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Simpson Bay

$60+ Cheap flights from Simpson Bay

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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MIA
Aug 23 — Aug 301
Sun 8/23
Sun 8/30
1 adult, Economy
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Find flights from Simpson Bay within your budget

 
Find flights departing from Simpson Bay that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on July 24, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Fri 9/18

12:20 pm-12:35 pm

Nonstop0h 15m

Gustavia St Barthelemy

Thu 9/24

4:25 pm-4:40 pm

Nonstop0h 15m

$206

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Sun 8/23

12:20 pm-12:35 pm

Nonstop0h 15m

Gustavia St Barthelemy

Sun 8/23

4:20 pm-4:35 pm

Nonstop0h 15m

$206

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Wed 8/12

11:10 am-11:25 am

Nonstop0h 15m

Gustavia St Barthelemy

Wed 8/19

5:30 pm-5:45 pm

Nonstop0h 15m

$206

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Wed 8/5

11:00 am-11:15 am

Nonstop0h 15m

Gustavia St Barthelemy

Thu 8/6

5:30 pm-5:45 pm

Nonstop0h 15m

$209

Simpson BayGustavia

SXM - SBH

SXMSBH

Simpson Bay Princess Juliana

Fri 11/13

9:00 am-9:20 am

Nonstop0h 20m

Gustavia St Barthelemy

Mon 11/16

4:25 pm-4:45 pm

Nonstop0h 20m

$346

Simpson BayOrlando

SXM - MCO

SXMMCO

Simpson Bay Princess Juliana

Fri 9/11

3:18 pm-11:06 pm

1 stop7h 48m

Orlando

Sun 9/20

8:50 pm-1:53 pm

1 stop17h 03m

$355

Simpson BayNew York

SXM - JFK

SXMJFK

Simpson Bay Princess Juliana

Sat 8/29

5:55 pm-10:11 pm

Nonstop4h 16m

New York John F Kennedy Intl

Sat 9/12

6:59 am-11:07 am

Nonstop4h 08m

$362

Simpson BayMiami

SXM - MIA

SXMMIA

Simpson Bay Princess Juliana

Fri 10/23

12:32 pm-10:29 pm

1 stop9h 57m

Miami

Sun 10/25

5:39 pm-11:32 am

1 stop17h 53m

$363

Simpson BayMiami

SXM - MIA

SXMMIA

Simpson Bay Princess Juliana

Fri 9/18

3:18 pm-12:55 am

1 stop9h 37m

Miami

Sun 9/27

7:40 pm-1:53 pm

1 stop18h 13m

$366

Simpson BayOrlando

SXM - MCO

SXMMCO

Simpson Bay Princess Juliana

Thu 8/27

3:18 pm-1:04 am

1 stop9h 46m

Orlando

Mon 8/31

5:30 am-1:53 pm

1 stop8h 23m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from 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 Simpson Bay in July
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
MytripPrice 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: Among all the travel providers offering deals on flights from Simpson Bay, FlightHub has been found to have the most accurate pricing. Users can find the same prices on deals on Cheapflights as FlightHub about >95% of the time. This is based on searches for flights from Simpson Bay made on Cheapflights over the past month and is updated monthly.
  • Most trusted provider: In terms of trustworthiness, Cheapflights users rate FlightHub the highest out of those offering flight deals from Simpson Bay. FlightHub has a user feedback rating of 3 out of 3 stars (3 being the best) and has received the most positive sentiment from Cheapflights users searching for flights from Simpson Bay. This info is gathered from Cheapflights searches over the past month.

Best time to book a flight from Simpson Bay

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

Travel insights for flights from Simpson Bay

Get recent, data-driven insights about flights from Simpson Bay including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Simpson Bay?

Currently, January is the cheapest month in which you can book a flight from Simpson Bay (average of $330). Flying from Simpson Bay in July will prove the most costly (average of $472). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Simpson Bay?

For flights departing from Simpson Bay check dates and pricing for the following: American Airlines. This airline departs to the following popular destinations: Miami.

Winair
Winair
From $191
American Airlines
American Airlines
From $269
JetBlue
JetBlue
From $191
Copa Airlines
Copa Airlines
From $270

What are popular destinations to fly to from Simpson Bay?

