HOU - SXM

$268 Find Cheap Flights from Houston Hobby Airport to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hobby to Simpson Bay departing on 7/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Simpson Bay, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Simpson Bay, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$557
Typical prices: $540-$749
Southwest
Sun 4/12Wed 4/15
HOU - SXM • 1 stop
Cheapest one-way
$268
Southwest
Tue 7/28
HOU - SXM • 1 stop
Top airlines
Cheapest • from $557 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Hobby and Simpson Bay. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $458 (round-trip)
Shortest trip • 6h 44m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 39% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hobby to Simpson Bay (HOU-SXM)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hobby to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hobby to Simpson Bay

Sun, Apr 12 - Wed, Apr 15
Southwest Logo
6:45 am - 2:25 pm
HOU
-
SXM
6h 40m
1 stop
Southwest Logo
2:25 pm - 10:45 pm
SXM
-
HOU
9h 20m
1 stop
$557Southwest
Sun, Apr 12 - Wed, Apr 15
Southwest Logo
5:05 am - 2:25 pm
HOU
-
SXM
8h 20m
1 stop
Southwest Logo
2:25 pm - 9:30 am
SXM
-
HOU
20h 05m
2 stops
$616Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
8:50 pm - 1:30 pm
HOU
-
SXM
15h 40m
2 stops
Southwest Logo
2:25 pm - 10:45 pm
SXM
-
HOU
9h 20m
1 stop
$643Southwest
Wed, Jun 3 - Sun, Jun 7
Southwest Logo
7:00 pm - 2:00 pm
HOU
-
SXM
18h 00m
2 stops
Southwest Logo
3:35 pm - 8:25 am
SXM
-
HOU
17h 50m
2 stops
$650Southwest
Fri, May 8 - Sat, May 16
Southwest Logo
5:00 am - 1:30 pm
HOU
-
SXM
7h 30m
1 stop
Southwest Logo
1:20 pm - 9:35 pm
SXM
-
HOU
9h 15m
1 stop
$665Southwest
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
7:50 pm - 1:30 pm
HOU
-
SXM
16h 40m
2 stops
Southwest Logo
2:25 pm - 10:10 am
SXM
-
HOU
20h 45m
2 stops
$670Southwest
Wed, May 6 - Thu, May 14
Delta Logo
6:00 am - 2:05 pm
HOU
-
SXM
7h 05m
1 stop
Delta Logo
3:20 pm - 10:26 pm
SXM
-
HOU
8h 06m
1 stop
$685Delta
Sat, May 9 - Sat, May 16
American Airlines Logo
4:19 pm - 11:37 am
HOU
-
SXM
18h 18m
2 stops
American Airlines Logo
12:41 pm - 11:47 pm
SXM
-
HOU
12h 06m
2 stops
$690American Airlines
Wed, May 6 - Thu, May 14
American Airlines Logo
4:18 pm - 11:37 am
HOU
-
SXM
18h 19m
2 stops
American Airlines Logo
12:41 pm - 11:47 pm
SXM
-
HOU
12h 06m
2 stops
$695American Airlines
Thu, Apr 9 - Mon, Apr 13
Southwest Logo
5:00 am - 1:30 pm
HOU
-
SXM
7h 30m
1 stop
Southwest Logo
2:25 pm - 11:30 pm
SXM
-
HOU
10h 05m
1 stop
$710Southwest
Booking Insights

KAYAK's insights & trends for Hobby to Simpson Bay flights

Get data-powered insights and trends into flights from Hobby to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Houston Hobby Airport to Simpson Bay?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Houston Hobby Airport to Simpson Bay departing in April.

What is the cheapest month to fly from Houston Hobby Airport to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Houston Hobby Airport to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Houston Hobby Airport to Simpson Bay is September, where tickets cost $383 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is $852 and $744 respectively.

Good to know

Low seasonFebruary
Cheapest flight$268
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly with an average 1% increase in price.
Flight from Houston Hobby Airport to Simpson Bay

When to book flights from Hobby to Simpson Bay

Are your dates flexible? Find out the best times to travel from Hobby to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Houston Hobby Airport to Simpson Bay flights

  • What is the cheapest flight from Houston Hobby Airport to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Houston Hobby Airport to Simpson Bay was $319 for a one-way ticket and $557 for a round-trip.

