$95+ 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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Mar 21 — Mar 281
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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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
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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 February 19, 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 February 19, 2026.
This Expedia deal was found by Cheapflights users on 2/15. 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$164
This eDestinos deal was found by Cheapflights users on 2/15. 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$166
This Orbitz deal was found by Cheapflights users on 2/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Wed 3/412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$171
This eDestinos deal was found by Cheapflights users on 2/16. 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.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$173
This Expedia deal was found by Cheapflights users on 2/16. 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.
Sat 2/2112:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$176
This eDestinos deal was found by Cheapflights users on 2/15. 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.
Mon 3/163:08 am
SJU
- ORD
1 stop21h 30m
Frontier
Tue 3/244:18 pm
ORD
- SJU
1 stop15h 36m
Frontier
Deal found 2/15![Frontier logo]()
$183
This Priceline deal was found by Cheapflights users on 2/18. 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.
Sat 5/27:00 am
SJU
- MKE
1 stop26h 38m
Frontier
Mon 5/117:42 pm
MKE
- SJU
1 stop16h 17m
Frontier
Deal found 2/18![Frontier logo]()
$202
This Priceline deal was found by Cheapflights users on 2/19. 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 5/143:19 pm
SJU
- MSP
1 stop19h 31m
Frontier
Sun 5/1710:45 am
MSP
- SJU
1 stop22h 09m
Frontier
Deal found 2/19![Frontier logo]()
$202
This Priceline deal was found by Cheapflights users on 2/18. 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 3/106:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Tue 3/176:35 pm
MKE
- SJU
1 stop6h 28m
Frontier
Deal found 2/18![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 2/15. 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.
Wed 3/45:25 pm
SJU
- MSP
1 stop28h 07m
Frontier
Mon 3/98:07 pm
MSP
- SJU
1 stop13h 05m
Frontier
Deal found 2/15![Frontier logo]()
$239
This Priceline deal was found by Cheapflights users on 2/17. 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 2/263:53 am
SJU
- MKE
1 stop7h 50m
Frontier
Sun 3/16:39 pm
MKE
- SJU
1 stop13h 30m
Frontier
Deal found 2/17![Frontier logo]()
$244
This Priceline deal was found by Cheapflights users on 2/19. 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 3/102:42 am
BQN
- ORD
1 stop13h 56m
Frontier
Tue 3/248:05 am
ORD
- BQN
1 stop16h 37m
Frontier
Deal found 2/19![Frontier logo]()
$244
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 February 19, 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 February 19, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 3/161:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/248:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$188
This Expedia deal was found by Cheapflights users on 2/15. 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.
Thu 4/1612:30 pm
SJU
- ORD
Nonstop5h 08m
Multiple Airlines
Sun 4/198:24 pm
ORD
- SJU
1 stop17h 18m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$196
This Orbitz deal was found by Cheapflights users on 2/18. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:19 pm
SJU
- MSP
1 stop19h 31m
Frontier
Sat 5/1610:45 am
MSP
- SJU
1 stop22h 09m
Frontier
Deal found 2/18![Frontier logo]()
$202
This Southwest deal was found by Cheapflights users on 2/15. 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 6/42:30 pm
SJU
- ORD
Nonstop5h 05m
Southwest
Mon 6/810:30 am
ORD
- SJU
Nonstop4h 50m
Southwest
Deal found 2/15![Southwest logo]()
$237
This Delta deal was found by Cheapflights users on 2/17. 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.
