$118+ Cheap flights from Puerto Rico to Chicago (CHI)
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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
jul. 20 — jul. 271
Round-trip
1 adult, Economy
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Cheapest flights from Puerto Rico to ChicagoExplore the most affordable flight options available from Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 20, 2026.
Explore the most affordable flight options available from Puerto Rico to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/76:00 am
SJU
- ORD
1 stop31h 15m
Frontier
sáb. 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/15![Frontier logo]()
$225
This Frontier deal was found by Cheapflights users on 6/16. 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.
jue. 9/36:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
dom. 9/612:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/16![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/266:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
mar. 9/112:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/15![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/216:00 am
SJU
- ORD
1 stop31h 25m
Frontier
vie. 9/412:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/15![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 6/16. 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.
jue. 8/276:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
vie. 8/2812:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/16![Frontier logo]()
$230
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/192:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
sáb. 8/228:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/15![United Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/196:45 am
SJU
- ORD
1 stop31h 15m
Frontier
dom. 8/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/17![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
lun. 9/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/17![Frontier logo]()
$234
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/258:20 am
SJU
- MDW
1 stop7h 25m
Southwest
lun. 8/315:00 am
MDW
- SJU
1 stop7h 45m
Southwest
Deal found 6/15![Southwest logo]()
$236
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/275:10 pm
SJU
- ORD
1 stop8h 25m
American Airlines
sáb. 8/296:59 pm
ORD
- SJU
1 stop13h 44m
American Airlines
Deal found 6/17![American Airlines logo]()
$236
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/187:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
mié. 8/265:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/17![American Airlines logo]()
$237
This Frontier deal was found by Cheapflights users on 6/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/46:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
dom. 9/612:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/17![Frontier logo]()
$238
Best flights from Puerto Rico to ChicagoDiscover carefully curated flight deals from Puerto Rico to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated junio 20, 2026.
Discover carefully curated flight deals from Puerto Rico to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated junio 20, 2026.
This Southwest deal was found by Cheapflights users on 6/19. 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.
jue. 9/35:30 am
SJU
- MDW
1 stop9h 35m
Southwest
lun. 9/73:15 pm
MDW
- SJU
1 stop6h 50m
Southwest
Deal found 6/19![Southwest logo]()
$246
This American Airlines deal was found by Cheapflights users on 6/19. 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.
jue. 8/207:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
lun. 8/316:00 am
ORD
- SJU
1 stop9h 11m
American Airlines
Deal found 6/19![American Airlines logo]()
$246
This Priceline deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
dom. 8/3012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/19![Frontier logo]()
$254
This Delta deal was found by Cheapflights users on 6/19. 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.
mié. 8/1912:56 pm
SJU
- MDW
1 stop10h 40m
Delta
vie. 8/2812:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/19![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/231:00 am
SJU
- ORD
1 stop9h 13m
United Airlines
lun. 8/315:30 am
ORD
- SJU
1 stop9h 12m
United Airlines
Deal found 6/15![United Airlines logo]()
$272
This Cheapflightsfares deal was found by Cheapflights users on 6/19. 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.
mar. 7/215:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
sáb. 8/82:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 6/19![JetBlue logo]()
$384
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/216:00 am
SJU
- MDW
1 stop7h 40m
Southwest
dom. 8/238:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/15![Southwest logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 7/127:35 am
MAZ
- ORD
1 stop16h 52m
Multiple Airlines
vie. 7/1712:44 am
ORD
- MAZ
1 stop11h 00m
Multiple Airlines
Deal found 6/15![Multiple Airlines logo]()
$562
This Southwest deal was found by Cheapflights users on 6/18. 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.
jue. 8/138:55 pm
SJU
- MDW
1 stop12h 50m
Southwest
sáb. 8/227:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Deal found 6/18![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 6/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/127:00 am
SJU
- MDW
1 stop10h 15m
Delta
mar. 8/186:05 am
MDW
- SJU
1 stop9h 33m
Delta
Deal found 6/18![Delta logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/16. 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.
vie. 6/267:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
mar. 6/306:29 pm
ORD
- SJU
1 stop10h 00m
United Airlines
Deal found 6/16![United Airlines logo]()
$357
This Southwest deal was found by Cheapflights users on 6/19. 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.
