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 Delta ($108), American Airlines ($108), and Frontier ($115).

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.

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).

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

To save on the cost of your flight from Wisconsin to Puerto Rico, book at least 34 days before your planned departure. Booking around this time can save you about 17% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $354 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $379.

What is the cheapest month to fly from Wisconsin to Puerto Rico?

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, September can be a great choice for travel to Puerto Rico. Flights to Puerto Rico from Wisconsin in September are about $438 on average during September, but can be found for as low as $175.

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.

$108+ Cheap Flights from Wisconsin to Puerto Rico

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Cheap flight deals from Wisconsin to Puerto Rico

Round-trip from	$214 (FlightHub)
One-way from	$108 (Delta)
Popular in	June
Cheapest in	September
Average price	$399

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).

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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).

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Average for round-trip flights in August 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 August 14, 2025.

Sat 9/206:30 amORD - SJU

1 stop6h 41mSpirit Airlines

Thu 9/2511:59 amSJU - ORD

1 stop6h 40mSpirit Airlines

Deal found 8/12

$214

Sat 9/205:08 pmMSN - SJU

2 stops17h 03mAmerican Airlines

Sat 9/274:45 pmSJU - MSN

2 stops18h 14mAmerican Airlines

Deal found 8/13

$215

Fri 9/266:00 amCWA - SJU

2 stops16h 37mAmerican Airlines

Tue 9/301:37 pmSJU - CWA

2 stops20h 44mAmerican Airlines

Deal found 8/14

$215

Tue 10/218:08 pmGRB - SJU

2 stops18h 46mAmerican Airlines

Tue 10/281:50 pmSJU - GRB

2 stops20h 24mAmerican Airlines

Deal found 8/14

$215

Tue 10/286:00 amATW - SJU

1 stop7h 08mAmerican Airlines

Wed 11/126:25 amSJU - ATW

2 stops10h 48mAmerican Airlines

Deal found 8/13

$215

Sun 9/215:40 amMKE - SJU

1 stop6h 36mDelta

Wed 9/245:41 pmSJU - MKE

1 stop7h 07mDelta

Deal found 8/13

$215

Sun 8/246:56 amORD - SJU

1 stop17h 00mSpirit Airlines

Thu 9/47:40 pmSJU - ORD

Nonstop5h 16mSpirit Airlines

Deal found 8/12

$220

Fri 10/36:18 pmATW - SJU

2 stops19h 35mAmerican Airlines

Tue 10/74:45 pmSJU - ATW

2 stops17h 38mAmerican Airlines

Deal found 8/14

$220

Sat 9/278:00 amMKE - SJU

2 stops14h 37mAmerican Airlines

Tue 10/73:00 pmSJU - MKE

1 stop9h 56mAmerican Airlines

Deal found 8/12

$220

Sat 8/236:56 amORD - SJU

1 stop16h 01mSpirit Airlines

Wed 8/271:39 pmSJU - ORD

Nonstop5h 11mSpirit Airlines

Deal found 8/12

$221

Mon 8/256:56 amORD - SJU

1 stop16h 01mSpirit Airlines

Fri 9/57:40 pmSJU - ORD

Nonstop5h 16mSpirit Airlines

Deal found 8/13

$223

Sun 8/245:05 amORD - SJU

1 stop15h 43mSpirit Airlines

Fri 8/2910:16 pmSJU - ORD

1 stop12h 06mSpirit Airlines

Deal found 8/13

$225

Best flights from Wisconsin to Puerto Rico
Discover carefully curated flight deals from Wisconsin to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 14, 2025.

