$114+ Cheap flights from O'Hare Intl (ORD) to Puerto Rico
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
jun 29 — jul 61
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Puerto Rico with Cheapflights
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Cheapest flights from O'Hare Intl to Puerto RicoExplore the most affordable flight options available from O'Hare Intl to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on maio 30, 2026.
Explore the most affordable flight options available from O'Hare Intl to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on maio 30, 2026.
This American Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 8/205:00 am
ORD
- SJU
1 stop12h 34m
American Airlines
sex 8/216:00 am
SJU
- ORD
1 stop10h 05m
American Airlines
Deal found 5/27![American Airlines logo]()
$231
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 8/175:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
qua 8/1910:33 am
SJU
- ORD
1 stop14h 57m
American Airlines
Deal found 5/29![American Airlines logo]()
$232
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 8/1912:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
qui 8/206:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/27![Frontier logo]()
$233
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 8/179:54 am
ORD
- SJU
1 stop11h 35m
Delta
qua 8/195:49 pm
SJU
- ORD
1 stop7h 13m
Delta
Deal found 5/29![Delta logo]()
$236
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
qua 8/1911:53 am
ORD
- SJU
1 stop11h 06m
American Airlines
ter 9/112:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 5/30![American Airlines logo]()
$237
This Frontier deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 8/1712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
seg 8/316:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/29![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 8/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
sáb 8/226:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/28![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 8/1712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
seg 8/246:00 am
SJU
- ORD
1 stop31h 25m
Frontier
Deal found 5/28![Frontier logo]()
$240
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 8/126:45 am
ORD
- SJU
1 stop14h 39m
American Airlines
seg 8/177:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Deal found 5/29![American Airlines logo]()
$241
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 8/154:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
seg 8/177:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Deal found 5/29![American Airlines logo]()
$242
This Frontier deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 8/1712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
sex 8/286:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/25![Frontier logo]()
$243
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
qua 8/127:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/27![Frontier logo]()
$245
Best flights from O'Hare Intl to Puerto RicoDiscover carefully curated flight deals from O'Hare Intl to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated maio 30, 2026.
Discover carefully curated flight deals from O'Hare Intl to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated maio 30, 2026.
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 8/1910:33 am
ORD
- SJU
1 stop10h 56m
Delta
qua 9/25:49 pm
SJU
- ORD
1 stop7h 13m
Delta
Deal found 5/26![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 8/148:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
sex 8/213:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 5/27![United Airlines logo]()
$307
This Cheapflightsfares deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 8/102:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
qui 8/135:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/27![JetBlue logo]()
$356
This Frontier deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 8/205:30 pm
ORD
- BQN
1 stop7h 34m
Frontier
dom 8/2312:28 pm
BQN
- ORD
1 stop11h 46m
Frontier
Deal found 5/26![Frontier logo]()
$436
This Priceline deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 7/44:59 pm
ORD
- BQN
1 stop8h 06m
Multiple Airlines
sáb 7/185:01 am
BQN
- ORD
2 stops17h 57m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$547
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 8/166:40 am
ORD
- SJU
1 stop8h 58m
Delta
qua 8/195:49 pm
SJU
- ORD
1 stop7h 13m
Delta
Deal found 5/26![Delta logo]()
$306
This Cheapflightsfares deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 7/252:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
sex 7/315:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/29![JetBlue logo]()
$356
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 8/86:00 am
ORD
- SJU
1 stop9h 33m
Delta
qua 8/122:59 pm
SJU
- ORD
1 stop10h 03m
Delta
Deal found 5/29![Delta logo]()
$361
This JetBlue deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 7/222:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
sáb 8/85:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/29![JetBlue logo]()
$375
This United Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 7/198:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
sáb 7/257:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 5/29![United Airlines logo]()
$429
This JetBlue deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 8/62:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
qui 8/135:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/25![JetBlue logo]()
$385
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 7/44:59 pm
ORD
- BQN
1 stop8h 06m
Frontier
dom 7/1212:04 pm
BQN
- ORD
1 stop12h 06m
Frontier
Deal found 5/27![Frontier logo]()
$466
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 6/26:07 am
ORD
- SJU
1 stop9h 22m
Delta
qui 7/22:14 pm
SJU
- ORD
1 stop7h 17m
Delta
Deal found 5/29![Delta logo]()
$401
This Cheapflightsfares deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 8/282:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
seg 8/315:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/28![JetBlue logo]()
$388
This JetBlue deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 7/312:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