mié. 8/121:20 pm
SJU
- MDW
1 stop6h 50m
Southwest
dom. 8/168:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Deal found 6/19![Southwest logo]()
$336
This JetBlue deal was found by Cheapflights users on 6/19. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/134:58 pm
SJU
- ORD
1 stop7h 46m
JetBlue
lun. 8/177:00 am
ORD
- SJU
1 stop10h 51m
JetBlue
Deal found 6/19![JetBlue logo]()
$416
This Frontier deal was found by Cheapflights users on 6/16. 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.
dom. 7/1212:04 pm
BQN
- ORD
1 stop12h 06m
Frontier
dom. 7/265:13 pm
ORD
- BQN
1 stop7h 57m
Frontier
Deal found 6/16![Frontier logo]()
$506
This Southwest deal was found by Cheapflights users on 6/18. 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.
vie. 6/2610:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
lun. 6/2911:35 am
MDW
- SJU
1 stop11h 50m
Southwest
Deal found 6/18![Southwest logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 6/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/27:35 am
MAZ
- ORD
2 stops33h 18m
Multiple Airlines
dom. 7/512:44 am
ORD
- MAZ
1 stop11h 00m
Multiple Airlines
Deal found 6/17![Multiple Airlines logo]()
$566
This Frontier deal was found by Cheapflights users on 6/16. 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.
sáb. 6/2712:19 pm
BQN
- ORD
1 stop12h 00m
Frontier
mié. 7/14:59 pm
ORD
- BQN
1 stop8h 44m
Frontier
Deal found 6/16![Frontier logo]()
$531
This FlightHub deal was found by Cheapflights users on 6/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/115:01 am
BQN
- ORD
2 stops12h 15m
JetBlue
vie. 7/242:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 6/17![JetBlue logo]()
$533
This United Airlines deal was found by Cheapflights users on 6/18. 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.
lun. 7/2012:15 am
BQN
- ORD
1 stop9h 45m
United Airlines
sáb. 8/812:11 pm
ORD
- BQN
1 stop9h 58m
United Airlines
Deal found 6/18![United Airlines logo]()
$566
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/2410:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
lun. 7/272:30 pm
MDW
- SJU
1 stop8h 50m
Southwest
Deal found 6/15![Southwest logo]()
$441
This Expedia deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/2512:19 pm
BQN
- ORD
1 stop12h 00m
Frontier
mar. 6/304:59 pm
ORD
- BQN
1 stop8h 06m
Frontier
Deal found 6/15![Frontier logo]()
$536
This United Airlines deal was found by Cheapflights users on 6/18. 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.
sáb. 9/52:55 pm
SJU
- ORD
1 stop11h 04m
United Airlines
mar. 9/81:00 pm
ORD
- SJU
2 stops9h 50m
United Airlines
Deal found 6/18![United Airlines logo]()
$590
This Southwest deal was found by Cheapflights users on 6/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/175:30 am
SJU
- MDW
2 stops9h 35m
Southwest
lun. 7/202:30 pm
MDW
- SJU
1 stop8h 50m
Southwest
Deal found 6/17![Southwest logo]()
$451
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
mar. 6/303:00 am
BQN
- ORD
1 stop21h 19m
Frontier
dom. 7/57:15 am
ORD
- BQN
2 stops41h 55m
Frontier
Deal found 6/16![Frontier logo]()
$615
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
lun. 6/293:00 am
BQN
- ORD
1 stop21h 19m
Frontier
dom. 7/57:05 am
ORD
- BQN
2 stops18h 05m
Frontier
Deal found 6/16![Frontier logo]()
$654
This United Airlines deal was found by Cheapflights users on 6/18. 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.
sáb. 8/291:19 pm
MAZ
- ORD
2 stops11h 21m
United Airlines
mié. 9/25:00 am
ORD
- MAZ
2 stops10h 11m
United Airlines
Deal found 6/18![United Airlines logo]()
$1,277
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/247:30 am
VQS
- ORD
1 stop13h 35m
United Airlines
mié. 8/268:55 am
ORD
- VQS
1 stop8h 35m
United Airlines
Deal found 6/17![United Airlines logo]()
$1,463
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/2310:48 am
CPX
- ORD
2 stops11h 11m
United Airlines
jue. 9/248:55 am
ORD
- CPX
1 stop7h 26m
United Airlines
Deal found 6/15![United Airlines logo]()
$1,553
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/141:19 pm
MAZ
- ORD
2 stops19h 21m
United Airlines
mar. 8/189:39 pm
ORD
- MAZ
2 stops17h 32m
United Airlines
Deal found 6/15![United Airlines logo]()
$1,702
This Delta deal was found by Cheapflights users on 6/19. 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.
