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St. Maarten

$531+ Cheap flights from Oshkosh, WI to St. Maarten

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SXM
Jan 18 — Jan 251
Sun 1/18
Sun 1/25
1 adult, Economy
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Cheap flight deals from Oshkosh to St. Maarten

Best flights from Oshkosh to St. Maarten
Discover carefully curated flight deals from Oshkosh to St. Maarten that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 19, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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 1/306:32 pmATW - SXM
1 stop18h 35mAmerican Airlines
Fri 2/64:24 pmSXM - ATW
1 stop8h 57mAmerican Airlines
Deal found 12/16$531
This American Airlines deal was found by Cheapflights users on 12/18. 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.
Sat 1/315:04 pmATW - SXM
2 stops17h 54mAmerican Airlines
Sat 2/75:33 pmSXM - ATW
2 stops19h 22mAmerican Airlines
Deal found 12/18$536
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Sat 5/24:47 pmATW - SXM
2 stops19h 23mAmerican Airlines
Fri 5/85:25 pmSXM - ATW
2 stops18h 19mAmerican Airlines
Deal found 12/16$592

Find flight deals from Oshkosh to St. Maarten

Keep the following information in mind while searching for Oshkosh to St. Maarten flight deals. Data was last updated December 19, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$536
(American Airlines)

Popular in

June

Cheapest in

October

Average price

$804
Provider with most accurate pricing for Appleton Intl-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Appleton Intl-Simpson Bay Princess Juliana flights.
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From Oshkosh to St. Maarten
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Highest demand for flights based on searches. 20% potential increase in price ($209 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($57 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Oshkosh to St. Maarten 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 December 19, 2025.
Use the filters below to find and compare flights from Oshkosh to St. Maarten that are best for you.

Fly from

Oshkosh

Fly to

St. Maarten

Route

Depart

Return

Price

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Fri 1/30

6:32 pm-3:07 pm

1 stop18h 35m

Simpson Bay Princess Juliana

Fri 2/6

4:24 pm-11:21 pm

1 stop8h 57m

$531

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Sat 1/31

5:04 pm-12:58 pm

2 stops17h 54m

Simpson Bay Princess Juliana

Sat 2/7

5:33 pm-10:55 am

2 stops19h 22m

$536

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Sat 5/2

4:47 pm-1:10 pm

2 stops19h 23m

Simpson Bay Princess Juliana

Fri 5/8

5:25 pm-10:44 am

2 stops18h 19m

$592

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Best time to book a flight from Oshkosh to St. Maarten

Have a flexible travel schedule? Discover the best time to fly to St. Maarten from Oshkosh 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 Oshkosh to St. Maarten

What is the cheapest month to book a flight from Oshkosh to St. Maarten?

Currently, March is the cheapest month in which you can book a flight from Oshkosh to St. Maarten (average of $584). Flying from Oshkosh to St. Maarten in November is currently the most expensive (average of $649). 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.

What is the cheapest time of day to fly from OS9 to SX?

Find hourly flight availability from Oshkosh to St. Maarten. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 19, 2025.

When flying from Oshkosh to St. Maarten, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 25% versus a flight in the evening.

Reviews of airlines servicing St. Maarten

Get insights into the airlines that provide service to St. Maarten. 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 St. Maarten. Reviews last updated December 19, 2025.
See what other customers who have flown with Delta and American Airlines from Oshkosh to St. Maarten have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Food

7.3

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,010 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Food

7.3

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,057 reviews
Delta
7.9
Good
8,010 reviews

Boarding

8.1

Food

7.3

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Oshkosh to St. Maarten. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Oshkosh to St. Maarten?

    For as low as $531, American Airlines can have you in St. Maarten from Oshkosh in 18h 35m. There are 2332 mi between Oshkosh and St. Maarten.

  • Can I find deals for flights from Oshkosh to St. Maarten that include hotel bookings?

    Yes. In addition to deals on Oshkosh to St. Maarten flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oshkosh to St. Maarten?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oshkosh to St. Maarten.

  • Can I find deals for business class flights from Oshkosh to St. Maarten?

    Yes. Cheapflights offers flight deals from Oshkosh to St. Maarten 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 Oshkosh to St. Maarten?

    Currently, March is the cheapest month in which you can book a flight from Oshkosh to St. Maarten (average of $584). Flying from Oshkosh to St. Maarten in November is currently the most expensive (average of $649). 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

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Top 2 airlines flying from Oshkosh to St. Maarten

Discover the top 2 airlines that operate flights from Oshkosh to St. Maarten. 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 December 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$584Average$708FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$587Average$793FlexibilityNo cancel feeOn-time71%

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