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Puerto Rico

$86+ 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 2/7. 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 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 December 18, 2025.

This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:45 amORD - SJU
1 stop10h 04mJetBlue
Sun 1/42:21 pmSJU - ORD
1 stop9h 43mJetBlue
Deal found 12/17$202
This Frontier deal was found by Cheapflights users on 12/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Thu 1/1511:55 amSJU - ORD
1 stop8h 30mFrontier
Deal found 12/15$205
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Thu 1/151:22 pmSJU - ORD
Nonstop5h 15mSpirit Airlines
Deal found 12/17$224
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:39 pmORD - SJU
1 stop9h 58mMultiple Airlines
Fri 1/1611:06 amSJU - ORD
1 stop10h 30mMultiple Airlines
Deal found 12/16$227
This Priceline deal was found by Cheapflights users on 12/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
Tue 12/238:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/15$230
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:14 pmORD - SJU
1 stop7h 49mFrontier
Wed 1/77:18 pmSJU - ORD
1 stop25h 59mFrontier
Deal found 12/16$234
This American Airlines deal was found by Cheapflights users on 12/15. 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.
Wed 12/3110:25 pmORD - SJU
Nonstop4h 35mAmerican Airlines
Thu 1/156:00 amSJU - ORD
Nonstop5h 35mAmerican Airlines
Deal found 12/15$236
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:05 pmORD - SJU
1 stop12h 34mMultiple Airlines
Fri 1/910:47 pmSJU - ORD
1 stop11h 31mMultiple Airlines
Deal found 12/16$240
This Priceline deal was found by Cheapflights users on 12/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:25 amORD - SJU
1 stop10h 29mMultiple Airlines
Mon 12/227:25 amSJU - ORD
1 stop13h 08mMultiple Airlines
Deal found 12/15$243
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:48 pmMKE - SJU
1 stop29h 02mFrontier
Thu 12/259:37 pmSJU - MKE
1 stop21h 44mFrontier
Deal found 12/17$264
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/218:06 pmMKE - SJU
1 stop28h 44mFrontier
Thu 12/259:37 pmSJU - MKE
1 stop21h 44mFrontier
Deal found 12/16$314
This Frontier deal was found by Cheapflights users on 12/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/207:48 pmMKE - SJU
1 stop11h 10mFrontier
Sun 12/213:55 amSJU - MKE
1 stop9h 18mFrontier
Deal found 12/15$334

Find 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 December 18, 2025.

Round-trip from

$195
(Kiwi.com)

One-way from

$86
(Priceline)

Popular in

June

Cheapest in

September

Average price

$532
From Wisconsin to Puerto Rico
Search Deals
One-way flight from Wisconsin to Puerto Rico
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($48 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 December 2025
Search Deals

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 December 18, 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 3/10

10:00 am-8:56 pm

1 stop9h 56m

San Juan Luis Munoz Marin Intl

Thu 3/12

3:26 am-11:25 am

1 stop8h 59m

$196

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/24

10:56 am-11:23 pm

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Thu 3/26

3:26 am-11:25 am

1 stop8h 59m

$196

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 1/8

8:27 pm-11:19 am

1 stop12h 52m

Ponce Mercedita

Thu 1/15

12:14 pm-7:41 pm

1 stop9h 27m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 5/11

10:35 am-8:03 pm

1 stop8h 28m

San Juan Luis Munoz Marin Intl

Tue 5/12

12:30 pm-7:26 pm

1 stop7h 56m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 2/27

12:41 pm-11:44 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Sat 3/7

5:10 am-11:58 am

1 stop8h 48m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 3/9

12:41 pm-9:31 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Wed 3/11

1:30 am-10:05 am

1 stop9h 35m

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 1/18

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Fri 1/23

11:06 am-7:36 pm

1 stop10h 30m

$205

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 3/17

10:56 am-11:23 pm

1 stop11h 27m

San Juan Luis Munoz Marin Intl

Thu 3/19

1:30 am-10:05 am

1 stop9h 35m

$211

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 2/27

3:11 pm-1:46 pm

1 stop20h 35m

Ponce Mercedita

Mon 3/2

11:30 am-11:15 pm

1 stop13h 45m

$216

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Thu 1/15

8:51 pm-11:20 am

1 stop12h 29m

Ponce Mercedita

Sun 1/18

12:14 pm-7:51 pm

1 stop9h 37m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 60 results
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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, March is the cheapest month in which you can book a flight from Wisconsin to Puerto Rico (average of $92). Flying from Wisconsin 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 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 December 18, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 50% on flights from Wisconsin to Puerto Rico by exploring options for tickets in the evening.

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

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

Travelers seeking maximum savings on their Wisconsin 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.

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.

  • How long is the flight from Wisconsin to Puerto Rico?

    JetBlue, Frontier, and United Airlines can get you from Wisconsin to Puerto Rico in just under 7h 10m. Your travel time can differ by up to 5h 42m. Airlines will cover a distance of 2180 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Frontier ($43), United Airlines ($108), and Delta ($108).

  • 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, March is the cheapest month in which you can book a flight from Wisconsin to Puerto Rico (average of $92). Flying from Wisconsin 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 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
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John F Kennedy Intl to Saint Thomas Island flights
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Fort Lauderdale 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$371FlexibilityNo cancel feeOn-time62%
DeltaCheapest$191Average$550FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$558FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$226Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$268Average$570FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$543FlexibilityNo cancel feeOn-time63%

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