HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$160+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oshkosh to Caribbean with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 enero 21, 2025.

Round-trip from

$342
(American Airlines)

One-way from

$160
(Kiwi.com)
From Oshkosh to Caribbean
Search Deals
One-way flight 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 enero 21, 2025.

This American Airlines deal was found by Cheapflights users on 1/21. 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.
mié. 5/75:00 amATW - SJU
1 stop7h 45mAmerican Airlines
mié. 5/146:30 amSJU - ATW
2 stops16h 01mAmerican Airlines
Deal found 1/21$342
This Delta deal was found by Cheapflights users on 1/20. 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.
mar. 3/47:05 amATW - SJU
2 stops14h 41mDelta
mié. 3/127:45 amSJU - ATW
2 stops14h 00mDelta
Deal found 1/20$397
This United Airlines deal was found by Cheapflights users on 1/20. 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.
sáb. 4/512:50 pmATW - SJU
1 stop10h 04mUnited Airlines
mar. 4/81:05 amSJU - ATW
2 stops11h 59mUnited Airlines
Deal found 1/20$457
This American Airlines deal was found by Cheapflights users on 1/20. 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.
sáb. 9/64:14 pmATW - STT
2 stops23h 16mAmerican Airlines
jue. 9/115:20 pmSTT - ATW
2 stops22h 02mAmerican Airlines
Deal found 1/20$509
This American Airlines deal was found by Cheapflights users on 1/21. 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.
lun. 4/285:00 amATW - NAS
1 stop7h 40mAmerican Airlines
sáb. 5/34:00 pmNAS - ATW
1 stop7h 32mAmerican Airlines
Deal found 1/21$540
This American Airlines deal was found by Cheapflights users on 1/21. 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.
mar. 2/45:38 amATW - STX
2 stops9h 25mAmerican Airlines
lun. 2/106:20 pmSTX - ATW
2 stops18h 52mAmerican Airlines
Deal found 1/21$584
This American Airlines deal was found by Cheapflights users on 1/21. 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.
dom. 4/64:36 pmATW - SXM
2 stops19h 38mAmerican Airlines
vie. 4/111:50 pmSXM - ATW
2 stops22h 00mAmerican Airlines
Deal found 1/21$590
This American Airlines deal was found by Cheapflights users on 1/21. 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.
mié. 12/106:07 amATW - UVF
2 stops30h 13mAmerican Airlines
mié. 12/175:05 pmUVF - ATW
1 stop30h 40mAmerican Airlines
Deal found 1/21$610
This United Airlines deal was found by Cheapflights users on 1/21. 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.
mié. 3/512:50 pmATW - NAS
2 stops23h 43mUnited Airlines
dom. 3/93:57 pmNAS - ATW
1 stop6h 22mUnited Airlines
Deal found 1/21$634
This Mytrip deal was found by Cheapflights users on 1/20. 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.
dom. 4/67:15 amATW - STT
2 stops25h 51mMultiple Airlines
jue. 4/102:38 pmSTT - ATW
3 stops30h 03mMultiple Airlines
Deal found 1/20$635
This Delta deal was found by Cheapflights users on 1/21. 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.
dom. 2/97:05 amATW - NAS
2 stops7h 56mDelta
jue. 2/135:26 pmNAS - ATW
1 stop6h 11mDelta
Deal found 1/21$639
This American Airlines deal was found by Cheapflights users on 1/19. 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.
mar. 4/15:39 amATW - KIN
2 stops13h 56mAmerican Airlines
mié. 4/912:45 pmKIN - ATW
2 stops22h 05mAmerican Airlines
Deal found 1/19$646

