$113+ Cheap flights from Wisconsin to Puerto Rico
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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Aug 9 — Aug 161
Round-trip
1 adult, Economy
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Find cheap flights from Wisconsin to Puerto Rico with Cheapflights
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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 Wisconsin to Puerto Rico
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Cheapest flights from Wisconsin to Puerto RicoExplore the most affordable flight options available from Wisconsin to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 10, 2026.
Explore the most affordable flight options available from Wisconsin to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 10, 2026.
This American Airlines deal was found by Cheapflights users on 7/7. 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 12/116:50 pm
MKE
- SJU
2 stops13h 45m
American Airlines
Wed 12/167:00 am
SJU
- MKE
1 stop12h 02m
American Airlines
Deal found 7/7![American Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 7/7. 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 8/126:28 am
MKE
- SJU
2 stops11h 05m
American Airlines
Mon 8/1712:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/7![American Airlines logo]()
$231
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.
Wed 8/268:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Sun 9/67:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/9![Frontier logo]()
$239
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 8/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 8/288:57 pm
SJU
- ORD
1 stop27h 11m
Frontier
Deal found 7/9![Frontier logo]()
$241
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 8/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$242
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.
Sat 8/158:52 pm
ORD
- SJU
1 stop25h 32m
Frontier
Thu 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$243
This Frontier deal was found by Cheapflights users on 7/7. 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.
Mon 7/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/7![Frontier logo]()
$244
This Super.com deal was found by Cheapflights users on 7/7. 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.
Wed 7/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/7![Frontier logo]()
$245
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 8/2610:33 am
ORD
- SJU
1 stop10h 56m
Delta
Fri 9/42:59 pm
SJU
- ORD
1 stop9h 58m
Delta
Deal found 7/8![Delta logo]()
$246
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 8/145:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Mon 8/1712:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 7/9![American Airlines logo]()
$247
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$248
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$249
Best flights from Wisconsin to Puerto RicoDiscover carefully curated flight deals from Wisconsin to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 10, 2026.
Discover carefully curated flight deals from Wisconsin to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 10, 2026.
This Delta deal was found by Cheapflights users on 7/7. 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 8/1910:33 am
ORD
- SJU
1 stop10h 56m
Delta
Wed 9/95:59 pm
SJU
- ORD
1 stop7h 00m
Delta
Deal found 7/7![Delta logo]()
$251
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.
Sat 9/198:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Wed 9/234:20 pm
SJU
- ORD
1 stop9h 08m
United Airlines
Deal found 7/8![United Airlines logo]()
$252
This Southwest deal was found by Cheapflights users on 7/6. 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.
Wed 8/2610:30 am
MKE
- SJU
1 stop6h 40m
Southwest
Sun 8/309:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/6![Southwest logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/98:27 pm
GRB
- SJU
2 stops18h 13m
American Airlines
Mon 9/142:58 pm
SJU
- GRB
2 stops19h 37m
American Airlines
Deal found 7/7![American Airlines logo]()
$331
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
ORD
- SJU
1 stop8h 59m
JetBlue
Tue 9/83:01 pm
SJU
- ORD
1 stop9h 43m
JetBlue
Deal found 7/9![JetBlue logo]()
$372
This Priceline deal was found by Cheapflights users on 7/7. 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 9/12:35 pm
ORD
- PSE
1 stop8h 24m
Multiple Airlines
Thu 10/19:58 am
PSE
- ORD
1 stop23h 23m
Multiple Airlines