Sat 5/95:15 pm
SJU
- ORD
1 stop7h 44m
Delta
Sat 5/166:00 am
ORD
- SJU
1 stop6h 18m
Delta
Deal found 2/17![Delta logo]()
$246
This American Airlines deal was found by Cheapflights users on 2/16. 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 5/142:42 pm
SJU
- MKE
1 stop7h 59m
American Airlines
Mon 5/186:42 pm
MKE
- SJU
1 stop16h 21m
American Airlines
Deal found 2/16![American Airlines logo]()
$266
This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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 4/3011:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Mon 5/412:18 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Deal found 2/18![Spirit Airlines logo]()
$200
This Priceline deal was found by Cheapflights users on 2/19. 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 5/143:19 pm
SJU
- MSP
1 stop19h 31m
Frontier
Sun 5/1710:45 am
MSP
- SJU
1 stop22h 09m
Frontier
Deal found 2/19![Frontier logo]()
$202
This Spirit deal was found by Cheapflights users on 2/17. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Sun 3/85:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/17![Spirit Airlines logo]()
$205
This Faresmojo deal was found by Cheapflights users on 2/16. 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 3/203:30 pm
SJU
- MSN
1 stop8h 28m
JetBlue
Mon 3/235:30 am
MSN
- SJU
1 stop6h 57m
JetBlue
Deal found 2/16![JetBlue logo]()
$486
This Delta deal was found by Cheapflights users on 2/15. 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 5/132:20 pm
SJU
- ORD
1 stop10h 39m
Delta
Sun 5/178:10 am
ORD
- SJU
1 stop10h 56m
Delta
Deal found 2/15![Delta logo]()
$246
This United Airlines deal was found by Cheapflights users on 2/16. 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 7/167:40 am
SJU
- MSN
1 stop8h 25m
United Airlines
Tue 7/288:15 am
MSN
- SJU
2 stops14h 35m
United Airlines
Deal found 2/16![United Airlines logo]()
$521
This CheapOair deal was found by Cheapflights users on 2/15. 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.
Wed 3/45:25 pm
SJU
- MSP
1 stop28h 07m
Frontier
Mon 3/98:07 pm
MSP
- SJU
1 stop13h 05m
Frontier
Deal found 2/15![Frontier logo]()
$239
This American Airlines deal was found by Cheapflights users on 2/15. 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 4/151:31 pm
SJU
- MKE
2 stops10h 26m
American Airlines
Wed 4/291:10 pm
MKE
- SJU
1 stop7h 55m
American Airlines
Deal found 2/15![American Airlines logo]()
$270
This Spirit deal was found by Cheapflights users on 2/18. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:45 pm
SJU
- ORD
1 stop8h 55m
Spirit Airlines
Sun 3/88:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 2/18![Spirit Airlines logo]()
$227
This OneTravel deal was found by Cheapflights users on 2/18. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:19 pm
SJU
- MSP
1 stop19h 31m
Multiple Airlines
Sat 5/169:00 am
MSP
- SJU
Nonstop5h 07m
Multiple Airlines
Deal found 2/18![Multiple Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 2/15. 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 4/157:30 am
SJU
- MKE
1 stop7h 22m
Delta
Wed 4/297:10 am
MKE
- SJU
1 stop8h 21m
Delta
Deal found 2/15![Delta logo]()
$266
This Priceline deal was found by Cheapflights users on 2/19. 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 3/102:42 am
BQN
- ORD
1 stop13h 56m
Frontier
Tue 3/248:05 am
ORD
- BQN
1 stop16h 37m
Frontier
Deal found 2/19![Frontier logo]()
$244
This American Airlines deal was found by Cheapflights users on 2/17. 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 4/177:25 am
SJU
- MSN
1 stop17h 30m
American Airlines
Sun 4/266:20 am
MSN
- SJU
2 stops10h 50m
American Airlines
Deal found 2/17![American Airlines logo]()
$272
This Delta deal was found by Cheapflights users on 2/17. 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 4/242:45 pm
SJU
- MKE
1 stop6h 50m
Delta
Mon 4/275:30 am
MKE
- SJU
1 stop9h 53m
Delta
Deal found 2/17![Delta logo]()
$266
This Priceline deal was found by Cheapflights users on 2/18. 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 4/226:30 am
SJU
- MSP
1 stop28h 09m
Frontier
Sun 4/266:11 pm
MSP
- SJU
1 stop14h 43m
Frontier
Deal found 2/18![Frontier logo]()
$244
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/102:42 am
BQN
- ORD
1 stop13h 56m
Multiple Airlines
Tue 3/246:36 pm
ORD
- BQN
2 stops30h 06m
Multiple Airlines
Deal found 2/19![Multiple Airlines logo]()
$298
This Spirit deal was found by Cheapflights users on 2/17. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 3/85:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/17![Spirit Airlines logo]()
$256
This Delta deal was found by Cheapflights users on 2/15. 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.
