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Cheap flights from Oakland, California to Simpson Bay from $767

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Oakland, California to Simpson Bay departing on 5/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Oakland, California to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:35 pm - 12:25 pm
OAK
-
SXM
14h 50m
2 stops
Southwest Logo
2:25 pm - 9:35 am
SXM
-
OAK
22h 10m
2 stops
$767Southwest
Fri, May 29 - Sat, Jun 6
Delta Logo
12:35 pm - 1:20 pm
OAK
-
SXM
21h 45m
2 stops
Delta Logo
3:30 pm - 4:24 pm
SXM
-
OAK
27h 54m
2 stops
$1,154Delta
Fri, Apr 10 - Mon, Apr 13
Delta Logo
4:49 pm - 1:20 pm
OAK
-
SXM
17h 31m
2 stops
Delta Logo
3:30 pm - 4:24 pm
SXM
-
OAK
27h 54m
2 stops
$1,332Delta
Fri, Apr 10 - Tue, Apr 14
Delta Logo
5:55 am - 11:29 am
OAK
-
SXM
26h 34m
2 stops
Delta Logo
3:30 pm - 4:24 pm
SXM
-
OAK
27h 54m
2 stops
$1,341Delta
Sat, Apr 11 - Mon, Apr 13
Delta Logo
5:55 am - 1:54 pm
OAK
-
SXM
28h 59m
2 stops
Delta Logo
3:30 pm - 4:24 pm
SXM
-
OAK
27h 54m
2 stops
$1,470Delta
Thu, Apr 9 - Mon, Apr 13
Delta Logo
5:55 am - 11:29 am
OAK
-
SXM
26h 34m
2 stops
Delta Logo
3:30 pm - 11:54 pm
SXM
-
OAK
35h 24m
2 stops
$1,560Delta
Sat, Apr 11 - Tue, Apr 14
Delta Logo
5:55 am - 11:29 am
OAK
-
SXM
26h 34m
2 stops
Delta Logo
3:30 pm - 11:54 pm
SXM
-
OAK
35h 24m
2 stops
$1,573Delta
Thu, Apr 9 - Tue, Apr 14
Delta Logo
4:49 pm - 1:54 pm
OAK
-
SXM
18h 05m
2 stops
Delta Logo
11:55 am - 11:46 pm
SXM
-
OAK
14h 51m
2 stops
$1,768Delta
Thu, Apr 9 - Sun, Apr 12
Multiple Airlines Logo
11:16 pm - 1:50 pm
OAK
-
SXM
35h 34m
3 stops
Multiple Airlines Logo
3:05 pm - 9:44 pm
SXM
-
OAK
33h 39m
2 stops
$2,409Multiple Airlines
Fri, May 29 - Sat, Jun 6
Delta Logo
5:06 pm - 2:27 pm
OAK
-
SXM
18h 21m
2 stops
Delta Logo
3:20 pm - 12:24 pm
SXM
-
OAK
24h 04m
2 stops
$4,566Delta
Fri, May 29 - Sat, Jun 6

Delta flights from Oakland, California to Simpson Bay

Our best Delta deals on Oakland, California to Simpson Bay flight tickets
Delta
Apr 10
OAK12:35 pmOakland
21h 45m
2 stops
SXM1:20 pmSimpson Bay Princess Juliana
Apr 13
SXM3:30 pmSimpson Bay Princess Juliana
27h 54m
2 stops
OAK4:24 pmOakland
$1,154
Delta
Apr 10
OAK4:49 pmOakland
17h 31m
2 stops
SXM1:20 pmSimpson Bay Princess Juliana
Apr 14
SXM3:30 pmSimpson Bay Princess Juliana
27h 54m
2 stops
OAK4:24 pmOakland
$1,332
Delta
Apr 11
OAK5:55 amOakland
26h 34m
2 stops
SXM11:29 amSimpson Bay Princess Juliana
Apr 13
SXM3:30 pmSimpson Bay Princess Juliana
27h 54m
2 stops
OAK4:24 pmOakland
$1,341

momondo Fare Finder

 
Customize your flight search to find flights from Oakland, California 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, momondo users made 832,500 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Oakland, California to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Fri 5/29

