$88+ 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 4/20. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 20 — Apr 271
Round-trip
1 adult, Economy
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Find cheap flights from Wisconsin to Puerto Rico with Cheapflights
1. Tell us where you want to go
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 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 March 21, 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 March 21, 2026.
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Sun 5/172:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/20![Frontier logo]()
$196
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$202
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Thu 4/303:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Wed 5/66:41 pm
SJU
- ORD
1 stop15h 56m
Frontier
Deal found 3/21![Frontier logo]()
$205
This Frontier deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:34 pm
ORD
- SJU
1 stop7h 18m
Frontier
Fri 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Deal found 3/19![Frontier logo]()
$206
This CheapOair deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/95:30 pm
ORD
- SJU
1 stop13h 34m
Frontier
Sat 5/166:41 pm
SJU
- ORD
1 stop15h 56m
Frontier
Deal found 3/20![Frontier logo]()
$207
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:05 am
ORD
- SJU
1 stop12h 50m
Multiple Airlines
Thu 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$208
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 5/155:30 pm
ORD
- SJU
1 stop13h 34m
Frontier
Fri 5/296:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 3/20![Frontier logo]()
$209
This Priceline deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/306:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$210
This Frontier deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:25 am
ORD
- SJU
1 stop9h 14m
Frontier
Sat 4/181:59 am
SJU
- ORD
1 stop12h 33m
Frontier
Deal found 3/21![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$212
This CheapOair deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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.
Fri 4/1011:55 am
ORD
- SJU
1 stop11h 30m
Multiple Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$213
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 March 21, 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 March 21, 2026.
This Orbitz deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Sat 5/162:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/20![Frontier logo]()
$222
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1210:40 am
GRB
- SJU
1 stop8h 54m
United Airlines
Thu 4/161:00 am
SJU
- GRB
2 stops11h 59m
United Airlines
Deal found 3/18![United Airlines logo]()
$270
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:19 am
ORD
- SJU
1 stop10h 53m
Delta
Fri 4/2412:55 pm
SJU
- ORD
1 stop8h 21m
Delta
Deal found 3/20![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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 4/125:24 pm
GRB
- SJU
2 stops16h 24m
American Airlines
Fri 4/177:25 am
SJU
- GRB
2 stops17h 06m
American Airlines
Deal found 3/21![American Airlines logo]()
$326
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:25 pm
MKE
- SJU
1 stop10h 50m
Southwest
Fri 7/245:15 pm
SJU
- MKE
1 stop7h 35m
Southwest
Deal found 3/19![Southwest logo]()
$326
This CheapOair deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Fri 5/155:30 pm
ORD
- BQN
1 stop7h 32m
Multiple Airlines
Wed 5/272:48 pm
BQN
- ORD
2 stops24h 42m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$405
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:55 pm
ORD
- PSE
1 stop16h 12m
Frontier
Tue 5/1210:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 3/17![Frontier logo]()
$264
This United Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:20 am
MKE
- SJU
1 stop9h 14m
United Airlines
Wed 8/52:05 am
SJU
- MKE
2 stops11h 43m
United Airlines
Deal found 3/16![United Airlines logo]()
$305
This CheapOair deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/203:55 pm
ORD
- BQN
1 stop18h 36m
Frontier
Sun 5/312:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/21![Frontier logo]()
$284
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/219:50 am
ORD
- SJU
1 stop9h 34m
Delta
Fri 4/242:03 pm
SJU
- ORD
1 stop7h 37m
Delta
Deal found 3/20![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:50 am
MSN
- SJU
1 stop15h 42m
American Airlines
Wed 4/291:31 pm
SJU
- MSN
2 stops11h 24m
American Airlines
Deal found 3/21![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:19 am
ORD
- SJU
1 stop10h 53m
Delta
Sat 5/27:30 am
SJU
- ORD
1 stop10h 12m
Delta
Deal found 3/20![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:30 pm
MKE
- SJU
1 stop7h 10m
Southwest
Tue 5/195:05 am
SJU
- MKE
1 stop7h 50m
Southwest
Deal found 3/19![Southwest logo]()
$349
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/285:00 am
GRB
- SJU
1 stop8h 44m
United Airlines
Thu 4/307:20 am
SJU
- GRB
