$88+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
May 9 — May 161
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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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 April 9, 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 April 9, 2026.
This eDestinos deal was found by Cheapflights users on 4/5. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:13 am
SJU
- ORD
1 stop21h 00m
Frontier
Sun 5/105:49 pm
ORD
- SJU
1 stop22h 37m
Frontier
Deal found 4/5![Frontier logo]()
$159
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:30 am
SJU
- ORD
1 stop26h 35m
Multiple Airlines
Sat 5/21:27 pm
ORD
- SJU
1 stop21h 56m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$173
This Cheapflightsfares deal was found by Cheapflights users on 4/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/244:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sun 4/267:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Deal found 4/5![Spirit Airlines logo]()
$174
This Expedia deal was found by Cheapflights users on 4/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/244:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 4/277:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Deal found 4/4![Spirit Airlines logo]()
$175
This Priceline deal was found by Cheapflights users on 4/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/293:21 am
SJU
- MKE
1 stop9h 05m
Frontier
Mon 5/412:21 pm
MKE
- SJU
1 stop12h 40m
Frontier
Deal found 4/8![Frontier logo]()
$176
This Expedia deal was found by Cheapflights users on 4/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:41 pm
SJU
- ORD
1 stop23h 09m
Frontier
Wed 5/133:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Deal found 4/6![Frontier logo]()
$176
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 4/2710:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$177
This eDestinos deal was found by Cheapflights users on 4/5. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Tue 5/123:55 pm
ORD
- SJU
1 stop20h 20m
Frontier
Deal found 4/5![Frontier logo]()
$178
This eDestinos deal was found by Cheapflights users on 4/8. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Sat 4/256:40 am
ORD
- SJU
1 stop17h 18m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$179
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Sat 5/21:27 pm
ORD
- SJU
1 stop21h 56m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 4/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:00 pm
SJU
- ORD
1 stop19h 05m
Spirit Airlines
Sun 4/267:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Deal found 4/5![Spirit Airlines logo]()
$182
This Expedia deal was found by Cheapflights users on 4/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:03 pm
SJU
- ORD
1 stop8h 36m
Multiple Airlines
Mon 4/277:50 am
ORD
- SJU
1 stop16h 08m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$183
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 April 9, 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 April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:38 am
BQN
- ORD
1 stop11h 22m
Multiple Airlines
Sun 4/266:40 am
ORD
- BQN
1 stop18h 03m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$301
This Delta deal was found by Cheapflights users on 4/9. 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.
Wed 7/82:42 pm
SJU
- ORD
1 stop10h 11m
Delta
Wed 7/156:00 am
ORD
- SJU
1 stop9h 38m
Delta
Deal found 4/9![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 4/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:45 am
SJU
- ATW
1 stop17h 02m
American Airlines
Mon 5/116:30 pm
ATW
- SJU
2 stops16h 33m
American Airlines
Deal found 4/6![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/5. 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.
Thu 4/303:56 pm
SJU
- MKE
1 stop7h 37m
United Airlines
Tue 5/59:37 am
MKE
- SJU
2 stops10h 47m
United Airlines
Deal found 4/5![United Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 4/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:50 am
SJU
- MKE
1 stop13h 20m
Southwest
Tue 5/59:15 am
MKE
- SJU
2 stops10h 50m
Southwest
Deal found 4/7![Southwest logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/62:59 am
BQN
- ORD
2 stops21h 02m
Frontier
Thu 5/145:30 pm
ORD
- BQN
1 stop7h 44m
Frontier
Deal found 4/6![Frontier logo]()
$399
This Delta deal was found by Cheapflights users on 4/9. 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.
