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Islamorada

$63+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MIA
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 46 days in advance, depart on a Thursday or Tuesday and return on a Thursday

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 October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Wed 12/3111:09 amBOS - MIA
1 stop8h 21mMultiple Airlines
Thu 1/88:00 amMIA - BOS
Nonstop3h 25mMultiple Airlines
Deal found 10/27$111
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Wed 12/3111:09 amBOS - MIA
1 stop8h 21mMultiple Airlines
Sat 1/101:58 pmMIA - BOS
Nonstop3h 24mMultiple Airlines
Deal found 10/26$113
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Wed 12/3111:09 amBOS - MIA
1 stop8h 21mFrontier
Wed 1/143:24 pmMIA - BOS
1 stop7h 45mFrontier
Deal found 10/26$120
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Wed 12/3111:09 amBOS - MIA
1 stop8h 21mFrontier
Thu 1/85:35 amMIA - BOS
1 stop19h 29mFrontier
Deal found 10/27$121
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Thu 11/1310:04 amBOS - MIA
1 stop14h 30mFrontier
Sat 11/156:35 pmMIA - BOS
1 stop14h 25mFrontier
Deal found 10/27$123
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Wed 12/3111:09 amBOS - MIA
1 stop8h 21mMultiple Airlines
Fri 1/97:12 pmMIA - BOS
1 stop5h 52mMultiple Airlines
Deal found 10/28$126
This Cheapflightsfares deal was found by Cheapflights users on 10/27. 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.
Wed 11/195:53 pmBOS - MIA
Nonstop3h 37mSpirit Airlines
Fri 11/286:46 amMIA - BOS
1 stop5h 49mSpirit Airlines
Deal found 10/27$129
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/178:40 amBOS - MIA
1 stop9h 27mFrontier
Thu 11/209:59 pmMIA - BOS
1 stop9h 30mFrontier
Deal found 10/28$130
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/158:28 amBOS - MIA
1 stop11h 11mFrontier
Wed 12/247:05 pmMIA - BOS
1 stop15h 03mFrontier
Deal found 10/28$132
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sat 11/1511:43 amBOS - MIA
1 stop23h 17mMultiple Airlines
Tue 11/186:25 amMIA - BOS
2 stops17h 34mMultiple Airlines
Deal found 10/27$133

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 October 29, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$109
(Kiwi.com)

One-way from

$63
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$249
Provider with most accurate pricing for Boston Logan Intl-Miami flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Miami flights.
Search Deals
From Boston Logan Intl to Islamorada
Search Deals
One-way flight from Boston Logan Intl to Islamorada
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($0 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 29, 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

Mon 11/17

7:10 am-10:47 am

Nonstop3h 37m

Miami

Wed 11/19

6:55 am-10:18 am

Nonstop3h 23m

$147

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sun 11/16

7:10 am-10:47 am

Nonstop3h 37m

Miami

Tue 11/18

7:35 pm-11:01 pm

Nonstop3h 26m

$152

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sun 12/7

7:59 pm-11:37 pm

Nonstop3h 38m

Miami

Sat 12/13

6:53 am-10:15 am

Nonstop3h 22m

$159

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 11/12

7:55 pm-11:32 pm

Nonstop3h 37m

Miami

Sat 11/15

7:20 am-1:23 pm

1 stop6h 03m

$167

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Tue 11/18

3:59 pm-7:37 pm

Nonstop3h 38m

Miami

Tue 11/25

11:42 am-2:59 pm

Nonstop3h 17m

$167

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 2/18

7:50 pm-11:31 pm

Nonstop3h 41m

Miami

Wed 2/25

7:00 pm-12:59 am

1 stop5h 59m

$168

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Fri 1/9

3:30 pm-7:16 pm

Nonstop3h 46m

Miami

Sat 1/17

8:05 am-3:57 pm

1 stop7h 52m

$169

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Tue 1/6

7:05 am-10:53 am

Nonstop3h 48m

Miami

Fri 1/16

8:25 pm-11:58 pm

Nonstop3h 33m

$179

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sat 12/13

7:00 am-2:25 pm

1 stop7h 25m

Miami

Sat 12/20

7:59 pm-11:25 pm

Nonstop3h 26m

$188

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Mon 11/24

7:10 am-10:47 am

Nonstop3h 37m

Miami

Wed 12/3

7:59 pm-11:25 pm

Nonstop3h 26m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 19 results
1
2

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 October 24, 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 46 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, January is the cheapest month in which you can book a flight from Boston to Islamorada (average of $41). Flying from Boston to Islamorada in August is currently the most expensive (average of $94). 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 October 29, 2025.

When flying from Boston to Islamorada, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 26% versus a flight at noon.

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 October 26, 2025.

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

How much does it cost to fly round-trip from Boston to Islamorada?

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 October 29, 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
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

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
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

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
11,032 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

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
2,907 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

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
8,114 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

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
3,124 reviews
Delta
7.9
Good
7,992 reviews

Overall

7.9

Boarding

8.2

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

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 13 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 156 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 37m. Delta provides one of the quickest options available for as low as $147. Airlines will cover a distance of 1259 mi. Most flights are nonstop.

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

    Consider Etihad Airways (100%), Japan Airlines (98%) or JetBlue (92%) 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 $696, our data indicates the cheapest price to be $74. The most popular route (Boston Logan Intl - Miami), is priced around $98.

  • 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, January is the cheapest month in which you can book a flight from Boston to Islamorada (average of $41). Flying from Boston to Islamorada in August is currently the most expensive (average of $94). 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$36Average$121FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$59Average$152FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$91Average$353FlexibilityNo cancel feeOn-time62%
DeltaCheapest$96Average$286FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$135Average$308FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$147Average$361FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$166Average$257FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$166Average$425FlexibilityNo cancel feeOn-time63%

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