2 stops12h 41m
United Airlines
Deal found 3/20![United Airlines logo]()
$326
This Priceline deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Thu 5/142:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/16![Frontier logo]()
$304
This Southwest deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:15 pm
ORD
- SJU
2 stops17h 20m
Southwest
Wed 5/135:05 am
SJU
- ORD
2 stops17h 50m
Southwest
Deal found 3/18![Southwest logo]()
$366
This Frontier deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:05 pm
ORD
- BQN
1 stop7h 48m
Frontier
Fri 4/172:38 am
BQN
- ORD
1 stop13h 45m
Frontier
Deal found 3/16![Frontier logo]()
$304
This United Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Wed 5/137:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/16![United Airlines logo]()
$336
This Delta deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/35:15 am
GRB
- SJU
1 stop10h 08m
Delta
Sat 5/92:35 pm
SJU
- GRB
1 stop6h 59m
Delta
Deal found 3/19![Delta logo]()
$338
This Trip.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:16 am
ORD
- BQN
2 stops15h 27m
Multiple Airlines
Sun 4/192:38 am
BQN
- ORD
2 stops31h 58m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$410
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:30 pm
ORD
- BQN
1 stop7h 32m
Multiple Airlines
Wed 5/272:48 pm
BQN
- ORD
2 stops24h 42m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$418
This Southwest deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:35 am
MKE
- SJU
1 stop9h 10m
Southwest
Wed 7/295:00 am
SJU
- MKE
1 stop7h 50m
Southwest
Deal found 3/19![Southwest logo]()
$387
This American Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:24 pm
GRB
- SJU
2 stops18h 05m
American Airlines
Mon 4/203:10 pm
SJU
- GRB
1 stop9h 21m
American Airlines
Deal found 3/16![American Airlines logo]()
$429
This CheapOair deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Sun 5/102:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/16![Frontier logo]()
$326
This United Airlines deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sat 5/167:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/16![United Airlines logo]()
$363
This Delta deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/305:55 am
MKE
- SJU
1 stop9h 43m
Delta
Fri 7/102:35 pm
SJU
- MKE
1 stop7h 30m
Delta
Deal found 3/17![Delta logo]()
$377
This CheapOair deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
- PSE
1 stop18h 28m
Multiple Airlines
Wed 4/158:39 am
PSE
- ORD
2 stops14h 00m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$426
This American Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:20 am
ATW
- SJU
1 stop15h 42m
American Airlines
Mon 4/2011:59 pm
SJU
- ATW
2 stops11h 28m
American Airlines
Deal found 3/19![American Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/2510:40 am
GRB
- SJU
2 stops9h 44m
United Airlines
Tue 4/287:20 am
SJU
- GRB
2 stops12h 53m
United Airlines
Deal found 3/20![United Airlines logo]()
$368
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:55 pm
ORD
- PSE
1 stop16h 12m
Frontier
Wed 5/1310:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 3/17![Frontier logo]()
$335
Last-minute flights from Wisconsin to Puerto RicoDiscover last-minute flight deals from Wisconsin to Puerto Rico. Data last updated March 21, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Puerto Rico. Data last updated March 21, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/74:34 pm
ORD
- SJU
1 stop7h 18m
Frontier
Fri 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Deal found 3/19![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$212
This CheapOair deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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.
Fri 4/1011:55 am
ORD
- SJU
1 stop11h 30m
Multiple Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$214
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$202
This Frontier deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:25 am
ORD
- SJU
1 stop9h 14m
Frontier
Sat 4/181:59 am
SJU
- ORD
1 stop12h 33m
Frontier
Deal found 3/21![Frontier logo]()
$211
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:17 am
ORD
- SJU
1 stop10h 38m
Multiple Airlines
Fri 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$208
This Priceline deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/306:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$210
This Frontier deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/172:20 pm
ORD
- SJU
1 stop9h 09m
Frontier
Sat 4/188:00 am
SJU
- ORD
1 stop8h 23m
Frontier
Deal found 3/20![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/205:48 pm
ORD
- SJU
1 stop14h 12m
Multiple Airlines
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$215
This CheapOair deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Thu 4/303:52 pm
ORD
- SJU
1 stop25h 07m
Frontier
Wed 5/66:41 pm
SJU
- ORD
1 stop15h 56m
Frontier
Deal found 3/21![Frontier logo]()
$205
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 March 21, 2026.