Mon 5/185:15 pm
SJU
- MKE
1 stop7h 41m
Delta
Sat 5/305:30 am
MKE
- SJU
1 stop6h 48m
Delta
Deal found 2/15![Delta logo]()
$266
This Frontier deal was found by Cheapflights users on 2/15. 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 7/158:10 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sun 7/1912:59 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 2/15![Frontier logo]()
$246
This Mytrip deal was found by Cheapflights users on 2/18. 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.
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Mon 3/94:43 pm
ORD
- SJU
2 stops22h 49m
Spirit Airlines
Deal found 2/18![Spirit Airlines logo]()
$260
This Southwest deal was found by Cheapflights users on 2/16. 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.
Tue 7/285:00 am
SJU
- MSP
1 stop11h 05m
Southwest
Tue 8/47:15 am
MSP
- SJU
2 stops10h 45m
Southwest
Deal found 2/16![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 2/17. 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 5/712:50 pm
SJU
- MKE
1 stop9h 12m
Delta
Tue 5/127:00 am
MKE
- SJU
1 stop8h 15m
Delta
Deal found 2/17![Delta logo]()
$266
This Priceline deal was found by Cheapflights users on 2/15. 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.
Mon 3/23:59 am
BQN
- ORD
1 stop13h 53m
Frontier
Sat 3/74:23 pm
ORD
- BQN
1 stop9h 19m
Frontier
Deal found 2/15![Frontier logo]()
$249
This Kiwi.com deal was found by Cheapflights users on 2/15. 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 4/1410:53 am
SJU
- MSP
2 stops38h 05m
Multiple Airlines
Tue 5/267:20 am
MSP
- SJU
1 stop10h 50m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$348
Last-minute flights from Puerto Rico to WisconsinDiscover last-minute flight deals from Puerto Rico to Wisconsin. Data last updated February 19, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Wisconsin. Data last updated February 19, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 2/16. 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.
Sat 2/2112:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$176
This Expedia deal was found by Cheapflights users on 2/15. 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$164
This eDestinos deal was found by Cheapflights users on 2/15. 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$166
This Priceline deal was found by Cheapflights users on 2/17. 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 2/263:53 am
SJU
- MKE
1 stop7h 50m
Frontier
Sun 3/16:39 pm
MKE
- SJU
1 stop13h 30m
Frontier
Deal found 2/17![Frontier logo]()
$244
This Orbitz deal was found by Cheapflights users on 2/15. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Wed 3/412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$171
This eDestinos deal was found by Cheapflights users on 2/16. 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.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$173
This Priceline deal was found by Cheapflights users on 2/15. 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.
Mon 3/23:59 am
BQN
- ORD
1 stop13h 53m
Frontier
Sat 3/74:23 pm
ORD
- BQN
1 stop9h 19m
Frontier
Deal found 2/15![Frontier logo]()
$249
This Priceline deal was found by Cheapflights users on 2/17. 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 3/33:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Sun 3/89:01 pm
MKE
- SJU
1 stop10h 53m
Frontier
Deal found 2/17![Frontier logo]()
$249
This CheapOair deal was found by Cheapflights users on 2/15. 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.
Wed 3/45:25 pm
SJU
- MSP
1 stop28h 07m
Frontier
Mon 3/98:07 pm
MSP
- SJU
1 stop13h 05m
Frontier
Deal found 2/15![Frontier logo]()
$239
This Priceline deal was found by Cheapflights users on 2/18. 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 3/106:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Tue 3/176:35 pm
MKE
- SJU
1 stop6h 28m
Frontier
Deal found 2/18![Frontier logo]()
$223
This Priceline deal was found by Cheapflights users on 2/19. 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 3/102:42 am
BQN
- ORD
1 stop13h 56m
Frontier
Tue 3/248:05 am
ORD
- BQN
1 stop16h 37m
Frontier
Deal found 2/19![Frontier logo]()
$244
This eDestinos deal was found by Cheapflights users on 2/15. 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.
Mon 3/163:08 am
SJU
- ORD
1 stop21h 30m
Frontier
Tue 3/244:18 pm
ORD
- SJU
1 stop15h 36m
Frontier
Deal found 2/15![Frontier logo]()
$183
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 February 19, 2026.
