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$128+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:23 pm
ATW
-
SJU
2 stops10h 48m
United Airlines
Thu 2/262:05 am
SJU
-
ATW
2 stops13h 53m
United Airlines
Deal found 1/28$256
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sun 5/3112:26 pm
ATW
-
SJU
1 stop7h 08m
United Airlines
Fri 6/51:00 am
SJU
-
ATW
2 stops14h 00m
United Airlines
Deal found 1/27$317
This American Airlines deal was found by Cheapflights users on 1/26. 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 10/196:25 pm
ATW
-
SJU
2 stops17h 15m
American Airlines
Mon 10/263:50 pm
SJU
-
ATW
2 stops18h 13m
American Airlines
Deal found 1/26$319
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/101:42 pm
ATW
-
SJU
2 stops20h 11m
American Airlines
Mon 4/205:45 am
SJU
-
ATW
2 stops17h 58m
American Airlines
Deal found 1/27$324
This Delta deal was found by Cheapflights users on 1/27. 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 9/125:29 am
ATW
-
SJU
1 stop10h 02m
Delta
Sat 9/197:00 am
SJU
-
ATW
2 stops14h 40m
Delta
Deal found 1/27$326
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/178:00 am
ATW
-
SJU
2 stops11h 50m
American Airlines
Tue 3/245:28 am
SJU
-
ATW
1 stop8h 29m
American Airlines
Deal found 1/27$359
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 5/3012:26 pm
ATW
-
SJU
1 stop7h 08m
United Airlines
Fri 6/51:00 am
SJU
-
ATW
2 stops14h 00m
United Airlines
Deal found 1/27$367
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/264:55 pm
ATW
-
SJU
2 stops17h 00m
American Airlines
Fri 5/2912:59 am
SJU
-
ATW
1 stop10h 25m
American Airlines
Deal found 1/27$368
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Sat 2/216:35 pm
ATW
-
SJU
1 stop8h 49m
American Airlines
Fri 2/276:33 am
SJU
-
ATW
1 stop13h 19m
American Airlines
Deal found 1/28$382
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/245:30 pm
ATW
-
SJU
2 stops10h 59m
United Airlines
Sat 6/132:05 am
SJU
-
ATW
2 stops12h 55m
United Airlines
Deal found 1/28$385
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:25 am
ATW
-
STX
1 stop7h 31m
Delta
Wed 3/43:58 pm
STX
-
ATW
1 stop7h 52m
Delta
Deal found 1/28$388
This American Airlines deal was found by Cheapflights users on 1/28. 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.
Wed 2/256:39 pm
ATW
-
STX
2 stops20h 58m
American Airlines
Mon 3/26:27 pm
STX
-
ATW
2 stops25h 25m
American Airlines
Deal found 1/28$392

Find flight deals from Oshkosh to Caribbean

Keep the following information in mind while searching for Oshkosh to Caribbean flight deals. Data was last updated January 29, 2026.

Round-trip from

$256
(United Airlines)

One-way from

$128
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$613
From Oshkosh to Caribbean
Search Deals
One-way flight from Oshkosh to Caribbean
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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

Sun 5/31

12:26 pm-8:34 pm

1 stop7h 08m

San Juan Luis Munoz Marin Intl

Fri 6/5

1:00 am-2:00 pm

2 stops14h 00m

$317

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 4/11

6:20 pm-1:49 pm

2 stops18h 29m

San Juan Luis Munoz Marin Intl

Fri 4/17

2:42 pm-10:14 am

2 stops20h 32m

$324

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 5/30

12:26 pm-8:34 pm

1 stop7h 08m

San Juan Luis Munoz Marin Intl

Fri 6/5

1:00 am-2:00 pm

2 stops14h 00m

$367

AppletonChristiansted

ATW - STX

ATWSTX

Appleton Intl

Sun 2/22

5:25 am-2:56 pm

1 stop7h 31m

Christiansted Henry Rohlsen

Wed 3/4

3:58 pm-9:50 pm

1 stop7h 52m

$388

AppletonChristiansted

ATW - STX

ATWSTX

Appleton Intl

Sun 2/22

5:25 am-2:56 pm

1 stop7h 31m

Christiansted Henry Rohlsen

Tue 3/3

3:58 pm-9:50 pm

1 stop7h 52m

$388

AppletonChristiansted

ATW - STX

ATWSTX

Appleton Intl

Tue 2/24

5:25 am-2:56 pm

1 stop7h 31m

Christiansted Henry Rohlsen

Wed 3/4

3:58 pm-9:50 pm

1 stop7h 52m

$388

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Thu 4/16

6:10 am-6:06 pm

2 stops34h 56m

San Juan Luis Munoz Marin Intl

Mon 4/20

5:45 am-10:43 pm

2 stops17h 58m

$394

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Fri 4/10

1:42 pm-10:53 am

2 stops20h 11m

San Juan Luis Munoz Marin Intl

Wed 4/15

7:25 am-9:54 pm

1 stop15h 29m

$408

AppletonChristiansted

ATW - STX

ATWSTX

Appleton Intl

Thu 2/26

5:25 am-2:56 pm

1 stop7h 31m

Christiansted Henry Rohlsen

Wed 3/4

3:58 pm-9:50 pm

1 stop7h 52m

$413

AppletonChristiansted

ATW - STX

ATWSTX

Appleton Intl

Thu 2/26

5:25 am-2:56 pm

1 stop7h 31m

Christiansted Henry Rohlsen

Tue 3/3

3:58 pm-9:50 pm

1 stop7h 52m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 41 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.

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, November is the cheapest month in which you can book a flight from Oshkosh to Caribbean (average of $113). Flying from Oshkosh to Caribbean in June 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 January 29, 2026.

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 January 29, 2026.
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
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,128 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,215 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,205 reviews
Delta
7.9
Good
8,128 reviews

Entertainment

7.8

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Oshkosh to Caribbean?

    Departing from Oshkosh to Caribbean will take you 7h 08m. Airlines will cover a distance of 2207 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 - Simpson Bay Princess Juliana, 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, November is the cheapest month in which you can book a flight from Oshkosh to Caribbean (average of $113). Flying from Oshkosh to Caribbean in June 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

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$291FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$679FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$623FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$208Average$402FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$266Average$667FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$736FlexibilityNo cancel feeOn-time63%
Sun Country AirCheapest$497Average$652FlexibilityNo cancel feeOn-time83%

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