Fri 7/107:30 am
SJU
- ORD
1 stop10h 14m
Delta
Mon 7/209:45 am
ORD
- SJU
1 stop11h 44m
Delta
Deal found 4/9![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 4/5. 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 9/242:35 pm
SJU
- MKE
1 stop7h 10m
Southwest
Mon 9/281:55 pm
MKE
- SJU
1 stop7h 20m
Southwest
Deal found 4/5![Southwest logo]()
$326
This American Airlines deal was found by Cheapflights users on 4/5. 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 6/56:20 am
SJU
- MSN
1 stop12h 02m
American Airlines
Mon 6/86:01 am
MSN
- SJU
1 stop16h 00m
American Airlines
Deal found 4/5![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/7. 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 4/227:40 am
SJU
- MSN
1 stop7h 11m
United Airlines
Wed 4/298:30 am
MSN
- SJU
2 stops11h 54m
United Airlines
Deal found 4/7![United Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 4/9. 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.
Wed 7/155:56 pm
SJU
- ORD
1 stop6h 57m
Delta
Mon 7/209:45 am
ORD
- SJU
1 stop11h 44m
Delta
Deal found 4/9![Delta logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:35 am
MAZ
- ORD
2 stops30h 30m
Multiple Airlines
Sun 4/2610:00 am
ORD
- MAZ
1 stop22h 42m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 4/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:45 pm
SJU
- MKE
1 stop6h 40m
Delta
Mon 8/315:55 am
MKE
- SJU
1 stop9h 40m
Delta
Deal found 4/4![Delta logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/96:00 am
SJU
- ATW
1 stop27h 46m
Multiple Airlines
Sun 7/192:44 pm
ATW
- SJU
2 stops33h 00m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$369
This Priceline deal was found by Cheapflights users on 4/9. 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.
Tue 5/262:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Sat 6/65:11 pm
ORD
- BQN
1 stop7h 51m
Frontier
Deal found 4/9![Frontier logo]()
$414
This American Airlines deal was found by Cheapflights users on 4/8. 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.
Thu 5/76:00 am
SJU
- MSN
1 stop18h 28m
American Airlines
Tue 5/126:00 am
MSN
- SJU
2 stops11h 10m
American Airlines
Deal found 4/8![American Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 4/7. 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.
Fri 5/13:56 pm
SJU
- MSN
1 stop7h 58m
United Airlines
Wed 5/66:30 am
MSN
- SJU
2 stops13h 54m
United Airlines
Deal found 4/7![United Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 4/7. 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.
Thu 7/92:05 pm
SJU
- MKE
1 stop7h 15m
Delta
Tue 8/412:56 pm
MKE
- SJU
1 stop8h 33m
Delta
Deal found 4/7![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 4/6. 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 5/65:05 am
SJU
- ORD
2 stops17h 50m
Southwest
Mon 5/114:15 pm
ORD
- SJU
2 stops17h 20m
Southwest
Deal found 4/6![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 4/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:56 pm
SJU
- MSN
1 stop8h 53m
United Airlines
Sat 4/2510:50 am
MSN
- SJU
1 stop8h 44m
United Airlines
Deal found 4/4![United Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 4/8. 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.
Thu 7/232:05 pm
SJU
- MKE
1 stop7h 15m
Delta
Wed 7/2910:11 am
MKE
- SJU
1 stop9h 34m
Delta
Deal found 4/8![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 4/5. 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 6/56:20 am
SJU
- MSN
1 stop12h 02m
American Airlines
Wed 6/177:00 am
MSN
- SJU
1 stop14h 45m
American Airlines
Deal found 4/5![American Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 4/5. 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 5/75:35 am
SJU
- MSP
2 stops10h 25m
Southwest
Mon 5/112:25 pm
MSP
- SJU
2 stops8h 30m
Southwest
Deal found 4/5![Southwest logo]()
$408
This Priceline deal was found by Cheapflights users on 4/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/92:59 am
BQN
- ORD
1 stop21h 14m
Multiple Airlines
Sun 5/176:00 am
ORD
- BQN
2 stops42h 52m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$416
This Frontier deal was found by Cheapflights users on 4/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:25 am
SJU
- MSP
1 stop10h 49m
Frontier
Mon 6/295:09 pm
MSP
- SJU
1 stop10h 46m
Frontier
Deal found 4/4![Frontier logo]()
$471
This Delta deal was found by Cheapflights users on 4/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1112:54 pm
SJU
- MKE
1 stop8h 58m
Delta
Mon 6/153:00 pm
MKE
- SJU
1 stop6h 27m
Delta
Deal found 4/4![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 4/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/261:20 pm
SJU
- MSP
2 stops10h 00m
Southwest
Fri 9/412:15 pm
MSP
- SJU
1 stop9h 35m
Southwest
Deal found 4/4![Southwest logo]()
$408
This Delta deal was found by Cheapflights users on 4/5. 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.
