$113+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Aug 13 — Aug 201
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico to Wisconsin with Cheapflights
1. Tell us where you want to go
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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 14, 2026.
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 14, 2026.
This Frontier deal was found by Cheapflights users on 7/11. 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 8/57:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 8/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/11![Frontier logo]()
$193
This Frontier deal was found by Cheapflights users on 7/10. 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 7/177:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 7/1812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/10![Frontier logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 7/11. 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.
Thu 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 8/2212:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/11![Frontier logo]()
$196
This Travelocity deal was found by Cheapflights users on 7/12. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 7/1812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/12![Frontier logo]()
$197
This Priceline deal was found by Cheapflights users on 7/10. 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.
Thu 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/2412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/10![Frontier logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Thu 7/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 7/2012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/13![Frontier logo]()
$201
This deal was found by Cheapflights users on 7/10. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:59 am
SJU
- ORD
1 stop11h 42m
Frontier
Sun 9/206:30 am
ORD
- SJU
1 stop7h 55m
Frontier
Deal found 7/10![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 7/10. 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.
Thu 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 8/2512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/10![Frontier logo]()
$203
This CheapOair deal was found by Cheapflights users on 7/13. 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.
Tue 8/257:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 8/2912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/13![Frontier logo]()
$208
This Frontier deal was found by Cheapflights users on 7/10. 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 7/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 8/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/10![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 7/13. 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.
Thu 8/277:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sun 8/3012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/13![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 7/13. 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.
Wed 8/266:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Tue 9/112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/13![Frontier logo]()
$215
Best flights from Puerto Rico to WisconsinDiscover carefully curated flight deals from Puerto Rico to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 14, 2026.
Discover carefully curated flight deals from Puerto Rico to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 14, 2026.
This Delta deal was found by Cheapflights users on 7/10. 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 8/2712:56 pm
SJU
- MKE
1 stop8h 57m
Delta
Mon 8/317:03 am
MKE
- SJU
1 stop8h 35m
Delta
Deal found 7/10![Delta logo]()
$226
This American Airlines deal was found by Cheapflights users on 7/9. 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 8/273:47 pm
SJU
- MKE
1 stop7h 00m
American Airlines
Mon 8/316:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Deal found 7/9![American Airlines logo]()
$226
This United Airlines deal was found by Cheapflights users on 7/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:20 pm
SJU
- ORD
1 stop9h 08m
United Airlines
Sun 9/208:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 7/13![United Airlines logo]()
$252
This Southwest deal was found by Cheapflights users on 7/11. 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 8/208:55 pm
SJU
- MKE
1 stop13h 00m
Southwest
Tue 8/2510:30 am
MKE
- SJU
1 stop6h 40m
Southwest
Deal found 7/11![Southwest logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 7/10. 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 8/412:04 pm
BQN
- ORD
1 stop12h 06m
Frontier
Tue 8/187:10 am
ORD
- BQN
2 stops18h 00m
Frontier
Deal found 7/10![Frontier logo]()
$324
This Faresmojo deal was found by Cheapflights users on 7/9. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:00 am
SJU
- MSN
1 stop10h 20m
JetBlue
Wed 8/265:43 am
MSN
- SJU
1 stop9h 55m
JetBlue
Deal found 7/9![JetBlue logo]()
$336
This Delta deal was found by Cheapflights users on 7/13. 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.
Fri 9/42:59 pm
SJU
- ORD
1 stop9h 58m
Delta
Sun 9/136:40 am
ORD
- SJU
1 stop9h 09m
Delta
Deal found 7/13![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 7/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Tue 9/158:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 7/13![United Airlines logo]()
$287
This American Airlines deal was found by Cheapflights users on 7/9. 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 8/55:45 am
SJU
- MKE
1 stop18h 12m
American Airlines
Fri 8/141:17 pm
MKE
- SJU
1 stop8h 58m
American Airlines
Deal found 7/9![American Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 7/8. 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.
Wed 9/27:30 am
SJU
- MSN
2 stops14h 49m
Delta
Sat 9/59:32 am
MSN
- SJU
2 stops11h 57m
Delta
Deal found 7/8![Delta logo]()
$296
This Southwest deal was found by Cheapflights users on 7/13. 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.
