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$169+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$169
(Delta)

Popular in

March

Cheapest in

October

Average price

$630
From Oshkosh to Caribbean
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One-way flight from Oshkosh to Caribbean
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Highest demand for flights based on searches. 7% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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.
Mon 11/37:42 pmATW - SJU
2 stops18h 05mAmerican Airlines
Tue 11/116:00 amSJU - ATW
2 stops19h 25mAmerican Airlines
Deal found 9/15$298
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sun 11/167:42 pmATW - SJU
2 stops15h 56mAmerican Airlines
Thu 11/204:44 pmSJU - ATW
1 stop8h 04mAmerican Airlines
Deal found 9/15$350
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 11/77:42 pmATW - SJU
1 stop17h 11mAmerican Airlines
Tue 11/116:00 amSJU - ATW
2 stops19h 25mAmerican Airlines
Deal found 9/15$357
This Delta deal was found by Cheapflights users on 9/15. 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.
Fri 10/35:35 amATW - SJU
1 stop9h 56mDelta
Tue 10/77:00 amSJU - ATW
2 stops14h 45mDelta
Deal found 9/15$362
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/36:18 pmATW - SJU
2 stops19h 35mAmerican Airlines
Tue 10/75:30 amSJU - ATW
2 stops19h 13mAmerican Airlines
Deal found 9/15$365
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/39:39 amATW - SJU
2 stops10h 30mAmerican Airlines
Thu 12/117:00 amSJU - ATW
2 stops14h 13mAmerican Airlines
Deal found 9/14$390
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Sun 9/286:30 amATW - SJU
1 stop7h 14mUnited Airlines
Wed 10/11:05 amSJU - ATW
2 stops11h 56mUnited Airlines
Deal found 9/13$399
This United Airlines deal was found by Cheapflights users on 9/14. 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 12/313:24 pmATW - SJU
2 stops12h 47mUnited Airlines
Tue 1/138:10 amSJU - ATW
2 stops10h 38mUnited Airlines
Deal found 9/14$409
This Mytrip deal was found by Cheapflights users on 9/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/175:03 pmATW - SJU
2 stops14h 49mMultiple Airlines
Wed 11/192:59 amSJU - ATW
2 stops20h 32mMultiple Airlines
Deal found 9/15$414
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/77:42 pmATW - STX
2 stops17h 30mAmerican Airlines
Tue 11/116:42 pmSTX - ATW
2 stops16h 34mAmerican Airlines
Deal found 9/14$429
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/166:58 amATW - NAS
1 stop6h 01mAmerican Airlines
Wed 11/193:02 pmNAS - ATW
1 stop9h 23mAmerican Airlines
Deal found 9/14$465
This Mytrip deal was found by Cheapflights users on 9/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/175:03 pmATW - NAS
2 stops20h 42mMultiple Airlines
Sun 11/2311:30 amNAS - ATW
1 stop11h 01mMultiple Airlines
Deal found 9/12$479

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 September 15, 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

Wed 1/28

6:07 am-11:40 pm

2 stops15h 33m

San Juan Luis Munoz Marin Intl

Wed 2/4

2:25 pm-9:50 pm

1 stop9h 25m

$235

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 2/1

2:45 pm-6:11 am

2 stops13h 26m

San Juan Luis Munoz Marin Intl

Fri 2/6

8:10 am-4:48 pm

2 stops10h 38m

$262

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 1/24

5:23 pm-6:11 am

2 stops10h 48m

San Juan Luis Munoz Marin Intl

Fri 1/30

8:10 am-4:48 pm

2 stops10h 38m

$272

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Fri 11/7

7:42 pm-2:53 pm

1 stop17h 11m

San Juan Luis Munoz Marin Intl

Tue 11/11

6:00 am-11:25 pm

2 stops19h 25m

$357

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Fri 10/3

5:35 am-4:31 pm

1 stop9h 56m

San Juan Luis Munoz Marin Intl

Tue 10/7

7:00 am-8:45 pm

2 stops14h 45m

$362

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 11/16

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Wed 11/19

2:05 am-1:57 pm

2 stops13h 52m

$362

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 2/3

12:35 pm-12:36 am

2 stops10h 01m

San Juan Luis Munoz Marin Intl

Fri 2/13

8:35 am-4:50 pm

1 stop10h 15m

$370

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 9/28

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Wed 10/1

1:05 am-12:01 pm

2 stops11h 56m

$399

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Sun 11/16

6:53 am-1:59 pm

1 stop6h 06m

Nassau Intl

Wed 11/19

3:02 pm-11:25 pm

1 stop9h 23m

$465

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Sat 10/11

6:13 pm-1:25 pm

2 stops18h 12m

Nassau Intl

Sat 10/18

2:27 pm-9:23 am

2 stops19h 56m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, September is the cheapest month in which you can book a flight from Oshkosh to Caribbean (average of $254). Flying from Oshkosh to Caribbean in June is currently the most expensive (average of $339). 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 September 15, 2025.

When flying from Oshkosh to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 15, 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
8.0
Very good
7,954 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,929 reviews
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 8h 25m. Airlines will cover a distance of 2248 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, September is the cheapest month in which you can book a flight from Oshkosh to Caribbean (average of $254). Flying from Oshkosh to Caribbean in June is currently the most expensive (average of $339). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$230FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$391FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$660FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$673FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$274Average$675FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$750FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$540Average$652FlexibilityNo cancel feeOn-time83%

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