Deal found 7/7![Multiple Airlines logo]()
$406
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:13 pm
ORD
- PSE
1 stop14h 53m
Frontier
Sat 8/1510:32 am
PSE
- ORD
1 stop13h 38m
Frontier
Deal found 7/9![Frontier logo]()
$416
This United Airlines deal was found by Cheapflights users on 7/7. 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 8/52:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Wed 9/23:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 7/7![United Airlines logo]()
$292
This Delta deal was found by Cheapflights users on 7/5. 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 8/156:40 am
ORD
- SJU
1 stop8h 58m
Delta
Sat 8/295:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Deal found 7/5![Delta logo]()
$311
This United Airlines deal was found by Cheapflights users on 7/5. 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 9/155:00 am
MSN
- SJU
1 stop8h 44m
United Airlines
Fri 9/181:00 am
SJU
- MSN
2 stops13h 42m
United Airlines
Deal found 7/5![United Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 7/7. 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 8/2210:24 am
MKE
- SJU
1 stop11h 05m
Delta
Wed 9/97:00 am
SJU
- MKE
1 stop7h 50m
Delta
Deal found 7/7![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/5. 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 8/285:48 pm
ATW
- SJU
2 stops18h 36m
American Airlines
Sat 9/512:55 am
SJU
- ATW
1 stop17h 33m
American Airlines
Deal found 7/5![American Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 7/6. 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 8/86:00 am
MKE
- SJU
1 stop9h 40m
Southwest
Fri 8/146:00 am
SJU
- MKE
1 stop11h 10m
Southwest
Deal found 7/6![Southwest logo]()
$366
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/172:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
Thu 8/205:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 7/8![JetBlue logo]()
$393
This United Airlines deal was found by Cheapflights users on 7/5. 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 8/287:00 am
ATW
- SJU
2 stops12h 38m
United Airlines
Sun 9/63:56 pm
SJU
- ATW
1 stop8h 22m
United Airlines
Deal found 7/5![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 7/6. 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 9/210:22 am
MKE
- SJU
1 stop11h 07m
Delta
Sun 9/65:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 7/6![Delta logo]()
$326
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/74:10 pm
ATW
- SJU
2 stops20h 09m
American Airlines
Wed 10/144:29 pm
SJU
- ATW
2 stops19h 31m
American Airlines
Deal found 7/8![American Airlines logo]()
$371
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:49 pm
ORD
- PSE
1 stop15h 14m
Frontier
Mon 10/59:58 am
PSE
- ORD
1 stop14h 57m
Frontier
Deal found 7/8![Frontier logo]()
$416
This Southwest deal was found by Cheapflights users on 7/5. 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 12/107:20 pm
MKE
- SJU
1 stop13h 10m
Southwest
Wed 12/166:45 am
SJU
- MKE
1 stop7h 15m
Southwest
Deal found 7/5![Southwest logo]()
$383
This Delta deal was found by Cheapflights users on 7/7. 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.
Tue 8/256:45 am
MKE
- SJU
1 stop8h 48m
Delta
Fri 9/42:59 pm
SJU
- MKE
1 stop9h 54m
Delta
Deal found 7/7![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 7/7. 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 8/186:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Tue 8/252:20 pm
SJU
- MKE
1 stop9h 19m
United Airlines
Deal found 7/7![United Airlines logo]()
$326
This JetBlue deal was found by Cheapflights users on 7/6. 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 8/252:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
Thu 8/275:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 7/6![JetBlue logo]()
$399
This Frontier deal was found by Cheapflights users on 7/6. 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 8/207:44 pm
ORD
- PSE
1 stop13h 18m
Frontier
Thu 8/2710:47 am
PSE
- ORD
1 stop13h 21m
Frontier
Deal found 7/6![Frontier logo]()
$417
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/151:55 pm
ORD
- BQN
2 stops16h 54m
Multiple Airlines
Fri 8/283:10 am
BQN
- ORD
1 stop20h 58m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$467
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.
Thu 8/2012:15 pm
MSP
- SJU
1 stop9h 35m
Southwest
Thu 8/272:35 pm
SJU
- MSP
2 stops8h 50m
Southwest
Deal found 7/9![Southwest logo]()
$388
This JetBlue deal was found by Cheapflights users on 7/7. 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.
