$114+ 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 8/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Jun 28 — Jul 51
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico to Wisconsin with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 May 29, 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 May 29, 2026.
This Frontier deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sun 9/612:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 5/24![Frontier logo]()
$223
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Sun 8/2312:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Mon 8/315:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 5/28![American Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 5/28. 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 8/201:38 pm
SJU
- ORD
1 stop10h 52m
American Airlines
Sun 8/235:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 5/28![American Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 5/28. 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 8/204:53 pm
SJU
- ORD
1 stop8h 37m
American Airlines
Tue 8/255:00 am
ORD
- SJU
1 stop6h 48m
American Airlines
Deal found 5/28![American Airlines logo]()
$236
This American Airlines deal was found by Cheapflights users on 5/27. 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 8/57:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Mon 8/175:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 5/27![American Airlines logo]()
$237
This Frontier deal was found by Cheapflights users on 5/28. 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 8/276:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Fri 8/2812:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 5/28![Frontier logo]()
$238
This American Airlines deal was found by Cheapflights users on 5/28. 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 8/67:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Wed 8/126:45 am
ORD
- SJU
1 stop14h 39m
American Airlines
Deal found 5/28![American Airlines logo]()
$241
This American Airlines deal was found by Cheapflights users on 5/26. 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 8/127:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Wed 8/195:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 5/26![American Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 5/25. 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 8/67:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Tue 8/118:37 am
ORD
- SJU
1 stop12h 18m
American Airlines
Deal found 5/25![American Airlines logo]()
$243
This American Airlines deal was found by Cheapflights users on 5/28. 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 8/274:53 pm
SJU
- ORD
1 stop8h 37m
American Airlines
Sat 8/298:22 am
ORD
- SJU
1 stop12h 33m
American Airlines
Deal found 5/28![American Airlines logo]()
$246
This American Airlines deal was found by Cheapflights users on 5/25. 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 8/57:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Wed 8/126:59 am
ORD
- SJU
1 stop13h 56m
American Airlines
Deal found 5/25![American Airlines logo]()
$248
This FlightHub deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sat 9/512:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 5/25![Frontier logo]()
$251
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 May 29, 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 May 29, 2026.
This Southwest deal was found by Cheapflights users on 5/24. 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 8/255:15 am
SJU
- MKE
1 stop6h 40m
Southwest
Mon 8/311:55 pm
MKE
- SJU
1 stop8h 55m
Southwest
Deal found 5/24![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 5/28. 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 8/55:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Fri 8/1410:22 am
MKE
- SJU
1 stop11h 07m
Delta
Deal found 5/28![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 5/24. 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 10/12:22 pm
SJU
- MSN
1 stop10h 02m
American Airlines
Sun 10/48:05 pm
MSN
- SJU
2 stops17h 35m
American Airlines
Deal found 5/24![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 5/27. 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 9/151:00 am
SJU
- MSN
2 stops13h 42m
United Airlines
Sat 9/196:30 am
MSN
- SJU
2 stops13h 08m
United Airlines
Deal found 5/27![United Airlines logo]()
$371
This JetBlue deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
Sat 9/191:00 pm
ORD
- BQN
1 stop8h 39m
JetBlue
Deal found 5/23![JetBlue logo]()
$381
This Priceline deal was found by Cheapflights users on 5/26. 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 7/135:01 am
BQN
- ORD
2 stops28h 49m
Multiple Airlines
Fri 7/175:13 pm
ORD
- BQN
