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Islamorada

$50+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — MIA
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Islamorada are usually found in September or October, booked 23 days in advance, depart on a Sunday or Monday and return on a Wednesday

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 October 20, 2025.

Round-trip from

$169
(Southwest)

One-way from

$50
(Southwest)

Popular in

December

Cheapest in

September

Average price

$150
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. 8% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 20, 2025.

This Southwest deal was found by Cheapflights users on 10/17. 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.
Wed 11/122:00 pmHOU - MIA
1 stop4h 50mSouthwest
Fri 11/147:35 pmMIA - HOU
Nonstop3h 05mSouthwest
Deal found 10/17$169
This Southwest deal was found by Cheapflights users on 10/19. 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 12/82:00 pmHOU - MIA
1 stop4h 50mSouthwest
Thu 12/114:55 pmMIA - HOU
1 stop6h 30mSouthwest
Deal found 10/19$174
This Southwest deal was found by Cheapflights users on 10/19. 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 12/155:35 amHOU - MIA
1 stop9h 25mSouthwest
Tue 12/167:40 amMIA - HOU
1 stop8h 40mSouthwest
Deal found 10/19$178
This Southwest deal was found by Cheapflights users on 10/19. 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.
Tue 11/112:00 pmHOU - MIA
1 stop4h 50mSouthwest
Tue 11/186:55 amMIA - HOU
1 stop5h 15mSouthwest
Deal found 10/19$183
This Southwest deal was found by Cheapflights users on 10/19. 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 12/176:00 amHOU - MIA
1 stop9h 10mSouthwest
Wed 12/246:55 amMIA - HOU
1 stop5h 15mSouthwest
Deal found 10/19$190
This Delta deal was found by Cheapflights users on 10/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/710:39 amHOU - MIA
1 stop6h 46mDelta
Tue 12/93:50 pmMIA - HOU
1 stop7h 58mDelta
Deal found 10/20$197
This Southwest deal was found by Cheapflights users on 10/19. 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.
Fri 11/148:05 pmHOU - MIA
Nonstop2h 20mSouthwest
Tue 11/186:55 amMIA - HOU
1 stop5h 15mSouthwest
Deal found 10/19$207
This Southwest deal was found by Cheapflights users on 10/19. 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.
Thu 11/68:05 pmHOU - MIA
Nonstop2h 20mSouthwest
Thu 11/137:35 pmMIA - HOU
Nonstop3h 05mSouthwest
Deal found 10/19$212

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 October 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

Sun 12/7

10:39 am-6:25 pm

1 stop6h 46m

Miami

Sat 12/13

7:00 am-1:28 pm

1 stop7h 28m

$197

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Mon 11/10

6:48 pm-12:46 am

1 stop4h 58m

Miami

Sat 11/15

7:00 am-1:28 pm

1 stop7h 28m

$197

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Fri 11/14

8:05 pm-11:25 pm

Nonstop2h 20m

Miami

Tue 11/18

6:55 am-11:10 am

1 stop5h 15m

$207

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Mon 1/5

8:05 pm-11:25 pm

Nonstop2h 20m

Miami

Wed 1/7

2:35 pm-10:40 pm

1 stop9h 05m

$233

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Mon 12/15

12:30 pm-9:50 pm

2 stops8h 20m

Miami

Tue 12/16

7:40 am-4:30 pm

2 stops9h 50m

$247

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Thu 11/6

8:05 pm-11:25 pm

Nonstop2h 20m

Miami

Sat 11/8

6:50 am-11:35 am

1 stop5h 45m

$257

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Mon 11/3

5:40 am-4:10 pm

2 stops9h 30m

Miami

Fri 11/7

7:35 pm-9:40 pm

Nonstop3h 05m

$262

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Tue 12/16

6:47 pm-12:46 am

1 stop4h 59m

Miami

Thu 1/1

6:00 am-10:01 am

1 stop5h 01m

$268

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Fri 11/7

8:05 pm-11:25 pm

Nonstop2h 20m

Miami

Tue 11/11

5:15 pm-8:55 pm

1 stop4h 40m

$268

HoustonMiami

HOU - MIA

HOUMIA

Houston Hobby

Sat 11/8

3:05 pm-9:25 pm

1 stop5h 20m

Miami

Mon 11/10

7:35 pm-9:40 pm

Nonstop3h 05m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/19

Showing 1-10 of 23 results
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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 October 17, 2025.

Booking 23 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, October is the cheapest month in which you can book a flight from Houston Hobby Airport to Islamorada (average of $58). Flying from Houston Hobby Airport to Islamorada in December is currently the most expensive (average of $111). 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 October 20, 2025.

It’s optimal to fly from Houston Hobby Airport to Islamorada in the afternoon. By choosing this option you can save up to 58% on the cost of your flight, compared to a flight in the evening.

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 Tuesday mornings when fares are most often at their lowest. Tuesday evenings 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 October 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
4,239 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

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
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

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
8,991 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

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
11,024 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

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
8,095 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

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
3,130 reviews
Southwest
8.0
Very good
4,239 reviews

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Overall

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 Delta or Southwest to get the fastest option. There are 953 mi between Houston Hobby Airport and Islamorada. This flight may include one or multiple stops.

  • 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, October is the cheapest month in which you can book a flight from Houston Hobby Airport to Islamorada (average of $58). Flying from Houston Hobby Airport to Islamorada in December is currently the most expensive (average of $111). 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 October 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$54Average$163FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$80Average$165FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$127Average$334FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$128Average$376FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$315FlexibilityNo cancel feeOn-time63%
DeltaCheapest$220Average$322FlexibilityNo cancel feeOn-timeN/A

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