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Wisconsin

$90+ Cheap flights from Puerto Rico to Wisconsin

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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
1 adult, Economy
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Cheap flight deals from Puerto Rico to Wisconsin

Cheapest flights from Puerto Rico to Wisconsin
Explore the most affordable flight options available from Puerto Rico to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 2, 2026.

This JetBlue deal was found by Cheapflights users on 12/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:21 pmSJU - ORD
1 stop9h 43mJetBlue
Thu 1/16:45 amORD - SJU
1 stop10h 04mJetBlue
Deal found 12/31$327
This JetBlue deal was found by Cheapflights users on 12/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:21 pmSJU - ORD
1 stop9h 43mJetBlue
Sun 1/46:45 amORD - SJU
1 stop10h 04mJetBlue
Deal found 12/30$335
This Expedia deal was found by Cheapflights users on 12/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Tue 1/69:35 amORD - SJU
1 stop7h 48mMultiple Airlines
Deal found 12/31$358
This Mytrip deal was found by Cheapflights users on 12/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:08 pmSJU - ORD
Nonstop5h 17mMultiple Airlines
Mon 1/52:15 pmORD - SJU
1 stop8h 27mMultiple Airlines
Deal found 12/31$365
This eDestinos deal was found by Cheapflights users on 12/31. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Tue 1/65:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/31$369
This eDestinos deal was found by Cheapflights users on 12/31. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Thu 1/15:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/31$396
This FlightHub deal was found by Cheapflights users on 12/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:08 pmSJU - ORD
Nonstop5h 17mSpirit Airlines
Sun 1/45:45 amORD - SJU
Nonstop4h 41mSpirit Airlines
Deal found 12/30$408
This Priceline deal was found by Cheapflights users on 12/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/312:21 pmSJU - ORD
1 stop9h 43mMultiple Airlines
Thu 1/15:45 amORD - SJU
Nonstop4h 41mMultiple Airlines
Deal found 12/30$433

Find flight deals from Puerto Rico to Wisconsin

Keep the following information in mind while searching for Puerto Rico to Wisconsin flight deals. Data was last updated January 2, 2026.

Round-trip from

$161
(Expedia)

One-way from

$90
(Expedia)

Popular in

July

Cheapest in

February

Average price

$305
From Puerto Rico to Wisconsin
Search Deals
One-way flight from Puerto Rico to Wisconsin
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($109 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Wisconsin 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 January 2, 2026.
Use the filters below to find and compare flights from Puerto Rico to Wisconsin that are best for you.

Fly from

Puerto Rico

Fly to

Wisconsin

Route

Depart

Return

Price

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 1/15

11:06 am-7:36 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 1/19

10:15 am-7:26 pm

1 stop7h 11m

$190

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 1/13

9:00 am-4:52 pm

1 stop9h 52m

Chicago O'Hare Intl

Fri 1/16

10:00 am-11:35 pm

1 stop11h 35m

$215

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 2/26

11:52 am-6:18 pm

1 stop8h 26m

Chicago O'Hare Intl

Tue 3/3

7:00 am-1:37 am

2 stops16h 37m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Tue 3/24

3:26 am-11:25 am

1 stop8h 59m

Chicago O'Hare Intl

Sun 3/29

12:20 pm-8:26 pm

1 stop7h 06m

$228

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sat 2/14

6:33 am-2:32 pm

1 stop9h 59m

Madison Truax Field

Sat 2/14

5:17 pm-11:40 am

1 stop16h 23m

$230

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Fri 2/13

6:15 am-11:13 am

1 stop6h 58m

Milwaukee-Mitchell

Mon 2/16

12:20 pm-11:58 pm

1 stop9h 38m

$235

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 3/5

6:33 am-3:51 pm

1 stop11h 18m

Milwaukee-Mitchell

Sun 3/8

6:37 pm-10:40 am

1 stop15h 03m

$235

San JuanMinneapolis

SJU - MSP

SJUMSP

San Juan Luis Munoz Marin Intl

Fri 2/27

12:27 pm-6:41 pm

1 stop8h 14m

Minneapolis St Paul

Mon 3/2

11:26 am-2:53 am

1 stop13h 27m

$236

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Sat 2/28

6:33 am-7:01 pm

1 stop14h 28m

Milwaukee-Mitchell

Thu 3/5

6:01 am-11:34 pm

1 stop15h 33m

$236

San JuanMilwaukee

SJU - MKE

SJUMKE

San Juan Luis Munoz Marin Intl

Thu 1/29

2:28 pm-8:24 pm

1 stop7h 56m

Milwaukee-Mitchell

Mon 2/2

9:33 am-11:59 pm

2 stops12h 26m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

Showing 1-10 of 60 results
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Best time to book a flight from Puerto Rico to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Puerto Rico 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 Puerto Rico to Wisconsin

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

Currently, September is the cheapest month in which you can book a flight from Puerto Rico to Wisconsin (average of $113). Flying from Puerto Rico to Wisconsin in July is currently the most expensive (average of $289). 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.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated January 2, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Puerto Rico to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,021 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,132 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,074 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Spirit Airlines
6.3
Okay
8,258 reviews
Southwest
8.0
Very good
4,254 reviews

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Puerto Rico to Wisconsin. 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 Puerto Rico to Wisconsin?

    Airlines like JetBlue, Frontier, and Spirit Airlines fly from Puerto Rico to Wisconsin in about 8h 26m. The time it takes to get you to your destination can typically vary by up to 2h 04m. Puerto Rico and Wisconsin are separated by a distance of 2073 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Puerto Rico to Wisconsin one-way?

    The cheapest airlines for a one-way flight from Puerto Rico to Wisconsin are Frontier ($64), United Airlines ($112), and Southwest ($112).

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

    Yes. In addition to deals on Puerto Rico to Wisconsin flights, Cheapflights offers vacation packages that include both flights and hotel.

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Puerto Rico to Wisconsin.

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

    Yes. Cheapflights offers flight deals from Puerto Rico to Wisconsin 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 Puerto Rico to Wisconsin?

    Currently, September is the cheapest month in which you can book a flight from Puerto Rico to Wisconsin (average of $113). Flying from Puerto Rico to Wisconsin in July is currently the most expensive (average of $289). 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 Puerto Rico to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Puerto Rico to Wisconsin

Discover the top 5 airlines that operate flights from Puerto Rico to Wisconsin. 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 January 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$118Average$398FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$182Average$301FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$215Average$382FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$235Average$471FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$305Average$485FlexibilityNo cancel feeOn-time63%

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