1 stop7h 57m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$578
This Southwest deal was found by Cheapflights users on 5/27. 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 8/206:30 am
SJU
- MKE
1 stop10h 50m
Southwest
Tue 8/256:05 am
MKE
- SJU
1 stop6h 30m
Southwest
Deal found 5/27![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 5/26. 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 8/67:30 am
SJU
- MSN
2 stops14h 49m
Delta
Mon 8/105:43 am
MSN
- SJU
1 stop9h 55m
Delta
Deal found 5/26![Delta logo]()
$378
This JetBlue deal was found by Cheapflights users on 5/27. 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 9/12:30 pm
BQN
- ORD
1 stop10h 14m
JetBlue
Wed 9/29:39 am
ORD
- BQN
1 stop7h 57m
JetBlue
Deal found 5/27![JetBlue logo]()
$391
This United Airlines deal was found by Cheapflights users on 5/26. 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 7/284:55 pm
SJU
- ORD
1 stop7h 36m
United Airlines
Fri 8/72:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/26![United Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 5/28. 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 9/255:41 pm
SJU
- MSP
1 stop7h 39m
Delta
Mon 9/2810:35 am
MSP
- SJU
1 stop10h 25m
Delta
Deal found 5/28![Delta logo]()
$378
This Faresmojo deal was found by Cheapflights users on 5/24. 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 7/262:21 pm
SJU
- MSN
1 stop7h 38m
JetBlue
Sun 8/211:07 am
MSN
- SJU
1 stop8h 38m
JetBlue
Deal found 5/24![JetBlue logo]()
$416
This United Airlines deal was found by Cheapflights users on 5/27. 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 6/267:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sun 6/282:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/27![United Airlines logo]()
$424
This American Airlines deal was found by Cheapflights users on 5/24. 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 7/77:25 am
SJU
- MSN
2 stops11h 47m
American Airlines
Tue 7/146:00 am
MSN
- SJU
1 stop15h 57m
American Airlines
Deal found 5/24![American Airlines logo]()
$489
This Southwest deal was found by Cheapflights users on 5/26. 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 6/197:00 am
SJU
- MKE
1 stop12h 50m
Southwest
Tue 6/239:35 am
MKE
- SJU
1 stop12h 10m
Southwest
Deal found 5/26![Southwest logo]()
$456
This Delta deal was found by Cheapflights users on 5/28. 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 7/232:21 pm
SJU
- MKE
1 stop6h 59m
Delta
Thu 7/3012:58 pm
MKE
- SJU
1 stop6h 47m
Delta
Deal found 5/28![Delta logo]()
$434
This Faresmojo deal was found by Cheapflights users on 5/25. 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.
Tue 7/2112:56 pm
SJU
- ATW
1 stop10h 35m
JetBlue
Sun 8/95:31 am
ATW
- SJU
1 stop10h 06m
JetBlue
Deal found 5/25![JetBlue logo]()
$461
This United Airlines deal was found by Cheapflights users on 5/27. 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 7/83:56 pm
SJU
- MKE
1 stop7h 33m
United Airlines
Tue 7/148:50 am
MKE
- SJU
2 stops11h 34m
United Airlines
Deal found 5/27![United Airlines logo]()
$462
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am
SJU
- MSP
1 stop16h 54m
American Airlines
Sat 11/146:40 am
MSP
- SJU
2 stops12h 52m
American Airlines
Deal found 5/29![American Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 5/28. 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 7/97:35 am
SJU
- MKE
1 stop12h 49m
Delta
Sun 7/1210:11 am
MKE
- SJU
1 stop11h 18m
Delta
Deal found 5/28![Delta logo]()
$434
This Priceline deal was found by Cheapflights users on 5/27. 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.
Fri 6/124:15 pm
BQN
- ORD
2 stops21h 45m
Multiple Airlines
Tue 6/164:59 pm
ORD
- BQN
1 stop8h 06m
Multiple Airlines
Deal found 5/27![Multiple Airlines logo]()
$635
This Southwest deal was found by Cheapflights users on 5/27. 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 7/295:30 am
SJU
- MSP
2 stops10h 35m
Southwest
Tue 8/47:15 am
MSP
- SJU
2 stops10h 45m
Southwest
Deal found 5/27![Southwest logo]()
$532
This United Airlines deal was found by Cheapflights users on 5/26. 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 10/287:10 am
SJU
- ATW
1 stop9h 00m
United Airlines
Sat 10/318:20 am
ATW
- SJU
2 stops14h 16m
United Airlines
Deal found 5/26![United Airlines logo]()
$484
This American Airlines deal was found by Cheapflights users on 5/28. 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 7/147:25 am
SJU
- MSN
1 stop17h 17m
American Airlines
Wed 7/296:00 am
MSN
- SJU
1 stop15h 57m
American Airlines
Deal found 5/28![American Airlines logo]()
$534
This United Airlines deal was found by Cheapflights users on 5/28. 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 9/291:00 am
SJU
- ATW
2 stops11h 18m
United Airlines
Sat 10/38:20 am
ATW
- SJU
2 stops11h 18m
