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$209+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 30 — Dec 71
Sun 11/30
Sun 12/7
1 adult, Economy
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Find 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 October 31, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 11/166:00 amATW - SJU
2 stops9h 52mAmerican Airlines
Thu 11/206:25 amSJU - ATW
2 stops10h 48mAmerican Airlines
Deal found 10/28$380
This Delta deal was found by Cheapflights users on 10/27. 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 11/111:11 amATW - SJU
2 stops11h 45mDelta
Thu 11/67:00 amSJU - ATW
2 stops15h 45mDelta
Deal found 10/27$399
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 11/37:42 pmATW - SJU
2 stops16h 01mAmerican Airlines
Tue 11/115:59 pmSJU - ATW
1 stop7h 26mAmerican Airlines
Deal found 10/30$439
This Delta deal was found by Cheapflights users on 10/29. 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 12/135:31 amATW - NAS
1 stop9h 12mDelta
Sat 12/203:30 pmNAS - ATW
1 stop8h 39mDelta
Deal found 10/29$445
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/135:10 amATW - NAS
2 stops9h 17mAmerican Airlines
Sat 12/206:45 pmNAS - ATW
2 stops15h 36mAmerican Airlines
Deal found 10/29$449
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/18:15 amATW - SJU
2 stops12h 07mUnited Airlines
Wed 11/52:05 amSJU - ATW
2 stops13h 52mUnited Airlines
Deal found 10/28$460
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:53 pmATW - SJU
1 stop20h 39mMultiple Airlines
Sat 12/64:10 amSJU - ATW
1 stop19h 38mMultiple Airlines
Deal found 10/28$471
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/35:20 pmATW - NAS
2 stops19h 13mUnited Airlines
Mon 12/82:55 pmNAS - ATW
2 stops21h 55mUnited Airlines
Deal found 10/28$484
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/34:06 pmATW - NAS
2 stops19h 07mAmerican Airlines
Mon 12/82:55 pmNAS - ATW
1 stop9h 29mAmerican Airlines
Deal found 10/28$489
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/58:15 amATW - SJU
2 stops12h 07mUnited Airlines
Sun 12/78:10 amSJU - ATW
1 stop8h 57mUnited Airlines
Deal found 10/28$493
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Tue 12/26:58 amATW - NAS
1 stop5h 48mAmerican Airlines
Mon 12/82:55 pmNAS - ATW
1 stop9h 29mAmerican Airlines
Deal found 10/28$510
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 12/165:10 amATW - SJU
2 stops10h 42mAmerican Airlines
Thu 1/86:30 amSJU - ATW
2 stops13h 21mAmerican Airlines
Deal found 10/29$545

Cheap flight deals from Oshkosh to Caribbean

Keep the following information in mind while searching for Oshkosh to Caribbean flight deals. Data was last updated October 31, 2025.

Round-trip from

$380
(American Airlines)

One-way from

$209
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$592
From Oshkosh to Caribbean
Search Deals
One-way flight from Oshkosh to Caribbean
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($63 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 October 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 October 31, 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

Sun 11/16

6:00 am-5:52 pm

2 stops9h 52m

San Juan Luis Munoz Marin Intl

Thu 11/20

6:25 am-3:13 pm

2 stops10h 48m

$380

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Sat 12/13

5:31 am-3:43 pm

1 stop9h 12m

Nassau Intl

Sat 12/20

3:30 pm-11:09 pm

1 stop8h 39m

$445

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Thu 1/22

11:25 am-9:57 am

2 stops21h 32m

Nassau Intl

Wed 1/28

2:22 pm-11:21 pm

1 stop9h 59m

$449

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Thu 2/5

6:32 pm-12:12 pm

2 stops16h 40m

Nassau Intl

Mon 2/9

1:12 pm-11:21 pm

1 stop11h 09m

$449

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Sat 12/13

5:10 am-3:27 pm

2 stops9h 17m

Nassau Intl

Sat 12/20

6:45 pm-9:21 am

2 stops15h 36m

$449

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Fri 1/23

6:32 pm-12:34 pm

1 stop17h 02m

Nassau Intl

Mon 1/26

7:40 am-11:21 pm

2 stops16h 41m

$449

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 1/24

3:39 pm-6:11 am

2 stops12h 32m

San Juan Luis Munoz Marin Intl

Sat 1/31

2:05 am-2:09 pm

2 stops14h 04m

$465

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Thu 12/4

1:53 pm-12:32 pm

1 stop20h 39m

San Juan Luis Munoz Marin Intl

Sat 12/6

4:10 am-9:48 pm

1 stop19h 38m

$471

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 1/10

11:21 am-11:49 pm

1 stop10h 28m

San Juan Luis Munoz Marin Intl

Sat 1/17

5:00 pm-10:18 pm

1 stop31h 18m

$480

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Wed 12/3

5:20 pm-1:33 pm

2 stops19h 13m

Nassau Intl

Mon 12/8

2:55 pm-11:50 am

2 stops21h 55m

$484

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 37 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, October is the cheapest month in which you can book a flight from Oshkosh to Caribbean (average of $143). 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 October 31, 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 October 31, 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
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 9h 12m. 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 - Simpson Bay Princess Juliana, 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, October is the cheapest month in which you can book a flight from Oshkosh to Caribbean (average of $143). 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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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 October 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$243FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$658FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$644FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$409FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$269Average$673FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$755FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$651FlexibilityNo cancel feeOn-time83%

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