Search for one-way flight options from Puerto Rico to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 19, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 3/231:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 2/16. 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 3/1711:03 am
SJU
- ORD
1 stop8h 28m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$98
This Frontier deal was found by Cheapflights users on 2/15. 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 7/288:10 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 2/15![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 2/17. 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 4/1611:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Deal found 2/17![Spirit Airlines logo]()
$100
This Priceline deal was found by Cheapflights users on 2/15. 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 3/102:42 am
BQN
- ORD
1 stop13h 56m
Frontier
Deal found 2/15![Frontier logo]()
$101
This Priceline deal was found by Cheapflights users on 2/15. 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 3/106:30 am
SJU
- ORD
1 stop18h 08m
Frontier
Deal found 2/15![Frontier logo]()
$101
This Expedia deal was found by Cheapflights users on 2/17. 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.
Sat 3/712:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/17![Spirit Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$105
This Mytrip deal was found by Cheapflights users on 2/17. 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 3/46:27 pm
SJU
- ORD
2 stops18h 55m
Spirit Airlines
Deal found 2/17![Spirit Airlines logo]()
$106
This Expedia deal was found by Cheapflights users on 2/17. 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.
Fri 4/174:11 pm
SJU
- MKE
1 stop27h 47m
Frontier
Deal found 2/17![Frontier logo]()
$107
This Priceline deal was found by Cheapflights users on 2/19. 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 5/63:19 pm
SJU
- ORD
1 stop18h 56m
Frontier
Deal found 2/19![Frontier logo]()
$107
This Trip.com deal was found by Cheapflights users on 2/17. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/287:05 am
SJU
- ORD
1 stop17h 34m
Frontier
Deal found 2/17![Frontier logo]()
$108
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 February 19, 2026.
Round-trip from | $176 (Expedia) |
|---|---|
One-way from | $95 (Cheapflightsfares) |
Popular in | August |
Cheapest in | January |
Average price | $279 |
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 February 19, 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
Mon 3/16
1:29 am-5:45 am
Nonstop5h 16m
Chicago O'Hare Intl
Tue 3/24
8:56 pm-2:29 am
Nonstop4h 33m
$188
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 4/16
12:30 pm-4:38 pm
Nonstop5h 08m
Chicago O'Hare Intl
Sun 4/19
8:24 pm-2:42 pm
1 stop17h 18m
$196
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 4/30
11:07 am-6:15 pm
1 stop8h 08m
Chicago O'Hare Intl
Mon 5/4
12:18 pm-5:54 pm
Nonstop4h 36m
$200
San JuanMinneapolis
SJU - MSP
SJUMSP
San Juan Luis Munoz Marin Intl
Thu 5/14
3:19 pm-9:50 am
1 stop19h 31m
Minneapolis St Paul
Sat 5/16
10:45 am-9:54 am
1 stop22h 09m
$202
San JuanMinneapolis
SJU - MSP
SJUMSP
San Juan Luis Munoz Marin Intl
Thu 5/14
3:19 pm-9:50 am
1 stop19h 31m
Minneapolis St Paul
Sun 5/17
10:45 am-9:54 am
1 stop22h 09m
$202
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 3/5
11:52 am-6:18 pm
1 stop8h 26m
Chicago O'Hare Intl
Sun 3/8
5:15 am-2:31 pm
1 stop8h 16m
$205
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 3/6
5:45 pm-12:40 am
1 stop8h 55m
Chicago O'Hare Intl
Sun 3/8
8:16 pm-2:31 pm
1 stop17h 15m
$227
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 6/4
2:30 pm-6:35 pm
Nonstop5h 05m
Chicago O'Hare Intl
Mon 6/8
10:30 am-4:20 pm
Nonstop4h 50m
$237
San JuanMinneapolis
SJU - MSP
SJUMSP
San Juan Luis Munoz Marin Intl
Wed 3/4
5:25 pm-7:32 pm
1 stop28h 07m
Minneapolis St Paul
Mon 3/9
8:07 pm-10:12 am
1 stop13h 05m
$239
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Tue 3/10
2:42 am-3:38 pm
1 stop13h 56m
Chicago O'Hare Intl
Tue 3/24
8:05 am-1:42 am
1 stop16h 37m
$244
Showing 1-10 of 60 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.
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, 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 June is currently the most expensive (average of $355). 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 February 19, 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.
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - 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
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 February 19, 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 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 February 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$140 | Average$299 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$215 | Average$356 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$472 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$399 | FlexibilityNo cancel fee | On-time63% |