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$264+ Cheap flights from Oshkosh, WI to Caribbean

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Dec 27 — Jan 31
Fri 12/27
Fri 1/3
1 adult, Economy
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Cheap flight deals from Oshkosh to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from Oshkosh (OS9) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$264
(American Airlines)
From Oshkosh to Caribbean
Search Deals

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 December 22, 2024.

This American Airlines deal was found by Cheapflights users on 12/21. 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 12/275:40 amATW - SJU
1 stop15h 30mAmerican Airlines
Thu 1/26:20 amSJU - ATW
2 stops14h 38mAmerican Airlines
Deal found 12/21$865
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/2911:20 amATW - STX
2 stops28h 05mAmerican Airlines
Tue 1/76:20 pmSTX - ATW
2 stops18h 52mAmerican Airlines
Deal found 12/21$1,186
This Delta deal was found by Cheapflights users on 12/21. 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 12/285:30 amATW - STX
1 stop6h 50mDelta
Sat 1/43:21 pmSTX - ATW
1 stop8h 25mDelta
Deal found 12/21$1,480
This United Airlines deal was found by Cheapflights users on 12/21. 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.
Thu 12/268:20 amATW - SJU
2 stops19h 52mUnited Airlines
Fri 1/38:35 amSJU - ATW
1 stop12h 30mUnited Airlines
Deal found 12/21$1,618
This Delta deal was found by Cheapflights users on 12/20. 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 12/276:20 amATW - SJU
2 stops12h 52mDelta
Wed 1/13:13 amSJU - ATW
2 stops11h 12mDelta
Deal found 12/20$1,866

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 December 22, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Thu 1/30

12:30 pm-12:04 am

2 stops9h 34m

San Juan Luis Munoz Marin Intl

Thu 2/6

2:25 pm-11:22 pm

2 stops10h 57m

$264

AppletonChristiansted

ATW - STX

ATWSTX

Appleton Intl

Tue 1/14

5:38 am-5:03 pm

2 stops9h 25m

Christiansted Henry Rohlsen

Tue 1/21

6:20 pm-11:12 am

2 stops18h 52m

$398

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 2/22

11:30 am-11:46 pm

2 stops10h 16m

San Juan Luis Munoz Marin Intl

Wed 2/26

6:15 am-4:35 pm

2 stops12h 20m

$404

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

Tue 2/11

6:10 am-5:41 pm

2 stops9h 31m

Saint Thomas Island Cyril E King

Wed 2/19

4:30 pm-11:16 pm

1 stop8h 46m

$508

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Fri 1/31

6:15 am-12:36 am

2 stops16h 21m

San Juan Luis Munoz Marin Intl

Mon 2/3

2:05 am-11:50 am

2 stops11h 45m

$514

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Thu 6/5

4:18 pm-9:25 am

1 stop16h 07m

Nassau Intl

Mon 6/9

10:50 am-3:43 pm

1 stop5h 53m

$563

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Tue 1/28

12:30 pm-2:00 pm

2 stops23h 30m

Simpson Bay Princess Juliana

Tue 2/4

2:55 pm-11:22 pm

1 stop10h 27m

$567

AppletonCastries

ATW - UVF

ATWUVF

Appleton Intl

Wed 3/12

4:37 pm-2:50 pm

2 stops21h 13m

Castries Hewanorra

Wed 3/19

3:10 pm-11:12 pm

1 stop9h 02m

$599

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Thu 6/5

6:35 am-1:50 pm

2 stops30h 15m

Nassau Intl

Mon 6/9

4:55 pm-7:16 pm

2 stops27h 21m

$608

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 1/5

3:40 pm-5:53 pm

2 stops24h 13m

San Juan Luis Munoz Marin Intl

Thu 1/9

10:09 pm-10:40 pm

3 stops26h 31m

$648

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/20

Showing 1-10 of 19 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.

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 $380). 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 December 22, 2024.

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 December 22, 2024.
Delta
8.0
Very good
8,597 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

8.0

Food

7.3

Overall

8.0

Reviews

1 / 10

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

Delta
8.0
Very good
8,597 reviews
Delta
8.0
Very good
8,597 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

8.0

Food

7.3

Overall

8.0

Reviews

1 / 10

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

United Airlines
7.4
Good
9,035 reviews
Delta
8.0
Very good
8,597 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

8.0

Food

7.3

Overall

8.0

Reviews

1 / 10

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
8,597 reviews

Boarding

8.2

Crew

8.6

Entertainment

7.9

Comfort

8.0

Food

7.3

Overall

8.0

Reviews

1 / 10

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 American Airlines ($277), Delta ($397), and United Airlines ($502).

  • 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 March is currently the most expensive (average of $380). 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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$146Average$352FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$168Average$409FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$258Average$653FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$274Average$651FlexibilityNo cancel feeOn-time69%
DeltaCheapest$284Average$664FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$360Average$573FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$379Average$725FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$498Average$670FlexibilityNo cancel feeOn-time83%
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