United Airlines
Deal found 5/28![United Airlines logo]()
$515
This Southwest deal was found by Cheapflights users on 5/27. 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 10/186:00 am
SJU
- MSP
2 stops10h 50m
Southwest
Sat 11/145:05 am
MSP
- SJU
2 stops9h 05m
Southwest
Deal found 5/27![Southwest logo]()
$568
This United Airlines deal was found by Cheapflights users on 5/28. 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 6/103:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Mon 6/152:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 5/28![United Airlines logo]()
$517
This Southwest deal was found by Cheapflights users on 5/26. 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 7/285:30 am
SJU
- MSP
2 stops10h 35m
Southwest
Sun 8/26:15 am
MSP
- SJU
2 stops9h 10m
Southwest
Deal found 5/26![Southwest logo]()
$606
This United Airlines deal was found by Cheapflights users on 5/24. 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 6/101:00 am
SJU
- ORD
1 stop7h 42m
United Airlines
Sun 6/141:30 pm
ORD
- SJU
1 stop6h 54m
United Airlines
Deal found 5/24![United Airlines logo]()
$565
This Southwest deal was found by Cheapflights users on 5/25. 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 7/85:30 am
SJU
- MSP
2 stops10h 35m
Southwest
Fri 7/174:00 pm
MSP
- SJU
2 stops8h 25m
Southwest
Deal found 5/25![Southwest logo]()
$630
Last-minute flights from Puerto Rico to WisconsinDiscover last-minute flight deals from Puerto Rico to Wisconsin. Data last updated May 29, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Wisconsin. Data last updated May 29, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 5/25. 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 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sat 5/3012:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/25![Frontier logo]()
$349
This Frontier deal was found by Cheapflights users on 5/25. 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 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Sun 5/3112:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/25![Frontier logo]()
$368
This American Airlines deal was found by Cheapflights users on 5/28. 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 6/210:29 am
SJU
- ORD
1 stop8h 16m
American Airlines
Fri 6/55:00 am
ORD
- SJU
1 stop6h 57m
American Airlines
Deal found 5/28![American Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 5/24. 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 6/410:29 am
SJU
- ORD
1 stop14h 01m
American Airlines
Sat 7/45:50 pm
ORD
- SJU
Nonstop4h 58m
American Airlines
Deal found 5/24![American Airlines logo]()
$361
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:21 am
SJU
- ORD
1 stop14h 08m
American Airlines
Tue 6/98:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 5/29![American Airlines logo]()
$351
This Frontier deal was found by Cheapflights users on 5/27. 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 6/116:00 am
SJU
- ORD
1 stop7h 24m
Frontier
Mon 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/27![Frontier logo]()
$367
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 6/166:00 am
SJU
- ORD
1 stop7h 24m
Frontier
Mon 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/24![Frontier logo]()
$303
This Faresmojo deal was found by Cheapflights users on 5/28. 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.
Thu 6/1812:54 pm
SJU
- MSN
1 stop10h 49m
JetBlue
Mon 6/225:52 am
MSN
- SJU
1 stop6h 39m
JetBlue
Deal found 5/28![JetBlue logo]()
$381
This eDestinos deal was found by Cheapflights users on 5/26. 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 6/204:20 pm
SJU
- MSP
Nonstop5h 30m
Sun Country Air
Wed 7/89:00 am
MSP
- SJU
Nonstop5h 18m
Sun Country Air
Deal found 5/26![Sun Country Air logo]()
$380
This American Airlines deal was found by Cheapflights users on 5/26. 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 6/256:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Mon 6/296:00 am
MKE
- SJU
1 stop16h 00m
American Airlines
Deal found 5/26![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 5/28. 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 6/266:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Sun 6/286:00 am
MKE
- SJU
1 stop16h 00m
American Airlines
Deal found 5/28![American Airlines logo]()
$366
This Expedia deal was found by Cheapflights users on 5/27. 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 6/279:37 pm
SJU
- ORD
1 stop11h 26m
Frontier
Sat 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/27![Frontier logo]()
$347
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 May 29, 2026.
Search for one-way flight options from Puerto Rico to Wisconsin. Find affordable one-way fares based on user searches. Data last updated May 29, 2026.
