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Islamorada

$67+ 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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — MIA
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 Friday 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 July 30, 2025.

Round-trip from

$122
(American Airlines)

One-way from

$67
(FlightHub)

Popular in

April

Cheapest in

September

Average price

$247
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 July 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 July 30, 2025.

This Booking.com deal was found by Cheapflights users on 7/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/112:18 pmBOS - MIA
Nonstop3h 32mSpirit Airlines
Thu 9/189:56 amMIA - BOS
Nonstop3h 27mSpirit Airlines
Deal found 7/28$119
This American Airlines deal was found by Cheapflights users on 7/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:13 pmBOS - MIA
Nonstop3h 37mAmerican Airlines
Tue 9/169:40 pmMIA - BOS
Nonstop3h 19mAmerican Airlines
Deal found 7/27$120
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 11/117:50 pmBOS - MIA
Nonstop3h 41mDelta
Wed 11/193:35 pmMIA - BOS
1 stop6h 54mDelta
Deal found 7/29$127
This Orbitz deal was found by Cheapflights users on 7/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1911:25 amBOS - MIA
Nonstop3h 36mMultiple Airlines
Sat 10/259:56 amMIA - BOS
Nonstop3h 27mMultiple Airlines
Deal found 7/28$133
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/3011:25 amBOS - MIA
Nonstop3h 36mFrontier
Sun 11/27:05 amMIA - BOS
Nonstop3h 25mFrontier
Deal found 7/30$135
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/15:00 amBOS - MIA
1 stop5h 50mSouthwest
Thu 9/411:35 amMIA - BOS
1 stop6h 25mSouthwest
Deal found 7/28$173

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 July 30, 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

Thu 9/11

2:18 pm-5:50 pm

Nonstop3h 32m

Miami

Thu 9/18

9:56 am-1:23 pm

Nonstop3h 27m

$119

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sat 9/13

6:13 pm-9:50 pm

Nonstop3h 37m

Miami

Tue 9/16

9:40 pm-12:59 am

Nonstop3h 19m

$120

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 9/10

5:35 am-1:33 pm

1 stop7h 58m

Miami

Wed 9/17

7:59 pm-11:26 pm

Nonstop3h 27m

$127

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sun 10/19

11:25 am-3:01 pm

Nonstop3h 36m

Miami

Sat 10/25

9:56 am-1:23 pm

Nonstop3h 27m

$133

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Thu 10/16

11:25 am-3:01 pm

Nonstop3h 36m

Miami

Sun 10/19

7:05 am-10:30 am

Nonstop3h 25m

$135

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Mon 9/1

5:00 am-10:50 am

1 stop5h 50m

Miami

Thu 9/4

11:35 am-6:00 pm

1 stop6h 25m

$173

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Sun 8/17

3:25 pm-7:06 pm

Nonstop3h 41m

$67

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 9/3

11:00 am-6:42 pm

1 stop7h 42m

$69

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Thu 10/9

11:25 am-3:01 pm

Nonstop3h 36m

$73

BostonMiami

BOS - MIA

BOSMIA

Boston Logan Intl

Wed 10/1

2:50 pm-9:15 pm

1 stop6h 25m

$76

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 12 results
1
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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 July 25, 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 July 30, 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 July 27, 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 July 30, 2025.

The most flights from BOS to I5L are scheduled on a Wednesday (31 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (17 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 July 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Spirit Airlines
6.3
Okay
8,048 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 23 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 150 times in the past calendar month.

  • 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 $67. However, be on the lookout for offers from Delta and Frontier, 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 (92%), Spirit Airlines (87%) or American Airlines (75%) 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 $867, our data indicates the cheapest price to be $78. The most popular route (Boston Logan Intl - Miami), is priced around $100.

  • 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$36Average$123FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$149FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$84Average$348FlexibilityNo cancel feeOn-time62%
DeltaCheapest$89Average$273FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$138Average$359FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$145Average$335FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$156Average$459FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$166Average$257FlexibilityNo cancel feeOn-time75%

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