Search for one-way flight options from Wisconsin to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated March 21, 2026.
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/202:47 pm
MKE
- SJU
1 stop7h 42m
Frontier
Deal found 3/20![Frontier logo]()
$88
This WAYA deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:51 pm
ORD
- SJU
1 stop7h 28m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$98
This Priceline deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$99
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$101
This Super.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3010:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/19![Spirit Airlines logo]()
$104
This Priceline deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/199:33 am
MKE
- SJU
1 stop23h 21m
Frontier
Deal found 3/20![Frontier logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$105
This eDestinos deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:04 pm
ORD
- SJU
1 stop27h 44m
Frontier
Deal found 3/17![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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 4/148:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$108
This Cheapflightsfares deal was found by Cheapflights users on 3/21. Clicking the “Pick Dates” 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.
Sun 4/128:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 3/21![Spirit Airlines logo]()
$109
This CheapOair deal was found by Cheapflights users on 3/20. Clicking the “Pick Dates” 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.
Thu 4/98:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 3/20![Spirit Airlines logo]()
$110
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 March 21, 2026.
Round-trip from | $196 (Priceline) |
|---|---|
One-way from | $88 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $498 |
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 March 21, 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
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 5/8
5:30 pm-2:02 am
1 stop7h 32m
Aguadilla Borinquen
Sat 5/16
2:59 am-11:13 pm
1 stop21h 14m
$222
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Wed 5/6
3:55 pm-9:07 am
1 stop16h 12m
Ponce Mercedita
Tue 5/12
10:02 am-11:13 pm
1 stop14h 11m
$264
Green BaySan Juan
GRB - SJU
GRBSJU
Green Bay Austin-Straubel
Sun 4/12
10:40 am-8:34 pm
1 stop8h 54m
San Juan Luis Munoz Marin Intl
Thu 4/16
1:00 am-11:59 am
2 stops11h 59m
$270
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 5/20
3:55 pm-11:31 am
1 stop18h 36m
Aguadilla Borinquen
Sun 5/31
2:59 am-11:13 pm
1 stop21h 14m
$284
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 5/8
5:30 pm-2:02 am
1 stop7h 32m
Aguadilla Borinquen
Thu 5/14
2:59 am-11:13 pm
1 stop21h 14m
$304
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 4/10
5:05 pm-1:53 am
1 stop7h 48m
Aguadilla Borinquen
Fri 4/17
2:38 am-3:23 pm
1 stop13h 45m
$304
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 5/6
10:20 am-8:34 pm
1 stop9h 14m
San Juan Luis Munoz Marin Intl
Wed 8/5
2:05 am-12:48 pm
2 stops11h 43m
$305
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/22
11:19 am-11:12 pm
1 stop10h 53m
San Juan Luis Munoz Marin Intl
Fri 4/24
12:55 pm-8:16 pm
1 stop8h 21m
$316
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/21
9:50 am-8:24 pm
1 stop9h 34m
San Juan Luis Munoz Marin Intl
Fri 4/24
2:03 pm-8:40 pm
1 stop7h 37m
$316
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/22
11:19 am-11:12 pm
1 stop10h 53m
San Juan Luis Munoz Marin Intl
Sat 5/2
7:30 am-4:42 pm
1 stop10h 12m
$316
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.
MKE-SJU
ORD-SJU
ORD-BQN
GRB-SJU
ORD-PSE
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
MKE-SJU
ORD-SJU
ORD-BQN
GRB-SJU
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 $102). Flying from Wisconsin to Puerto Rico in June is currently the most expensive (average of $359). 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.
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Return Flight Options
Top destinations
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 March 21, 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 6 airlines flying from Wisconsin to Puerto Rico
Discover the top 6 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 March 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$559 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$117 | Average$420 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$202 | Average$532 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$208 | Average$366 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$215 | Average$554 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$483 | FlexibilityNo cancel fee | On-time63% |