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Puerto Rico

$372+ Cheap flights from Oshkosh, WI to Puerto Rico

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 12/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap 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 October 30, 2025.

Round-trip from

$380
(American Airlines)

One-way from

$372
(Mytrip)

Popular in

March

Cheapest in

November

Average price

$592
From Oshkosh to Puerto Rico
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One-way flight from Oshkosh to Puerto Rico
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Highest demand for flights based on searches. 8% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sun 11/166:00 amATW - SJU
2 stops9h 52mAmerican Airlines
Thu 11/206:25 amSJU - ATW
2 stops10h 48mAmerican Airlines
Deal found 10/28$380
This Delta deal was found by Cheapflights users on 10/27. 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 11/111:11 amATW - SJU
2 stops11h 45mDelta
Thu 11/67:00 amSJU - ATW
2 stops15h 45mDelta
Deal found 10/27$399
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/37:42 pmATW - SJU
2 stops16h 01mAmerican Airlines
Tue 11/115:59 pmSJU - ATW
1 stop7h 26mAmerican Airlines
Deal found 10/30$439
This United Airlines deal was found by Cheapflights users on 10/28. 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 11/18:15 amATW - SJU
2 stops12h 07mUnited Airlines
Wed 11/52:05 amSJU - ATW
2 stops13h 52mUnited Airlines
Deal found 10/28$460
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:53 pmATW - SJU
1 stop20h 39mMultiple Airlines
Sat 12/64:10 amSJU - ATW
1 stop19h 38mMultiple Airlines
Deal found 10/28$471
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Fri 12/58:15 amATW - SJU
2 stops12h 07mUnited Airlines
Sun 12/78:10 amSJU - ATW
1 stop8h 57mUnited Airlines
Deal found 10/28$493
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/165:10 amATW - SJU
2 stops10h 42mAmerican Airlines
Thu 1/86:30 amSJU - ATW
2 stops13h 21mAmerican Airlines
Deal found 10/29$545

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 October 30, 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

Sun 11/16

6:00 am-5:52 pm

2 stops9h 52m

San Juan Luis Munoz Marin Intl

Thu 11/20

6:25 am-3:13 pm

2 stops10h 48m

$380

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 1/24

3:39 pm-6:11 am

2 stops12h 32m

San Juan Luis Munoz Marin Intl

Sat 1/31

2:05 am-2:09 pm

2 stops14h 04m

$465

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Thu 12/4

1:53 pm-12:32 pm

1 stop20h 39m

San Juan Luis Munoz Marin Intl

Sat 12/6

4:10 am-9:48 pm

1 stop19h 38m

$471

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 1/10

11:21 am-11:49 pm

1 stop10h 28m

San Juan Luis Munoz Marin Intl

Sat 1/17

5:00 pm-10:18 pm

1 stop31h 18m

$480

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 1/10

3:39 pm-6:11 am

2 stops12h 32m

San Juan Luis Munoz Marin Intl

Fri 1/16

2:05 am-2:09 pm

2 stops14h 04m

$492

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 12/6

9:39 am-11:52 pm

2 stops12h 13m

San Juan Luis Munoz Marin Intl

Sun 12/7

6:00 am-10:47 pm

2 stops18h 47m

$529

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 12/16

5:10 am-5:52 pm

2 stops10h 42m

San Juan Luis Munoz Marin Intl

Thu 1/8

6:30 am-5:51 pm

2 stops13h 21m

$545

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 12/20

5:28 pm-11:58 am

2 stops16h 30m

$372

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 12/20

6:15 am-6:11 am

2 stops21h 56m

$503

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sat 12/20

5:00 am-1:54 pm

1 stop6h 54m

$675

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 $87). 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 October 30, 2025.

It’s optimal to fly from Oshkosh to Puerto Rico in the evening. By choosing this option you can save up to 50% 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 October 30, 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
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,035 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 9h 52m. 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 $87). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$314FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$512FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$523FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$414FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$269Average$561FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$573FlexibilityNo cancel feeOn-time63%

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