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Puerto Rico

$114+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jun 28 — Jul 51
Sun 6/28
Sun 7/5
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 May 29, 2026.

This American Airlines deal was found by Cheapflights users on 5/27. 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 8/205:00 am
ORD
-
SJU
1 stop12h 34m
American Airlines
Fri 8/216:00 am
SJU
-
ORD
1 stop10h 05m
American Airlines
Deal found 5/27$231
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Mon 8/175:20 pm
ORD
-
SJU
Nonstop4h 55m
American Airlines
Wed 8/191:38 pm
SJU
-
ORD
1 stop7h 25m
American Airlines
Deal found 5/29$232
This Frontier deal was found by Cheapflights users on 5/27. 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 8/1912:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Thu 8/206:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 5/27$233
This Delta deal was found by Cheapflights users on 5/28. 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 8/171:00 pm
ORD
-
SJU
1 stop9h 52m
Delta
Wed 8/261:19 pm
SJU
-
ORD
1 stop9h 33m
Delta
Deal found 5/28$236
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Wed 8/195:00 am
ORD
-
SJU
1 stop10h 03m
American Airlines
Tue 9/112:55 am
SJU
-
ORD
Nonstop5h 05m
American Airlines
Deal found 5/29$237
This Frontier deal was found by Cheapflights users on 5/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Mon 8/316:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 5/29$238
This Kiwi.com deal was found by Cheapflights users on 5/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sat 8/226:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 5/28$239
This Frontier deal was found by Cheapflights users on 5/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:29 am
ORD
-
SJU
Nonstop4h 57m
Frontier
Mon 8/246:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 5/28$240
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Wed 8/126:45 am
ORD
-
SJU
1 stop14h 39m
American Airlines
Mon 8/177:24 pm
SJU
-
ORD
1 stop13h 10m
American Airlines
Deal found 5/29$241
This American Airlines deal was found by Cheapflights users on 5/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:59 pm
ORD
-
SJU
Nonstop4h 55m
American Airlines
Thu 8/201:38 pm
SJU
-
ORD
1 stop11h 52m
American Airlines
Deal found 5/28$242
This Priceline deal was found by Cheapflights users on 5/24. 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 8/1612:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Sun 8/306:11 pm
SJU
-
ORD
Nonstop5h 15m
Frontier
Deal found 5/24$243
This Frontier deal was found by Cheapflights users on 5/27. 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 8/812:44 am
ORD
-
SJU
Nonstop5h 00m
Frontier
Wed 8/127:14 pm
SJU
-
ORD
Nonstop5h 13m
Frontier
Deal found 5/27$245

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 May 29, 2026.

Round-trip from

$231
(American Airlines)

One-way from

$114
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$416
From Wisconsin to Puerto Rico
Search Deals
One-way flight from Wisconsin to Puerto Rico
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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 May 29, 2026.
Use the filters below to find and compare flights from Wisconsin to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 8/19

10:33 am-10:29 pm

1 stop10h 56m

San Juan Luis Munoz Marin Intl

Wed 9/2

5:49 pm-12:02 am

1 stop7h 13m

$236

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 9/6

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Tue 9/15

1:00 am-9:41 am

2 stops9h 41m

$246

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Mon 8/17

5:28 am-4:38 pm

1 stop10h 10m

San Juan Luis Munoz Marin Intl

Wed 8/19

12:56 pm-8:50 pm

1 stop8h 54m

$276

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 8/16

6:40 am-4:38 pm

1 stop8h 58m

San Juan Luis Munoz Marin Intl

Wed 8/19

5:49 pm-12:02 am

1 stop7h 13m

$306

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 8/22

1:45 pm-10:29 pm

1 stop7h 44m

San Juan Luis Munoz Marin Intl

Tue 8/25

12:56 pm-10:32 pm

1 stop10h 36m

$321

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 10/19

8:25 pm-1:45 pm

1 stop16h 20m

San Juan Luis Munoz Marin Intl

Wed 10/28

3:25 pm-11:05 pm

1 stop8h 40m

$326

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Mon 11/16

7:42 pm-1:41 pm

2 stops15h 59m

San Juan Luis Munoz Marin Intl

Thu 12/3

6:25 am-3:18 pm

2 stops10h 53m

$326

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Fri 9/25

6:49 am-2:44 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Fri 10/2

1:00 am-1:37 pm

2 stops13h 37m

$348

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Mon 8/10

2:35 pm-11:59 pm

1 stop8h 24m

Ponce Mercedita

Thu 8/13

5:01 am-1:39 pm

1 stop9h 38m

$356

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Mon 11/16

10:34 am-9:00 pm

1 stop8h 26m

San Juan Luis Munoz Marin Intl

Thu 12/3

4:52 pm-12:26 am

1 stop9h 34m

$359

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/25

Showing 1-10 of 60 resultsSorted by cheapest first
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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, October is the cheapest month in which you can book a flight from Wisconsin to Puerto Rico (average of $108). Flying from Wisconsin to Puerto Rico in January is currently the most expensive (average of $2,255). 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.

How far ahead should I book a flight from Wisconsin to Puerto Rico?

To ensure you get the cheapest price possible for a flight from Wisconsin to Puerto Rico, you should look to book at least 28 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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?

    Delta, United Airlines, and American Airlines can get you from Wisconsin to Puerto Rico in just under 7h 14m. Your travel time can differ by up to 9h 06m. 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 ($90), Southwest ($108), and Delta ($112).

  • 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, October is the cheapest month in which you can book a flight from Wisconsin to Puerto Rico (average of $108). Flying from Wisconsin to Puerto Rico in January is currently the most expensive (average of $2,255). 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.
Newark to Luis Munoz Marin Intl flights
Orlando to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
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John F Kennedy Intl to Punta Cana flights
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Dallas/Fort Worth to Luis Munoz Marin Intl flights
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Atlanta to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Baltimore to Luis Munoz Marin Intl flights
John F Kennedy Intl to Oranjestad flights
Newark to Santo Domingo flights
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Dulles Intl to Luis Munoz Marin Intl flights
Tampa to Luis Munoz Marin Intl flights
Newark to Montego Bay flights
Reagan-National to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Hobby to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
John F Kennedy Intl to Montego Bay flights
Boston to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
LaGuardia to Santo Domingo flights
LaGuardia to Santiago de los Caballeros flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Atlanta to Montego Bay flights
John F Kennedy Intl to Kingston flights
Raleigh to Luis Munoz Marin Intl flights
Miami to Luis Munoz Marin Intl flights
Newark to Nassau flights
Atlanta to Punta Cana flights
Dallas/Fort Worth to Punta Cana flights
Orlando to Punta Cana flights
Boston to Punta Cana flights
LaGuardia to Montego Bay flights
Newark to Providenciales flights
John F Kennedy Intl to Bridgetown flights
Newark to Simpson Bay flights
Baltimore to Punta Cana flights
Boston to Oranjestad flights
Fort Lauderdale to Montego Bay 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 May 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$112Average$556FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$117Average$423FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$219Average$366FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$225Average$510FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$235Average$562FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$484FlexibilityNo cancel feeOn-time63%

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