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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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MIA
Apr 11 — Apr 181
Sat 4/11
Sat 4/18
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Islamorada are usually found in September or October, booked 24 days in advance, depart on a Thursday or Saturday and return on a Thursday

Cheap 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 March 12, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 3/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:01 am
BOS
-
MIA
Nonstop3h 33m
Spirit Airlines
Wed 4/153:49 pm
MIA
-
BOS
Nonstop3h 17m
Spirit Airlines
Deal found 3/7$88
This Spirit deal was found by Cheapflights users on 3/7. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:01 am
BOS
-
MIA
Nonstop3h 33m
Spirit Airlines
Thu 4/1610:00 am
MIA
-
BOS
Nonstop3h 17m
Spirit Airlines
Deal found 3/7$90
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/316:01 am
BOS
-
MIA
Nonstop3h 33m
Spirit Airlines
Sat 4/410:39 am
MIA
-
BOS
Nonstop3h 16m
Spirit Airlines
Deal found 3/9$93
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Thu 4/96:01 am
BOS
-
MIA
Nonstop3h 33m
Spirit Airlines
Wed 4/153:49 pm
MIA
-
BOS
Nonstop3h 17m
Spirit Airlines
Deal found 3/8$96
This Expedia deal was found by Cheapflights users on 3/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/296:01 am
BOS
-
MIA
Nonstop3h 33m
Spirit Airlines
Wed 4/110:39 am
MIA
-
BOS
Nonstop3h 16m
Spirit Airlines
Deal found 3/9$97
This Super.com deal was found by Cheapflights users on 3/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:20 am
BOS
-
MIA
Nonstop3h 24m
Spirit Airlines
Wed 4/2210:00 am
MIA
-
BOS
Nonstop3h 17m
Spirit Airlines
Deal found 3/9$98
This CheapOair deal was found by Cheapflights users on 3/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:49 pm
BOS
-
MIA
Nonstop3h 31m
Spirit Airlines
Tue 4/213:49 pm
MIA
-
BOS
Nonstop3h 17m
Spirit Airlines
Deal found 3/9$100
This WAYA deal was found by Cheapflights users on 3/9. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2412:36 pm
BOS
-
MIA
1 stop7h 31m
Multiple Airlines
Thu 4/210:39 am
MIA
-
BOS
Nonstop3h 16m
Multiple Airlines
Deal found 3/9$101
This Cheapflightsfares deal was found by Cheapflights users on 3/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:01 am
BOS
-
MIA
Nonstop3h 33m
Spirit Airlines
Thu 4/1610:00 am
MIA
-
BOS
Nonstop3h 17m
Spirit Airlines
Deal found 3/8$102
This Cheapflightsfares deal was found by Cheapflights users on 3/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:01 am
BOS
-
MIA
Nonstop3h 33m
Spirit Airlines
Mon 4/2010:00 am
MIA
-
BOS
Nonstop3h 17m
Spirit Airlines
Deal found 3/7$104
This Super.com deal was found by Cheapflights users on 3/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/136:01 am
BOS
-
MIA
Nonstop3h 33m
Spirit Airlines
Wed 4/153:49 pm
MIA
-
BOS
Nonstop3h 17m
Spirit Airlines
Deal found 3/9$105

Find flight deals from Boston to Islamorada

Keep the following information in mind while searching for Boston to Islamorada flight deals. Data was last updated March 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$88
(Cheapflightsfares)

One-way from

$54
(Cheapflightsfares)

Popular in

December

Cheapest in

September

Average price

$252
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. 14% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 March 12, 2026.
Use the filters below to find and compare flights from Boston to Islamorada that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Mon 4/6

7:05 am-10:46 am

Nonstop3h 41m

Miami

Wed 4/8

7:59 pm-11:33 pm

Nonstop3h 34m

$197

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 5/20

7:15 am-10:44 am

Nonstop3h 29m

Miami

Wed 6/3

12:40 pm-8:04 pm

1 stop7h 24m

$227

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Fri 6/5

7:15 am-10:44 am

Nonstop3h 29m

Miami

Tue 6/9

7:55 pm-11:25 pm

Nonstop3h 30m

$257

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sun 4/5

3:15 pm-6:59 pm

Nonstop3h 44m

Miami

Thu 4/9

6:00 am-11:28 am

1 stop5h 28m

$267

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 4/22

3:24 pm-6:59 pm

Nonstop3h 35m

Miami

Tue 4/28

7:00 am-10:21 am

Nonstop3h 21m

$277

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Thu 5/14

3:20 pm-6:59 pm

Nonstop3h 39m

Miami

Mon 5/18

7:39 pm-1:28 am

1 stop5h 49m

$287

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Mon 4/27

5:45 am-2:27 pm

2 stops8h 42m

Miami

Thu 4/30

6:10 pm-11:59 pm

1 stop5h 49m

$302

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Mon 4/27

10:05 am-10:45 pm

2 stops12h 40m

Miami

Wed 4/29

12:24 pm-11:59 pm

2 stops11h 35m

$307

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Thu 6/4

5:20 pm-11:15 pm

1 stop5h 55m

Miami

Sun 6/7

5:35 am-3:30 pm

2 stops9h 55m

$322

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 4/8

10:45 am-8:40 pm

2 stops9h 55m

Miami

Tue 4/14

7:00 am-3:55 pm

2 stops8h 55m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 24 resultsSorted by cheapest first
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 March 6, 2026.

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 24 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 $60). Flying from Boston to Islamorada in December is currently the most expensive (average of $108). 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 March 12, 2026.

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 evening, which can drop the price by up to 42% 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 March 12, 2026.

Travelers seeking maximum savings on their Boston to Islamorada flight should consider departing on Tuesday at noon when fares are most often at their lowest. Friday mornings 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 March 12, 2026.

The most flights from BOS to I5L are scheduled on a Thursday (25 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

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 March 12, 2026.
Peruse reviews from past customers who have flown with Delta,JetBlue, andAmerican Airlines 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
8,286 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

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
8,286 reviews
Delta
7.9
Good
8,286 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

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
2,903 reviews
Delta
7.9
Good
8,286 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

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
7.1
Good
11,432 reviews
Delta
7.9
Good
8,286 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

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
8,518 reviews
Delta
7.9
Good
8,286 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

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
5.7
Fair
3,035 reviews
Delta
7.9
Good
8,286 reviews

Boarding

8.1

Overall

7.9

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

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 21 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 174 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 41m. Delta provides one of the quickest options available for as low as $197. Airlines will cover a distance of 1259 mi. Most flights are nonstop.

  • What are the cheapest airlines to fly from Boston to Islamorada one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $36. However, be on the lookout for offers from Frontier and JetBlue, as they are both options that can get you from Boston to Islamorada for a low price.

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

    Consider Japan Airlines (85%), EL AL (83%) or Iberia (79%) 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 $555, our data indicates the cheapest price to be $49. The most popular route (Boston Logan Intl - Miami), is priced around $82.

  • 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 $60). Flying from Boston to Islamorada in December is currently the most expensive (average of $108). 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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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 March 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$44Average$155FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$53Average$198FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$88Average$305FlexibilityNo cancel feeOn-time62%
DeltaCheapest$98Average$301FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$153Average$296FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$348FlexibilityNo cancel feeOn-time71%
Alaska AirlinesCheapest$166Average$257FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$166Average$414FlexibilityNo cancel feeOn-time63%

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