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$108+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$220
(American Airlines)

One-way from

$108
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$775
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 ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/31. 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.
jue. 10/26:19 pmATW - SJU
2 stops19h 34mAmerican Airlines
lun. 10/61:35 pmSJU - ATW
2 stops20h 48mAmerican Airlines
Deal found 7/31$220
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 11/96:30 amATW - SJU
1 stop7h 10mUnited Airlines
vie. 11/148:10 amSJU - ATW
1 stop7h 47mUnited Airlines
Deal found 7/29$415
This Delta deal was found by Cheapflights users on 7/31. 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.
mié. 12/105:29 amATW - NAS
1 stop8h 56mDelta
mié. 12/174:50 pmNAS - ATW
1 stop6h 09mDelta
Deal found 7/31$515
This Delta deal was found by Cheapflights users on 7/31. 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.
sáb. 9/65:34 amATW - SJU
1 stop6h 56mDelta
sáb. 9/137:00 amSJU - ATW
2 stops16h 17mDelta
Deal found 7/31$562
This American Airlines deal was found by Cheapflights users on 7/31. 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.
vie. 8/153:25 pmATW - STX
2 stops20h 33mAmerican Airlines
mar. 8/191:38 pmSTX - ATW
2 stops20h 28mAmerican Airlines
Deal found 7/31$574
This American Airlines deal was found by Cheapflights users on 7/31. 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.
vie. 9/266:18 pmATW - NAS
2 stops18h 11mAmerican Airlines
dom. 9/282:09 pmNAS - ATW
2 stops19h 57mAmerican Airlines
Deal found 7/31$574
This American Airlines deal was found by Cheapflights users on 7/30. 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.
dom. 9/286:19 pmATW - STT
2 stops20h 41mAmerican Airlines
vie. 10/35:10 pmSTT - ATW
2 stops25h 38mAmerican Airlines
Deal found 7/30$579
This Delta deal was found by Cheapflights users on 7/31. 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.
dom. 9/75:34 amATW - SXM
1 stop7h 22mDelta
dom. 9/143:20 pmSXM - ATW
1 stop8h 20mDelta
Deal found 7/31$612
This American Airlines deal was found by Cheapflights users on 7/31. 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.
dom. 9/76:19 pmATW - SXM
2 stops18h 00mAmerican Airlines
dom. 9/142:20 pmSXM - ATW
2 stops19h 46mAmerican Airlines
Deal found 7/31$661
This American Airlines deal was found by Cheapflights users on 7/30. 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.
lun. 12/86:20 amATW - UVF
2 stops28h 40mAmerican Airlines
vie. 12/125:05 pmUVF - ATW
2 stops29h 54mAmerican Airlines
Deal found 7/30$706
This Delta deal was found by Cheapflights users on 7/31. 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.
dom. 9/285:35 amATW - STT
1 stop6h 58mDelta
vie. 10/32:43 pmSTT - ATW
1 stop8h 57mDelta
Deal found 7/31$798
This American Airlines deal was found by Cheapflights users on 7/28. 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.
lun. 8/186:35 pmATW - EIS
2 stops17h 41mAmerican Airlines
jue. 8/211:56 pmEIS - ATW
2 stops32h 27mAmerican Airlines
Deal found 7/28$1,145

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 julio 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

jue. 10/2

6:19 pm-2:53 pm

2 stops19h 34m

San Juan Luis Munoz Marin Intl

lun. 10/6

1:35 pm-9:23 am

2 stops20h 48m

$220

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

sáb. 11/15

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

dom. 11/23

8:10 am-1:57 pm

1 stop7h 47m

$455

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

mié. 12/10

5:29 am-3:25 pm

1 stop8h 56m

Nassau Intl

mié. 12/17

4:50 pm-9:59 pm

1 stop6h 09m

$515

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

jue. 1/8

6:55 am-11:15 am

1 stop27h 20m

Nassau Intl

mar. 1/13

12:55 pm-9:50 pm

1 stop9h 55m

$552

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

sáb. 9/6

5:34 am-1:30 pm

1 stop6h 56m

San Juan Luis Munoz Marin Intl

sáb. 9/13

7:00 am-10:17 pm

2 stops16h 17m

$562

AppletonChristiansted

ATW - STX

ATWSTX

Appleton Intl

vie. 8/15

3:25 pm-12:58 pm

2 stops20h 33m

Christiansted Henry Rohlsen

mar. 8/19

1:38 pm-9:06 am

2 stops20h 28m

$574

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

dom. 9/28

6:19 pm-4:00 pm

2 stops20h 41m

Saint Thomas Island Cyril E King

vie. 10/3

5:10 pm-5:48 pm

2 stops25h 38m

$579

AppletonCastries

ATW - UVF

ATWUVF

Appleton Intl

sáb. 1/24

6:55 am-2:30 pm

2 stops29h 35m

Castries Hewanorra

mar. 2/3

4:50 pm-10:42 am

2 stops19h 52m

$596

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

dom. 9/7

5:34 am-1:56 pm

1 stop7h 22m

Simpson Bay Princess Juliana

dom. 9/14

3:20 pm-10:40 pm

1 stop8h 20m

$612

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

dom. 9/7

6:19 pm-1:19 pm

2 stops18h 00m

Simpson Bay Princess Juliana

dom. 9/14

2:20 pm-9:06 am

2 stops19h 46m

$661

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Showing 1-10 of 19 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 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 julio 31, 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 julio 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
8.0
Very good
7,981 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
7,981 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

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.

  • 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 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$230FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$394FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$663FlexibilityNo cancel feeOn-time69%
DeltaCheapest$225Average$663FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$269Average$682FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$325Average$744FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$519Average$649FlexibilityNo cancel feeOn-time83%

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