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Puerto Rico

$200+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$200
(Delta)

Popular in

March

Cheapest in

October

Average price

$630
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. 7% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 16, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 stops18h 05mAmerican Airlines
Tue 11/116:00 amSJU - ATW
2 stops19h 25mAmerican Airlines
Deal found 9/15$298
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/33:45 pmATW - SJU
2 stops18h 26mAmerican Airlines
Tue 10/75:30 amSJU - ATW
2 stops19h 13mAmerican Airlines
Deal found 9/16$324
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/167:42 pmATW - SJU
2 stops18h 11mAmerican Airlines
Thu 11/206:00 amSJU - ATW
2 stops11h 13mAmerican Airlines
Deal found 9/15$350
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/77:42 pmATW - SJU
1 stop17h 11mAmerican Airlines
Tue 11/116:00 amSJU - ATW
2 stops19h 25mAmerican Airlines
Deal found 9/15$357
This Delta deal was found by Cheapflights users on 9/16. 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.
Fri 10/35:35 amATW - SJU
1 stop9h 56mDelta
Tue 10/77:00 amSJU - ATW
2 stops10h 47mDelta
Deal found 9/16$362
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/36:39 amATW - SJU
1 stop13h 30mAmerican Airlines
Thu 12/116:25 amSJU - ATW
2 stops14h 48mAmerican Airlines
Deal found 9/14$390
This United Airlines deal was found by Cheapflights users on 9/14. 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 12/313:24 pmATW - SJU
2 stops12h 47mUnited Airlines
Tue 1/138:10 amSJU - ATW
2 stops10h 38mUnited Airlines
Deal found 9/14$409
This American Airlines deal was found by Cheapflights users on 9/15. 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 11/176:00 amATW - SJU
2 stops12h 48mAmerican Airlines
Thu 11/204:44 pmSJU - ATW
1 stop8h 04mAmerican Airlines
Deal found 9/15$413
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Mon 11/175:03 pmATW - SJU
2 stops14h 49mMultiple Airlines
Wed 11/192:59 amSJU - ATW
2 stops20h 32mMultiple Airlines
Deal found 9/15$414

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 September 16, 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

Fri 10/3

3:45 pm-11:11 am

2 stops18h 26m

San Juan Luis Munoz Marin Intl

Tue 10/7

5:30 am-11:43 pm

2 stops19h 13m

$324

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Fri 11/7

7:42 pm-2:53 pm

1 stop17h 11m

San Juan Luis Munoz Marin Intl

Tue 11/11

6:00 am-11:25 pm

2 stops19h 25m

$357

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Mon 11/3

7:42 pm-1:43 pm

2 stops16h 01m

San Juan Luis Munoz Marin Intl

Tue 11/11

5:59 pm-9:16 am

2 stops17h 17m

$361

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 11/16

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Wed 11/19

2:05 am-1:57 pm

2 stops13h 52m

$362

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Fri 10/3

5:35 am-4:31 pm

1 stop9h 56m

San Juan Luis Munoz Marin Intl

Tue 10/7

7:00 am-8:45 pm

2 stops14h 45m

$362

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Wed 12/3

6:39 am-10:09 pm

1 stop13h 30m

San Juan Luis Munoz Marin Intl

Thu 12/11

6:25 am-7:13 pm

2 stops14h 48m

$390

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Mon 11/17

6:00 am-8:48 pm

2 stops12h 48m

San Juan Luis Munoz Marin Intl

Thu 11/20

6:00 am-3:13 pm

2 stops11h 13m

$413

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 9/28

5:35 am-4:31 pm

1 stop9h 56m

$200

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 9/28

6:19 pm-2:15 pm

2 stops18h 56m

$240

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 9/28

3:20 pm-9:35 pm

3 stops29h 15m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, September is the cheapest month in which you can book a flight from Oshkosh to Puerto Rico (average of $254). Flying from Oshkosh to Puerto Rico in June is currently the most expensive (average of $339). 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 September 16, 2025.

When flying from Oshkosh to Puerto Rico, 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 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 September 16, 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
8.0
Very good
7,954 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,929 reviews
Delta
8.0
Very good
7,954 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Boarding

8.2

Food

7.3

Overall

8.0

Entertainment

7.9

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 7h 10m. Fly via American Airlines, United Airlines, or Delta 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, September is the cheapest month in which you can book a flight from Oshkosh to Puerto Rico (average of $254). Flying from Oshkosh to Puerto Rico in June is currently the most expensive (average of $339). 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 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$308FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$402FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$569FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$510FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$274Average$585FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$601FlexibilityNo cancel feeOn-time63%

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