ter 8/45:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/27![JetBlue logo]()
$405
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 7/1611:20 am
ORD
- SJU
1 stop8h 25m
Delta
dom 7/192:21 pm
SJU
- ORD
1 stop7h 10m
Delta
Deal found 5/25![Delta logo]()
$446
This Priceline deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
qui 7/24:59 pm
ORD
- BQN
1 stop8h 06m
Multiple Airlines
seg 7/65:09 am
BQN
- ORD
2 stops29h 57m
Multiple Airlines
Deal found 5/30![Multiple Airlines logo]()
$611
This United Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 8/71:30 pm
ORD
- BQN
1 stop8h 39m
United Airlines
ter 8/1812:15 am
BQN
- ORD
2 stops15h 45m
United Airlines
Deal found 5/27![United Airlines logo]()
$573
This JetBlue deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 7/282:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
seg 8/175:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/27![JetBlue logo]()
$405
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 7/25:30 am
ORD
- SJU
1 stop10h 16m
Delta
seg 7/66:00 am
SJU
- ORD
1 stop9h 16m
Delta
Deal found 5/25![Delta logo]()
$466
This JetBlue deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 7/162:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
qua 7/225:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/26![JetBlue logo]()
$405
This Priceline deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 7/19:35 am
ORD
- BQN
2 stops21h 23m
Multiple Airlines
dom 7/512:04 pm
BQN
- ORD
1 stop22h 07m
Multiple Airlines
Deal found 5/25![Multiple Airlines logo]()
$658
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 8/191:00 pm
ORD
- SJU
2 stops9h 50m
United Airlines
qua 9/24:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Deal found 5/28![United Airlines logo]()
$606
This JetBlue deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 7/232:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
seg 7/275:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/28![JetBlue logo]()
$409
This CheapOair deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 6/2610:16 am
ORD
- BQN
1 stop14h 49m
Multiple Airlines
dom 7/54:45 am
BQN
- ORD
2 stops39h 46m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$668
This United Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 6/192:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
seg 6/227:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 5/28![United Airlines logo]()
$617
This JetBlue deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 7/282:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
sáb 8/155:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/27![JetBlue logo]()
$419
This United Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 8/207:20 am
ORD
- BQN
2 stops14h 49m
United Airlines
sáb 8/2212:15 am
BQN
- ORD
1 stop10h 29m
United Airlines
Deal found 5/29![United Airlines logo]()
$648
This JetBlue deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 7/122:35 pm
ORD
- PSE
1 stop8h 24m
JetBlue
sex 7/175:01 am
PSE
- ORD
1 stop9h 38m
JetBlue
Deal found 5/26![JetBlue logo]()
$423
This Cheapflightsfares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 7/172:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
sex 7/245:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
Deal found 5/26![JetBlue logo]()
$431
Last-minute flights from O'Hare Intl to Puerto RicoDiscover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated maio 30, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated maio 30, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 5/2812:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
sáb 5/307:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/27![Frontier logo]()
$328
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 5/2812:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
qua 6/104:05 pm
SJU
- ORD
1 stop8h 14m
Frontier
Deal found 5/27![Frontier logo]()
$337
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 6/16:00 pm
ORD
- SJU
1 stop14h 39m
American Airlines
sáb 6/66:21 am
SJU
- ORD
1 stop12h 24m
American Airlines
Deal found 5/29![American Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
seg 6/16:00 pm
ORD
- SJU
1 stop14h 39m
American Airlines
seg 6/2912:44 am
SJU
- ORD
1 stop8h 46m
American Airlines
Deal found 5/30![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
ter 6/27:00 am
ORD
- SJU
1 stop10h 25m
American Airlines
ter 6/96:21 am
SJU
- ORD
1 stop11h 39m
American Airlines
Deal found 5/30![American Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 6/312:00 pm
ORD
- SJU
1 stop10h 01m
American Airlines
sáb 6/137:00 am
SJU
- ORD
1 stop10h 43m
American Airlines
Deal found 5/29![American Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 6/68:10 am
ORD
- SJU
1 stop11h 20m
Delta
qua 6/102:14 pm
SJU
- ORD
1 stop7h 17m
Delta
Deal found 5/28![Delta logo]()
$286
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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.
sáb 6/61:29 pm
ORD
- SJU
1 stop8h 31m
American Airlines
sáb 6/207:00 am
SJU
- ORD
1 stop13h 45m
American Airlines
Deal found 5/30![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 6/146:10 am
ORD
- SJU
1 stop11h 15m
American Airlines
sáb 6/207:00 am
SJU
- ORD
1 stop11h 50m
American Airlines
Deal found 5/29![American Airlines logo]()
$338
This Frontier deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 6/174:59 pm
ORD
- SJU
1 stop8h 10m
Frontier
qua 7/87:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/27![Frontier logo]()
$307
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 6/178:00 am
ORD
- SJU
1 stop13h 45m
American Airlines
qui 6/251:47 pm
SJU
- ORD
1 stop11h 47m
American Airlines
Deal found 5/29![American Airlines logo]()
$326
This Super.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 6/276:55 am
ORD
- SJU
1 stop12h 37m
Frontier
sáb 7/47:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/27![Frontier logo]()
$327
One-way flights from O'Hare Intl to Puerto RicoSearch for one-way flight options from O'Hare Intl to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated maio 30, 2026.
Search for one-way flight options from O'Hare Intl to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated maio 30, 2026.
