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San Juan

$109+ Cheap flights from Wisconsin to San Juan

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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Nov 22 — Nov 291
Sat 11/22
Sat 11/29
1 adult, Economy
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Find flight deals from Wisconsin to San Juan

Cheapest flights from Wisconsin to San Juan
Explore the most affordable flight options available from Wisconsin to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:40 amORD - SJU
Nonstop4h 42mSpirit Airlines
Sat 12/137:08 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 10/21$209
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/172:31 pmORD - SJU
1 stop11h 02mMultiple Airlines
Fri 11/213:23 pmSJU - ORD
1 stop21h 12mMultiple Airlines
Deal found 10/22$210
This Frontier deal was found by Cheapflights users on 10/20. 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 10/296:40 amORD - SJU
1 stop10h 14mFrontier
Mon 11/34:24 pmSJU - ORD
1 stop9h 47mFrontier
Deal found 10/20$211
This Expedia deal was found by Cheapflights users on 10/23. 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 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Tue 1/134:06 pmSJU - ORD
1 stop7h 53mFrontier
Deal found 10/23$213
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:40 amORD - SJU
1 stop9h 14mMultiple Airlines
Thu 12/410:42 amSJU - ORD
1 stop9h 54mMultiple Airlines
Deal found 10/22$214
This Frontier deal was found by Cheapflights users on 10/22. 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 10/296:40 amORD - SJU
1 stop10h 14mFrontier
Thu 11/137:30 amSJU - ORD
1 stop8h 29mFrontier
Deal found 10/22$216
This Cheapflightsfares deal was found by Cheapflights users on 10/23. 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 12/18:41 amORD - SJU
Nonstop4h 36mSpirit Airlines
Mon 12/89:47 pmSJU - ORD
Nonstop5h 12mSpirit Airlines
Deal found 10/23$217
This Priceline deal was found by Cheapflights users on 10/21. 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 10/285:28 pmORD - SJU
1 stop7h 16mSpirit Airlines
Fri 10/313:19 pmSJU - ORD
1 stop7h 14mSpirit Airlines
Deal found 10/21$218
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:40 amORD - SJU
Nonstop4h 42mSpirit Airlines
Tue 12/167:08 pmSJU - ORD
Nonstop5h 22mSpirit Airlines
Deal found 10/21$220
This Frontier deal was found by Cheapflights users on 10/22. 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 12/312:15 pmORD - SJU
1 stop8h 14mFrontier
Thu 1/86:00 amSJU - ORD
1 stop12h 55mFrontier
Deal found 10/22$223
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/117:34 pmORD - SJU
2 stops51h 58mMultiple Airlines
Fri 11/143:41 pmSJU - ORD
Nonstop5h 10mMultiple Airlines
Deal found 10/21$225
This Frontier deal was found by Cheapflights users on 10/21. 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 10/286:40 amORD - SJU
1 stop10h 14mFrontier
Fri 10/315:51 pmSJU - ORD
2 stops18h 39mFrontier
Deal found 10/21$227

Cheap flight deals from Wisconsin to San Juan

Keep the following information in mind while searching for Wisconsin to San Juan flight deals. Data was last updated October 23, 2025.

Round-trip from

$209
(Kiwi.com)

One-way from

$109
(Priceline)

Popular in

June

Cheapest in

September

Average price

$338
From Wisconsin to San Juan
Search Deals
One-way flight from Wisconsin to San Juan
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to San Juan 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 October 23, 2025.
Use the filters below to find and compare flights from Wisconsin to San Juan that are best for you.

