$110+ Cheap flights from O'Hare Intl (ORD) to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 12 — Nov 191
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 October 13, 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 October 13, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:51 am -
1 stop23h 26m
Sun 12/133:47 am -
1 stop23h 14m
Deal found 10/12![Frontier logo]()
$210
This Frontier deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Sat 12/55:24 pm -
1 stop7h 28m
Mon 12/73:09 pm -
1 stop11h 52m
Deal found 10/12![Frontier logo]()
$212
This Justfly.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/610:38 am -
1 stop26h 21m
Wed 12/911:48 am -
1 stop15h 13m
Deal found 10/12![Frontier logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:26 am -
1 stop13h 33m
Tue 11/37:26 pm -
1 stop23h 41m
Deal found 10/9![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:51 am -
1 stop14h 55m
Wed 11/187:23 am -
1 stop11h 44m
Deal found 10/11![Frontier logo]()
$225
This Cheapflightsfares deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:51 am -
1 stop6h 29m
Sat 10/317:23 am -
1 stop27h 23m
Deal found 10/8![Frontier logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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.
Sat 10/318:00 am -
1 stop28h 25m
Fri 11/63:55 am -
1 stop21h 36m
Deal found 10/13![Frontier logo]()
$228
This JetBlue deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/142:59 pm -
1 stop9h 00m
Mon 12/216:24 pm -
1 stop7h 09m
Deal found 10/8![JetBlue logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/55:24 pm -
1 stop6h 49m
Sat 12/127:17 am -
1 stop19h 44m
Deal found 10/12![Frontier logo]()
$230
This Booking.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:26 am -
1 stop13h 33m
Sun 11/17:23 am -
1 stop27h 23m
Deal found 10/9![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/37:35 pm -
2 stops17h 44m
Wed 11/113:55 pm -
1 stop19h 05m
Deal found 10/12![Frontier logo]()
$232
This JetBlue deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/52:59 pm -
1 stop9h 00m
Sat 12/126:01 am -
1 stop9h 29m
Deal found 10/8![JetBlue logo]()
$233
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 October 13, 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 October 13, 2026.
This JetBlue deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Sun 12/132:59 pm -
1 stop9h 00m
Sun 12/206:15 am -
1 stop9h 15m
Deal found 10/12![JetBlue logo]()
$262
This United Airlines deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/711:56 am -
1 stop10h 01m
Fri 11/131:09 am -
1 stop8h 38m
Deal found 10/11![United Airlines logo]()
$270
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:35 am -
1 stop6h 39m
Mon 12/143:47 am -
1 stop23h 14m
Deal found 10/9![Frontier logo]()
$373
This Justfly.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/97:00 am -
2 stops24h 22m
Mon 11/1610:54 am -
2 stops33h 36m
Deal found 10/12![Multiple Airlines logo]()
$469
This JetBlue deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:00 pm -
1 stop10h 13m
Tue 11/105:30 pm -
1 stop8h 06m
Deal found 10/9![JetBlue logo]()
$262
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1211:56 am -
1 stop10h 01m
Fri 11/131:09 am -
1 stop9h 53m
Deal found 10/10![United Airlines logo]()
$270
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:43 pm -
1 stop7h 14m
Tue 11/31:09 am -
1 stop10h 36m
Deal found 10/9![United Airlines logo]()
$270
This JetBlue deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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.
Sat 11/71:00 pm -
1 stop10h 13m
Sat 11/146:25 am -
1 stop9h 17m
Deal found 10/11![JetBlue logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:49 am -
2 stops40h 58m
Tue 12/13:47 am -
1 stop23h 12m
Deal found 10/8![Frontier logo]()
$386
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/92:16 pm -
Nonstop4h 44m
Wed 11/181:00 pm -
1 stop10h 30m
Deal found 10/8![United Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/32:16 pm -
Nonstop4h 44m
Wed 11/118:25 am -
Nonstop5h 22m
Deal found 10/12![United Airlines logo]()
$337
This Priceline deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 10/307:00 am -
1 stop16h 11m
Mon 11/210:54 am -
2 stops30h 37m
Deal found 10/10![Multiple Airlines logo]()
$483
This FlightHub deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:00 am -
1 stop16h 50m
Thu 11/195:01 am -
1 stop10h 31m
Deal found 10/9![JetBlue logo]()
$412
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/218:55 am -
Nonstop4h 49m
Wed 10/287:25 am -
Nonstop5h 22m
Deal found 10/8![United Airlines logo]()
$358
This Mytrip deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:26 am -
2 stops22h 51m
Mon 11/212:37 pm -
2 stops13h 44m
Deal found 10/10![Frontier logo]()
$485
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:16 pm -
Nonstop4h 44m
Sat 12/122:05 am -
1 stop8h 44m
Deal found 10/8![United Airlines logo]()
$369
This JetBlue deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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.
Mon 11/22:50 pm -
1 stop9h 00m
Tue 11/175:01 am -
1 stop10h 41m
Deal found 10/10![JetBlue logo]()
$473
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:32 am -
1 stop9h 50m
Wed 12/28:25 am -
Nonstop5h 24m
Deal found 10/9![United Airlines logo]()
$376
This Cheapflightsfares deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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.
