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$153+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 30 — May 71
Wed 4/30
Wed 5/7
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 April 25, 2025.

Round-trip from

$298
(American Airlines)

One-way from

$153
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$668
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. 3% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 25, 2025.

This American Airlines deal was found by Cheapflights users on 4/24. 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.
Thu 10/24:14 pmATW - SJU
2 stops21h 33mAmerican Airlines
Mon 10/65:27 pmSJU - ATW
2 stops16h 48mAmerican Airlines
Deal found 4/24$298
This United Airlines deal was found by Cheapflights users on 4/25. 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 10/36:41 amATW - SJU
1 stop7h 03mUnited Airlines
Mon 10/61:05 amSJU - ATW
2 stops14h 01mUnited Airlines
Deal found 4/25$458
This American Airlines deal was found by Cheapflights users on 4/25. 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 5/115:00 amATW - NAS
1 stop7h 45mAmerican Airlines
Fri 5/162:45 pmNAS - ATW
1 stop8h 47mAmerican Airlines
Deal found 4/25$514
This Delta deal was found by Cheapflights users on 4/25. 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 8/155:29 amATW - NAS
1 stop7h 12mDelta
Wed 8/273:06 pmNAS - ATW
1 stop7h 53mDelta
Deal found 4/25$540
This Delta deal was found by Cheapflights users on 4/25. 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 9/197:00 amATW - SJU
2 stops14h 08mDelta
Mon 9/292:15 pmSJU - ATW
1 stop7h 27mDelta
Deal found 4/25$565
This United Airlines deal was found by Cheapflights users on 4/24. 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 8/153:45 pmATW - NAS
2 stops21h 05mUnited Airlines
Wed 8/272:33 pmNAS - ATW
2 stops24h 33mUnited Airlines
Deal found 4/24$592
This American Airlines deal was found by Cheapflights users on 4/25. 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 12/64:47 pmATW - STT
2 stops17h 23mAmerican Airlines
Sat 12/133:20 pmSTT - ATW
1 stop8h 12mAmerican Airlines
Deal found 4/25$651
This American Airlines deal was found by Cheapflights users on 4/25. 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 7/226:11 pmATW - UVF
2 stops18h 43mAmerican Airlines
Tue 7/293:00 pmUVF - ATW
2 stops31h 39mAmerican Airlines
Deal found 4/25$681
This United Airlines deal was found by Cheapflights users on 4/24. 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 5/2312:55 pmATW - STT
1 stop24h 59mUnited Airlines
Tue 5/271:19 pmSTT - ATW
2 stops23h 51mUnited Airlines
Deal found 4/24$1,121
This Delta deal was found by Cheapflights users on 4/25. 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 12/125:29 amATW - STT
1 stop6h 53mDelta
Fri 12/193:32 pmSTT - ATW
1 stop8h 27mDelta
Deal found 4/25$1,182
This Delta deal was found by Cheapflights users on 4/24. 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.
Mon 12/295:30 amATW - UVF
1 stop7h 37mDelta
Sat 1/33:03 pmUVF - ATW
1 stop9h 00mDelta
Deal found 4/24$1,897

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 April 25, 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

Thu 10/2

4:14 pm-2:47 pm

2 stops21h 33m

San Juan Luis Munoz Marin Intl

Mon 10/6

5:27 pm-9:15 am

2 stops16h 48m

$298

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Fri 10/3

6:41 am-2:44 pm

1 stop7h 03m

San Juan Luis Munoz Marin Intl

Mon 10/6

1:05 am-2:06 pm

2 stops14h 01m

$458

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Sun 5/11

6:19 am-3:00 pm

1 stop7h 41m

Nassau Intl

Fri 5/16

2:45 pm-10:32 pm

1 stop8h 47m

$514

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Fri 8/15

5:29 am-1:41 pm

1 stop7h 12m

Nassau Intl

Wed 8/27

3:06 pm-9:59 pm

1 stop7h 53m

$540

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Fri 9/19

7:00 am-10:08 pm

2 stops14h 08m

San Juan Luis Munoz Marin Intl

Mon 9/29

2:15 pm-8:42 pm

1 stop7h 27m

$565

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Fri 8/15

3:45 pm-1:50 pm

2 stops21h 05m

Nassau Intl

Wed 8/27

2:33 pm-2:06 pm

2 stops24h 33m

$592

AppletonCastries

ATW - UVF

ATWUVF

Appleton Intl

Tue 7/22

6:11 pm-1:54 pm

2 stops18h 43m

Castries Hewanorra

Tue 7/29

3:00 pm-9:39 pm

2 stops31h 39m

$681

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

Fri 5/23

5:40 am-4:20 pm

2 stops9h 40m

Saint Thomas Island Cyril E King

Tue 5/27

3:40 pm-10:56 am

2 stops20h 16m

$1,022

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

Fri 5/23

12:55 pm-2:54 pm

1 stop24h 59m

Saint Thomas Island Cyril E King

Tue 5/27

1:19 pm-12:10 pm

2 stops23h 51m

$1,121

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

Fri 5/23

5:35 am-3:10 pm

1 stop8h 35m

Saint Thomas Island Cyril E King

Tue 5/27

1:17 pm-10:26 pm

1 stop10h 09m

$1,344

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 13 results
1
2

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 December is currently the most expensive (average of $336). 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 April 25, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 25, 2025.
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,920 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,685 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,920 reviews

Comfort

7.9

Boarding

8.2

Crew

8.5

Overall

8.0

Entertainment

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    While some choose either Appleton Intl - San Juan Luis Munoz Marin Intl or Appleton Intl - Saint Thomas Island Cyril E King, Appleton Intl - Nassau 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 December is currently the most expensive (average of $336). 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

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Top 8 airlines flying from Oshkosh to Caribbean

Discover the top 8 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 April 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$245FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$195Average$451FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$248Average$463FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$258Average$664FlexibilityNo cancel feeOn-time69%
DeltaCheapest$264Average$628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$266Average$665FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$375Average$765FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$495Average$646FlexibilityNo cancel feeOn-time83%

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