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$163+ Cheap flights from Oshkosh, WI to Caribbean

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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Oshkosh to Caribbean

Cheapest flights from Oshkosh to Caribbean
Explore the most affordable flight options available from Oshkosh to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:31 amATW - NAS
1 stop5h 23mDelta
Mon 12/221:31 pmNAS - ATW
1 stop8h 32mDelta
Deal found 12/15$423
This Delta deal was found by Cheapflights users on 12/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:05 pmATW - NAS
2 stops20h 38mDelta
Tue 12/234:28 pmNAS - ATW
1 stop6h 13mDelta
Deal found 12/17$510
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/172:32 pmATW - NAS
2 stops22h 01mUnited Airlines
Tue 12/231:05 pmNAS - ATW
2 stops26h 28mUnited Airlines
Deal found 12/17$523
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:20 pmATW - NAS
2 stops19h 13mUnited Airlines
Mon 12/223:35 pmNAS - ATW
1 stop7h 02mUnited Airlines
Deal found 12/15$532
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:00 amATW - SJU
1 stop6h 47mDelta
Sat 12/274:45 pmSJU - ATW
1 stop8h 24mDelta
Deal found 12/16$577
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/319:51 amATW - SJU
1 stop17h 09mAmerican Airlines
Tue 1/68:20 amSJU - ATW
1 stop17h 01mAmerican Airlines
Deal found 12/17$622
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/174:06 pmATW - NAS
2 stops19h 06mAmerican Airlines
Mon 12/226:45 pmNAS - ATW
2 stops15h 36mAmerican Airlines
Deal found 12/15$636
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/179:39 amATW - NAS
1 stop26h 31mAmerican Airlines
Tue 12/232:00 pmNAS - ATW
1 stop20h 21mAmerican Airlines
Deal found 12/17$656
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:10 amATW - SJU
2 stops14h 26mUnited Airlines
Tue 1/67:00 amSJU - ATW
2 stops10h 04mUnited Airlines
Deal found 12/17$679
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 12/205:39 amATW - SJU
2 stops14h 26mAmerican Airlines
Sat 12/277:00 amSJU - ATW
2 stops13h 56mAmerican Airlines
Deal found 12/16$680
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/165:20 pmATW - SJU
2 stops26h 06mUnited Airlines
Wed 1/72:05 amSJU - ATW
2 stops14h 04mUnited Airlines
Deal found 12/16$845
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:23 pmATW - STT
2 stops19h 07mUnited Airlines
Wed 12/313:05 pmSTT - ATW
1 stop8h 32mUnited Airlines
Deal found 12/18$971

Find flight deals from Oshkosh to Caribbean

Keep the following information in mind while searching for Oshkosh to Caribbean flight deals. Data was last updated December 18, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$163
(Delta)

Popular in

March

Cheapest in

November

Average price

$695
From Oshkosh to Caribbean
Search Deals
One-way flight from Oshkosh to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oshkosh to Caribbean 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 18, 2025.
Use the filters below to find and compare flights from Oshkosh to Caribbean that are best for you.

Fly from

Oshkosh

Fly to

Caribbean

Route

Depart

Return

Price

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 2/3

7:15 am-9:39 pm

1 stop12h 24m

San Juan Luis Munoz Marin Intl

Fri 2/13

6:00 am-7:42 pm

1 stop15h 42m

$235

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Thu 5/28

2:43 pm-5:30 am

2 stops13h 47m

San Juan Luis Munoz Marin Intl

Tue 6/2

2:05 am-2:07 pm

2 stops13h 02m

$325

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Wed 4/15

6:35 am-8:38 pm

2 stops13h 03m

San Juan Luis Munoz Marin Intl

Mon 4/20

7:40 am-4:50 pm

1 stop10h 10m

$325

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 4/26

6:17 am-12:10 am

2 stops16h 53m

San Juan Luis Munoz Marin Intl

Wed 4/29

5:40 am-9:34 pm

2 stops16h 54m

$350

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 2/3

6:30 am-10:26 pm

1 stop13h 56m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:00 am-6:01 pm

1 stop14h 01m

$361

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Mon 2/2

12:35 pm-12:36 am

2 stops10h 01m

San Juan Luis Munoz Marin Intl

Thu 2/5

8:35 am-4:48 pm

1 stop10h 13m

$370

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Sun 2/8

5:20 am-5:02 pm

1 stop10h 42m

Nassau Intl

Thu 2/12

1:15 pm-9:50 pm

1 stop9h 35m

$393

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Wed 1/7

5:20 am-1:31 pm

1 stop7h 11m

Nassau Intl

Tue 1/13

2:56 pm-9:47 pm

1 stop7h 51m

$393

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Wed 1/7

5:20 am-11:50 am

1 stop5h 30m

Nassau Intl

Wed 1/14

1:41 pm-8:49 pm

1 stop8h 08m

$393

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Mon 1/26

5:20 am-1:31 pm

1 stop7h 11m

Nassau Intl

Fri 1/30

1:41 pm-8:49 pm

1 stop8h 08m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 35 results
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Best time to book a flight from Oshkosh to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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 Caribbean

What is the cheapest month to book a flight from Oshkosh to Caribbean?

Currently, November is the cheapest month in which you can book a flight from Oshkosh to Caribbean (average of $113). Flying from Oshkosh to Caribbean in June is currently the most expensive (average of $379). 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 CB?

Find hourly flight availability from Oshkosh to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

It’s typically best to fly out from Oshkosh to Caribbean at noon. Doing so could potentially save you 20% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Oshkosh to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Oshkosh to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oshkosh to Caribbean flight should consider departing on Sunday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated December 18, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Oshkosh to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,005 reviews

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

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
8,005 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

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.
United Airlines
7.4
Good
9,091 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

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
11,054 reviews
Delta
7.9
Good
8,005 reviews

Food

7.3

Entertainment

7.9

Comfort

7.9

Crew

8.5

Overall

7.9

Boarding

8.1

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 Caribbean. 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 Caribbean?

    Departing from Oshkosh to Caribbean will take you 10h 42m. Airlines will cover a distance of 1464 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Oshkosh to Caribbean?

    While some choose either Appleton Intl - Saint Thomas Island Cyril E King or Appleton Intl - Christiansted Henry Rohlsen, Appleton Intl - San Juan Luis Munoz Marin Intl is the most popular route from Oshkosh to Caribbean.

  • Can I find deals for flights from Oshkosh to Caribbean that include hotel bookings?

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

  • How can I find direct flights from Oshkosh to Caribbean?

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

  • Can I find deals for business class flights from Oshkosh to Caribbean?

    Yes. Cheapflights offers flight deals from Oshkosh to Caribbean 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 Caribbean?

    Currently, November is the cheapest month in which you can book a flight from Oshkosh to Caribbean (average of $113). Flying from Oshkosh to Caribbean in June is currently the most expensive (average of $379). 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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Alternative routes for Oshkosh to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Oshkosh to Caribbean

Discover the top 7 airlines that operate flights from Oshkosh to Caribbean. 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$256FlexibilityNo cancel feeOn-time62%
DeltaCheapest$191Average$673FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$660FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$226Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$268Average$665FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$754FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$497Average$652FlexibilityNo cancel feeOn-time83%

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