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Puerto Rico

$127+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
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 February 3, 2026.

This American Airlines deal was found by Cheapflights users on 2/1. 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 11/147:42 pm
ATW
-
SJU
1 stop17h 20m
American Airlines
Sat 11/216:25 am
SJU
-
ATW
2 stops14h 46m
American Airlines
Deal found 2/1$319
This United Airlines deal was found by Cheapflights users on 2/1. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/155:23 pm
ATW
-
SJU
2 stops10h 48m
United Airlines
Thu 2/262:05 am
SJU
-
ATW
2 stops13h 53m
United Airlines
Deal found 2/1$338
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/76:35 pm
ATW
-
SJU
1 stop8h 49m
American Airlines
Tue 3/101:30 am
SJU
-
ATW
2 stops12h 19m
American Airlines
Deal found 2/2$359
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/2$366
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Wed 4/226:00 am
ATW
-
SJU
2 stops15h 05m
American Airlines
Tue 4/287:25 am
SJU
-
ATW
1 stop14h 59m
American Airlines
Deal found 2/1$382
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Sun 2/156:40 pm
ATW
-
SJU
1 stop8h 44m
American Airlines
Fri 2/276:00 am
SJU
-
ATW
2 stops13h 52m
American Airlines
Deal found 2/1$401
This Delta deal was found by Cheapflights users on 2/2. 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 2/35:20 am
ATW
-
SJU
1 stop9h 57m
Delta
Fri 2/132:12 pm
SJU
-
ATW
1 stop9h 38m
Delta
Deal found 2/2$420
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/46:39 pm
ATW
-
SJU
1 stop8h 45m
American Airlines
Thu 3/127:40 am
SJU
-
ATW
2 stops11h 12m
American Airlines
Deal found 2/2$422
This American Airlines deal was found by Cheapflights users on 2/1. 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 4/76:31 pm
ATW
-
SJU
2 stops15h 17m
American Airlines
Mon 4/1311:59 pm
SJU
-
ATW
2 stops11h 18m
American Airlines
Deal found 2/1$438
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Mon 2/166:39 pm
ATW
-
SJU
1 stop8h 45m
American Airlines
Fri 2/207:33 am
SJU
-
ATW
1 stop16h 04m
American Airlines
Deal found 2/1$445

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 February 3, 2026.

Round-trip from

$256
(United Airlines)

One-way from

$127
(Kiwi.com)

Popular in

March

Cheapest in

November

Average price

$645
From Oshkosh to Puerto Rico
Search Deals
One-way flight from Oshkosh to Puerto Rico
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($50 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($28 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 3, 2026.
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

Mon 4/20

12:34 pm-11:50 pm

2 stops10h 16m

San Juan Luis Munoz Marin Intl

Tue 4/28

1:00 am-11:48 am

2 stops11h 48m

$256

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 4/19

10:30 am-8:34 pm

1 stop9h 04m

San Juan Luis Munoz Marin Intl

Mon 4/27

1:00 am-2:00 pm

2 stops14h 00m

$318

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Mon 3/2

6:39 pm-5:24 am

1 stop8h 45m

San Juan Luis Munoz Marin Intl

Tue 3/10

9:50 am-11:19 pm

2 stops14h 29m

$319

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 3/1

1:25 pm-5:24 am

1 stop13h 59m

San Juan Luis Munoz Marin Intl

Fri 3/6

6:33 am-12:51 pm

1 stop8h 18m

$319

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 2/15

5:23 pm-6:11 am

2 stops10h 48m

San Juan Luis Munoz Marin Intl

Thu 2/26

2:05 am-1:58 pm

2 stops13h 53m

$338

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 2/15

6:40 pm-5:24 am

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Fri 2/27

8:40 am-5:52 pm

2 stops11h 12m

$401

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Sun 4/26

6:30 am-12:33 pm

1 stop29h 03m

$127

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Mon 4/13

10:30 am-8:34 pm

1 stop9h 04m

$128

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 4/21

7:06 am-8:51 pm

1 stop12h 45m

$128

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Tue 4/14

10:30 am-8:34 pm

1 stop9h 04m

$128

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 15 results
1
2

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 $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.

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 February 3, 2026.
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
8,132 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Crew

8.5

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
8,132 reviews
Delta
7.9
Good
8,132 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Crew

8.5

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
9,229 reviews
Delta
7.9
Good
8,132 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Crew

8.5

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
11,212 reviews
Delta
7.9
Good
8,132 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Overall

7.9

Boarding

8.1

Crew

8.5

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 10h 48m. Fly via United Airlines, American 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, 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 $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

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 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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$341FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$568FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$182Average$481FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$208Average$402FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$266Average$553FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$515FlexibilityNo cancel feeOn-time63%

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