Sat 9/205:08 pmMSN - SJU

2 stops17h 03mAmerican Airlines

Sat 9/273:05 pmSJU - MSN

1 stop9h 22mAmerican Airlines

Deal found 8/13

$215

Tue 12/92:45 pmMKE - SJU

1 stop6h 32mDelta

Wed 12/171:50 pmSJU - MKE

1 stop7h 13mDelta

Deal found 8/14

$215

Sat 11/1512:05 pmMKE - SJU

2 stops10h 31mUnited Airlines

Tue 11/184:52 pmSJU - MKE

1 stop7h 51mUnited Airlines

Deal found 8/14

$215

Sun 9/285:45 amMKE - SJU

1 stop6h 30mSouthwest

Wed 10/86:10 amSJU - MKE

1 stop11h 05mSouthwest

Deal found 8/12

$215

Mon 8/256:56 amORD - SJU

1 stop16h 01mSpirit Airlines

Sat 8/304:05 pmSJU - ORD

1 stop7h 17mSpirit Airlines

Deal found 8/12

$235

Mon 10/65:10 amORD - SJU

1 stop8h 01mMultiple Airlines

Fri 10/107:40 pmSJU - ORD

Nonstop5h 16mMultiple Airlines

Deal found 8/12

$253

Sat 9/208:00 amORD - BQN

1 stop17h 27mFrontier

Fri 9/263:32 amBQN - ORD

1 stop12h 45mFrontier

Deal found 8/12

$262

Sat 11/89:00 amMSP - SJU

Nonstop5h 14mSun Country Air

Sat 11/155:15 pmSJU - MSP

Nonstop5h 54mSun Country Air

Deal found 8/14

$269

Fri 9/266:00 amCWA - SJU

2 stops16h 37mAmerican Airlines

Tue 9/301:37 pmSJU - CWA

2 stops20h 44mAmerican Airlines

Deal found 8/14

$215

Wed 1/212:45 pmMKE - SJU

1 stop7h 04mDelta

Fri 1/302:12 pmSJU - MKE

1 stop8h 00mDelta

Deal found 8/13

$215

Tue 2/1012:53 pmGRB - SJU

1 stop7h 02mAmerican Airlines

Wed 2/186:50 pmSJU - GRB

2 stops17h 54mAmerican Airlines

Deal found 8/13

$215

Tue 1/2710:25 amMKE - SJU

1 stop8h 05mDelta

Thu 1/292:12 pmSJU - MKE

1 stop8h 00mDelta

Deal found 8/13

$215

Last-minute flights from Wisconsin to Puerto Rico
Discover last-minute flight deals from Wisconsin to Puerto Rico. Data last updated August 14, 2025 and is based on user searches.

Fri 8/225:16 pmORD - BQN

1 stop8h 28mMultiple Airlines

Mon 8/253:43 amBQN - ORD

1 stop13h 27mMultiple Airlines

Deal found 8/12

$335

Sat 8/236:56 amORD - SJU

1 stop16h 01mSpirit Airlines

Wed 8/271:39 pmSJU - ORD

Nonstop5h 11mSpirit Airlines

Deal found 8/12

$221

Sat 8/236:56 amORD - SJU

1 stop16h 01mSpirit Airlines

Tue 8/261:39 pmSJU - ORD

Nonstop5h 11mSpirit Airlines

Deal found 8/12

$226

Sat 8/236:56 amORD - SJU

1 stop16h 01mSpirit Airlines

Mon 8/2510:16 pmSJU - ORD

1 stop12h 06mSpirit Airlines

Deal found 8/14

$243

Sat 8/236:56 amORD - SJU

1 stop16h 01mMultiple Airlines

Sat 8/303:21 pmSJU - ORD

1 stop9h 12mMultiple Airlines

Deal found 8/14

$244

Sun 8/246:56 amORD - SJU

1 stop17h 00mSpirit Airlines

Thu 9/47:40 pmSJU - ORD

Nonstop5h 16mSpirit Airlines

Deal found 8/12

$220

Sun 8/245:05 amORD - SJU

1 stop15h 43mSpirit Airlines

Fri 8/2910:16 pmSJU - ORD

1 stop12h 06mSpirit Airlines

Deal found 8/13

$225

Sun 8/245:05 amORD - SJU

1 stop15h 43mMultiple Airlines

Thu 9/43:16 pmSJU - ORD

1 stop9h 54mMultiple Airlines

Deal found 8/12

$233

Sun 8/245:05 amORD - SJU

1 stop15h 43mSpirit Airlines

Sat 8/304:05 pmSJU - ORD

1 stop7h 17mSpirit Airlines

Deal found 8/12

$235

Sun 8/245:05 amORD - SJU

1 stop15h 43mSpirit Airlines

Tue 8/261:39 pmSJU - ORD

Nonstop5h 11mSpirit Airlines

Deal found 8/12

$236

Sun 8/245:05 amORD - SJU

1 stop15h 43mMultiple Airlines

Sun 8/243:59 amSJU - ORD

1 stop15h 42mMultiple Airlines

Deal found 8/11

$245

Sun 8/249:22 amMSP - SJU

1 stop26h 35mSpirit Airlines

Fri 8/2910:16 pmSJU - MSP

2 stops24h 12mSpirit Airlines

Deal found 8/13

$322

One-way flights from Wisconsin to Puerto Rico
Search for one-way flight options from Wisconsin to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated August 14, 2025.

