HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Puerto Rico

$113+ Cheap flights from Wisconsin 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 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Puerto Rico with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Wisconsin to Puerto Rico

Keep the following information in mind while searching for Wisconsin to Puerto Rico flight deals. Data was last updated July 1, 2025.

Round-trip from

$207
(Priceline)

One-way from

$113
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$479
From Wisconsin to Puerto Rico
Search Deals
One-way flight from Wisconsin to Puerto Rico
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from Wisconsin to Puerto Rico

Cheapest flights from Wisconsin to Puerto Rico
Explore the most affordable flight options available from Wisconsin to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2025.

This Priceline deal was found by Cheapflights users on 6/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/511:28 amORD - SJU
1 stop29h 34mMultiple Airlines
Wed 8/133:55 pmSJU - ORD
Nonstop5h 04mMultiple Airlines
Deal found 6/29$205
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/85:10 amORD - SJU
1 stop8h 01mFrontier
Thu 9/251:11 amSJU - ORD
1 stop11h 52mFrontier
Deal found 6/30$207
This FlightHub deal was found by Cheapflights users on 6/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/205:05 amORD - SJU
1 stop15h 04mSpirit Airlines
Sat 8/22:28 pmSJU - ORD
Nonstop5h 19mSpirit Airlines
Deal found 6/30$213
This American Airlines deal was found by Cheapflights users on 6/30. 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 9/296:40 pmMSN - SJU
2 stops17h 06mAmerican Airlines
Tue 10/73:00 pmSJU - MSN
1 stop9h 51mAmerican Airlines
Deal found 6/30$225
This American Airlines deal was found by Cheapflights users on 6/29. 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.
Thu 10/26:19 pmATW - SJU
2 stops19h 34mAmerican Airlines
Mon 10/65:02 pmSJU - ATW
2 stops17h 21mAmerican Airlines
Deal found 6/29$230
This Priceline deal was found by Cheapflights users on 6/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/74:37 pmORD - BQN
1 stop8h 24mFrontier
Sun 8/102:59 amBQN - ORD
1 stop22h 06mFrontier
Deal found 6/30$244
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2710:51 amMSN - SJU
2 stops12h 06mUnited Airlines
Thu 10/23:56 pmSJU - MSN
1 stop7h 32mUnited Airlines
Deal found 6/30$260
This Cheapflightsfares deal was found by Cheapflights users on 7/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:00 amMSP - SJU
1 stop6h 58mSpirit Airlines
Sun 9/72:53 pmSJU - MSP
1 stop7h 42mSpirit Airlines
Deal found 7/1$276
This FlightHub deal was found by Cheapflights users on 6/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:00 amMSP - SJU
1 stop6h 58mMultiple Airlines
Sat 10/44:15 pmSJU - MSP
Nonstop5h 38mMultiple Airlines
Deal found 6/30$280
This Cheapflightsfares deal was found by Cheapflights users on 6/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/189:00 amMSP - SJU
Nonstop5h 11mSun Country Air
Sat 10/254:15 pmSJU - MSP
Nonstop5h 38mSun Country Air
Deal found 6/29$291
This Delta deal was found by Cheapflights users on 6/28. 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.
Mon 8/256:05 amMSN - SJU
2 stops15h 02mDelta
Sat 9/67:30 amSJU - MSN
2 stops15h 28mDelta
Deal found 6/28$295
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Sat 10/256:00 amGRB - SJU
2 stops16h 05mAmerican Airlines
Sun 11/96:25 pmSJU - GRB
2 stops17h 03mAmerican Airlines
Deal found 6/30$342

Cheapflights Fare Finder

Customize your flight search to find flights from Wisconsin 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 July 1, 2025.
Use the filters below to find and compare flights from Wisconsin to Puerto Rico that are best for you.