Fri 5/87:30 am
SJU
- MKE
1 stop8h 46m
Delta
Mon 5/187:09 am
MKE
- SJU
1 stop8h 24m
Delta
Deal found 4/5![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/283:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Tue 5/52:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 4/4![United Airlines logo]()
$447
This Priceline deal was found by Cheapflights users on 4/9. 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.
Tue 5/262:59 am
BQN
- ORD
1 stop21h 14m
Multiple Airlines
Sat 6/61:55 pm
ORD
- BQN
2 stops12h 02m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$456
Last-minute flights from Puerto Rico to WisconsinDiscover last-minute flight deals from Puerto Rico to Wisconsin. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Wisconsin. Data last updated April 9, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 4/8. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Sat 4/256:40 am
ORD
- SJU
1 stop17h 18m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 4/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:00 pm
SJU
- ORD
1 stop19h 05m
Spirit Airlines
Sun 4/267:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Deal found 4/5![Spirit Airlines logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 4/2710:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$177
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Sat 5/21:27 pm
ORD
- SJU
1 stop21h 56m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$181
This Expedia deal was found by Cheapflights users on 4/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/233:03 pm
SJU
- ORD
1 stop8h 36m
Multiple Airlines
Mon 4/277:50 am
ORD
- SJU
1 stop16h 08m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 4/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/244:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sun 4/267:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Deal found 4/5![Spirit Airlines logo]()
$174
This Expedia deal was found by Cheapflights users on 4/4. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/244:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 4/277:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Deal found 4/4![Spirit Airlines logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:30 am
SJU
- ORD
1 stop26h 35m
Multiple Airlines
Sat 5/21:27 pm
ORD
- SJU
1 stop21h 56m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$173
This Priceline deal was found by Cheapflights users on 4/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/293:21 am
SJU
- MKE
1 stop9h 05m
Frontier
Mon 5/412:21 pm
MKE
- SJU
1 stop12h 40m
Frontier
Deal found 4/8![Frontier logo]()
$176
This eDestinos deal was found by Cheapflights users on 4/5. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:13 am
SJU
- ORD
1 stop21h 00m
Frontier
Sun 5/105:49 pm
ORD
- SJU
1 stop22h 37m
Frontier
Deal found 4/5![Frontier logo]()
$159
This Expedia deal was found by Cheapflights users on 4/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:41 pm
SJU
- ORD
1 stop23h 09m
Frontier
Wed 5/133:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Deal found 4/6![Frontier logo]()
$176
This eDestinos deal was found by Cheapflights users on 4/5. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Tue 5/123:55 pm
ORD
- SJU
1 stop20h 20m
Frontier
Deal found 4/5![Frontier logo]()
$178
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 April 9, 2026.
