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$235+ Cheap flights from Oshkosh, WI to Puerto Rico

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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Oshkosh to Puerto Rico

Cheapest flights from Oshkosh to Puerto Rico
Explore the most affordable flight options available from Oshkosh to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 18, 2025.

This Delta deal was found by Cheapflights users on 12/16. 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 12/207:00 amATW - SJU
1 stop6h 47mDelta
Sat 12/274:45 pmSJU - ATW
1 stop8h 24mDelta
Deal found 12/16$577
This American Airlines deal was found by Cheapflights users on 12/17. 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 12/319:51 amATW - SJU
1 stop17h 09mAmerican Airlines
Tue 1/68:20 amSJU - ATW
1 stop17h 01mAmerican Airlines
Deal found 12/17$622
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/318:10 amATW - SJU
2 stops14h 26mUnited Airlines
Tue 1/67:00 amSJU - ATW
2 stops10h 04mUnited Airlines
Deal found 12/17$679
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/205:00 amATW - SJU
1 stop15h 05mAmerican Airlines
Sat 12/277:00 amSJU - ATW
2 stops13h 56mAmerican Airlines
Deal found 12/16$680
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/165:20 pmATW - SJU
2 stops26h 06mUnited Airlines
Wed 1/72:05 amSJU - ATW
2 stops14h 04mUnited Airlines
Deal found 12/16$845
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/265:00 amATW - SJU
1 stop9h 17mAmerican Airlines
Fri 12/268:35 pmSJU - ATW
2 stops14h 46mAmerican Airlines
Deal found 12/16$1,379

Find flight deals from Oshkosh to Puerto Rico

Keep the following information in mind while searching for Oshkosh to Puerto Rico flight deals. Data was last updated December 18, 2025.

Round-trip from

$235
(American Airlines)

Popular in

March

Cheapest in

November

Average price

$695
From Oshkosh to Puerto Rico
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($52 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 December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oshkosh to Puerto Rico 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 18, 2025.
Use the filters below to find and compare flights from Oshkosh to Puerto Rico that are best for you.

Fly from

Oshkosh

Fly to

Puerto Rico

Route

Depart

Return

Price

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 2/3

7:15 am-9:39 pm

1 stop12h 24m

San Juan Luis Munoz Marin Intl

Fri 2/13

6:00 am-7:42 pm

1 stop15h 42m

$235

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Thu 5/28

2:43 pm-5:30 am

2 stops13h 47m

San Juan Luis Munoz Marin Intl

Tue 6/2

2:05 am-2:07 pm

2 stops13h 02m

$325

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Wed 4/15

6:35 am-8:38 pm

2 stops13h 03m

San Juan Luis Munoz Marin Intl

Mon 4/20

7:40 am-4:50 pm

1 stop10h 10m

$325

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 4/26

6:17 am-12:10 am

2 stops16h 53m

San Juan Luis Munoz Marin Intl

Wed 4/29

5:40 am-9:34 pm

2 stops16h 54m

$350

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 2/3

6:30 am-10:26 pm

1 stop13h 56m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:00 am-6:01 pm

1 stop14h 01m

$361

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Mon 2/2

12:35 pm-12:36 am

2 stops10h 01m

San Juan Luis Munoz Marin Intl

Thu 2/5

8:35 am-4:48 pm

1 stop10h 13m

$370

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Best time to book a flight from Oshkosh to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico 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 Puerto Rico

What is the cheapest month to book a flight from Oshkosh to Puerto Rico?

Currently, March is the cheapest month in which you can book a flight from Oshkosh to Puerto Rico (average of $92). Flying from Oshkosh to Puerto Rico in June is currently the most expensive (average of $379). 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 PR?

Find hourly flight availability from Oshkosh to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 18, 2025.

It’s optimal to fly from Oshkosh to Puerto Rico in the evening. By choosing this option you can save up to 51% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Oshkosh to Puerto Rico?

Use this chart to determine the cheapest time to fly round-trip from Oshkosh to Puerto Rico. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oshkosh to Puerto Rico flight should consider departing on Tuesday mornings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated December 18, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Oshkosh to Puerto Rico by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.1

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
8,004 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.1

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
9,092 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.1

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
11,055 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Food

7.3

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.1

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 Puerto Rico. 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 Puerto Rico?

    There are many flights that can get you from Oshkosh to Puerto Rico in 12h 24m. Fly via American Airlines or United Airlines to get the fastest option. The distance between Oshkosh and Puerto Rico is about 2207 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Oshkosh to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Oshkosh to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oshkosh to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oshkosh to Puerto Rico.

  • Can I find deals for business class flights from Oshkosh to Puerto Rico?

    Yes. Cheapflights offers flight deals from Oshkosh to Puerto Rico 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 Puerto Rico?

    Currently, March is the cheapest month in which you can book a flight from Oshkosh to Puerto Rico (average of $92). Flying from Oshkosh to Puerto Rico in June is currently the most expensive (average of $379). 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

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Alternative routes for Oshkosh to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Top 6 airlines flying from Oshkosh to Puerto Rico

Discover the top 6 airlines that operate flights from Oshkosh to Puerto Rico. 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 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$371FlexibilityNo cancel feeOn-time62%
DeltaCheapest$191Average$550FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$507FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$226Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$268Average$557FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$543FlexibilityNo cancel feeOn-time63%

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