  • Do I need a passport to fly between Houston Hobby Airport and Simpson Bay?

    Yes

  • Which aircraft models fly most regularly from Houston Hobby Airport to Simpson Bay?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Houston Hobby Airport to Simpson Bay?

    SkyTeam, and oneworld are the airline alliances operating flights between Houston Hobby Airport and Simpson Bay, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Houston to Simpson Bay, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Houston to Simpson Bay are Delta and American Airlines. With an average price for the route of $727 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $692 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Houston Hobby Airport to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Houston Hobby Airport to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Houston Hobby Airport to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Houston Hobby Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Houston Hobby Airport to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Houston Hobby Airport with another airline. Booking your flights between Houston Hobby Airport and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Houston Hobby Airport to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Houston Hobby Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Hobby to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Houston to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hobby to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8303 reviews
7.9Comfort
7.2Food
8.5Crew
7.8Entertainment
8.1Boarding
Airline reviews

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

6.0 GoodCarl, Mar 2026
ATL - ATW
Read more Delta reviews

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Poor communication ahead of time about flight delays and old planes/other equipment.

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

The crew was excellent and overall the flight was good. No complaints.

Like all of the flights I took to get down to Dallas. They were delayed

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

Horrendous and unprofessional staff and will never fly spirit again

When I arrived at the airport at 4:00 in the morning, I was notified that I "hadn't paid" for my ticket (I had paid and had a boarding pass). Then I was told that while I had paid, the ticket was $600 more than it actually was, and that I needed to pay that so I could board. None of this was true, of course, but it took 20 minutes, two crew members behind the desk, and one on the phone to clear up.

First off, I had a conversation with a flight attendant that was working this flight. I overheard her telling another flight attendant while we were in line for Chic-Fil-A that the flight was not going to land until 12:47 pm. I found this odd since the flight was to take off at 1:03. I commented to the flight attendant that was going to mess up the on-time take-off She said. if you fly alot you will notice that it's a good thing if the flight even arrives at all. I said that was a low bar. I think that flight attendants represent their airlines whether on board or in the airport ordering food. I was surprised to hear such negativity. However, I have noticed that Spirit flight attendants are usually in a sour mood.. Eventually the flight arrived and I boarded and the flight took off an hour late. There was no direction about the on-board wi-fi. Nor was there any info in the seat back pocket. I don't know if there was wi-fi or not, There were no complimentary snacks or drinks for my row 36 as there was turbulence and the captain asked the flight attendants to stop serving just as they were close to my row. When the turbulence stopped, they did have time to serve us but they did not. Upon arriving, the flight attendant asked anyone not having to catch a flight to Ft. Laudersle which was a tight connection to sit down and let those people pass. I complied but I could not help thinking that if Spirit would have took off on time that they would not have to inconvenience their passengers. All in all, I think Spirit is a mediocre airline at best. There are so many things they could do to improve. Yet, since I only fly Spirit infrequently preferring Southwest and Delta, I like to see if they are improving and sadly no, they are not. One good thing - nice modern seats and interiors.

My flight was cancelled I missed time at work and got a parking ticket

Went as planned. No wifi included and no screens. No free snacks. Didn't buy food so can't rate that. Unable to charge devices on plane. Staff were friendly and flight was fast, cheap and convenient.

I purchased extra legroom so I will be comfortable but the guy behind me is a big guy who keeps on moving and since he is big I can feel his movement at the back of my chair.

Spirit was on time. They maintained updates and information. The crew was friendly and professional. Because this is a budget friendly airline, they have dispensed with a lot of frills and part of that comes with a price, for example, the seats are not quite as comfortable as others. I am ok with a pay for beverage and snack service as I prefer my own anyway so this was not a concern. I thought overall, having a great flight crew and on time service was definitely worth losing some of the frills from other carriers.

Sadly there was a crew member very rude with my kid and with me.

They canceled the flight and didn't assist in getting a new flight on any airline. I had to spend 10 hrs in the airport after getting a ticket On Delta for twice as much. I've flown Spirit many times and this was my worst experience I've had.

Late taking off. ATC sent us circling around Chicago for almost an hour, after landing taxied for 40 minutes.

Everything you need to know for your flight from Hobby to Simpson Bay

Information on your arrival and departure airports