Fri 8/212:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
Fri 8/285:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 7/7![JetBlue logo]()
$399
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am
ORD
- SJU
1 stop9h 33m
Delta
Sat 9/52:31 pm
SJU
- ORD
1 stop6h 59m
Delta
Deal found 7/9![Delta logo]()
$336
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.
Wed 9/28:10 am
MSN
- SJU
2 stops11h 28m
United Airlines
Sat 9/57:00 am
SJU
- MSN
2 stops12h 56m
United Airlines
Deal found 7/8![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 7/5. 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.
Wed 10/72:55 pm
MSP
- SJU
1 stop7h 10m
Southwest
Tue 10/135:50 am
SJU
- MSP
1 stop10h 00m
Southwest
Deal found 7/5![Southwest logo]()
$388
This JetBlue deal was found by Cheapflights users on 7/4. 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 8/259:40 am
ORD
- BQN
1 stop7h 48m
JetBlue
Wed 8/265:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
Deal found 7/4![JetBlue logo]()
$403
Last-minute flights from Wisconsin to Puerto RicoDiscover last-minute flight deals from Wisconsin to Puerto Rico. Data last updated July 10, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Puerto Rico. Data last updated July 10, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 7/7. 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.
Wed 7/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/7![Frontier logo]()
$245
This Frontier deal was found by Cheapflights users on 7/7. 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.
Mon 7/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/7![Frontier logo]()
$244
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$248
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.
Sun 8/912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 8/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/9![Frontier logo]()
$250
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 8/217:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$242
This American Airlines deal was found by Cheapflights users on 7/7. 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 8/126:28 am
MKE
- SJU
2 stops11h 05m
American Airlines
Mon 8/1712:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/7![American Airlines logo]()
$231
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 8/145:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Mon 8/1712:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 7/9![American Airlines logo]()
$247
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.
Sat 8/158:52 pm
ORD
- SJU
1 stop25h 32m
Frontier
Thu 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$243
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/8![Frontier logo]()
$249
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 8/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 8/288:57 pm
SJU
- ORD
1 stop27h 11m
Frontier
Deal found 7/9![Frontier logo]()
$241
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.
Wed 8/268:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Sun 9/67:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/9![Frontier logo]()
$239
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 8/266:00 am
ORD
- SJU
1 stop9h 33m
Delta
Wed 9/27:30 am
SJU
- ORD
1 stop10h 31m
Delta
Deal found 7/8![Delta logo]()
$246
One-way flights from Wisconsin to Puerto RicoSearch for one-way flight options from Wisconsin to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated July 10, 2026.
Search for one-way flight options from Wisconsin to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated July 10, 2026.
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.
Sat 8/1510:19 am
MKE
- SJU
2 stops12h 31m
United Airlines
Deal found 7/8![United Airlines logo]()
$113
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 8/76:00 am
MKE
- SJU
1 stop16h 15m
American Airlines
Deal found 7/9![American Airlines logo]()
$115
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:20 am
MKE
- SJU
2 stops11h 13m
American Airlines
Deal found 7/8![American Airlines logo]()
$116
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 9/21:17 pm
MKE
- SJU
1 stop8h 58m
American Airlines
Deal found 7/9![American Airlines logo]()
$118
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.
Mon 9/218:14 pm
MKE
- SJU
2 stops17h 36m
American Airlines
Deal found 7/9![American Airlines logo]()
$119
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.
Tue 7/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/9![Frontier logo]()
$125
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/9![Frontier logo]()
$126
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/9![Frontier logo]()
$128
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/9![Frontier logo]()
$130
This eDestinos deal was found by Cheapflights users on 7/7. 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.
Tue 7/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/7![Frontier logo]()
$132
This United Airlines deal was found by Cheapflights users on 7/7. 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 9/16:30 am
MSN
- SJU
2 stops13h 08m
United Airlines
Deal found 7/7![United Airlines logo]()
$133
This Delta deal was found by Cheapflights users on 7/5. 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 8/201:50 pm
ORD
- SJU
1 stop7h 39m
Delta
Deal found 7/5![Delta logo]()
$133
Find flight deals from Wisconsin to Puerto Rico
Keep the following information in mind while searching for Wisconsin to Puerto Rico flight deals. Data was last updated July 10, 2026.