vie. 9/47:30 am
SJU
- ORD
2 stops11h 59m
Delta
dom. 9/137:00 am
ORD
- SJU
2 stops14h 00m
Delta
Deal found 6/19![Delta logo]()
$3,394
Last-minute flights from Puerto Rico to ChicagoDiscover last-minute flight deals from Puerto Rico to Chicago. Data last updated junio 20, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to Chicago. Data last updated junio 20, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/196:30 pm
SJU
- MDW
1 stop7h 10m
Southwest
lun. 6/225:10 pm
MDW
- SJU
1 stop7h 10m
Southwest
Deal found 6/15![Southwest logo]()
$371
This United Airlines deal was found by Cheapflights users on 6/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/241:00 am
SJU
- ORD
1 stop7h 42m
United Airlines
sáb. 6/2711:15 am
ORD
- SJU
1 stop9h 09m
United Airlines
Deal found 6/17![United Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 6/19. 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.
mié. 6/246:21 am
SJU
- ORD
1 stop8h 56m
American Airlines
mar. 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/19![American Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/247:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
lun. 6/296:40 pm
ORD
- SJU
1 stop9h 49m
United Airlines
Deal found 6/15![United Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 6/19. 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.
mié. 6/246:21 am
SJU
- ORD
1 stop8h 56m
American Airlines
sáb. 6/278:00 am
ORD
- SJU
1 stop13h 45m
American Airlines
Deal found 6/19![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 6/19. 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.
jue. 6/251:47 pm
SJU
- ORD
1 stop11h 47m
American Airlines
sáb. 6/2711:40 am
ORD
- SJU
1 stop10h 20m
American Airlines
Deal found 6/19![American Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 6/19. 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.
jue. 6/257:00 am
SJU
- ORD
1 stop11h 42m
American Airlines
mar. 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/19![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/267:00 am
SJU
- ORD
1 stop11h 42m
American Airlines
mar. 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/17![American Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 6/19. 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.
vie. 6/2610:20 pm
SJU
- MDW
1 stop12h 30m
Southwest
lun. 7/63:00 pm
MDW
- SJU
1 stop8h 35m
Southwest
Deal found 6/19![Southwest logo]()
$366
This Frontier deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/279:37 pm
SJU
- ORD
1 stop11h 26m
Frontier
vie. 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/15![Frontier logo]()
$369
This eDestinos deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/296:00 am
SJU
- ORD
1 stop18h 19m
Frontier
lun. 7/2012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/16![Frontier logo]()
$367
This Southwest deal was found by Cheapflights users on 6/19. 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.
vie. 7/1710:20 pm
SJU
- MDW
1 stop11h 30m
Southwest
lun. 7/205:10 pm
MDW
- SJU
1 stop7h 15m
Southwest
Deal found 6/19![Southwest logo]()
$346
One-way flights from Puerto Rico to ChicagoSearch for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Data last updated junio 20, 2026.
Search for one-way flight options from Puerto Rico to Chicago. Find affordable one-way fares based on user searches. Data last updated junio 20, 2026.
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/2610:33 am
SJU
- ORD
1 stop15h 02m
American Airlines
Deal found 6/17![American Airlines logo]()
$118
This eDestinos deal was found by Cheapflights users on 6/18. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/46:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/15![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/186:45 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/19![Frontier logo]()
$122
This Southwest deal was found by Cheapflights users on 6/19. 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.
jue. 8/138:55 pm
SJU
- MDW
2 stops15h 30m
Southwest
Deal found 6/19![Southwest logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/19. 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.
dom. 8/237:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Deal found 6/19![American Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/18. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/147:00 am
SJU
- ORD
1 stop13h 46m
American Airlines
Deal found 6/18![American Airlines logo]()
$126
This Super.com deal was found by Cheapflights users on 6/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/177:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$127
This Southwest deal was found by Cheapflights users on 6/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/172:35 pm
SJU
- MDW
1 stop9h 05m
Southwest
Deal found 6/20![Southwest logo]()
$128
This Southwest deal was found by Cheapflights users on 6/19. 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.
lun. 9/78:55 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 6/19![Southwest logo]()
$133
This Southwest deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/2510:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Deal found 6/15![Southwest logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 6/18. 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.
dom. 9/138:30 am
SJU
- MDW
2 stops38h 28m
Frontier
Deal found 6/18![Frontier logo]()
$170
Find flight deals from Puerto Rico to Chicago
Keep the following information in mind while searching for Puerto Rico to Chicago flight deals. Data was last updated junio 20, 2026.