Mon 9/295:40 amMSN - SJU

1 stop6h 36mDelta

Deal found 8/14

$108

Tue 10/286:00 amATW - SJU

1 stop7h 08mAmerican Airlines

Deal found 8/13

$108

Tue 9/167:20 amMKE - SJU

1 stop7h 57mDelta

Deal found 8/14

$108

Sat 9/64:36 pmGRB - SJU

2 stops20h 39mAmerican Airlines

Deal found 8/14

$110

Mon 9/228:00 amMKE - SJU

2 stops14h 37mAmerican Airlines

Deal found 8/14

$110

Tue 9/306:16 pmCWA - SJU

2 stops22h 58mAmerican Airlines

Deal found 8/13

$114

Tue 9/163:47 pmMKE - SJU

2 stops18h 24mAmerican Airlines

Deal found 8/14

$114

Sat 10/112:45 pmORD - SJU

1 stop9h 00mFrontier

Deal found 8/13

$115

Sat 9/66:44 pmORD - SJU

1 stop15h 20mSpirit Airlines

Deal found 8/12

$116

Sat 8/236:56 amORD - SJU

1 stop16h 01mSpirit Airlines

Deal found 8/14

$117

Sat 9/136:44 pmORD - SJU

1 stop15h 20mSpirit Airlines

Deal found 8/12

$119

Tue 9/162:04 pmORD - SJU

3 stops23h 07mSpirit Airlines

Deal found 8/14

$121

Cheapflights Fare Finder

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

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 9/20

5:08 pm-11:11 am

2 stops17h 03m

San Juan Luis Munoz Marin Intl

Sat 9/27

3:05 pm-11:27 pm

1 stop9h 22m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 12/9

2:45 pm-11:17 pm

1 stop6h 32m

San Juan Luis Munoz Marin Intl

Wed 12/17

1:50 pm-7:03 pm

1 stop7h 13m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sat 11/15

12:05 pm-12:36 am

2 stops10h 31m

San Juan Luis Munoz Marin Intl

Tue 11/18

4:52 pm-10:43 pm

1 stop7h 51m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Sun 9/28

5:45 am-1:15 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

Wed 10/8

6:10 am-4:15 pm

1 stop11h 05m

$215

WausauSan Juan

CWA - SJU

CWASJU

Wausau Central Wisconsin

Fri 9/26

6:00 am-11:37 pm

2 stops16h 37m

San Juan Luis Munoz Marin Intl

Tue 9/30

1:37 pm-9:21 am

2 stops20h 44m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Wed 1/21

2:45 pm-11:49 pm

1 stop7h 04m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:12 pm-8:12 pm

1 stop8h 00m

$215

Green BaySan Juan

GRB - SJU

GRBSJU

Green Bay Austin-Straubel

Tue 2/10

12:53 pm-9:55 pm

1 stop7h 02m

San Juan Luis Munoz Marin Intl

Wed 2/18

6:50 pm-10:44 am

2 stops17h 54m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 1/27

10:25 am-8:30 pm

1 stop8h 05m

San Juan Luis Munoz Marin Intl

Thu 1/29

2:12 pm-8:12 pm

1 stop8h 00m

$215

Green BaySan Juan

GRB - SJU

GRBSJU

Green Bay Austin-Straubel

Tue 10/21

8:08 pm-3:55 pm

2 stops18h 47m

San Juan Luis Munoz Marin Intl

Tue 10/28

1:50 pm-9:14 am

2 stops20h 24m

$215

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Mon 1/26

7:00 am-4:51 pm

1 stop7h 51m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:12 pm-8:12 pm

1 stop8h 00m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 60 results

...

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 June is currently the most expensive (average of $339). 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?

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.

Related info for your journey

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 Delta ($108), American Airlines ($108), and Frontier ($115).
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 June is currently the most expensive (average of $339). 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

Top 6 airlines flying from Wisconsin to Puerto Rico

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$129	Average$309	FlexibilityNo cancel fee	On-time62%
Spirit Airlines	Cheapest$208	Average$402	FlexibilityNo cancel fee	On-time65%
United Airlines	Cheapest$215	Average$598	FlexibilityNo cancel fee	On-time69%
Delta	Cheapest$225	Average$509	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$271	Average$564	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$323	Average$603	FlexibilityNo cancel fee	On-time63%

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$108+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Wisconsin to Puerto Rico with Cheapflights

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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 August 14, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Wisconsin to Puerto Rico

Cheapest flights from Wisconsin to Puerto RicoExplore 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 August 14, 2025.

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 August 14, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Wisconsin to Puerto Rico that are best for you.

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.

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?

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 August 14, 2025.

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?

Can I find deals for flights from Wisconsin to Puerto Rico that include hotel bookings?

How can I find direct flights from Wisconsin to Puerto Rico?

Can I find deals for business class flights from Wisconsin to Puerto Rico?

What is the cheapest month to book a flight from Wisconsin to Puerto Rico?

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.

Top 6 airlines flying from Wisconsin to Puerto Rico

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Travel Smart

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 August 14, 2025.