Fri 8/146:00 am
SJU
- MKE
1 stop11h 10m
Southwest
Sat 8/299:05 am
MKE
- SJU
1 stop6h 35m
Southwest
Deal found 7/13![Southwest logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 7/9. 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.
Thu 8/273:10 am
BQN
- ORD
1 stop11h 10m
Frontier
Sun 9/136:30 am
ORD
- BQN
2 stops26h 27m
Frontier
Deal found 7/9![Frontier logo]()
$346
This Cheapflightsfares deal was found by Cheapflights users on 7/10. 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.
Tue 8/45:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
Tue 8/182:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 7/10![JetBlue logo]()
$347
This American Airlines deal was found by Cheapflights users on 7/12. 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 9/244:19 pm
SJU
- MSN
1 stop19h 32m
American Airlines
Mon 9/288:05 pm
MSN
- SJU
2 stops16h 52m
American Airlines
Deal found 7/12![American Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 7/10. 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.
Fri 8/285:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Mon 8/3110:33 am
ORD
- SJU
1 stop10h 56m
Delta
Deal found 7/10![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 7/11. 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.
Fri 8/147:03 am
SJU
- MSN
1 stop11h 14m
American Airlines
Sun 8/239:52 am
MSN
- SJU
1 stop12h 23m
American Airlines
Deal found 7/11![American Airlines logo]()
$326
This JetBlue deal was found by Cheapflights users on 7/12. 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.
Tue 8/252:30 pm
BQN
- ORD
1 stop10h 14m
JetBlue
Wed 8/262:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 7/12![JetBlue logo]()
$362
This United Airlines deal was found by Cheapflights users on 7/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/13:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Wed 9/28:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 7/8![United Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 7/12. 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.
Fri 11/64:00 pm
SJU
- MSP
2 stops9h 20m
Southwest
Mon 11/92:50 pm
MSP
- SJU
1 stop8h 15m
Southwest
Deal found 7/12![Southwest logo]()
$382
This Faresmojo deal was found by Cheapflights users on 7/10. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:00 am
SJU
- MSN
1 stop10h 51m
JetBlue
Sun 8/25:48 am
MSN
- SJU
1 stop6h 44m
JetBlue
Deal found 7/10![JetBlue logo]()
$366
This United Airlines deal was found by Cheapflights users on 7/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Sun 9/138:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 7/12![United Airlines logo]()
$377
This Southwest deal was found by Cheapflights users on 7/12. 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.
Fri 9/253:20 pm
SJU
- MSP
1 stop7h 45m
Southwest
Wed 9/307:15 am
MSP
- SJU
2 stops9h 55m
Southwest
Deal found 7/12![Southwest logo]()
$382
This Delta deal was found by Cheapflights users on 7/12. 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 9/247:00 am
SJU
- MSN
1 stop10h 23m
Delta
Mon 9/286:00 am
MSN
- SJU
1 stop9h 49m
Delta
Deal found 7/12![Delta logo]()
$362
This American Airlines deal was found by Cheapflights users on 7/12. 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 8/107:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Sun 8/234:25 pm
MKE
- SJU
1 stop6h 50m
American Airlines
Deal found 7/12![American Airlines logo]()
$364
This Frontier deal was found by Cheapflights users on 7/10. 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.
Sat 11/711:52 am
BQN
- ORD
1 stop13h 58m
Frontier
Sun 11/154:44 pm
ORD
- BQN
1 stop8h 09m
Frontier
Deal found 7/10![Frontier logo]()
$462
This United Airlines deal was found by Cheapflights users on 7/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/251:00 am
SJU
- MSN
2 stops13h 37m
United Airlines
Tue 9/298:10 am
MSN
- SJU
2 stops11h 28m
United Airlines
Deal found 7/10![United Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 7/12. 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.
Sun 10/255:30 am
SJU
- MSP
1 stop7h 45m
Southwest
Sat 10/316:20 am
MSP
- SJU
2 stops12h 45m
Southwest
Deal found 7/12![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 7/12. 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.