Round-trip from | $231 (American Airlines) |
|---|---|
One-way from | $113 (United Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $489 |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin to Puerto Rico 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 10, 2026.
Use the filters below to find and compare flights from Wisconsin to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 8/19
10:33 am-10:29 pm
1 stop10h 56m
San Juan Luis Munoz Marin Intl
Wed 9/9
5:59 pm-11:59 pm
1 stop7h 00m
$251
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 9/19
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Wed 9/23
4:20 pm-12:28 am
1 stop9h 08m
$252
Quickest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 8/5
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Wed 9/2
3:56 pm-8:05 pm
Nonstop5h 09m
$292
MadisonSan Juan
MSN - SJU
MSNSJU
Madison Truax Field
Tue 9/15
5:00 am-2:44 pm
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Fri 9/18
1:00 am-1:42 pm
2 stops13h 42m
$296
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 8/15
6:40 am-4:38 pm
1 stop8h 58m
San Juan Luis Munoz Marin Intl
Sat 8/29
5:49 pm-11:57 pm
1 stop7h 08m
$311
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 8/26
10:30 am-6:10 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Sun 8/30
9:25 pm-8:55 am
1 stop12h 30m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/22
10:24 am-10:29 pm
1 stop11h 05m
San Juan Luis Munoz Marin Intl
Wed 9/9
7:00 am-1:50 pm
1 stop7h 50m
$326
AppletonSan Juan
ATW - SJU
ATWSJU
Appleton Intl
Fri 8/28
7:00 am-8:38 pm
2 stops12h 38m
San Juan Luis Munoz Marin Intl
Sun 9/6
3:56 pm-11:18 pm
1 stop8h 22m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/2
10:22 am-10:29 pm
1 stop11h 07m
San Juan Luis Munoz Marin Intl
Sun 9/6
5:49 pm-11:53 pm
1 stop7h 04m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/25
6:45 am-4:33 pm
1 stop8h 48m
San Juan Luis Munoz Marin Intl
Fri 9/4
2:59 pm-11:53 pm
1 stop9h 54m
$326
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Wisconsin to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Wisconsin with our price prediction graph.
ORD-SJU
MKE-SJU
GRB-SJU
ORD-PSE
MSN-SJU
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 Puerto Rico
USWI-PR0
ORD-SJU
MKE-SJU
GRB-SJU
ORD-PSE
What is the cheapest month to book a flight from Wisconsin to Puerto Rico?
Currently, January is the cheapest month in which you can book a flight from Wisconsin to Puerto Rico (average of $90). Flying from Wisconsin to Puerto Rico in June is currently the most expensive (average of $326). 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 Wisconsin to Puerto Rico?
To ensure you get the cheapest price possible for a flight from Wisconsin to Puerto Rico, you should look to book at least 28 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Related info for your journey
Find useful and relevant information for your journey from Wisconsin to Puerto Rico. 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 Wisconsin to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Wisconsin to Puerto Rico by cabin class
Find flights from Wisconsin to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Wisconsin and Puerto Rico flights
Browse other Wisconsin and Puerto Rico flight options. Last updated on July 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Puerto Rico
Find the right flight back to Wisconsin after your stay in Puerto Rico
Wisconsin to Puerto Rico flights
Consider these flights traveling from Wisconsin to Puerto Rico.
Top 5 airlines flying from Wisconsin to Puerto Rico
Discover the top 5 airlines that operate flights from Wisconsin to Puerto Rico. 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$117 | Average$423 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$143 | Average$553 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$230 | Average$504 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$571 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$316 | Average$488 | FlexibilityNo cancel fee | On-time63% |