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Simpson Bay

$294+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SXM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Houston Hobby to Simpson Bay Princess Juliana are usually found in September or January, booked 4 days in advance, depart on a Tuesday or Friday and return on a Tuesday

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 September 17, 2025.

Round-trip from

$632
(American Airlines)

One-way from

$294
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$383
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. 8% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/16. 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 10/168:11 pmHOU - SXM
2 stops18h 04mAmerican Airlines
Thu 10/234:24 pmSXM - HOU
2 stops18h 18mAmerican Airlines
Deal found 9/16$632
This American Airlines deal was found by Cheapflights users on 9/15. 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 12/46:29 pmHOU - SXM
2 stops17h 23mAmerican Airlines
Mon 12/85:25 pmSXM - HOU
2 stops18h 13mAmerican Airlines
Deal found 9/15$672
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/28:20 pmHOU - SXM
2 stops18h 02mAmerican Airlines
Sun 11/95:24 pmSXM - HOU
2 stops17h 13mAmerican Airlines
Deal found 9/15$682
This American Airlines deal was found by Cheapflights users on 9/16. 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.
Mon 10/138:11 pmHOU - SXM
2 stops16h 26mAmerican Airlines
Thu 10/164:24 pmSXM - HOU
2 stops18h 09mAmerican Airlines
Deal found 9/16$717
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/314:41 pmHOU - SXM
2 stops21h 34mAmerican Airlines
Fri 11/75:24 pmSXM - HOU
2 stops18h 17mAmerican Airlines
Deal found 9/16$792
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/316:00 amHOU - SXM
1 stop6h 49mDelta
Fri 11/74:14 pmSXM - HOU
1 stop8h 46mDelta
Deal found 9/16$807
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/128:11 pmHOU - SXM
2 stops16h 26mAmerican Airlines
Sun 10/194:24 pmSXM - HOU
2 stops18h 09mAmerican Airlines
Deal found 9/16$812
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/286:22 pmHOU - SXM
2 stops17h 57mAmerican Airlines
Sun 10/52:20 pmSXM - HOU
2 stops20h 13mAmerican Airlines
Deal found 9/15$862
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/286:22 pmHOU - SXM
2 stops17h 57mAmerican Airlines
Thu 10/22:20 pmSXM - HOU
2 stops10h 28mAmerican Airlines
Deal found 9/15$897
This Delta deal was found by Cheapflights users on 9/16. 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 10/126:00 amHOU - SXM
1 stop6h 49mDelta
Sun 10/193:14 pmSXM - HOU
1 stop8h 46mDelta
Deal found 9/16$1,017
This American Airlines deal was found by Cheapflights users on 9/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/34:28 pmHOU - SXM
2 stops20h 12mAmerican Airlines
Sat 10/114:24 pmSXM - HOU
2 stops17h 05mAmerican Airlines
Deal found 9/17$1,052
This Delta deal was found by Cheapflights users on 9/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/36:00 amHOU - SXM
1 stop6h 50mDelta
Sat 10/113:14 pmSXM - HOU
1 stop8h 46mDelta
Deal found 9/17$1,077

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 September 17, 2025.
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

Thu 10/16

8:11 pm-3:15 pm

2 stops18h 04m

Simpson Bay Princess Juliana

Thu 10/23

4:24 pm-9:42 am

2 stops18h 18m

$632

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Mon 10/27

6:11 pm-1:37 pm

2 stops18h 26m

Simpson Bay Princess Juliana

Fri 10/31

2:40 pm-8:28 am

2 stops18h 48m

$672

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Thu 12/4

6:29 pm-1:52 pm

2 stops17h 23m

Simpson Bay Princess Juliana

Mon 12/8

5:25 pm-9:38 am

2 stops18h 13m

$672

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Sun 11/2

8:20 pm-4:22 pm

2 stops18h 02m

Simpson Bay Princess Juliana

Sun 11/9

5:24 pm-8:37 am

2 stops17h 13m

$682

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Sun 11/2

5:00 am-1:49 pm

1 stop6h 49m

Simpson Bay Princess Juliana

Sun 11/9

4:20 pm-11:46 pm

1 stop9h 26m

$717

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Mon 10/13

8:11 pm-1:37 pm

2 stops16h 26m

Simpson Bay Princess Juliana

Thu 10/16

4:24 pm-9:33 am

2 stops18h 09m

$717

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Wed 1/14

6:25 pm-2:05 pm

2 stops17h 40m

Simpson Bay Princess Juliana

Sun 1/18

4:15 pm-8:38 am

2 stops18h 23m

$752

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Fri 10/31

4:41 pm-3:15 pm

2 stops21h 34m

Simpson Bay Princess Juliana

Fri 11/7

5:24 pm-9:41 am

2 stops18h 17m

$792

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Fri 10/31

6:00 am-1:49 pm

1 stop6h 49m

Simpson Bay Princess Juliana

Fri 11/7

4:14 pm-11:00 pm

1 stop8h 46m

$807

HoustonSimpson Bay

HOU - SXM

HOUSXM

Houston Hobby

Sun 10/12

8:11 pm-1:37 pm

2 stops16h 26m

Simpson Bay Princess Juliana

Sun 10/19

4:24 pm-9:33 am

2 stops18h 09m

$812

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 16 results
1
2

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 September 12, 2025.

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, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Simpson Bay (average of $459). Flying from Houston Hobby Airport to Simpson Bay in March is currently the most expensive (average of $652). 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.

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 September 17, 2025.
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
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,023 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Food

7.3

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 $632, American Airlines can have you in Simpson Bay from Houston Hobby Airport in 18h 04m. There are 2175 mi between Houston Hobby Airport and Simpson Bay.

  • 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 $301. Other airlines that can offer you cheap pricing are Delta, from $587, and American Airlines, from $599. These flights start at 54% 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, September is the cheapest month in which you can book a flight from Houston Hobby Airport to Simpson Bay (average of $459). Flying from Houston Hobby Airport to Simpson Bay in March is currently the most expensive (average of $652). 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$301Average$423FlexibilityNo cancel feeOn-time65%
DeltaCheapest$587Average$727FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$599Average$696FlexibilityNo cancel feeOn-time71%

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