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$42+ 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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — BOS
fev 27 — mar 61
qui 2/27
qui 3/6
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 fevereiro 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$54
(FlightHub)

One-way from

$42
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$421
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. 8% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($21 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 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 fevereiro 22, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 3/267:23 pmMIA - BOS
Nonstop3h 27mSpirit Airlines
dom 3/308:20 amBOS - MIA
Nonstop3h 41mSpirit Airlines
Deal found 2/21$67
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 3/110:32 amMIA - BOS
Nonstop3h 18mMultiple Airlines
ter 3/411:33 amBOS - MIA
Nonstop3h 42mMultiple Airlines
Deal found 2/21$68
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 3/273:32 pmMIA - BDL
Nonstop3h 10mFrontier
dom 3/307:48 pmBDL - MIA
Nonstop3h 23mFrontier
Deal found 2/21$83
This Frontier deal was found by Cheapflights users on 2/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 3/47:05 amMIA - BOS
Nonstop3h 28mFrontier
sáb 3/89:36 amBOS - MIA
1 stop11h 15mFrontier
Deal found 2/21$99
This Delta deal was found by Cheapflights users on 2/21. 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.
sex 3/287:20 pmMIA - BOS
Nonstop3h 24mDelta
ter 4/87:05 amBOS - MIA
Nonstop3h 33mDelta
Deal found 2/21$137
This JetBlue deal was found by Cheapflights users on 2/21. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 3/86:00 amMIA - BOS
Nonstop3h 10mJetBlue
seg 3/106:59 pmBOS - MIA
Nonstop3h 35mJetBlue
Deal found 2/21$138
This American Airlines deal was found by Cheapflights users on 2/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 3/288:28 pmMIA - BDL
Nonstop3h 15mAmerican Airlines
dom 3/305:19 amBDL - MIA
Nonstop3h 30mAmerican Airlines
Deal found 2/21$179
This Mytrip deal was found by Cheapflights users on 2/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 4/49:55 amMIA - BDL
2 stops23h 55mMultiple Airlines
dom 4/61:41 pmBDL - MIA
1 stop25h 53mMultiple Airlines
Deal found 2/21$203
This Delta deal was found by Cheapflights users on 2/21. 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.
dom 5/257:30 amMIA - MVY
1 stop6h 33mDelta
ter 6/34:45 pmMVY - MIA
1 stop5h 44mDelta
Deal found 2/21$206
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.
sex 4/46:10 pmMIA - BDL
1 stop6h 08mDelta
ter 4/82:24 pmBDL - MIA
1 stop5h 29mDelta
Deal found 2/20$217
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.
sáb 3/86:00 amMIA - ALB
1 stop7h 16mDelta
qua 4/166:28 pmALB - MIA
1 stop6h 20mDelta
Deal found 2/20$217
This Mytrip deal was found by Cheapflights users on 2/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 3/111:52 amMIA - BDL
2 stops22h 30mSpirit Airlines
seg 3/311:17 amBDL - MIA
2 stops30h 58mSpirit Airlines
Deal found 2/21$218

Find flights from Florida Keys to Massachusetts within your budget

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 fevereiro 22, 2025.

Fly from

Florida Keys

Fly to

Massachusetts

Route

Depart

Return

Price

MiamiBoston

MIA - BOS

MIABOS

Miami

ter 3/4

7:05 am-10:33 am

Nonstop3h 28m

Boston Logan Intl

sáb 3/8

4:00 pm-7:40 pm

Nonstop3h 40m

$61

MiamiBoston

MIA - BOS

MIABOS

Miami

qua 3/19

2:35 pm-9:16 pm

1 stop6h 41m

Boston Logan Intl

seg 3/24

5:20 pm-9:04 pm

Nonstop3h 44m

$63

MiamiBoston

MIA - BOS

MIABOS

Miami

ter 3/4

7:05 am-10:33 am

Nonstop3h 28m

Boston Logan Intl

qui 3/13

11:33 am-3:15 pm

Nonstop3h 42m

$65

MiamiHartford

MIA - BDL

MIABDL

Miami

qui 3/27

3:32 pm-6:42 pm

Nonstop3h 10m

Hartford Bradley Intl

dom 3/30

7:48 pm-11:11 pm

Nonstop3h 23m

$83

MiamiBoston

MIA - BOS

MIABOS

Miami

sex 3/28

7:20 pm-10:44 pm

Nonstop3h 24m

Boston Logan Intl

ter 4/8

7:05 am-10:38 am

Nonstop3h 33m

$137

MiamiBoston

MIA - BOS

MIABOS

Miami

sáb 3/8

6:00 am-9:10 am

Nonstop3h 10m

Boston Logan Intl

seg 3/10

6:59 pm-10:34 pm

Nonstop3h 35m

$138

MiamiHartford

MIA - BDL

MIABDL

Miami

sex 3/28

8:28 pm-11:43 pm

Nonstop3h 15m

Hartford Bradley Intl

dom 3/30

5:19 am-8:49 am

Nonstop3h 30m

$179

MiamiHartford

MIA - BDL

MIABDL

Miami

sex 4/4

9:55 am-9:50 am

2 stops23h 55m

Hartford Bradley Intl

dom 4/6

1:41 pm-3:34 pm

1 stop25h 53m

$203

MiamiWest Tisbury

MIA - MVY

MIAMVY

Miami

dom 5/25

7:30 am-2:03 pm

1 stop6h 33m

West Tisbury Martha's Vineyard

ter 6/3

4:45 pm-10:29 pm

1 stop5h 44m

$206

MiamiHartford

MIA - BDL

MIABDL

Miami

sex 4/4

6:10 pm-12:18 am

1 stop6h 08m

Hartford Bradley Intl

dom 4/6

6:52 pm-12:52 am

1 stop6h 00m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 57 results
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2
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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.

Travel insights for flights from Florida Keys to Massachusetts

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

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 fevereiro 22, 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 fevereiro 22, 2025.
To help decide which airline to fly from Florida Keys to Massachusetts, see what other customers have to say about Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

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
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

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
9,700 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

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
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

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
3,068 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

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.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Overall

8.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Food

7.1

Boarding

8.2

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 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 $42. Frontier flights start at $44 while deals on Southwest start at $74 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 fevereiro 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$209Average$577FlexibilityNo cancel feeOn-time62%
DeltaCheapest$216Average$371FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$246Average$328FlexibilityNo cancel feeOn-time71%
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