pm-11:51 pm

Nonstop3h 52m

$167

MiamiBoston

MIA - BOS

MIABOS

Miami

jue. 1/22

11:31 am-2:56 pm

Nonstop3h 25m

Boston Logan Intl

sáb. 1/24

7:59 pm-11:51 pm

Nonstop3h 52m

$167

MiamiBoston

MIA - BOS

MIABOS

Miami

jue. 1/22

11:31 am-2:56 pm

Nonstop3h 25m

Boston Logan Intl

lun. 1/26

3:50 pm-7:33 pm

Nonstop3h 43m

$167

MiamiAlbany

MIA - ALB

MIAALB

Miami

vie. 3/13

5:05 am-6:29 pm

1 stop13h 24m

Albany Intl

dom. 3/15

12:01 pm-12:32 am

1 stop12h 31m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

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, November is the cheapest month in which you can book a flight from Florida Keys to Massachusetts (average of $170). Flying from Florida Keys to Massachusetts in May is currently the most expensive (average of $320). 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 enero 8, 2026.

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.

Weekly flight availability from Florida Keys to Massachusetts

Explore weekly flight availability from Florida Keys to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated enero 8, 2026.

The most flights from zzEOA to USMA are scheduled on a Thursday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 enero 8, 2026.
Read reviews from past customers who have flown Delta, American Airlines, and JetBlue from Florida Keys to Massachusetts. 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.
Delta
7.9
Good
8,032 reviews

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,032 reviews
Delta
7.9
Good
8,032 reviews

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,097 reviews
Delta
7.9
Good
8,032 reviews

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
JetBlue
7.2
Good
2,892 reviews
Delta
7.9
Good
8,032 reviews

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Spirit Airlines
6.3
Okay
8,289 reviews
Delta
7.9
Good
8,032 reviews

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Frontier
5.7
Fair
3,060 reviews
Delta
7.9
Good
8,032 reviews

Crew

8.5

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Entertainment

7.8

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

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.

  • How long is the flight from Florida Keys to Massachusetts?

    For as low as $147, Southwest can have you in Massachusetts from Florida Keys in 3h 29m. There are 1259 mi between Florida Keys and Massachusetts. Both multi-stop and nonstop flights can be found to your destination and back.

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

    To fly one-way, consider booking your trip with Frontier, which is currently one of the cheapest options available, starting at $29. Spirit Airlines flights start at $40 while deals on Delta start at $77 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, November is the cheapest month in which you can book a flight from Florida Keys to Massachusetts (average of $170). Flying from Florida Keys to Massachusetts in May is currently the most expensive (average of $320). 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

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Top 2 airlines flying from Florida Keys to Massachusetts

Discover the top 2 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 enero 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$182Average$346FlexibilityNo cancel feeOn-time71%
JetBlueCheapest$277Average$442FlexibilityNo cancel feeOn-time62%

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