HOU - SXM

$150 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 7/7. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$389
Typical prices: $812-$615
Southwest
Fri 8/7Sun 8/16
HOU - SXM • 1 stop
Cheapest one-way
$150
Southwest
Tue 7/7
HOU - SXM • 1 stop
Top airlines
Cheapest • from $389 (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 $460 (round-trip)
Shortest trip • 6h 53m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 41% 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

Fri, Aug 7 - Sun, Aug 16
Southwest Logo
5:05 am - 2:05 pm
HOU
-
SXM
8h 00m
1 stop
Southwest Logo
3:05 pm - 11:15 pm
SXM
-
HOU
9h 10m
1 stop
$389Southwest
Fri, Aug 7 - Sun, Aug 16
Southwest Logo
5:05 am - 2:05 pm
HOU
-
SXM
8h 00m
1 stop
Southwest Logo
3:05 pm - 11:15 pm
SXM
-
HOU
9h 10m
1 stop
$399Southwest
Mon, Jul 20 - Wed, Jul 22
Southwest Logo
5:05 am - 1:25 pm
HOU
-
SXM
7h 20m
1 stop
Southwest Logo
3:00 pm - 11:15 pm
SXM
-
HOU
9h 15m
1 stop
$415Southwest
Wed, Aug 12 - Sun, Aug 16
Southwest Logo
8:50 pm - 2:05 pm
HOU
-
SXM
16h 15m
2 stops
Southwest Logo
3:05 pm - 11:15 pm
SXM
-
HOU
9h 10m
1 stop
$420Southwest
Mon, Jul 20 - Wed, Jul 22
Southwest Logo
5:05 am - 1:25 pm
HOU
-
SXM
7h 20m
1 stop
Southwest Logo
3:00 pm - 11:15 pm
SXM
-
HOU
9h 15m
1 stop
$425Southwest
Mon, Jul 20 - Wed, Jul 22
Southwest Logo
5:05 am - 1:25 pm
HOU
-
SXM
7h 20m
1 stop
Southwest Logo
3:00 pm - 9:00 am
SXM
-
HOU
19h 00m
2 stops
$475Southwest
Mon, Jul 20 - Wed, Jul 22
Southwest Logo
8:35 pm - 2:00 pm
HOU
-
SXM
16h 25m
2 stops
Southwest Logo
3:00 pm - 11:15 pm
SXM
-
HOU
9h 15m
1 stop
$485Southwest
Fri, Aug 21 - Mon, Aug 24
Southwest Logo
5:05 am - 2:05 pm
HOU
-
SXM
8h 00m
1 stop
Southwest Logo
3:05 pm - 10:20 pm
SXM
-
HOU
8h 15m
1 stop
$495Southwest
Mon, Oct 5 - Fri, Oct 23
Southwest Logo
5:05 am - 2:00 pm
HOU
-
SXM
7h 55m
1 stop
Southwest Logo
3:00 pm - 12:25 am
SXM
-
HOU
10h 25m
1 stop
$496Southwest
Sat, Sep 19 - Thu, Sep 24
Southwest Logo
7:40 pm - 2:05 pm
HOU
-
SXM
17h 25m
2 stops
Southwest Logo
3:05 pm - 9:25 am
SXM
-
HOU
19h 20m
2 stops
$500Southwest
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 August.

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 December and June, where the average cost of round-trip tickets is $807 and $765 respectively.

Good to know

Low seasonFebruary
Cheapest flight$150
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly with an average 2% 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 5 days, the lowest price for a flight from Houston Hobby Airport to Simpson Bay was $150 for a one-way ticket and $389 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?

    oneworld is the only airline alliance operating flights between Houston Hobby Airport and Simpson Bay.

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

    The two airlines most popular with KAYAK users for flights from Houston to Simpson Bay are Southwest and American Airlines. With an average price for the route of $725 and an overall rating of 7.9, Southwest is the most popular choice. American Airlines is also a great choice for the route, with an average price of $717 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
SouthwestOverall score based on 4237 reviews
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

Another uncoordinated American experience. Always surprises me at DFW for them of all places. Have to take this flight as there are no other good time options. We knew from the start that something was wrong, but the pilot wouldn't tell us. I just watched my Kayak app grow the delay by 10 minutes as it went to 3.5 hours. They were uncoordinated with maintenance (as maintenance, when finally arriving, knew within 15 minutes the plane wasn't going. No 'sorry' or 'this is what is going on' comment. The pilot seemed unfazed / didn't care about the process we were going through.

The seats. The seat in front of me was awful and when the guy sat down, it flew back and hit my head when I was putting my backpack under the seat, It didn't make for a pleasant experience,

The flight back to Dallas was delayed, which has happened to me several times with American Airlines. There was no announcement, no update sent out, no compensation offered for the inconvenience.

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

The flight from Dallas to Tokyo was not on Japan Airlines. It was on American Airlines. Very disappointed that we did not fly on Japan Airlines. Will not be using you liars again. I’ll just book direct from the airline next time. Wish you could make this right and has us fly on Japan Air when heading back home to the US.

They made nearly everyone check their bag because the overhead bins are way too small. Extremely inconvenient

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

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

Information on your arrival and departure airports