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Islamorada

$54+ Cheap flights from Boston (BOS) to Islamorada, FL

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MIA
out 11 — out 181
sáb 10/11
sáb 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Islamorada are usually found in September or January, booked 30 days in advance, depart on a Thursday or Tuesday and return on a Thursday

Cheap flight deals from Boston to Islamorada

Keep the following information in mind while searching for Boston to Islamorada flight deals. Data was last updated setembro 11, 2025.

Round-trip from

$97
(Cheapflightsfares)

One-way from

$54
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$177
From Boston Logan Intl to Islamorada
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One-way flight from Boston Logan Intl to Islamorada
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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 September 2025
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Find flight deals from Boston to Islamorada

Cheapest flights from Boston to Islamorada
Explore the most affordable flight options available from Boston to Islamorada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on setembro 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
sex 10/314:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
dom 11/97:00 amMIA - BOS
Nonstop3h 23mSpirit Airlines
Deal found 9/10$97
This Spirit deal was found by Cheapflights users on 9/9. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 11/1311:18 amBOS - MIA
Nonstop3h 32mSpirit Airlines
dom 11/167:00 amMIA - BOS
Nonstop3h 23mSpirit Airlines
Deal found 9/9$98
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
qui 9/252:18 pmBOS - MIA
Nonstop3h 32mMultiple Airlines
dom 10/57:25 amMIA - BOS
1 stop24h 27mMultiple Airlines
Deal found 9/10$99
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/272:18 pmBOS - MIA
Nonstop3h 32mMultiple Airlines
dom 10/57:25 amMIA - BOS
1 stop24h 27mMultiple Airlines
Deal found 9/10$100
This Southwest deal was found by Cheapflights users on 9/9. 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.
sáb 10/251:30 pmBOS - MIA
1 stop7h 00mSouthwest
qua 10/294:35 pmMIA - BOS
1 stop4h 35mSouthwest
Deal found 9/9$101
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
qui 9/252:18 pmBOS - MIA
Nonstop3h 32mSpirit Airlines
seg 10/612:40 pmMIA - BOS
Nonstop3h 16mSpirit Airlines
Deal found 9/11$102
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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 9/252:18 pmBOS - MIA
Nonstop3h 32mSpirit Airlines
dom 9/289:56 amMIA - BOS
Nonstop3h 27mSpirit Airlines
Deal found 9/9$106
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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.
sex 10/244:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
seg 10/2712:40 pmMIA - BOS
Nonstop3h 16mSpirit Airlines
Deal found 9/10$107
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
sex 10/174:54 pmBOS - MIA
Nonstop3h 38mSpirit Airlines
seg 10/2012:40 pmMIA - BOS
Nonstop3h 16mSpirit Airlines
Deal found 9/11$108
This Mytrip deal was found by Cheapflights users on 9/10. 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.
qui 9/252:18 pmBOS - MIA
Nonstop3h 32mMultiple Airlines
qui 10/27:25 amMIA - BOS
1 stop24h 27mMultiple Airlines
Deal found 9/10$109
This Southwest deal was found by Cheapflights users on 9/10. 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.
qua 10/225:00 amBOS - MIA
1 stop9h 30mSouthwest
sáb 10/255:45 amMIA - BOS
1 stop8h 45mSouthwest
Deal found 9/10$111

Cheapflights Fare Finder

 
Customize your flight search to find flights from Boston to Islamorada 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 setembro 11, 2025.
Use the filters below to find and compare flights from Boston to Islamorada that are best for you.

