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$90+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 12, 2025.

This Priceline deal was found by Cheapflights users on 12/10. 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.
Wed 12/177:00 amORD - SJU
1 stop9h 53mMultiple Airlines
Wed 12/248:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Deal found 12/10$201
This Frontier deal was found by Cheapflights users on 12/11. 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 12/3111:23 amORD - SJU
1 stop7h 04mFrontier
Thu 1/154:35 pmSJU - ORD
1 stop8h 09mFrontier
Deal found 12/11$205
This Trip.com deal was found by Cheapflights users on 12/10. 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.
Sat 12/137:00 amORD - SJU
1 stop9h 53mMultiple Airlines
Thu 12/185:09 pmSJU - ORD
1 stop17h 43mMultiple Airlines
Deal found 12/10$206
This WAYA deal was found by Cheapflights users on 12/10. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:15 pmORD - SJU
1 stop8h 35mMultiple Airlines
Fri 1/95:18 pmSJU - ORD
1 stop8h 28mMultiple Airlines
Deal found 12/10$208
This Trip.com deal was found by Cheapflights users on 12/11. 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.
Sat 12/137:00 amORD - SJU
1 stop9h 53mJetBlue
Mon 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/11$215
This Trip.com deal was found by Cheapflights users on 12/10. 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.
Fri 12/127:00 amORD - SJU
1 stop9h 52mJetBlue
Mon 12/151:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/10$220
This Trip.com deal was found by Cheapflights users on 12/11. 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.
Sat 12/137:00 amORD - SJU
1 stop9h 53mJetBlue
Sun 12/141:45 pmSJU - ORD
1 stop10h 07mJetBlue
Deal found 12/11$221
This Priceline deal was found by Cheapflights users on 12/11. 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 12/236:25 amSJU - ORD
1 stop7h 40mMultiple Airlines
Deal found 12/11$223
This CheapOair deal was found by Cheapflights users on 12/10. 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 12/10$224
This Frontier deal was found by Cheapflights users on 12/9. 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.
Tue 12/301:27 pmORD - SJU
1 stop15h 07mFrontier
Fri 1/97:10 amSJU - ORD
1 stop11h 57mFrontier
Deal found 12/9$227
This Trip.com deal was found by Cheapflights users on 12/11. 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.
Sat 12/137:00 amORD - SJU
1 stop9h 53mMultiple Airlines
Mon 12/158:45 pmSJU - ORD
Nonstop5h 14mMultiple Airlines
Deal found 12/11$228
This CheapOair deal was found by Cheapflights users on 12/10. 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.
Sat 12/132:26 pmORD - PSE
1 stop16h 54mFrontier
Thu 12/1812:29 pmPSE - ORD
1 stop22h 23mFrontier
Deal found 12/10$244

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 12, 2025.

Round-trip from

$180
(Frontier)

One-way from

$90
(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 ($47 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
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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 12, 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

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Sat 1/10

8:27 pm-11:19 am

1 stop12h 52m

Ponce Mercedita

Thu 1/15

12:14 pm-7:41 pm

1 stop9h 27m

$201

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

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

$202

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Tue 6/2

3:15 pm-1:59 am

1 stop9h 44m

San Juan Luis Munoz Marin Intl

Tue 6/9

12:30 pm-7:26 pm

1 stop7h 56m

$214

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sun 2/22

1:17 pm-2:57 am

1 stop11h 40m

Aguadilla Borinquen

Fri 2/27

3:58 am-3:37 pm

1 stop13h 39m

$215

ChicagoAguadilla

ORD - BQN

ORDBQN

Chicago O'Hare Intl

Sun 2/22

1:17 pm-2:57 am

1 stop11h 40m

Aguadilla Borinquen

Mon 3/2

3:58 am-3:52 pm

1 stop13h 54m

$215

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 3/6

4:18 pm-11:40 am

1 stop17h 22m

Ponce Mercedita

Thu 3/12

11:35 am-11:38 pm

1 stop13h 03m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 2/21

6:04 am-4:56 pm

1 stop8h 52m

San Juan Luis Munoz Marin Intl

Sun 3/1

5:10 am-11:48 am

1 stop8h 38m

$216

ChicagoPonce

ORD - PSE

ORDPSE

Chicago O'Hare Intl

Fri 2/20

9:07 pm-11:25 am

1 stop12h 18m

Ponce Mercedita

Mon 3/2

11:30 am-3:52 pm

1 stop30h 22m

$216

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sat 1/31

7:45 am-6:05 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Mon 2/2

11:06 am-7:36 pm

1 stop10h 30m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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 December 12, 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?

    Frontier, JetBlue, and United Airlines can get you from Wisconsin to Puerto Rico in just under 9h 03m. Your travel time can differ by up to 3h 49m. 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 ($60), 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 $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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$367FlexibilityNo cancel feeOn-time62%
DeltaCheapest$203Average$549FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$215Average$560FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$226Average$406FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$269Average$571FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$550FlexibilityNo cancel feeOn-time63%

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