Sat 9/55:55 am
SJU
- MSP
1 stop9h 30m
Southwest
Sat 9/126:45 am
MSP
- SJU
1 stop14h 10m
Southwest
Deal found 7/12![Southwest logo]()
$388
This American Airlines deal was found by Cheapflights users on 7/13. 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 8/67:03 am
SJU
- MSP
1 stop15h 50m
American Airlines
Mon 8/106:15 am
MSP
- SJU
1 stop11h 18m
American Airlines
Deal found 7/13![American Airlines logo]()
$408
This United Airlines deal was found by Cheapflights users on 7/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Thu 9/248:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 7/10![United Airlines logo]()
$417
Last-minute flights from Puerto Rico to WisconsinDiscover last-minute flight deals from Puerto Rico to Wisconsin. Data last updated July 14, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Wisconsin. Data last updated July 14, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 7/12. 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 7/187:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sun 7/2612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/12![Frontier logo]()
$274
This Frontier deal was found by Cheapflights users on 7/12. 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.
Sun 7/197:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Wed 7/2212:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/12![Frontier logo]()
$272
This Frontier deal was found by Cheapflights users on 7/10. 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 7/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 8/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/10![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 7/10. 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 7/227:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 7/2712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/10![Frontier logo]()
$215
This Frontier deal was found by Cheapflights users on 7/10. 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 7/227:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Fri 8/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/10![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 7/11. 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 7/227:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 7/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/11![Frontier logo]()
$273
This eDestinos deal was found by Cheapflights users on 7/11. 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 7/227:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sun 7/2612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/11![Frontier logo]()
$285
This Super.com deal was found by Cheapflights users on 7/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/237:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 7/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/11![Frontier logo]()
$233
This Faresmojo deal was found by Cheapflights users on 7/8. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/512:56 pm
SJU
- MKE
1 stop8h 13m
JetBlue
Wed 8/125:34 am
MKE
- SJU
1 stop7h 08m
JetBlue
Deal found 7/8![JetBlue logo]()
$296
This American Airlines deal was found by Cheapflights users on 7/9. 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.
Fri 8/72:33 pm
SJU
- MKE
1 stop9h 41m
American Airlines
Sun 8/96:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Deal found 7/9![American Airlines logo]()
$230
This Southwest deal was found by Cheapflights users on 7/10. 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 8/208:55 pm
SJU
- MKE
1 stop13h 00m
Southwest
Tue 8/2510:30 am
MKE
- SJU
1 stop9h 35m
Southwest
Deal found 7/10![Southwest logo]()
$276
This Delta deal was found by Cheapflights users on 7/10. 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 8/2712:56 pm
SJU
- MKE
1 stop8h 57m
Delta
Mon 8/317:03 am
MKE
- SJU
1 stop8h 35m
Delta
Deal found 7/10![Delta logo]()
$226
One-way flights from Puerto Rico to WisconsinSearch for one-way flight options from Puerto Rico to Wisconsin. Find affordable one-way fares based on user searches. Data last updated July 14, 2026.
Search for one-way flight options from Puerto Rico to Wisconsin. Find affordable one-way fares based on user searches. Data last updated July 14, 2026.
This Southwest deal was found by Cheapflights users on 7/9. 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.
Sat 8/296:25 am
SJU
- MKE
1 stop9h 45m
Southwest
Deal found 7/9![Southwest logo]()
$113
This Southwest deal was found by Cheapflights users on 7/9. 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.
Sun 8/305:00 am
SJU
- MKE
1 stop7h 10m
Southwest
Deal found 7/9![Southwest logo]()
$129
This United Airlines deal was found by Cheapflights users on 7/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:56 pm
SJU
- MKE
1 stop8h 03m
United Airlines
Deal found 7/10![United Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 7/8. 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.
Thu 8/135:45 pm
SJU
- ORD
1 stop27h 08m
Frontier
Deal found 7/8![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 7/10. 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.
Thu 9/101:59 am
SJU
- ORD
1 stop11h 42m
Frontier
Deal found 7/10![Frontier logo]()
$142
This Frontier deal was found by Cheapflights users on 7/11. 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 7/287:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/11![Frontier logo]()
$146
This eDestinos deal was found by Cheapflights users on 7/12. 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 8/57:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/12![Frontier logo]()
$147
This Super.com deal was found by Cheapflights users on 7/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/244:15 pm
SJU
- MSP
Nonstop5h 31m
Sun Country Air
Deal found 7/10![Sun Country Air logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 7/9. 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.