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Sun 8/2312:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 5/28![American Airlines logo]()
$114
This Delta deal was found by Cheapflights users on 5/28. 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 8/261:19 pm
SJU
- ORD
1 stop9h 33m
Delta
Deal found 5/28![Delta logo]()
$118
This Frontier deal was found by Cheapflights users on 5/27. 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 8/206:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/27![Frontier logo]()
$119
This American Airlines deal was found by Cheapflights users on 5/28. 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 8/127:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Deal found 5/28![American Airlines logo]()
$121
This American Airlines deal was found by Cheapflights users on 5/24. 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 8/133:47 pm
SJU
- ORD
1 stop9h 12m
American Airlines
Deal found 5/24![American Airlines logo]()
$122
This American Airlines deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:47 pm
SJU
- ORD
1 stop14h 47m
American Airlines
Deal found 5/26![American Airlines logo]()
$128
This Delta deal was found by Cheapflights users on 5/28. 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 6/102:14 pm
SJU
- ORD
1 stop7h 17m
Delta
Deal found 5/28![Delta logo]()
$138
This Orbitz deal was found by Cheapflights users on 5/27. 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 7/97:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/27![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 7/47:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/27![Frontier logo]()
$143
This Delta deal was found by Cheapflights users on 5/24. 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 6/21:14 pm
SJU
- ORD
1 stop8h 12m
Delta
Deal found 5/24![Delta logo]()
$148
This FlightHub deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:15 pm
SJU
- MSP
Nonstop5h 31m
Sun Country Air
Deal found 5/29![Sun Country Air logo]()
$149
This American Airlines deal was found by Cheapflights users on 5/28. 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 8/2412:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 5/28![American Airlines logo]()
$149
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 May 29, 2026.
Round-trip from | $223 (Frontier) |
|---|---|
One-way from | $114 (American Airlines) |
Popular in | March |
Cheapest in | January |
Average price | $416 |
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 May 29, 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
Tue 8/25
5:15 am-10:55 am
1 stop6h 40m
Milwaukee-Mitchell
Mon 8/31
1:55 pm-11:50 pm
1 stop8h 55m
$326
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Wed 8/5
5:49 pm-11:53 pm
1 stop7h 04m
Milwaukee-Mitchell
Fri 8/14
10:22 am-10:29 pm
1 stop11h 07m
$326
San JuanMadison
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Thu 10/1
2:22 pm-11:24 pm
1 stop10h 02m
Madison Truax Field
Sun 10/4
8:05 pm-2:40 pm
2 stops17h 35m
$326
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 8/20
6:30 am-4:20 pm
1 stop10h 50m
Milwaukee-Mitchell
Tue 8/25
6:05 am-1:35 pm
1 stop6h 30m
$326
San JuanMadison
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Tue 9/15
1:00 am-1:42 pm
2 stops13h 42m
Madison Truax Field
Sat 9/19
6:30 am-8:38 pm
2 stops13h 08m
$371
San JuanMadison
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Thu 8/6
7:30 am-9:19 pm
2 stops14h 49m
Madison Truax Field
Mon 8/10
5:43 am-4:38 pm
1 stop9h 55m
$378
San JuanMinneapolis
SJU - MSP
SJUMSP
San Juan Luis Munoz Marin Intl
Fri 9/25
5:41 pm-12:20 am
1 stop7h 39m
Minneapolis St Paul
Mon 9/28
10:35 am-10:00 pm
1 stop10h 25m
$378
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Wed 9/16
5:01 am-1:39 pm
1 stop9h 38m
Chicago O'Hare Intl
Sat 9/19
1:00 pm-10:39 pm
1 stop8h 39m
$381
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Tue 9/1
2:30 pm-11:44 pm
1 stop10h 14m
Chicago O'Hare Intl
Wed 9/2
9:39 am-6:36 pm
1 stop7h 57m
$391
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 7/28
4:55 pm-11:31 pm
1 stop7h 36m
Chicago O'Hare Intl
Fri 8/7
2:38 pm-8:34 pm
Nonstop4h 56m
$393
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-MKE
SJU-MSN
BQN-ORD
SJU-ORD
SJU-MSP
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-MKE
SJU-MSN
BQN-ORD
SJU-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 March is currently the most expensive (average of $256). 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 64 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 May 29, 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.
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 May 29, 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 May 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$108 | Average$399 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$399 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$521 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$439 | FlexibilityNo cancel fee | On-time63% |