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Simpson Bay

$605+ Cheap flights from Hobby (HOU) to Simpson Bay (SXM)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SXM
Feb 24 — Mar 31
Tue 2/24
Tue 3/3
1 adult, Economy
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Cheap flight deals from Hobby to Simpson Bay

Cheapest flights from Hobby to Simpson Bay
Explore the most affordable flight options available from Hobby to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 25, 2026.

This Southwest deal was found by Cheapflights users on 1/24. 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 5/135:50 am
HOU
-
SXM
1 stop6h 50m
Southwest
Wed 5/202:35 pm
SXM
-
HOU
1 stop9h 10m
Southwest
Deal found 1/24$605
This American Airlines deal was found by Cheapflights users on 1/23. 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.
Wed 5/64:19 pm
HOU
-
SXM
2 stops18h 18m
American Airlines
Thu 5/144:35 pm
SXM
-
HOU
2 stops17h 51m
American Airlines
Deal found 1/23$620
This Southwest deal was found by Cheapflights users on 1/24. 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 4/135:00 am
HOU
-
SXM
1 stop7h 40m
Southwest
Thu 4/162:35 pm
SXM
-
HOU
1 stop9h 55m
Southwest
Deal found 1/24$625
This Southwest deal was found by Cheapflights users on 1/24. 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 4/97:50 pm
HOU
-
SXM
2 stops16h 50m
Southwest
Sun 4/123:20 pm
SXM
-
HOU
2 stops19h 15m
Southwest
Deal found 1/24$635
This Southwest deal was found by Cheapflights users on 1/23. 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 6/17:50 pm
HOU
-
SXM
2 stops16h 50m
Southwest
Mon 6/83:00 pm
SXM
-
HOU
1 stop9h 45m
Southwest
Deal found 1/23$650
This American Airlines deal was found by Cheapflights users on 1/24. 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.
Thu 8/68:25 pm
HOU
-
SXM
2 stops16h 02m
American Airlines
Mon 8/102:22 pm
SXM
-
HOU
2 stops18h 59m
American Airlines
Deal found 1/24$660
This American Airlines deal was found by Cheapflights users on 1/23. 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.
Tue 5/54:19 pm
HOU
-
SXM
2 stops18h 18m
American Airlines
Sat 5/94:35 pm
SXM
-
HOU
2 stops17h 51m
American Airlines
Deal found 1/23$700
This American Airlines deal was found by Cheapflights users on 1/22. 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.
Thu 3/268:20 pm
HOU
-
SXM
2 stops15h 56m
American Airlines
Mon 3/3012:29 pm
SXM
-
HOU
2 stops12h 29m
American Airlines
Deal found 1/22$705
This Delta deal was found by Cheapflights users on 1/23. 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.
Wed 4/296:00 am
HOU
-
SXM
1 stop7h 09m
Delta
Sun 5/31:50 pm
SXM
-
HOU
1 stop9h 54m
Delta
Deal found 1/23$725
This Southwest deal was found by Cheapflights users on 1/23. 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 6/87:25 pm
HOU
-
SXM
2 stops17h 35m
Southwest
Mon 6/153:00 pm
SXM
-
HOU
2 stops18h 35m
Southwest
Deal found 1/23$730
This Southwest deal was found by Cheapflights users on 1/24. 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 4/258:20 pm
HOU
-
SXM
2 stops17h 05m
Southwest
Sat 5/21:20 pm
SXM
-
HOU
1 stop9h 15m
Southwest
Deal found 1/24$735

Find flight deals from Hobby to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$605
(Southwest)

Popular in

June

Cheapest in

September

Average price

$612
Provider with most accurate pricing for Houston Hobby-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Houston Hobby-Simpson Bay Princess Juliana flights.
Search Deals
From Houston Hobby to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hobby to Simpson Bay 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 January 25, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to Simpson Bay that are best for you.

