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Simpson Bay

$293+ Cheap flights from Hobby (HOU) to Simpson Bay (SXM)

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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SXM
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap 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 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$595
(Southwest)

One-way from

$293
(Delta)

Popular in

June

Cheapest in

September

Average price

$612
Provider with most accurate pricing for Houston Hobby-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Houston Hobby-Simpson Bay Princess Juliana flights.
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From Houston Hobby to Simpson Bay Princess Juliana
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One-way flight from Houston Hobby to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 9% potential increase in price ($69 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find 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 8, 2026.

This Southwest deal was found by Cheapflights users on 1/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:00 amHOU - SXM
1 stop7h 40mSouthwest
Fri 4/242:35 pmSXM - HOU
1 stop9h 55mSouthwest
Deal found 1/7$595
This Southwest deal was found by Cheapflights users on 1/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:50 amHOU - SXM
1 stop6h 50mSouthwest
Thu 5/142:35 pmSXM - HOU
2 stops20h 05mSouthwest
Deal found 1/8$600
This Delta deal was found by Cheapflights users on 1/6. 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 3/256:00 amHOU - SXM
1 stop6h 54mDelta
Tue 3/3112:55 pmSXM - HOU
1 stop10h 47mDelta
Deal found 1/6$630
This American Airlines deal was found by Cheapflights users on 1/6. 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 7/26:23 pmHOU - SXM
2 stops18h 22mAmerican Airlines
Wed 7/84:36 pmSXM - HOU
2 stops17h 27mAmerican Airlines
Deal found 1/6$640
This American Airlines deal was found by Cheapflights users on 1/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/128:20 pmHOU - SXM
2 stops15h 56mAmerican Airlines
Sun 3/154:28 pmSXM - HOU
2 stops20h 20mAmerican Airlines
Deal found 1/7$645
This American Airlines deal was found by Cheapflights users on 1/6. 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.
Fri 2/138:16 pmHOU - SXM
2 stops17h 43mAmerican Airlines
Fri 2/205:28 pmSXM - HOU
2 stops18h 15mAmerican Airlines
Deal found 1/6$650
This American Airlines deal was found by Cheapflights users on 1/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:20 pmHOU - SXM
2 stops18h 08mAmerican Airlines
Fri 3/134:28 pmSXM - HOU
2 stops20h 20mAmerican Airlines
Deal found 1/7$680
This American Airlines deal was found by Cheapflights users on 1/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/74:21 pmHOU - SXM
2 stops17h 08mAmerican Airlines
Wed 3/114:28 pmSXM - HOU
2 stops18h 15mAmerican Airlines
Deal found 1/7$685
This American Airlines deal was found by Cheapflights users on 1/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/304:55 pmHOU - SXM
2 stops18h 03mAmerican Airlines
Mon 2/25:33 pmSXM - HOU
2 stops18h 32mAmerican Airlines
Deal found 1/8$690
This American Airlines deal was found by Cheapflights users on 1/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/128:16 pmHOU - SXM
2 stops18h 12mAmerican Airlines
Tue 2/174:01 pmSXM - HOU
2 stops19h 42mAmerican Airlines
Deal found 1/7$780
This Southwest deal was found by Cheapflights users on 1/6. 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 6/75:00 amHOU - SXM
1 stop8h 35mSouthwest
Fri 6/123:00 pmSXM - HOU
1 stop9h 45mSouthwest
Deal found 1/6$790
This Delta deal was found by Cheapflights users on 1/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/296:00 amHOU - SXM
1 stop7h 09mDelta
Sun 5/31:50 pmSXM - HOU
1 stop9h 54mDelta
Deal found 1/7$795

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 8, 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 5/6

5:50 am-1:40 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Thu 5/14

2:35 pm-11:30 pm

1 stop9h 55m

$595

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Fri 3/20

4:20 pm-11:29 am

2 stops18h 09m

Simpson Bay Princess Juliana

Tue 3/24

4:28 pm-9:43 am

2 stops18h 15m

$600

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Fri 2/6

4:55 pm-12:58 pm

2 stops18h 03m

Simpson Bay Princess Juliana

Tue 2/10

5:33 pm-10:05 am

2 stops18h 32m

$600

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Mon 4/20

8:15 pm-1:40 pm

2 stops16h 25m

Simpson Bay Princess Juliana

Fri 4/24

2:35 pm-10:25 am

2 stops20h 50m

$600

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

$600

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Wed 3/25

6:00 am-1:54 pm

1 stop6h 54m

Simpson Bay Princess Juliana

Tue 3/31

12:55 pm-10:42 pm

1 stop10h 47m

$630

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Thu 7/2

6:23 pm-1:45 pm

2 stops18h 22m

Simpson Bay Princess Juliana

Wed 7/8

4:36 pm-9:03 am

2 stops17h 27m

$640

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Thu 3/12

8:20 pm-1:16 pm

2 stops15h 56m

Simpson Bay Princess Juliana

Sun 3/15

4:28 pm-11:48 am

2 stops20h 20m

$645

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Sun 2/15

5:25 am-2:50 pm

1 stop7h 25m

$293

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Sun 2/15

4:21 pm-12:29 pm

2 stops18h 08m

$293

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 12 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 Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Houston Hobby Airport-Simpson Bay flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 2, 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 4 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 $589). 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 8, 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
8,026 reviews

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

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
8,026 reviews
Delta
7.9
Good
8,026 reviews

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

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
11,097 reviews
Delta
7.9
Good
8,026 reviews

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

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
8,288 reviews
Delta
7.9
Good
8,026 reviews

Boarding

8.1

Comfort

7.9

Food

7.2

Crew

8.5

Entertainment

7.8

Overall

7.9

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 $595, Southwest can have you in Simpson Bay from Houston Hobby Airport in 6h 50m. 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 $589). 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 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$300Average$382FlexibilityNo cancel feeOn-time65%
DeltaCheapest$587Average$741FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$587Average$691FlexibilityNo cancel feeOn-time71%

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