Fly from

Boston

Fly to

Islamorada

Route

Depart

Return

Price

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

qua 11/12

5:30 am-1:05 pm

1 stop7h 35m

Miami

sáb 11/15

9:55 am-5:05 pm

1 stop7h 10m

$126

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

seg 11/10

8:11 pm-11:50 pm

Nonstop3h 39m

Miami

sáb 11/15

7:00 am-10:20 am

Nonstop3h 20m

$137

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

ter 10/21

4:26 pm-8:00 pm

Nonstop3h 34m

Miami

ter 10/28

12:05 pm-3:26 pm

Nonstop3h 21m

$137

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

qua 10/22

4:26 pm-8:00 pm

Nonstop3h 34m

Miami

ter 10/28

3:10 pm-9:27 pm

1 stop6h 17m

$147

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

qua 11/5

4:26 pm-8:00 pm

Nonstop3h 34m

Miami

ter 11/11

8:05 am-3:56 pm

1 stop7h 51m

$147

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

sáb 10/25

4:26 pm-8:00 pm

Nonstop3h 34m

Miami

seg 11/3

5:25 pm-11:49 pm

1 stop6h 24m

$147

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

sex 10/3

7:10 am-10:43 am

Nonstop3h 33m

Miami

seg 10/6

3:33 pm-10:27 pm

1 stop6h 54m

$147

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

dom 10/26

5:00 am-10:55 am

1 stop5h 55m

Miami

seg 10/27

7:05 pm-11:55 pm

1 stop4h 50m

$151

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

qui 10/2

3:50 pm-10:35 pm

1 stop6h 45m

Miami

qua 10/8

3:15 pm-10:15 pm

1 stop7h 00m

$151

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

qui 9/25

8:35 am-6:10 pm

1 stop9h 35m

Miami

seg 9/29

7:35 am-1:50 pm

1 stop6h 15m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from Boston to Islamorada

Have a flexible travel schedule? Discover the best time to fly to Islamorada from Boston 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 Boston to Islamorada

How far ahead should I book a flight from Boston to Islamorada?

Use this chart to determine the optimal time to book a round-trip flight from Boston to Islamorada. Price data was last updated on August 29, 2025.

The price you pay for your flight from Boston to Islamorada may vary depending on when you book. For the best chance of a lower fare, look to book 30 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Boston to Islamorada?

Currently, September is the cheapest month in which you can book a flight from Boston to Islamorada (average of $232). Flying from Boston to Islamorada in March is currently the most expensive (average of $289). 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 BOS to I5L?

Find hourly flight availability from Boston to Islamorada. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated setembro 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Boston to Islamorada as you normally would.

What is the cheapest day to fly from Boston to Islamorada?

Use this chart to determine the cheapest time to fly round-trip from Boston to Islamorada. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their Boston to Islamorada flight should consider departing on Wednesday evenings when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Boston to Islamorada

Explore weekly flight availability from Boston to Islamorada. 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 setembro 11, 2025.

The most flights from BOS to I5L are scheduled on a Thursday (21 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (14 on average).

Reviews of airlines servicing Islamorada

Get insights into the airlines that provide service to Islamorada. 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 Islamorada. Reviews last updated setembro 11, 2025.
Peruse reviews from past customers who have flown with Delta, American Airlines, and JetBlue from Boston to Islamorada to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
JetBlue
7.2
Good
2,913 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Frontier
5.8
Fair
3,177 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Crew

8.5

Overall

8.0

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Boston to Islamorada. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Boston to Islamorada?

    Most people fly from Boston Logan Intl (BOS) if they book a flight from Boston to Islamorada. On average, Logan Intl has 17 outbound flights to Islamorada per day from 8 airlines. Boston Logan Intl is conveniently located just 2.6 mi from Boston’s city center.

  • How popular is this Boston to Islamorada flight route?

    Flights from Boston Logan Intl to Islamorada have been viewed 153 times in the past calendar month.

  • How long is the flight from Boston to Islamorada?

    A quick flight from Boston to Islamorada can take about 3h 39m. Southwest provides one of the quickest options available for as low as $137. Airlines will cover a distance of 1259 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most reliable airlines from Boston to Islamorada?

    Consider Japan Airlines (95%), American Airlines (81%) or GOL (78%) when booking your flight. These represent the most reliable airlines when flying from Boston to Islamorada.

  • What are the cheapest flights from Boston to Islamorada?

    Looking for the cheapest flight from Boston to Islamorada? While on average our users pay $542, our data indicates the cheapest price to be $59. The most popular route (Boston Logan Intl - Miami), is priced around $86.

  • Can I find deals for flights from Boston to Islamorada that include hotel bookings?

    Yes. In addition to deals on Boston to Islamorada flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Islamorada?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Islamorada.

  • Can I find deals for business class flights from Boston to Islamorada?

    Yes. Cheapflights offers flight deals from Boston to Islamorada 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 Boston to Islamorada?

    Currently, September is the cheapest month in which you can book a flight from Boston to Islamorada (average of $232). Flying from Boston to Islamorada in March is currently the most expensive (average of $289). 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.

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Top 8 airlines flying from Boston to Islamorada

Discover the top 8 airlines that operate flights from Boston to Islamorada. 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 setembro 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$36Average$132FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$151FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$87Average$349FlexibilityNo cancel feeOn-time62%
DeltaCheapest$91Average$281FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$142Average$347FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$145Average$332FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$166Average$257FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$166Average$435FlexibilityNo cancel feeOn-time63%

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