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Islamorada

$54+ Cheap flights from Hobby (HOU) 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MIA
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Islamorada are usually found in September or August, booked 81 days in advance, depart on a Sunday or Monday and return on a Tuesday

Cheap flight deals from Hobby to Islamorada

Keep the following information in mind while searching for Hobby to Islamorada flight deals. Data was last updated August 20, 2025.

Round-trip from

$107
(Southwest)

One-way from

$54
(Southwest)

Popular in

December

Cheapest in

September

Average price

$176
From Houston Hobby to Islamorada
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One-way flight from Houston Hobby to Islamorada
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Highest demand for flights based on searches. 10% potential increase in price ($24 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 August 2025
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Find flight deals from Hobby to Islamorada

Cheapest flights from Hobby to Islamorada
Explore the most affordable flight options available from Hobby to Islamorada. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Southwest deal was found by Cheapflights users on 8/19. 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 9/221:10 pmHOU - MIA
Nonstop2h 35mSouthwest
Thu 9/256:15 pmMIA - HOU
Nonstop2h 45mSouthwest
Deal found 8/19$107
This Southwest deal was found by Cheapflights users on 8/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:00 pmHOU - MIA
Nonstop2h 25mSouthwest
Sat 9/208:05 amMIA - HOU
Nonstop2h 40mSouthwest
Deal found 8/20$117
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sat 9/136:00 pmHOU - MIA
Nonstop2h 25mSouthwest
Mon 9/156:15 pmMIA - HOU
Nonstop2h 45mSouthwest
Deal found 8/19$127
This Southwest deal was found by Cheapflights users on 8/18. 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.
Wed 10/14:00 pmHOU - MIA
1 stop4h 45mSouthwest
Fri 10/37:30 pmMIA - HOU
Nonstop2h 50mSouthwest
Deal found 8/18$142
This Southwest deal was found by Cheapflights users on 8/19. 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.
Sun 9/213:10 pmHOU - MIA
Nonstop2h 30mSouthwest
Fri 9/265:05 pmMIA - HOU
1 stop7h 10mSouthwest
Deal found 8/19$143
This Southwest deal was found by Cheapflights users on 8/18. 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.
Wed 10/111:20 amHOU - MIA
2 stops8h 20mSouthwest
Sat 10/45:30 pmMIA - HOU
Nonstop2h 50mSouthwest
Deal found 8/18$147
This Southwest deal was found by Cheapflights users on 8/19. 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.
Wed 9/174:00 pmHOU - MIA
1 stop4h 45mSouthwest
Fri 9/196:15 pmMIA - HOU
Nonstop2h 45mSouthwest
Deal found 8/19$158
This Southwest deal was found by Cheapflights users on 8/17. 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.
Sat 9/611:00 amHOU - MIA
Nonstop2h 30mSouthwest
Mon 9/86:15 pmMIA - HOU
Nonstop2h 45mSouthwest
Deal found 8/17$162

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hobby 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 August 20, 2025.
Use the filters below to find and compare flights from Houston Hobby Airport to Islamorada that are best for you.

Fly from

Hobby

Fly to

Islamorada

Route

Depart

Return

Price

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Thu 11/13

8:05 pm-11:25 pm

Nonstop2h 20m

Miami

Fri 11/14

7:35 pm-9:40 pm

Nonstop3h 05m

$107

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Mon 9/22

1:10 pm-4:45 pm

Nonstop2h 35m

Miami

Fri 9/26

6:15 pm-8:00 pm

Nonstop2h 45m

$107

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Sun 9/21

3:10 pm-6:40 pm

Nonstop2h 30m

Miami

Fri 9/26

6:15 pm-8:00 pm

Nonstop2h 45m

$107

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Mon 9/22

1:10 pm-4:45 pm

Nonstop2h 35m

Miami

Thu 9/25

6:15 pm-8:00 pm

Nonstop2h 45m

$107

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Sat 9/13

6:00 pm-9:25 pm

Nonstop2h 25m

Miami

Sat 9/20

8:05 am-9:45 am

Nonstop2h 40m

$117

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Sat 9/13

6:00 pm-9:25 pm

Nonstop2h 25m

Miami

Mon 9/15

6:15 pm-8:00 pm

Nonstop2h 45m

$127

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Wed 10/1

2:30 pm-9:45 pm

1 stop6h 15m

Miami

Sat 10/4

5:30 pm-7:20 pm

Nonstop2h 50m

$142

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Sat 10/4

1:05 pm-4:25 pm

Nonstop2h 20m

$54

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Sun 11/16

8:05 pm-11:25 pm

Nonstop2h 20m

$54

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Mon 10/27

7:55 pm-11:15 pm

Nonstop2h 20m

$54

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 13 results
1
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Best time to book a flight from Hobby to Islamorada

Have a flexible travel schedule? Discover the best time to fly to Islamorada from Hobby 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 Houston Hobby Airport to Islamorada

How far ahead should I book a flight from Houston Hobby Airport to Islamorada?

Use this chart to determine the optimal time to book a round-trip flight from Hobby to Islamorada. Price data was last updated on August 8, 2025.

Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from Houston Hobby Airport to Islamorada. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Houston Hobby Airport to Islamorada?

Currently, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Islamorada (average of $232). Flying from Houston Hobby Airport 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 HOU to I5L?

Find hourly flight availability from Hobby 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 August 20, 2025.

When flying from Houston Hobby Airport to Islamorada, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Houston Hobby Airport to Islamorada?

Use this chart to determine the cheapest time to fly round-trip from Hobby to Islamorada. Price data was last updated on December 16, 2024.

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

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 August 20, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Houston Hobby Airport 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
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,928 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Spirit Airlines
6.3
Okay
8,039 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
5.8
Fair
3,207 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

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

  • How long is the flight from Houston Hobby Airport to Islamorada?

    There are many flights that can get you from Houston Hobby Airport to Islamorada in 2h 20m. Fly via Southwest to get the fastest option. There are 953 mi between Houston Hobby Airport and Islamorada. All flights are typically nonstop.

  • What are the cheapest flights from Houston Hobby Airport to Islamorada?

    The cheapest flight price from Houston Hobby Airport to Islamorada is $63. On average you can expect to pay $274. The most popular route, (Houston Hobby - Miami), can usually be booked for $60.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Hobby 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 Houston Hobby Airport to Islamorada?

    Currently, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Islamorada (average of $232). Flying from Houston Hobby Airport 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.

See more FAQs

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Top 6 airlines flying from Hobby to Islamorada

Discover the top 6 airlines that operate flights from Hobby 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$66Average$168FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$78Average$169FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$143Average$404FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$145Average$360FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$173Average$324FlexibilityNo cancel feeOn-time63%
DeltaCheapest$220Average$334FlexibilityNo cancel feeOn-timeN/A

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