This American Airlines deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 8/165:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 5/27![American Airlines logo]()
$114
This Delta deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 8/245:28 am
ORD
- SJU
1 stop7h 14m
Delta
Deal found 5/28![Delta logo]()
$118
This Frontier deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 8/2112:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 5/29![Frontier logo]()
$119
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 6/285:00 am
ORD
- SJU
1 stop12h 25m
American Airlines
Deal found 5/29![American Airlines logo]()
$121
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 8/198:37 am
ORD
- SJU
1 stop12h 18m
American Airlines
Deal found 5/29![American Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 8/154:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 5/29![American Airlines logo]()
$124
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 8/86:00 am
ORD
- SJU
1 stop9h 33m
Delta
Deal found 5/29![Delta logo]()
$128
This Frontier deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/29![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 8/2712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 5/29![Frontier logo]()
$130
This American Airlines deal was found by Cheapflights users on 5/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 6/55:00 am
ORD
- SJU
1 stop6h 57m
American Airlines
Deal found 5/28![American Airlines logo]()
$138
This SmartFares deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 8/187:00 am
ORD
- BQN
1 stop16h 33m
JetBlue
Deal found 5/26![JetBlue logo]()
$187
This Priceline deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 6/244:59 pm
ORD
- BQN
1 stop17h 34m
Frontier
Deal found 5/29![Frontier logo]()
$188
Find flight deals from O'Hare Intl to Puerto Rico
Keep the following information in mind while searching for O'Hare Intl to Puerto Rico flight deals. Data was last updated maio 30, 2026.
Round-trip from | $231 (American Airlines) |
|---|---|
One-way from | $114 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $374 |
Good round-trip deal | $412 or less |
Good one-way deal | $203 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 maio 30, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
qua 8/19
10:33 am-10:29 pm
1 stop10h 56m
San Juan Luis Munoz Marin Intl
qua 9/2
5:49 pm-12:02 am
1 stop7h 13m
$236
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
dom 8/16
6:40 am-4:38 pm
1 stop8h 58m
San Juan Luis Munoz Marin Intl
qua 8/19
5:49 pm-12:02 am
1 stop7h 13m
$306
Quickest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
sex 8/14
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
sex 8/21
3:56 pm-8:05 pm
Nonstop5h 09m
$307
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
seg 8/10
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
qui 8/13
5:01 am-1:39 pm
1 stop9h 38m
$356
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
sáb 7/25
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
sex 7/31
5:01 am-1:39 pm
1 stop9h 38m
$356
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
sáb 8/8
6:00 am-4:33 pm
1 stop9h 33m
San Juan Luis Munoz Marin Intl
qua 8/12
2:59 pm-12:02 am
1 stop10h 03m
$361
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
qua 7/22
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
sáb 8/8
5:01 am-1:39 pm
1 stop9h 38m
$375
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
qui 8/6
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
qui 8/13
5:01 am-1:39 pm
1 stop9h 38m
$385
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
sex 8/28
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
seg 8/31
5:01 am-1:39 pm
1 stop9h 38m
$388
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
ter 6/2
6:07 am-4:29 pm
1 stop9h 22m
San Juan Luis Munoz Marin Intl
qui 7/2
2:14 pm-8:31 pm
1 stop7h 17m
$401
Showing 1-10 of 58 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from O'Hare Intl with our price prediction graph.
ORD-SJU
ORD-PSE
ORD-BQN
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 Chicago O'Hare Intl Airport to Puerto Rico
ORD-PR0
ORD-SJU
ORD-PSE
ORD-BQN
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Puerto Rico?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $113). Flying from Chicago O'Hare Intl Airport to Puerto Rico in August is currently the most expensive (average of $944). 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 ORD to PR?
Find hourly flight availability from O'Hare Intl to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated maio 30, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Puerto Rico in the afternoon. If you’re flexible enough to do this you can expect to save up to 24% on your trip compared to booking a flight at noon.
Weekly flight availability from Chicago O'Hare Intl Airport to Puerto Rico
Explore weekly flight availability from O'Hare Intl to Puerto Rico. 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 maio 30, 2026.
The most flights from ORD to PR0 are scheduled on a Monday (9 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 21% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 140 minutes.
What is the most punctual flight time for Chicago to Puerto Rico flights?
Historically, flights departing in the morning 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 Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Puerto Rico flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 18% of flights being delayed.
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Puerto Rico?
The price you pay for your flight from Chicago O'Hare Intl Airport to Puerto Rico may vary depending on when you book. For the best chance of a lower fare, look to book 55 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Puerto Rico?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Puerto Rico. Price data was last updated on May 23, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Puerto Rico flight should consider departing on Monday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Puerto Rico
Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated maio 30, 2026.
Read reviews from past customers who have flown United Airlines,JetBlue, andAmerican Airlines from Chicago O'Hare Intl Airport to Puerto Rico. 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.
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Spirit Airlines
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for O'Hare Intl 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 O'Hare Intl to Puerto Rico by cabin class
Find flights from O'Hare Intl to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Puerto Rico flights
Browse other O'Hare Intl and Puerto Rico flight options. Last updated on maio 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from O'Hare Intl to Puerto Rico
Discover the top 7 airlines that operate flights from O'Hare Intl 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 maio 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$133 | Average$324 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$143 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$144 | Average$315 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$258 | Average$526 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$306 | Average$508 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$483 | FlexibilityNo cancel fee | On-time63% |