Fly from

Wisconsin

Fly to

Puerto Rico

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 8/5

11:28 am-6:02 pm

1 stop29h 34m

San Juan Luis Munoz Marin Intl

Wed 8/13

3:55 pm-7:59 pm

Nonstop5h 04m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 9/8

5:10 am-2:11 pm

1 stop8h 01m

San Juan Luis Munoz Marin Intl

Sun 9/14

1:11 am-11:53 am

1 stop11h 42m

$207

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 7/20

5:05 am-9:09 pm

1 stop15h 04m

San Juan Luis Munoz Marin Intl

Sat 8/2

2:28 pm-6:47 pm

Nonstop5h 19m

$213

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 9/29

6:40 pm-12:46 pm

2 stops17h 06m

San Juan Luis Munoz Marin Intl

Tue 10/7

3:00 pm-11:51 pm

1 stop9h 51m

$225

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Thu 8/7

4:37 pm-2:01 am

1 stop8h 24m

Aguadilla Borinquen

Sun 8/10

2:59 am-12:05 am

1 stop22h 06m

$244

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 9/27

10:51 am-11:57 pm

2 stops12h 06m

San Juan Luis Munoz Marin Intl

Thu 10/2

3:56 pm-10:28 pm

1 stop7h 32m

$260

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Thu 9/4

6:00 am-1:58 pm

1 stop6h 58m

San Juan Luis Munoz Marin Intl

Sun 9/7

2:53 pm-9:35 pm

1 stop7h 42m

$276

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Thu 9/18

6:00 am-1:58 pm

1 stop6h 58m

San Juan Luis Munoz Marin Intl

Sat 10/4

4:15 pm-8:53 pm

Nonstop5h 38m

$280

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 8/25

6:05 am-10:07 pm

2 stops15h 02m

San Juan Luis Munoz Marin Intl

Sat 9/6

7:30 am-9:58 pm

2 stops15h 28m

$295

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 7/26

9:00 am-3:16 pm

Nonstop5h 16m

San Juan Luis Munoz Marin Intl

Sat 8/9

4:20 pm-8:57 pm

Nonstop5h 37m

$340

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 57 results
1
2
3
...
6

Best time to book a flight from Wisconsin to Puerto Rico

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

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

Currently, September is the cheapest month in which you can book a flight from Wisconsin to Puerto Rico (average of $254). Flying from Wisconsin 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 WI to PR?

Find hourly flight availability from Wisconsin 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 July 1, 2025.

When flying from Wisconsin 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 July 1, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Wisconsin to Puerto Rico. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,273 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,858 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
JetBlue
7.3
Good
2,919 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,273 reviews

Entertainment

7.6

Food

7.0

Overall

8.0

Crew

8.6

Comfort

8.0

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Wisconsin to Puerto Rico one-way?

    The cheapest airlines for a one-way flight from Wisconsin to Puerto Rico are United Airlines ($113), Delta ($113), and Spirit Airlines ($115).

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Wisconsin to Puerto Rico (average of $254). Flying from Wisconsin 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

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 Wisconsin to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
Newark to Luis Munoz Marin Intl flights
Orlando to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
Philadelphia to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Dulles Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
O'Hare Intl to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
Boston to Luis Munoz Marin Intl flights
Newark to Santo Domingo flights
Newark to Punta Cana flights
Newark to Montego Bay flights
John F Kennedy Intl to Oranjestad flights
Reagan-National to Luis Munoz Marin Intl flights
Newark to Oranjestad flights
Atlanta to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Hobby to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Miami to Luis Munoz Marin Intl flights
Boston to Punta Cana flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
John F Kennedy Intl to Saint Thomas Island flights
LaGuardia to Punta Cana flights
LaGuardia to Oranjestad flights
Atlanta to Montego Bay flights
John F Kennedy Intl to Kingston flights
John F Kennedy Intl to Nassau flights
LaGuardia to Montego Bay flights
Dallas/Fort Worth to Punta Cana flights
Newark to Simpson Bay flights
John F Kennedy Intl to Port of Spain flights
John F Kennedy Intl to Simpson Bay flights
Newark to Nassau flights
Dulles Intl to Oranjestad flights
Boston to Oranjestad flights
John F Kennedy Intl to Bridgetown flights
Los Angeles to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
O'Hare Intl to Punta Cana flights
Boston to Santo Domingo flights

Top 6 airlines flying from Wisconsin to Puerto Rico

Discover the top 6 airlines that operate flights from Wisconsin 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$253FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$208Average$388FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$225Average$597FlexibilityNo cancel feeOn-time69%
DeltaCheapest$255Average$512FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$273Average$567FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$325Average$596FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.