Round-trip from | $225 (Kiwi.com) |
|---|---|
One-way from | $118 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $412 |
Good round-trip deal | $435 or less |
Good one-way deal | $194 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico to Chicago 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 junio 20, 2026.
Use the filters below to find and compare flights from Puerto Rico to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
jue. 9/3
5:30 am-2:05 pm
1 stop9h 35m
Chicago Midway
lun. 9/7
3:15 pm-11:05 pm
1 stop6h 50m
$246
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
jue. 8/20
7:24 pm-7:34 am
1 stop13h 10m
Chicago O'Hare Intl
lun. 8/31
6:00 am-4:11 pm
1 stop9h 11m
$246
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
jue. 8/20
7:14 pm-11:27 pm
Nonstop5h 13m
Chicago O'Hare Intl
dom. 8/30
12:44 am-6:44 am
Nonstop5h 00m
$254
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
mié. 8/19
12:56 pm-10:36 pm
1 stop10h 40m
Chicago Midway
vie. 8/28
12:46 pm-10:29 pm
1 stop8h 43m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
vie. 8/21
6:00 am-12:40 pm
1 stop7h 40m
Chicago Midway
dom. 8/23
8:05 pm-9:10 am
1 stop12h 05m
$256
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
jue. 8/13
8:55 pm-8:45 am
1 stop12h 50m
Chicago Midway
sáb. 8/22
7:50 am-4:40 pm
2 stops7h 50m
$256
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
dom. 8/23
1:00 am-9:13 am
1 stop9h 13m
Chicago O'Hare Intl
lun. 8/31
5:30 am-3:42 pm
1 stop9h 12m
$272
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
mié. 8/12
7:00 am-4:15 pm
1 stop10h 15m
Chicago Midway
mar. 8/18
6:05 am-4:38 pm
1 stop9h 33m
$316
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
mié. 8/12
1:20 pm-7:10 pm
1 stop6h 50m
Chicago Midway
dom. 8/16
8:05 pm-9:10 am
1 stop12h 05m
$336
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
vie. 6/26
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
mar. 6/30
6:29 pm-5:29 am
1 stop10h 00m
$357
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Puerto Rico with our price prediction graph.
SJU-MDW
SJU-ORD
BQN-ORD
MAZ-ORD
BQN-MDW
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 Chicago
PR0-CHI
SJU-MDW
SJU-ORD
BQN-ORD
MAZ-ORD
What is the cheapest month to book a flight from Puerto Rico to Chicago?
Currently, May is the cheapest month in which you can book a flight from Puerto Rico to Chicago (average of $64). Flying from Puerto Rico to Chicago in June is currently the most expensive (average of $915). 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.
What is the cheapest time of day to fly from PR to CHI?
Find hourly flight availability from Puerto Rico to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated junio 20, 2026.
When flying from Puerto Rico to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 22% versus a flight in the afternoon.
Weekly flight availability from Puerto Rico to Chicago
Explore weekly flight availability from Puerto Rico to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated junio 20, 2026.
The most flights from PR0 to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).
How often are flights from Puerto Rico to Chicago delayed?
About 8% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 183 minutes.
What is the most punctual flight time for Puerto Rico to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Puerto Rico to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 4% of flights being delayed.
How far ahead should I book a flight from Puerto Rico to Chicago?
Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from Puerto Rico to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Puerto Rico to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to Chicago. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their Puerto Rico to Chicago flight should consider departing on Sunday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated junio 20, 2026.
Read reviews from past customers who have flown United Airlines,American Airlines, andJetBlue from Puerto Rico to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Entertainment
7.1
Food
6.6
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Entertainment
7.1
Food
6.6
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Entertainment
7.1
Food
6.6
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Entertainment
7.1
Food
6.6
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Entertainment
7.1
Food
6.6
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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
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Alternative routes for Puerto Rico to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on junio 20, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Puerto Rico to Chicago by cabin class
Find flights from Puerto Rico to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Puerto Rico and Chicago flights
Browse other Puerto Rico and Chicago flight options. Last updated on junio 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Puerto Rico to Chicago
Discover the top 6 airlines that operate flights from Puerto Rico to Chicago. 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 junio 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$252 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$263 | Average$483 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$508 | FlexibilityNo cancel fee | On-time63% |