Some of the most frequent flights departing from Simpson Bay everyday are: Gustavia (245 flights per day), New York (56 flights per day), and Oranjestad (40 flights per day).

New York
New York
From $218
Miami
Miami
From $216
Fort Lauderdale
Fort Lauderdale
From $198
Toronto
Toronto
From $286

What is the cheapest place to fly to from Simpson Bay?

The cheapest city to fly to from Simpson Bay is Basseterre Robert Bradshaw Intl, with prices starting at $149. Explore other affordable destinations below.

Basseterre Robert Bradshaw Intl
Basseterre Robert Bradshaw Intl
From $149
Santo Domingo Las Americas
Santo Domingo Las Americas
From $173
Saba Island Juancho E. Yrausquin
Saba Island Juancho E. Yrausquin
From $181
St. John's V.C. Bird Intl
St. John's V.C. Bird Intl
From $185

When is the best time to book a flight from Simpson Bay?

To ensure you get the cheapest price possible for a flight from Simpson Bay, you should look to book at least 69 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Airline reviews for flights from Simpson Bay

Read reviews and ratings of airlines operating flights from Simpson Bay. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Simpson Bay travel. Please note that the reviews are sourced from user searches and were last updated on July 24, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Read reviews from past customers who have flown American Airlines from Simpson Bay. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,843 reviews

Food

6.4

Crew

7.9

Overall

7.1

Entertainment

6.8

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
6.0
Good

Charleen,May 2026

POS - MIA

If I had any other choice in getting to my destination, I would have used it
American Airlines
7.1
Good
11,843 reviews
American Airlines
7.1
Good
11,843 reviews

Food

6.4

Crew

7.9

Overall

7.1

Entertainment

6.8

Boarding

7.5

Comfort

7.2

Reviews

1 / 20
6.0
Good

Charleen,May 2026

POS - MIA

If I had any other choice in getting to my destination, I would have used it

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Popular international destinations from Simpson Bay

The most popular international flight routes departing from Simpson Bay we’ve come across at this time.
Flights from Simpson Bay to Miami
Flights from Simpson Bay to Fort Lauderdale

Related info for your journey

Access useful and relevant information related to your journey from Simpson Bay. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated July 24, 2026.

  • What are the most popular destinations to fly to from Simpson Bay?

    This month, the top selected destinations from Simpson Bay are Miami, Toronto, Paris. Throughout the year, Miami, Gustavia, Santo Domingo are some of the top choices made by users flying from Simpson Bay.

  • What is the cheapest flight from Simpson Bay to anywhere?

    Users have flown out of Simpson Bay for as low as $129 to Gustavia (prices may vary depending on the airline and departure time). On average, users have booked flights for $525 to fly from Simpson Bay.

  • What are the cheapest airlines flying from Simpson Bay to anywhere?

    Over the past few days, we've found that Frontier, Arajet, and FlexFlight have the cheapest prices from Simpson Bay. Frontier flights from Simpson Bay to Orlando ($122), Arajet flights from Simpson Bay to Bogotá El Dorado ($136), and FlexFlight flights from Simpson Bay to Gustavia St Barthelemy ($137).

  • What is the cheapest premium economy flight from Simpson Bay?

    Options for some of the cheapest premium economy flights from Simpson Bay we have found on Cheapflights are as follows:
    Fly from Simpson Bay Princess Juliana to Bridgetown starting at $632
    Fly from Simpson Bay Princess Juliana to Fort Lauderdale starting at $1,047
    Fly from Simpson Bay Princess Juliana to Paris Orly Airport starting at $1,353
    Fly from Simpson Bay Princess Juliana to Paris Charles de Gaulle Airport starting at $1,810

  • What is the cheapest first class flight from Simpson Bay?

    If you’re looking for a cheap first-class flight from Simpson Bay, consider Gustavia. Prices start at $671 so you can fly first-class even on a budget.

  • What is the cheapest month to fly from Simpson Bay?

    January is currently the cheapest month to fly from Simpson Bay. At this moment in time July is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Simpson Bay?

    Check out the cheapest flights from Simpson Bay to embark to:
    Fly from Simpson Bay to Miami from $329 round trip
    Fly from Simpson Bay to New York from $359 round trip
    Fly from Simpson Bay to Orlando from $396 round trip

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