HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$227+ 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 7 — Apr 141
Mon 4/7
Mon 4/14
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

Keep the following information in mind while searching for Oshkosh to Caribbean flight deals. Data was last updated April 2, 2025.

Round-trip from

$285
(American Airlines)

One-way from

$227
(Delta)

Popular in

December

Cheapest in

September

Average price

$635
From Oshkosh to Caribbean
Search Deals
One-way flight from Oshkosh to Caribbean
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($5 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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 April 2, 2025.

This American Airlines deal was found by Cheapflights users on 4/1. 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 10/49:49 amATW - SJU
2 stops27h 56mAmerican Airlines
Tue 10/144:05 pmSJU - ATW
2 stops19h 42mAmerican Airlines
Deal found 4/1$255
This Delta deal was found by Cheapflights users on 4/1. 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 10/45:29 amATW - SJU
1 stop9h 39mDelta
Tue 10/147:00 amSJU - ATW
2 stops14h 42mDelta
Deal found 4/1$390
This United deal was found by Cheapflights users on 4/1. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/112:50 pmATW - SJU
1 stop10h 04mUnited Airlines
Fri 4/41:05 amSJU - ATW
2 stops15h 03mUnited Airlines
Deal found 4/1$459
This American Airlines deal was found by Cheapflights users on 4/1. 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 5/274:37 pmATW - NAS
2 stops16h 03mAmerican Airlines
Wed 6/412:10 pmNAS - ATW
2 stops12h 24mAmerican Airlines
Deal found 4/1$486
This Delta deal was found by Cheapflights users on 3/31. 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.
Sun 5/115:35 amATW - NAS
1 stop9h 29mDelta
Fri 5/161:13 pmNAS - ATW
1 stop10h 13mDelta
Deal found 3/31$507
This American Airlines deal was found by Cheapflights users on 4/1. 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 6/203:40 pmATW - STT
2 stops19h 10mAmerican Airlines
Thu 6/265:00 pmSTT - ATW
2 stops23h 06mAmerican Airlines
Deal found 4/1$509
This United deal was found by Cheapflights users on 3/31. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/113:44 pmATW - NAS
2 stops21h 06mUnited Airlines
Fri 5/162:53 pmNAS - ATW
2 stops22h 11mUnited Airlines
Deal found 3/31$543
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Fri 5/95:00 amATW - SXM
1 stop7h 15mAmerican Airlines
Fri 5/162:05 pmSXM - ATW
1 stop9h 27mAmerican Airlines
Deal found 3/31$567
This Mytrip deal was found by Cheapflights users on 4/1. 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.
Fri 5/94:26 pmATW - KIN
2 stops20h 03mMultiple Airlines
Fri 5/161:34 pmKIN - ATW
2 stops32h 53mMultiple Airlines
Deal found 4/1$583
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Tue 4/85:00 amATW - STX
2 stops9h 31mAmerican Airlines
Sat 4/194:55 pmSTX - ATW
2 stops18h 59mAmerican Airlines
Deal found 3/31$594
This Mytrip deal was found by Cheapflights users on 3/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/94:26 pmATW - SXM
2 stops20h 34mMultiple Airlines
Fri 5/163:05 pmSXM - ATW
3 stops32h 22mMultiple Airlines
Deal found 3/31$641
This Delta deal was found by Cheapflights users on 4/1. 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.
Tue 5/205:35 amATW - STT
1 stop7h 06mDelta
Wed 5/282:51 pmSTT - ATW
1 stop8h 35mDelta
Deal found 4/1$653

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 2, 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

Tue 4/22

11:24 am-5:00 am

2 stops16h 36m

San Juan Luis Munoz Marin Intl

Wed 4/30

6:21 am-11:24 pm

2 stops18h 03m

$285

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 4/20

3:15 pm-10:32 am

3 stops42h 17m

San Juan Luis Munoz Marin Intl

Fri 4/25

10:27 am-6:50 pm

3 stops33h 23m

$480

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Tue 5/27

4:37 pm-9:40 am

2 stops16h 03m

Nassau Intl

Wed 6/4

12:10 pm-11:34 pm

2 stops12h 24m

$486

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Sun 5/11

5:35 am-4:04 pm

1 stop9h 29m

Nassau Intl

Fri 5/16

1:13 pm-10:26 pm

1 stop10h 13m

$507

AppletonSaint Thomas Island

ATW - STT

ATWSTT

Appleton Intl

Fri 6/20

3:40 pm-11:50 am

2 stops19h 10m

Saint Thomas Island Cyril E King

Thu 6/26

5:00 pm-3:06 pm

2 stops23h 06m

$509

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 4/22

3:43 pm-11:54 pm

1 stop7h 11m

San Juan Luis Munoz Marin Intl

Tue 4/29

1:05 am-12:04 pm

2 stops11h 59m

$510

AppletonNassau

ATW - NAS

ATWNAS

Appleton Intl

Sun 5/11

3:44 pm-1:50 pm

2 stops21h 06m

Nassau Intl

Fri 5/16

2:53 pm-12:04 pm

2 stops22h 11m

$543

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Mon 9/1

5:29 am-4:50 pm

1 stop10h 21m

San Juan Luis Munoz Marin Intl

Mon 9/8

7:00 am-8:42 pm

2 stops14h 42m

$555

AppletonSimpson Bay

ATW - SXM

ATWSXM

Appleton Intl

Fri 5/9

5:00 am-1:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Fri 5/16

2:05 pm-10:32 pm

1 stop9h 27m

$567

AppletonKingston

ATW - KIN

ATWKIN

Appleton Intl

Fri 5/9

4:26 pm-12:29 pm

2 stops20h 03m

Kingston Norman Manley

Fri 5/16

1:34 pm-10:27 pm

2 stops32h 53m

$583

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 17 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 2, 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 2, 2025.
Delta
8.0
Very good
7,899 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

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
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

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
8,615 reviews
Delta
8.0
Very good
7,899 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

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
7,899 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Food

7.3

Comfort

8.0

Overall

8.0

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 - 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 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

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 John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Mexico City flights
O'Hare Intl to Seattle flights
O'Hare Intl to Miami flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Heathrow flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Newark flights
O'Hare Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Orlando flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Charles de Gaulle flights
Minneapolis to Seattle flights
O'Hare Intl to Denver flights
Minneapolis to Las Vegas flights
O'Hare Intl to Athens flights
O'Hare Intl to Dulles Intl flights
Minneapolis to Dallas/Fort Worth flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Boston flights
O'Hare Intl to Honolulu flights
Minneapolis to LaGuardia flights
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Narita flights
O'Hare Intl to Haneda flights
O'Hare Intl to San Diego flights
Minneapolis to Sky Harbor Intl flights
Minneapolis to Denver flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to Dublin flights
Minneapolis to Orlando flights
O'Hare Intl to Hobby flights
O'Hare Intl to New Orleans flights
Minneapolis to Newark flights
O'Hare Intl to Austin flights
O'Hare Intl to Tampa flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Santa Ana flights
Minneapolis to John F Kennedy Intl flights
O'Hare Intl to Nashville flights
O'Hare Intl to Atlanta flights
Milwaukee to John F Kennedy Intl flights
O'Hare Intl to Vancouver Intl flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Charleston flights
O'Hare Intl to San Antonio 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$245FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$203Average$456FlexibilityNo cancel feeOn-time65%
DeltaCheapest$264Average$629FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$264Average$664FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$265Average$662FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$375Average$765FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$384Average$445FlexibilityNo cancel feeOn-time62%
Sun Country AirCheapest$495Average$646FlexibilityNo 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.