Search for one-way flight options from Puerto Rico to Wisconsin. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Priceline deal was found by Cheapflights users on 4/4. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/23:26 pm
SJU
- MKE
1 stop18h 12m
Frontier
Deal found 4/4![Frontier logo]()
$88
This Priceline deal was found by Cheapflights users on 4/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:30 am
SJU
- MKE
1 stop29h 56m
Frontier
Deal found 4/5![Frontier logo]()
$94
This Frontier deal was found by Cheapflights users on 4/8. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/43:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/8![Frontier logo]()
$98
This OneTravel deal was found by Cheapflights users on 4/7. 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2910:54 am
SJU
- MKE
1 stop25h 32m
Frontier
Deal found 4/7![Frontier logo]()
$111
This Priceline deal was found by Cheapflights users on 4/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/223:19 pm
SJU
- MKE
1 stop21h 07m
Frontier
Deal found 4/6![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:04 pm
SJU
- ORD
1 stop17h 33m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 4/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2512:57 pm
SJU
- ORD
1 stop9h 20m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$117
This Super.com deal was found by Cheapflights users on 4/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/5![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 4/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/164:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$119
This FlightHub deal was found by Cheapflights users on 4/6. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/121:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:00 pm
SJU
- ORD
2 stops34h 59m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$121
This Delta deal was found by Cheapflights users on 4/8. 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.
Fri 5/152:35 pm
SJU
- MSN
1 stop7h 14m
Delta
Deal found 4/8![Delta logo]()
$123
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 April 9, 2026.
Round-trip from | $159 (eDestinos) |
|---|---|
One-way from | $88 (Priceline) |
Popular in | March |
Cheapest in | January |
Average price | $329 |
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 April 9, 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
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Tue 4/21
2:38 am-1:00 pm
1 stop11h 22m
Chicago O'Hare Intl
Sun 4/26
6:40 am-1:43 am
1 stop18h 03m
$301
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 7/8
2:42 pm-11:53 pm
1 stop10h 11m
Chicago O'Hare Intl
Wed 7/15
6:00 am-4:38 pm
1 stop9h 38m
$316
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 7/10
7:30 am-4:44 pm
1 stop10h 14m
Chicago O'Hare Intl
Mon 7/20
9:45 am-10:29 pm
1 stop11h 44m
$316
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 7/15
5:56 pm-11:53 pm
1 stop6h 57m
Chicago O'Hare Intl
Mon 7/20
9:45 am-10:29 pm
1 stop11h 44m
$316
San JuanAppleton
SJU - ATW
SJUATW
San Juan Luis Munoz Marin Intl
Thu 5/7
6:45 am-10:47 pm
1 stop17h 02m
Appleton Intl
Mon 5/11
6:30 pm-12:03 pm
2 stops16h 33m
$326
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 4/30
3:56 pm-10:33 pm
1 stop7h 37m
Milwaukee-Mitchell
Tue 5/5
9:37 am-9:24 pm
2 stops10h 47m
$326
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Fri 5/1
6:50 am-7:10 pm
1 stop13h 20m
Milwaukee-Mitchell
Tue 5/5
9:15 am-9:05 pm
2 stops10h 50m
$326
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 9/24
2:35 pm-8:45 pm
1 stop7h 10m
Milwaukee-Mitchell
Mon 9/28
1:55 pm-10:15 pm
1 stop7h 20m
$326
San JuanMadison
SJU - MSN
SJUMSN
San Juan Luis Munoz Marin Intl
Fri 6/5
6:20 am-5:22 pm
1 stop12h 02m
Madison Truax Field
Mon 6/8
6:01 am-11:01 pm
1 stop16h 00m
$326
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 8/27
5:45 pm-11:25 pm
1 stop6h 40m
Milwaukee-Mitchell
Mon 8/31
5:55 am-4:35 pm
1 stop9h 40m
$326
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Puerto Rico with our price prediction graph.
SJU-ORD
SJU-MKE
BQN-ORD
SJU-ATW
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
BQN-ORD
SJU-ATW
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 $117). Flying from Puerto Rico to Wisconsin in June is currently the most expensive (average of $333). 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 April 9, 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.
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
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
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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 April 9, 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 April 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$399 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$215 | Average$399 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$464 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$399 | FlexibilityNo cancel fee | On-time63% |