$108+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Aug 5 — Aug 121
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap 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 July 31, 2025.
Round-trip from | $215 (Southwest) |
|---|---|
One-way from | $108 (American Airlines) |
Popular in | July |
Cheapest in | February |
Average price | $494 |
Find flight deals from Puerto Rico to Wisconsin
Cheapest flights from Puerto Rico to WisconsinExplore 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 July 31, 2025.
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 July 31, 2025.
This Southwest deal was found by Cheapflights users on 7/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/184:05 pmSJU - MKE
1 stop7h 55mSouthwest
Sun 9/285:45 amMKE - SJU
1 stop6h 30mSouthwest
Deal found 7/31![Southwest logo]()
$215
This American Airlines deal was found by Cheapflights users on 7/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/301:36 pmSJU - ATW
2 stops20h 41mAmerican Airlines
Sun 8/316:35 pmATW - SJU
2 stops17h 10mAmerican Airlines
Deal found 7/30![American Airlines logo]()
$219
This American Airlines deal was found by Cheapflights users on 7/29. 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.
Wed 9/104:43 pmSJU - MKE
2 stops18h 21mAmerican Airlines
Sun 9/146:23 pmMKE - SJU
2 stops17h 24mAmerican Airlines
Deal found 7/29![American Airlines logo]()
$220
This FlightHub deal was found by Cheapflights users on 7/31. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1510:16 pmSJU - ORD
1 stop12h 06mSpirit Airlines
Mon 8/1812:55 pmORD - SJU
Nonstop4h 45mSpirit Airlines
Deal found 7/31![Spirit Airlines logo]()
$221
This Delta deal was found by Cheapflights users on 7/29. 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.
Thu 11/66:43 pmSJU - MKE
1 stop7h 12mDelta
Tue 11/117:00 amMKE - SJU
1 stop8h 10mDelta
Deal found 7/29![Delta logo]()
$225
This KAYAK deal was found by Cheapflights users on 7/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/73:00 pmSJU - ORD
Nonstop5h 20mAmerican Airlines
Wed 10/87:11 amORD - SJU
2 stops15h 48mAmerican Airlines
Deal found 7/29![American Airlines logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 7/31. 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.
Thu 9/182:48 pmSJU - MSP
1 stop8h 20mSpirit Airlines
Sun 9/215:15 amMSP - SJU
1 stop7h 38mSpirit Airlines
Deal found 7/31![Spirit Airlines logo]()
$238
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/133:29 amSJU - ORD
1 stop12h 58mMultiple Airlines
Sun 8/176:56 amORD - SJU
1 stop7h 14mMultiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$242
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/123:40 amSJU - ORD
1 stop7h 34mFrontier
Sat 9/138:00 amORD - SJU
1 stop14h 59mFrontier
Deal found 7/30![Frontier logo]()
$248
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1612:45 pmSJU - MSN
2 stops10h 24mAmerican Airlines
Tue 1/1311:43 amMSN - SJU
1 stop9h 57mAmerican Airlines
Deal found 7/31![American Airlines logo]()
$255
This Frontier deal was found by Cheapflights users on 7/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/193:32 amBQN - ORD
1 stop12h 45mFrontier
Fri 10/38:49 pmORD - BQN
1 stop13h 07mFrontier
Deal found 7/30![Frontier logo]()
$258
This SmartFares deal was found by Cheapflights users on 7/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/144:12 pmSJU - MSP
1 stop28h 44mMultiple Airlines
Sat 8/239:22 amMSP - SJU
2 stops27h 55mMultiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$271
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 July 31, 2025.
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 JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 9/18
4:05 pm-11:00 pm
1 stop7h 55m
Milwaukee-Mitchell
Sun 9/28
5:45 am-1:15 pm
1 stop6h 30m
$215
San JuanAppleton
SJU - ATW
SJUATW
San Juan Luis Munoz Marin Intl
Sat 8/30
1:36 pm-9:17 am
2 stops20h 41m
Appleton Intl
Sun 8/31
6:35 pm-12:45 pm
2 stops17h 10m
$219
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Wed 9/10
4:43 pm-10:04 am
2 stops18h 21m
Milwaukee-Mitchell
Sun 9/14
6:23 pm-12:47 pm
2 stops17h 24m
$220
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 8/15
10:16 pm-9:22 am
1 stop12h 06m
Chicago O'Hare Intl
Mon 8/18
12:55 pm-6:40 pm
Nonstop4h 45m
$221
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 10/7
3:00 pm-7:20 pm
Nonstop5h 20m
Chicago O'Hare Intl
Wed 10/8
7:11 am-11:59 pm
2 stops15h 48m
$230
San JuanMinneapolis
SJU - MSP
SJUMSP
San Juan Luis Munoz Marin Intl
Thu 9/18
2:48 pm-10:08 pm
1 stop8h 20m
Minneapolis St Paul
Sun 9/21
5:15 am-1:53 pm
1 stop7h 38m
$238
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/13
3:29 am-3:27 pm
1 stop12h 58m
Chicago O'Hare Intl
Sun 8/17
6:56 am-3:10 pm
1 stop7h 14m
$242
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 8/12
3:40 am-10:14 am
1 stop7h 34m
Chicago O'Hare Intl
Sat 9/13
8:00 am-8:02 am
1 stop23h 02m
$248
San JuanMadison
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Tue 12/16
12:45 pm-9:09 pm
2 stops10h 24m
Madison Truax Field
Tue 1/13
11:43 am-11:40 pm
1 stop9h 57m
$255
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Fri 9/19
3:32 am-3:17 pm
1 stop12h 45m
Chicago O'Hare Intl
Fri 10/3
8:49 pm-10:56 am
1 stop13h 07m
$258
Showing 1-10 of 45 results
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, February is the cheapest month in which you can book a flight from Puerto Rico to Wisconsin (average of $280). Flying from Puerto Rico to Wisconsin in June is currently the most expensive (average of $376). 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 PR to WI?
Find hourly flight availability from Puerto Rico to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.
When flying from Puerto Rico to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
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 July 31, 2025.
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.
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentGina,Jul 2025
LAS - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentGina,Jul 2025
LAS - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentGina,Jul 2025
LAS - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentGina,Jul 2025
LAS - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentGina,Jul 2025
LAS - DEN
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Overall
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentGina,Jul 2025
LAS - DEN
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.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Puerto Rico to Wisconsin
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Puerto Rico to Wisconsin
Discover the top 4 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 July 31, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$215 | Average$419 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$265 | Average$390 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$265 | Average$458 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$323 | Average$485 | FlexibilityNo cancel fee | On-time63% |