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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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Round-trip from

$195
(Cheapflightsfares)

One-way from

$104
(FlightHub)

Popular in

December

Cheapest in

September

Average price

$370
From Wisconsin to Puerto Rico
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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).
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Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/129:55 amORD - SJU
1 stop7h 55mSpirit Airlines
Thu 5/298:12 pmSJU - ORD
1 stop13h 38mSpirit Airlines
Deal found 4/29$202
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 9/186:10 pmGRB - SJU
2 stops19h 35mAmerican Airlines
Tue 9/303:55 pmSJU - GRB
2 stops18h 26mAmerican Airlines
Deal found 4/29$225
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/162:45 pmMKE - SJU
1 stop6h 23mDelta
Tue 9/235:19 pmSJU - MKE
1 stop7h 06mDelta
Deal found 4/29$225
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Thu 10/26:11 pmATW - SJU
2 stops19h 34mAmerican Airlines
Mon 10/61:55 pmSJU - ATW
2 stops20h 20mAmerican Airlines
Deal found 4/29$231
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Mon 8/256:20 amMSN - SJU
2 stops16h 45mAmerican Airlines
Fri 9/51:55 pmSJU - MSN
2 stops22h 56mAmerican Airlines
Deal found 4/27$255
This eDestinos deal was found by Cheapflights users on 4/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/29:00 amMSP - SJU
Nonstop5h 16mSun Country Air
Sat 8/94:20 pmSJU - MSP
Nonstop5h 37mSun Country Air
Deal found 4/29$264
This eDestinos deal was found by Cheapflights users on 4/29. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/114:15 pmORD - SJU
1 stop20h 14mFrontier
Fri 5/163:56 amSJU - ORD
1 stop20h 36mFrontier
Deal found 4/29$270
This Mytrip deal was found by Cheapflights users on 4/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/105:48 pmMSP - SJU
1 stop27h 29mMultiple Airlines
Sat 5/247:45 pmSJU - MSP
2 stops18h 43mMultiple Airlines
Deal found 4/28$273
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/1511:30 amORD - SJU
Nonstop4h 46mMultiple Airlines
Mon 5/196:00 amSJU - ORD
1 stop13h 29mMultiple Airlines
Deal found 4/28$275
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/265:45 amMSN - SJU
1 stop6h 44mDelta
Sat 9/67:00 amSJU - MSN
2 stops15h 04mDelta
Deal found 4/27$292
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 9/165:20 amMKE - SJU
2 stops10h 00mAmerican Airlines
Tue 9/233:55 pmSJU - MKE
1 stop8h 34mAmerican Airlines
Deal found 4/29$302
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/254:50 pmMSP - SJU
1 stop17h 41mSpirit Airlines
Sat 5/318:12 pmSJU - MSP
2 stops18h 16mSpirit Airlines
Deal found 4/29$306

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 April 30, 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

Mon 5/12

9:55 am-6:50 pm

1 stop7h 55m

San Juan Luis Munoz Marin Intl

Thu 5/29

8:12 pm-8:50 am

1 stop13h 38m

$202

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

2:45 pm-10:08 pm

1 stop6h 23m

San Juan Luis Munoz Marin Intl

Tue 9/23

5:19 pm-11:25 pm

1 stop7h 06m

$225

AppletonSan Juan

ATW - SJU

ATWSJU

Appleton Intl

Thu 10/2

6:11 pm-2:45 pm

2 stops19h 34m

San Juan Luis Munoz Marin Intl

Mon 10/6

1:55 pm-9:15 am

2 stops20h 20m

$231

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 8/25

6:20 am-12:05 am

2 stops16h 45m

San Juan Luis Munoz Marin Intl

Fri 9/5

1:55 pm-11:51 am

2 stops22h 56m

$255

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 5/11

4:15 pm-1:29 pm

1 stop20h 14m

San Juan Luis Munoz Marin Intl

Fri 5/16

3:56 am-11:32 pm

1 stop20h 36m

$270

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 5/10

5:48 pm-10:17 pm

1 stop27h 29m

San Juan Luis Munoz Marin Intl

Sat 5/24

7:45 pm-1:28 pm

2 stops18h 43m

$273

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 5/15

11:30 am-5:16 pm

Nonstop4h 46m

San Juan Luis Munoz Marin Intl

Mon 5/19

6:00 am-6:29 pm

1 stop13h 29m

$275

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 5/10

9:00 am-3:11 pm

Nonstop5h 11m

San Juan Luis Munoz Marin Intl

Sat 5/24

2:50 pm-8:01 pm

Nonstop6h 11m

$291

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 8/26

5:45 am-1:29 pm

1 stop6h 44m

San Juan Luis Munoz Marin Intl

Sat 9/6

7:00 am-9:04 pm

2 stops15h 04m

$292

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 9/16

5:20 am-4:20 pm

2 stops10h 00m

San Juan Luis Munoz Marin Intl

Tue 9/23

3:55 pm-11:29 pm

1 stop8h 34m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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, September is the cheapest month in which you can book a flight from Wisconsin to Puerto Rico (average of $254). Flying from Wisconsin to Puerto Rico in December is currently the most expensive (average of $336). 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 April 30, 2025.

When flying from Wisconsin to Puerto Rico, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Puerto Rico. Reviews last updated April 30, 2025.
Read through reviews of airlines operating flights from Wisconsin to Puerto Rico, such as Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,929 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,696 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,922 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Boarding

8.2

Crew

8.5

Entertainment

7.1

Overall

8.0

Food

7.1

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

  • 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 Spirit Airlines ($104), Delta ($108), and Frontier ($135).

  • 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, September is the cheapest month in which you can book a flight from Wisconsin to Puerto Rico (average of $254). Flying from Wisconsin to Puerto Rico in December is currently the most expensive (average of $336). 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

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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 7 airlines flying from Wisconsin to Puerto Rico

Discover the top 7 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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$256FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$204Average$392FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$233Average$611FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$248Average$463FlexibilityNo cancel feeOn-time62%
DeltaCheapest$264Average$516FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$267Average$562FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$343Average$621FlexibilityNo cancel feeOn-time63%

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