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$151+ 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 6/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$329
(Mytrip)

One-way from

$151
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$564
From Oshkosh to Caribbean
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One-way flight from Oshkosh to Caribbean
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($1 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/19. 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 10/64:05 pmSJU - ATW
2 stops19h 42mAmerican Airlines
Deal found 2/19$281
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Sun 3/306:30 amATW - SJU
1 stop9h 04mMultiple Airlines
Thu 4/33:05 amSJU - ATW
2 stops21h 21mMultiple Airlines
Deal found 2/20$329
This United Airlines deal was found by Cheapflights users on 2/19. 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 2/268:15 amATW - SJU
2 stops12h 07mUnited Airlines
Thu 2/278:10 amSJU - ATW
2 stops10h 35mUnited Airlines
Deal found 2/19$364
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Sat 4/267:30 amATW - STT
3 stops25h 10mMultiple Airlines
Sat 5/312:29 pmSTT - ATW
3 stops31h 04mMultiple Airlines
Deal found 2/19$469
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/17:50 amATW - STT
2 stops26h 00mAmerican Airlines
Wed 4/95:50 pmSTT - ATW
2 stops22h 42mAmerican Airlines
Deal found 2/19$509
This Delta deal was found by Cheapflights users on 2/19. 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.
Thu 4/245:20 amATW - STT
1 stop8h 45mDelta
Fri 5/21:50 pmSTT - ATW
1 stop9h 44mDelta
Deal found 2/19$539
This American Airlines deal was found by Cheapflights users on 2/20. 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 4/15:00 amATW - NAS
1 stop5h 59mAmerican Airlines
Mon 4/73:55 pmNAS - ATW
1 stop7h 36mAmerican Airlines
Deal found 2/20$540
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Thu 3/66:30 amATW - NAS
1 stop7h 15mMultiple Airlines
Sun 3/911:30 amNAS - ATW
2 stops27h 03mMultiple Airlines
Deal found 2/20$587
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/15:22 pmATW - SXM
2 stops19h 58mAmerican Airlines
Tue 4/83:18 pmSXM - ATW
2 stops25h 14mAmerican Airlines
Deal found 2/19$592
This Delta deal was found by Cheapflights users on 2/20. 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 2/20$605
This American Airlines deal was found by Cheapflights users on 2/19. 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 9/154:14 pmATW - UVF
2 stops20h 29mAmerican Airlines
Thu 9/253:34 pmUVF - ATW
2 stops23h 48mAmerican Airlines
Deal found 2/19$618
This United Airlines deal was found by Cheapflights users on 2/20. 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 4/183:43 pmATW - NAS
2 stops21h 07mUnited Airlines
Sat 4/262:53 pmNAS - ATW
2 stops22h 10mUnited Airlines
Deal found 2/20$659

Find flights from Oshkosh to Caribbean within your budget

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 February 20, 2025.

Fly from

Oshkosh

Fly to

Caribbean

Route

Depart

Return

Price

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 3/30

6:30 am-4:34 pm

1 stop9h 04m

San Juan Luis Munoz Marin Intl

Thu 4/3

3:05 am-11:26 pm

2 stops21h 21m

$329

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 4/1

7:50 am-8:20 pm

2 stops11h 30m

San Juan Luis Munoz Marin Intl

Mon 4/7

5:30 am-9:43 pm

2 stops17h 13m

$444

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

Sat 4/26

7:30 am-9:40 am

3 stops25h 10m

Saint Thomas Island Cyril E King

Sat 5/3

12:29 pm-6:33 pm

3 stops31h 04m

$469

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

Tue 4/1

7:50 am-10:50 am

2 stops26h 00m

Saint Thomas Island Cyril E King

Wed 4/9

5:50 pm-3:32 pm

2 stops22h 42m

$509

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Thu 5/22

3:43 pm-11:54 pm

1 stop7h 11m

San Juan Luis Munoz Marin Intl

Thu 5/29

7:45 am-4:48 pm

1 stop10h 03m

$537

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

Thu 4/24

5:20 am-3:05 pm

1 stop8h 45m

Saint Thomas Island Cyril E King

Fri 5/2

1:50 pm-10:34 pm

1 stop9h 44m

$539

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Tue 4/1

5:00 am-11:59 am

1 stop5h 59m

Nassau Intl

Mon 4/7

3:55 pm-10:31 pm

1 stop7h 36m

$540

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Thu 3/6

6:30 am-2:45 pm

1 stop7h 15m

Nassau Intl

Sun 3/9

11:30 am-1:33 pm

2 stops27h 03m

$587

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Tue 4/1

5:22 pm-2:20 pm

2 stops19h 58m

Simpson Bay Princess Juliana

Tue 4/8

3:18 pm-3:32 pm

2 stops25h 14m

$592

AppletonCastries

ATW - UVF

ATWUVF

Appleton Intl

Wed 4/9

4:02 pm-2:28 pm

2 stops21h 26m

Castries Hewanorra

Tue 4/15

3:28 pm-9:43 pm

2 stops31h 15m

$657

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 20 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.

Travel insights for flights from Oshkosh to Caribbean

Get recent, data-driven insights about flights from Oshkosh to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 20, 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 February 20, 2025.
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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
8,220 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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
8,766 reviews
Delta
8.0
Very good
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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
8,220 reviews

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

Crew

8.5

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 cheapest airlines to fly from Oshkosh to Caribbean one-way?

    The cheapest airlines for a one-way flight from Oshkosh to Caribbean are United Airlines ($151), American Airlines ($209), and Delta ($343).

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

    While some choose either Appleton Intl - Nassau Intl or Appleton Intl - Saint Thomas Island Cyril E King, 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 March is currently the most expensive (average of $363). 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 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$258FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$157Average$420FlexibilityNo cancel feeOn-time65%
DeltaCheapest$264Average$656FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$264Average$665FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$268Average$675FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$379Average$767FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$397Average$463FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$495Average$648FlexibilityNo cancel feeOn-time83%
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