6:35 pm-12:25 pm

2 stops14h 50m

Simpson Bay Princess Juliana

Sat 6/6

2:25 pm-9:35 am

2 stops22h 10m

$767

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Fri 4/10

12:35 pm-1:20 pm

2 stops21h 45m

Simpson Bay Princess Juliana

Mon 4/13

3:30 pm-4:24 pm

2 stops27h 54m

$1,154

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Fri 4/10

4:49 pm-1:20 pm

2 stops17h 31m

Simpson Bay Princess Juliana

Tue 4/14

3:30 pm-4:24 pm

2 stops27h 54m

$1,332

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Sat 4/11

5:55 am-11:29 am

2 stops26h 34m

Simpson Bay Princess Juliana

Mon 4/13

3:30 pm-4:24 pm

2 stops27h 54m

$1,341

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Thu 4/9

5:55 am-1:54 pm

2 stops28h 59m

Simpson Bay Princess Juliana

Mon 4/13

3:30 pm-4:24 pm

2 stops27h 54m

$1,470

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Sat 4/11

5:55 am-11:29 am

2 stops26h 34m

Simpson Bay Princess Juliana

Tue 4/14

3:30 pm-11:54 pm

2 stops35h 24m

$1,560

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Thu 4/9

5:55 am-11:29 am

2 stops26h 34m

Simpson Bay Princess Juliana

Tue 4/14

3:30 pm-11:54 pm

2 stops35h 24m

$1,573

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Thu 4/9

4:49 pm-1:54 pm

2 stops18h 05m

Simpson Bay Princess Juliana

Sun 4/12

11:55 am-11:46 pm

2 stops14h 51m

$1,768

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Fri 5/29

11:16 pm-1:50 pm

3 stops35h 34m

Simpson Bay Princess Juliana

Sat 6/6

3:05 pm-9:44 pm

2 stops33h 39m

$2,409

OaklandSimpson Bay

OAK - SXM

OAKSXM

Oakland

Fri 5/29

5:06 pm-2:27 pm

2 stops18h 21m

Simpson Bay Princess Juliana

Sat 6/6

3:20 pm-12:24 pm

2 stops24h 04m

$4,566

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 11 resultsSorted by cheapest first
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See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Oakland, California to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Oakland to Simpson Bay Princess Juliana?

Delta is the most popular carrier operating from Oakland to Simpson Bay Princess Juliana

What airlines fly to Simpson Bay?

American Airlines, JetBlue and United Airlines are the top three most popular airlines that fly to Simpson Bay from Oakland, California according to our data. American Airlines is the first choice among our users, with 58% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 4 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

When to book flights from Oakland, California to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Oakland, California to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Oakland, California to Simpson Bay (OAK to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Simpson Bay

Fastest flight time

14h 50m

Direct flights

None
The fastest flight from Oakland, California to Simpson Bay takes 14h 50m
There are no direct flights from Oakland, California to Simpson Bay. There are no popular flight routes from Oakland, California to Simpson Bay.
Search flight deals

  • How far is Oakland to Simpson Bay Princess Juliana by plane?

    There are 3790.6 mi between Oakland and Simpson Bay Princess Juliana. Typically, this will take 14h 50m by plane in normal conditions.

  • When did momondo last update prices for flights from Oakland Airport to Simpson Bay Princess Juliana Airport?

    Prices for flights from Oakland Airport to Simpson Bay Princess Juliana Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Oakland Airport to Simpson Bay Princess Juliana Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Oakland Airport to Simpson Bay Princess Juliana Airport.

  • What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

    The travel and health documents you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Oakland to Simpson Bay?

It is quick and easy to find Oakland to Simpson Bay flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Simpson Bay that suits you.

Can I find flights from Oakland to Simpson Bay with flexible booking policies on momondo?

momondo does allow users to show only those flights to Simpson Bay from Oakland which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Oakland to Simpson Bay?

Once you have performed a search for Oakland to Simpson Bay flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Oakland to Simpson Bay right now. Can momondo alert me if prices change?

Price alerts on flights to Simpson Bay from Oakland are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Simpson Bay trip

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Delta