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 enero 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

mié. 5/7

5:00 am-1:45 pm

1 stop7h 45m

San Juan Luis Munoz Marin Intl

mié. 5/14

6:30 am-9:31 pm

2 stops16h 01m

$342

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

mar. 3/4

7:05 am-11:46 pm

2 stops14h 41m

San Juan Luis Munoz Marin Intl

mié. 3/12

7:45 am-8:45 pm

2 stops14h 00m

$397

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

sáb. 4/5

12:50 pm-11:54 pm

1 stop10h 04m

San Juan Luis Munoz Marin Intl

mar. 4/8

1:05 am-12:04 pm

2 stops11h 59m

$457

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

lun. 4/28

5:00 am-1:40 pm

1 stop7h 40m

Nassau Intl

sáb. 5/3

4:00 pm-10:32 pm

1 stop7h 32m

$540

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

mar. 2/18

1:02 pm-11:44 am

2 stops20h 42m

Saint Thomas Island Cyril E King

mar. 2/25

6:35 pm-12:37 pm

2 stops20h 02m

$544

AppletonChristiansted

ATW - STX

ATWSTX

Appleton Intl

mar. 2/4

5:38 am-5:03 pm

2 stops9h 25m

Christiansted Henry Rohlsen

lun. 2/10

6:20 pm-11:12 am

2 stops18h 52m

$584

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

dom. 4/6

4:36 pm-1:14 pm

2 stops19h 38m

Simpson Bay Princess Juliana

vie. 4/11

1:50 pm-10:50 am

2 stops22h 00m

$590

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

mié. 3/5

12:50 pm-1:33 pm

2 stops23h 43m

Nassau Intl

dom. 3/9

3:57 pm-9:19 pm

1 stop6h 22m

$634

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

dom. 4/6

7:15 am-10:06 am

2 stops25h 51m

Saint Thomas Island Cyril E King

jue. 4/10

2:38 pm-7:41 pm

3 stops30h 03m

$635

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

dom. 2/9

7:05 am-4:01 pm

2 stops7h 56m

Nassau Intl

jue. 2/13

5:26 pm-10:37 pm

1 stop6h 11m

$639

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/19

Showing 1-10 of 26 results
1
2
3

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 $378). 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 enero 21, 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 enero 21, 2025.
Delta
8.0
Very good
8,521 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Comfort

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
8,521 reviews
Delta
8.0
Very good
8,521 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Comfort

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
8,984 reviews
Delta
8.0
Very good
8,521 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Comfort

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
8,521 reviews

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.6

Boarding

8.2

Comfort

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 most popular routes from Oshkosh to Caribbean?

    While some choose either Appleton Intl - Saint Thomas Island Cyril E King or Appleton Intl - Nassau Intl, 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 $378). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oshkosh to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Cancún flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Orlando flights
O'Hare Intl to Sky Harbor Intl flights
Minneapolis to Sky Harbor Intl flights
Minneapolis to Las Vegas flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Dallas/Fort Worth flights
Minneapolis to Orlando flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Tampa flights
Minneapolis to Cancún flights
O'Hare Intl to Denver flights
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Seattle flights
Minneapolis to Fort Lauderdale flights
O'Hare Intl to LaGuardia flights
Minneapolis to Miami flights
O'Hare Intl to Boston flights
Minneapolis to Tampa flights
Minneapolis to Seattle flights
Minneapolis to Fort Myers flights
O'Hare Intl to Narita flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Newark flights
O'Hare Intl to Charles de Gaulle flights
Minneapolis to Dallas/Fort Worth flights
O'Hare Intl to Heathrow flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Haneda flights
O'Hare Intl to Cozumel flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Atlanta flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Austin flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Athens flights
O'Hare Intl to San Diego flights
Minneapolis to Denver flights
Milwaukee to Orlando flights
Minneapolis to Los Angeles flights
O'Hare Intl to Nashville flights
Minneapolis to LaGuardia flights
Minneapolis to San Diego flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Punta Cana flights

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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$364FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$168Average$410FlexibilityNo cancel feeOn-time65%
DeltaCheapest$264Average$652FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$264Average$655FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$274Average$645FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$360Average$558FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$379Average$738FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$498Average$670FlexibilityNo cancel feeOn-time83%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.