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Puerto Rico

$87+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Mar 4 — Mar 111
Wed 3/4
Wed 3/11
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 February 2, 2026.

This CheapOair deal was found by Cheapflights users on 1/31. 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 2/258:30 am
ORD
-
SJU
1 stop14h 13m
Multiple Airlines
Tue 3/103:36 pm
SJU
-
ORD
1 stop9h 11m
Multiple Airlines
Deal found 1/31$187
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
-
SJU
1 stop8h 44m
Frontier
Tue 2/243:53 am
SJU
-
ORD
1 stop13h 59m
Frontier
Deal found 2/1$188
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
ORD
-
BQN
1 stop16h 27m
Frontier
Mon 3/162:42 am
BQN
-
ORD
1 stop21h 56m
Frontier
Deal found 2/1$188
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Tue 2/2412:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/512:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/31$189
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:16 pm
ORD
-
SJU
1 stop17h 15m
Multiple Airlines
Tue 3/108:11 pm
SJU
-
ORD
2 stops22h 46m
Multiple Airlines
Deal found 2/1$190
This Kiwi.com deal was found by Cheapflights users on 1/31. 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.
Tue 3/36:02 pm
ORD
-
SJU
2 stops19h 29m
Multiple Airlines
Wed 3/1110:52 am
SJU
-
ORD
1 stop22h 33m
Multiple Airlines
Deal found 1/31$191
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2512:17 pm
ORD
-
SJU
Nonstop4h 32m
Spirit Airlines
Fri 3/611:52 am
SJU
-
ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/1$192
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 2/227:23 pm
ORD
-
SJU
1 stop21h 35m
Multiple Airlines
Sat 3/74:41 pm
SJU
-
ORD
1 stop9h 06m
Multiple Airlines
Deal found 1/31$193
This Orbitz deal was found by Cheapflights users on 1/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1010:48 am
ORD
-
SJU
1 stop10h 45m
Spirit Airlines
Thu 2/1212:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/30$194
This Cheapflightsfares deal was found by Cheapflights users on 1/31. 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.
Mon 2/910:48 am
ORD
-
SJU
1 stop10h 45m
Spirit Airlines
Thu 2/1212:32 pm
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/31$195
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:15 am
ORD
-
SJU
1 stop8h 16m
Spirit Airlines
Thu 3/121:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/1$196
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2410:55 am
ORD
-
SJU
1 stop12h 03m
Spirit Airlines
Tue 3/311:29 am
SJU
-
ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/1$197

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 February 2, 2026.

Round-trip from

$187
(CheapOair)

One-way from

$87
(Frontier)

Popular in

December

Cheapest in

September

Average price

$420
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 ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($20 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 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 February 2, 2026.
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

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Tue 3/3

8:30 am-2:57 am

1 stop16h 27m

Aguadilla Borinquen

Mon 3/16

2:42 am-11:38 pm

1 stop21h 56m

$188

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Fri 5/15

2:38 pm-8:34 pm

Nonstop4h 56m

San Juan Luis Munoz Marin Intl

Tue 5/19

7:40 am-11:53 am

Nonstop5h 13m

$237

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Mon 2/23

3:50 pm-2:57 am

1 stop9h 07m

Aguadilla Borinquen

Mon 3/9

2:43 am-5:46 pm

1 stop16h 03m

$240

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Tue 2/17

8:30 am-2:57 am

1 stop16h 27m

Aguadilla Borinquen

Mon 3/30

2:42 am-11:38 pm

1 stop21h 56m

$244

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

$247

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 2/25

11:20 am-11:58 pm

1 stop10h 38m

San Juan Luis Munoz Marin Intl

Wed 3/4

4:30 pm-10:48 pm

1 stop8h 18m

$256

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/24

5:00 am-4:52 pm

2 stops9h 52m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:42 pm-10:08 am

1 stop18h 26m

$256

Green BaySan Juan

GRB - SJU

GRBSJU

Green Bay Austin-Straubel

Sat 5/9

11:06 am-10:54 pm

2 stops10h 48m

San Juan Luis Munoz Marin Intl

Sat 5/23

7:00 am-8:34 pm

2 stops14h 34m

$256

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 4/25

9:43 am-8:34 pm

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Fri 5/1

1:00 am-10:04 am

1 stop10h 04m

$256

Green BaySan Juan

GRB - SJU

GRBSJU

Green Bay Austin-Straubel

Tue 3/3

11:13 am-9:12 pm

2 stops7h 59m

San Juan Luis Munoz Marin Intl

Tue 3/10

6:15 am-4:31 pm

2 stops11h 16m

$256

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

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 $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.

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?

    Frontier, United Airlines, and Delta can get you from Wisconsin to Puerto Rico in just under 4h 56m. Your travel time can differ by up to 11h 31m. 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 Frontier ($85), Southwest ($108), and United Airlines ($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 $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 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
Newark to Luis Munoz Marin Intl flights
LaGuardia to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santiago de los Caballeros flights
O'Hare Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Punta Cana flights
Dulles Intl to Luis Munoz Marin Intl flights
Boston to Luis Munoz Marin Intl flights
Newark to Santiago de los Caballeros flights
Newark to Punta Cana flights
Reagan-National to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Newark to Santo Domingo flights
John F Kennedy Intl to Oranjestad flights
Newark to Oranjestad flights
Philadelphia to Luis Munoz Marin Intl flights
Hartford to Luis Munoz Marin Intl flights
Baltimore to Luis Munoz Marin Intl flights
Atlanta to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
John F Kennedy Intl to Montego Bay flights
Boston to Oranjestad flights
Newark to Nassau flights
John F Kennedy Intl to Nassau flights
Orlando to Luis Munoz Marin Intl flights
Raleigh to Luis Munoz Marin Intl flights
Minneapolis to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
Boston to Punta Cana flights
Newark to Simpson Bay flights
Newark to Montego Bay flights
Hobby to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
Tampa to Luis Munoz Marin Intl flights
Detroit to Luis Munoz Marin Intl flights
LaGuardia to Nassau flights
John F Kennedy Intl to Providenciales flights
Newark to Saint Thomas Island flights
John F Kennedy Intl to Simpson Bay flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
George Bush Intcntl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Port of Spain flights
Atlanta to Punta Cana flights
LaGuardia to Oranjestad flights
LaGuardia to Santo Domingo flights
LaGuardia to Santiago de los Caballeros flights
Atlanta to Montego Bay flights
John F Kennedy Intl to Saint Thomas Island 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 February 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$85Average$341FlexibilityNo cancel feeOn-time62%
DeltaCheapest$118Average$568FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$182Average$512FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$208Average$402FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$215Average$558FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$515FlexibilityNo cancel feeOn-time63%

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