Fly from

Wisconsin

Fly to

San Juan

Route

Depart

Return

Price

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Wed 2/4

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Tue 2/10

3:46 pm-10:58 pm

1 stop9h 12m

$223

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

6:15 am-3:20 pm

1 stop7h 05m

San Juan Luis Munoz Marin Intl

Wed 1/28

3:55 pm-10:38 pm

1 stop8h 43m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

12:38 pm-12:36 am

2 stops9h 58m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-12:03 pm

2 stops11h 58m

$235

MilwaukeeSan Juan

MKE - SJU

MKESJU

Milwaukee-Mitchell

Tue 2/3

7:50 am-9:26 pm

1 stop11h 36m

San Juan Luis Munoz Marin Intl

Tue 2/10

7:45 am-2:55 pm

1 stop9h 10m

$235

MinneapolisSan Juan

MSP - SJU

MSPSJU

Minneapolis St Paul

Sat 11/8

9:00 am-4:14 pm

Nonstop5h 14m

San Juan Luis Munoz Marin Intl

Sat 11/15

5:15 pm-9:09 pm

Nonstop5h 54m

$239

WausauSan Juan

CWA - SJU

CWASJU

Wausau Central Wisconsin

Mon 11/10

5:01 pm-10:17 am

2 stops15h 16m

San Juan Luis Munoz Marin Intl

Tue 11/18

5:59 pm-10:58 am

2 stops18h 59m

$240

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/8

7:10 am-8:30 pm

1 stop11h 20m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:30 am-4:39 pm

1 stop11h 09m

$263

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Thu 1/29

2:27 pm-12:36 am

1 stop8h 09m

San Juan Luis Munoz Marin Intl

Sun 2/1

2:05 am-9:40 am

1 stop9h 35m

$267

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 2/14

2:48 pm-6:11 am

2 stops13h 23m

San Juan Luis Munoz Marin Intl

Wed 2/18

8:35 am-2:07 pm

1 stop7h 32m

$279

ChicagoSan Juan

ORD - SJU

ORDSJU

Chicago O'Hare Intl

Sun 2/8

2:20 pm-9:00 pm

Nonstop4h 40m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:45 am-5:08 pm

1 stop11h 23m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/23

Showing 1-10 of 60 results
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Best time to book a flight from Wisconsin to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan 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 San Juan

What is the cheapest month to book a flight from Wisconsin to San Juan?

Currently, October is the cheapest month in which you can book a flight from Wisconsin to San Juan (average of $143). Flying from Wisconsin to San Juan 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 SJU?

Find hourly flight availability from Wisconsin to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 23, 2025.

It’s typically best to fly out from Wisconsin to San Juan in the evening. Doing so could potentially save you 46% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from Wisconsin to San Juan?

Use this chart to determine the cheapest time to fly round-trip from Wisconsin to San Juan. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Wisconsin to San Juan 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 San Juan. 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 San Juan?

    A quick flight from Wisconsin to San Juan can take about 4h 40m. United Airlines provides one of the quickest options available for as low as $223. The distance between Wisconsin and San Juan is about 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 San Juan one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $109. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Wisconsin to San Juan for a low price.

  • What are the most popular routes from Wisconsin to San Juan?

    The most popular flight routes from Wisconsin to San Juan are Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Minneapolis St Paul - San Juan Luis Munoz Marin Intl and Milwaukee-Mitchell - San Juan Luis Munoz Marin Intl.

  • Can I find deals for flights from Wisconsin to San Juan that include hotel bookings?

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

  • How can I find direct flights from Wisconsin to San Juan?

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

  • Can I find deals for business class flights from Wisconsin to San Juan?

    Yes. Cheapflights offers flight deals from Wisconsin to San Juan 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 San Juan?

    Currently, October is the cheapest month in which you can book a flight from Wisconsin to San Juan (average of $143). Flying from Wisconsin to San Juan 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

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Alternative routes for Wisconsin to San Juan

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 San Juan

Discover the top 6 airlines that operate flights from Wisconsin to San Juan. 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 October 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$129Average$245FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$202Average$613FlexibilityNo cancel feeOn-time69%
DeltaCheapest$215Average$517FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$226Average$414FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$271Average$577FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$580FlexibilityNo cancel feeOn-time63%

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