Fly from

Hobby

Fly to

Simpson Bay

Route

Depart

Return

Price

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Wed 5/13

8:35 pm-1:40 pm

2 stops16h 05m

Simpson Bay Princess Juliana

Wed 5/20

2:35 pm-10:45 pm

1 stop9h 10m

$610

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Tue 3/10

4:20 pm-11:29 am

2 stops18h 09m

Simpson Bay Princess Juliana

Tue 3/17

4:28 pm-9:43 am

2 stops18h 15m

$620

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Wed 5/6

4:19 pm-11:37 am

2 stops18h 18m

Simpson Bay Princess Juliana

Thu 5/14

4:35 pm-9:26 am

2 stops17h 51m

$620

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Mon 4/13

5:00 am-1:40 pm

1 stop7h 40m

Simpson Bay Princess Juliana

Thu 4/16

2:35 pm-11:30 pm

1 stop9h 55m

$625

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Mon 6/1

5:00 am-1:40 pm

1 stop7h 40m

Simpson Bay Princess Juliana

Mon 6/8

3:00 pm-11:45 pm

1 stop9h 45m

$625

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Thu 4/9

7:50 pm-1:40 pm

2 stops16h 50m

Simpson Bay Princess Juliana

Sun 4/12

3:20 pm-9:35 am

2 stops19h 15m

$635

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Tue 5/5

4:19 pm-11:37 am

2 stops18h 18m

Simpson Bay Princess Juliana

Sat 5/9

4:35 pm-9:26 am

2 stops17h 51m

$700

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Mon 4/13

4:19 pm-11:37 am

2 stops18h 18m

Simpson Bay Princess Juliana

Thu 4/16

12:41 pm-11:47 pm

2 stops12h 06m

$700

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Mon 2/23

4:21 pm-12:29 pm

2 stops18h 08m

Simpson Bay Princess Juliana

Thu 2/26

5:28 pm-9:43 am

2 stops18h 15m

$700

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Thu 3/26

8:20 pm-1:16 pm

2 stops15h 56m

Simpson Bay Princess Juliana

Mon 3/30

12:29 pm-11:58 pm

2 stops12h 29m

$705

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

Showing 1-10 of 16 results
1
2

Compare providers for flights from Hobby to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hobby to Simpson Bay in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
CheapTicketsDealPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Houston Hobby Airport-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Houston Hobby Airport-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Houston Hobby Airport-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Houston Hobby Airport-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Houston Hobby Airport-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Hobby to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay 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 Simpson Bay

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

Use this chart to determine the optimal time to book a round-trip flight from Hobby to Simpson Bay. Price data was last updated on January 23, 2026.

The price you pay for your flight from Houston Hobby Airport to Simpson Bay may vary depending on when you book. For the best chance of a lower fare, look to book 71 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 Houston Hobby Airport to Simpson Bay?

Currently, August is the cheapest month in which you can book a flight from Houston Hobby Airport to Simpson Bay (average of $203). Flying from Houston Hobby Airport to Simpson Bay in June is currently the most expensive (average of $593). 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.

How much does it cost to fly round-trip from Houston Hobby Airport to Simpson Bay?

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. 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 Simpson Bay. Reviews last updated January 25, 2026.
Read through reviews of airlines operating flights from Houston Hobby Airport to Simpson Bay, such as Delta, American Airlines, and Spirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,112 reviews

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,112 reviews
Delta
7.9
Good
8,112 reviews

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,195 reviews
Delta
7.9
Good
8,112 reviews

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,375 reviews
Delta
7.9
Good
8,112 reviews

Entertainment

7.8

Overall

7.9

Comfort

7.9

Crew

8.5

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Hobby to Simpson Bay. 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 into for flights to Simpson Bay from Houston Hobby?

    Located just 0.5 mi from the city center, Simpson Bay Princess Juliana is the airport most travelers will use when flying to Simpson Bay from Houston Hobby. Booking flights from Houston Hobby to Princess Juliana (SXM) should be relatively easy as there are 0 daily inbound flights from Houston Hobby from 3 different airlines.

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

    For as low as $610, Southwest can have you in Simpson Bay from Houston Hobby Airport in 16h 05m. There are 2175 mi between Houston Hobby Airport and Simpson Bay. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Houston Hobby Airport to Simpson Bay round-trip?

    Cheapflights users have booked flights from Houston Hobby Airport to Simpson Bay round-trip from $203. Other airlines that can offer you cheap pricing are American Airlines, from $587, and Delta, from $587. These flights start at 68% lower than the current average price 3 months from now.

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

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

  • How can I find direct flights from Hobby to Simpson Bay?

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

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

    Yes. Cheapflights offers flight deals from Hobby to Simpson Bay 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 Simpson Bay?

    Currently, August is the cheapest month in which you can book a flight from Houston Hobby Airport to Simpson Bay (average of $203). Flying from Houston Hobby Airport to Simpson Bay in June is currently the most expensive (average of $593). 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

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

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Alternative routes for Hobby to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
George Bush Intcntl to Simpson Bay flights

Top 3 airlines flying from Hobby to Simpson Bay

Discover the top 3 airlines that operate flights from Hobby to Simpson Bay. 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 January 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$203Average$348FlexibilityNo cancel feeOn-time65%
DeltaCheapest$587Average$722FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$587Average$686FlexibilityNo cancel feeOn-time71%

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