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Puerto Rico

$104+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
nov. 21 — nov. 281
vie. 11/21
vie. 11/28
1 adult, Economy
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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 octubre 22, 2025.

Round-trip from

$207
(Kiwi.com)

One-way from

$104
(eDestinos)

Popular in

June

Cheapest in

September

Average price

$338
From Wisconsin to Puerto Rico
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One-way flight from Wisconsin to Puerto Rico
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Highest demand for flights based on searches. 11% potential increase in price ($53 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 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 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 octubre 22, 2025.

This Frontier deal was found by Cheapflights users on 10/20. 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.
mié. 10/296:40 amORD - SJU
1 stop10h 14mFrontier
sáb. 11/13:31 pmSJU - ORD
1 stop8h 58mFrontier
Deal found 10/20$207
This Cheapflightsfares deal was found by Cheapflights users on 10/20. 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.
lun. 11/178:00 amORD - SJU
Nonstop4h 36mSpirit Airlines
lun. 11/244:12 pmSJU - ORD
Nonstop5h 11mSpirit Airlines
Deal found 10/20$209
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
dom. 11/1612:17 pmORD - SJU
1 stop11h 15mMultiple Airlines
sáb. 11/224:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 10/19$210
This Frontier deal was found by Cheapflights users on 10/20. 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.
vie. 11/148:26 amORD - SJU
2 stops15h 06mFrontier
vie. 11/217:11 amSJU - ORD
1 stop12h 48mFrontier
Deal found 10/20$212
This Frontier deal was found by Cheapflights users on 10/19. 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.
lun. 11/246:15 pmORD - SJU
1 stop6h 39mFrontier
mar. 11/253:59 amSJU - ORD
1 stop7h 48mFrontier
Deal found 10/19$213
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
lun. 10/277:51 pmORD - SJU
1 stop17h 21mMultiple Airlines
lun. 11/39:00 amSJU - ORD
1 stop29h 45mMultiple Airlines
Deal found 10/19$214
This Frontier deal was found by Cheapflights users on 10/19. 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.
mar. 10/286:40 amORD - SJU
1 stop10h 14mFrontier
lun. 11/312:29 pmSJU - ORD
2 stops13h 42mFrontier
Deal found 10/19$216
This Cheapflightsfares deal was found by Cheapflights users on 10/21. 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.
lun. 12/18:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
sáb. 12/67:08 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 10/21$217
This Priceline deal was found by Cheapflights users on 10/20. 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.
dom. 12/75:55 amORD - SJU
Nonstop4h 41mSpirit Airlines
sáb. 12/137:08 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 10/20$218
This Trip.com deal was found by Cheapflights users on 10/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/186:40 amORD - SJU
1 stop9h 14mMultiple Airlines
jue. 11/204:12 pmSJU - ORD
Nonstop5h 11mMultiple Airlines
Deal found 10/20$219
This Kiwi.com deal was found by Cheapflights users on 10/21. 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.
mar. 12/95:40 amORD - SJU
Nonstop4h 42mSpirit Airlines
mar. 12/167:08 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 10/21$220
This Delta deal was found by Cheapflights users on 10/21. 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.
dom. 12/711:41 amMKE - SJU
1 stop9h 39mDelta
vie. 12/127:00 amSJU - MKE
1 stop11h 13mDelta
Deal found 10/21$235

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 octubre 22, 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

WausauSan Juan

CWA - SJU

CWASJU

Wausau Central Wisconsin

lun. 11/10

11:29 am-10:17 am

2 stops20h 48m

San Juan Luis Munoz Marin Intl

mar. 11/18

5:59 pm-10:58 am

2 stops18h 59m

$240

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom. 1/18

2:56 pm-6:11 am

2 stops13h 15m

San Juan Luis Munoz Marin Intl

jue. 1/22

8:35 am-2:52 pm

1 stop8h 17m

$257

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

dom. 12/7

3:45 pm-12:35 am

1 stop6h 50m

San Juan Luis Munoz Marin Intl

vie. 12/12

6:10 am-9:50 pm

2 stops17h 40m

$289

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

jue. 11/13

5:25 am-3:04 am

1 stop19h 39m

Aguadilla Borinquen

mié. 11/26

3:55 am-5:13 pm

1 stop15h 18m

$301

Green BaySan Juan

GRB - SJU

GRBSJU

Green Bay Austin-Straubel

mié. 2/4

6:31 am-9:26 pm

2 stops12h 55m

San Juan Luis Munoz Marin Intl

jue. 2/19

8:10 am-7:04 pm

2 stops12h 54m

$302

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

jue. 12/4

11:41 am-11:20 pm

1 stop9h 39m

San Juan Luis Munoz Marin Intl

jue. 12/11

6:38 pm-11:54 pm

1 stop7h 16m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

jue. 12/4

10:25 am-11:20 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

vie. 12/12

7:00 am-4:13 pm

1 stop11h 13m

$305

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

jue. 12/4

11:41 am-11:20 pm

1 stop9h 39m

San Juan Luis Munoz Marin Intl

mié. 12/10

3:32 pm-11:54 pm

1 stop10h 22m

$305

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

mié. 12/3

11:25 am-11:54 pm

1 stop10h 29m

San Juan Luis Munoz Marin Intl

sáb. 12/6

1:45 pm-9:52 pm

1 stop10h 07m

$308

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

vie. 11/21

11:50 am-1:15 am

1 stop11h 25m

San Juan Luis Munoz Marin Intl

sáb. 11/29

12:07 pm-7:27 pm

1 stop9h 20m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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 $87). 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 octubre 22, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 49% 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?

    American Airlines, United Airlines, and Southwest can get you from Wisconsin to Puerto Rico in just under 6h 50m. Your travel time can differ by up to 13h 58m. Airlines will cover a distance of 2073 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 American Airlines ($118), United Airlines ($118), and Southwest ($118).

  • 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 $87). 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.
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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 octubre 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$315FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$570FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$517FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$414FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$271Average$577FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$580FlexibilityNo cancel feeOn-time63%

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