Fri 8/146:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 7/9![Frontier logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/176:44 am
SJU
- ORD
1 stop14h 09m
Frontier
Deal found 7/9![Frontier logo]()
$150
This Super.com deal was found by Cheapflights users on 7/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/9![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 7/11. 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.
Wed 8/198:57 pm
SJU
- ORD
1 stop27h 11m
Frontier
Deal found 7/11![Frontier logo]()
$152
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 July 14, 2026.
Round-trip from | $193 (Frontier) |
|---|---|
One-way from | $113 (Southwest) |
Popular in | August |
Cheapest in | January |
Average price | $434 |
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 14, 2026.
Use the filters below to find and compare flights from Puerto Rico to Wisconsin that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 8/27
12:56 pm-8:53 pm
1 stop8h 57m
Milwaukee-Mitchell
Mon 8/31
7:03 am-4:38 pm
1 stop8h 35m
$226
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 8/27
3:47 pm-9:47 pm
1 stop7h 00m
Milwaukee-Mitchell
Mon 8/31
6:20 am-10:24 pm
1 stop15h 04m
$226
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 9/16
4:20 pm-12:28 am
1 stop9h 08m
Chicago O'Hare Intl
Sun 9/20
8:55 am-2:44 pm
Nonstop4h 49m
$252
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/4
2:59 pm-11:57 pm
1 stop9h 58m
Chicago O'Hare Intl
Sun 9/13
6:40 am-4:49 pm
1 stop9h 09m
$256
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 8/20
8:55 pm-8:55 am
1 stop13h 00m
Milwaukee-Mitchell
Tue 8/25
10:30 am-6:10 pm
1 stop6h 40m
$276
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/10
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Tue 9/15
8:55 am-2:44 pm
Nonstop4h 49m
$287
San JuanMadison
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Wed 9/2
7:30 am-9:19 pm
2 stops14h 49m
Madison Truax Field
Sat 9/5
9:32 am-10:29 pm
2 stops11h 57m
$296
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Wed 8/5
5:45 am-10:57 pm
1 stop18h 12m
Milwaukee-Mitchell
Fri 8/14
1:17 pm-11:15 pm
1 stop8h 58m
$316
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 8/28
5:49 pm-11:57 pm
1 stop7h 08m
Chicago O'Hare Intl
Mon 8/31
10:33 am-10:29 pm
1 stop10h 56m
$316
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Tue 8/4
12:04 pm-11:10 pm
1 stop12h 06m
Chicago O'Hare Intl
Tue 8/18
7:10 am-2:10 am
2 stops18h 00m
$324
Showing 1-10 of 60 resultsSorted by cheapest first
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.
SJU-ORD
SJU-MKE
SJU-MSP
BQN-ORD
SJU-MSN
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
PR0-USWI
SJU-ORD
SJU-MKE
SJU-MSP
BQN-ORD
What is the cheapest month to book a flight from Puerto Rico to Wisconsin?
Currently, May is the cheapest month in which you can book a flight from Puerto Rico to Wisconsin (average of $98). Flying from Puerto Rico to Wisconsin in June is currently the most expensive (average of $286). 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.
How far ahead should I book a flight from Puerto Rico to Wisconsin?
The price you pay for your flight from Puerto Rico to Wisconsin may vary depending on when you book. For the best chance of a lower fare, look to book 59 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
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 14, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Puerto Rico to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Overall
8.0
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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
Toggle through the tabs below to find thousands of 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.
Complete your trip
Complete your trip to Wisconsin by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Puerto Rico to Wisconsin by cabin class
Find flights from Puerto Rico to Wisconsin, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Puerto Rico and Wisconsin flights
Browse other Puerto Rico and Wisconsin flight options. Last updated on July 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Wisconsin
Find the right flight back to Puerto Rico after your stay in Wisconsin
Puerto Rico to Wisconsin flights
Consider these flights traveling from Puerto Rico to Wisconsin.
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 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$399 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$399 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$449 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$399 | FlexibilityNo cancel fee | On-time63% |