Wed 11/255:12 pm -
1 stop19h 22m
Sat 11/283:29 pm -
1 stop11h 14m
Deal found 10/12![Frontier logo]()
$552
This JetBlue deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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.
Mon 11/22:50 pm -
1 stop9h 00m
Wed 11/185:23 am -
1 stop10h 19m
Deal found 10/10![JetBlue logo]()
$473
This Justfly.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:15 am -
2 stops28h 08m
Sun 12/202:25 pm -
2 stops42h 40m
Deal found 10/13![Frontier logo]()
$555
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 12/911:55 am -
1 stop10h 02m
Fri 12/181:09 am -
1 stop8h 43m
Deal found 10/12![United Airlines logo]()
$390
This JetBlue deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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.
Fri 11/62:59 pm -
1 stop8h 51m
Thu 11/195:01 am -
1 stop10h 31m
Deal found 10/10![JetBlue logo]()
$484
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/282:16 pm -
Nonstop4h 44m
Sat 10/312:05 am -
1 stop8h 57m
Deal found 10/12![United Airlines logo]()
$402
This JetBlue deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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.
Sat 11/72:59 pm -
1 stop8h 51m
Mon 11/165:01 am -
1 stop10h 41m
Deal found 10/10![JetBlue logo]()
$518
This United Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1712:05 pm -
1 stop10h 04m
Fri 11/131:09 am -
1 stop8h 38m
Deal found 10/8![United Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:52 am -
Nonstop4h 48m
Sat 10/313:55 pm -
Nonstop5h 31m
Deal found 10/12![United Airlines logo]()
$421
This JetBlue deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:42 pm -
1 stop9h 08m
Sun 11/85:23 am -
1 stop10h 19m
Deal found 10/8![JetBlue logo]()
$565
This United Airlines deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/292:16 pm -
Nonstop4h 44m
Sat 10/312:05 am -
1 stop8h 57m
Deal found 10/12![United Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 12/52:16 pm -
Nonstop4h 44m
Fri 12/118:25 am -
Nonstop5h 24m
Deal found 10/10![United Airlines logo]()
$437
Last-minute flights from O'Hare Intl to Puerto RicoDiscover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated October 13, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated October 13, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:51 am -
1 stop6h 29m
Sat 10/317:23 am -
1 stop27h 23m
Deal found 10/8![Frontier logo]()
$226
This Booking.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2910:26 am -
1 stop13h 33m
Sun 11/17:23 am -
1 stop27h 23m
Deal found 10/9![Frontier logo]()
$231
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3010:26 am -
1 stop13h 33m
Tue 11/37:26 pm -
1 stop23h 41m
Deal found 10/9![Frontier logo]()
$224
This FlightHub deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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.
Fri 10/3010:26 am -
1 stop13h 33m
Sat 11/77:26 pm -
1 stop15h 20m
Deal found 10/11![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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.
Sat 10/318:00 am -
1 stop28h 25m
Fri 11/63:55 am -
1 stop21h 36m
Deal found 10/13![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” 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 11/37:35 pm -
2 stops17h 44m
Wed 11/113:55 pm -
1 stop19h 05m
Deal found 10/12![Frontier logo]()
$232
This JetBlue deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:00 pm -
1 stop10h 13m
Thu 11/126:25 am -
1 stop9h 17m
Deal found 10/9![JetBlue logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:00 am -
1 stop15h 28m
Mon 11/163:55 am -
2 stops16h 35m
Deal found 10/8![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 11/99:51 am -
1 stop14h 55m
Fri 11/2011:13 am -
1 stop15h 30m
Deal found 10/11![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/99:51 am -
1 stop14h 55m
Wed 11/114:52 pm -
2 stops18h 08m
Deal found 10/8![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/119:51 am -
1 stop14h 55m
Wed 11/187:23 am -
1 stop11h 44m
Deal found 10/11![Frontier logo]()
$225
This Cheapflightsfares deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/179:51 am -
1 stop23h 26m
Sun 12/133:47 am -
1 stop23h 14m
Deal found 10/12![Frontier logo]()
$210
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 October 13, 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 October 13, 2026.
This Super.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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.
Mon 11/99:51 am -
1 stop23h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop9h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Frontier logo]()
$121
This Cheapflightsfares deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/198:11 pm -
1 stop12h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$122
This Frontier deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:11 pm -
1 stop12h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 10/11. Clicking the “Pick Dates” 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 12/88:15 am -
1 stop14h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/11![Frontier logo]()
$125
This Super.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 am -
1 stop18h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$128
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/108:52 am -
Nonstop4h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![United Airlines logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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.
Sun 1/1012:17 am -
Nonstop4h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$131
This Frontier deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” 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 11/1310:19 am -
1 stop12h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/10![Frontier logo]()
$132
This JetBlue deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” 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.
Mon 12/142:59 pm -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![JetBlue logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:50 pm -
2 stops25h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:35 pm -
2 stops37h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Frontier logo]()
$156
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 October 13, 2026.
Round-trip from | $210 (Cheapflightsfares) |
|---|---|
One-way from | $110 (Super.com) |
Popular in | December |
Cheapest in | August |
Average price | $403 |
Good round-trip deal | $362 or less |
Good one-way deal | $185 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 7,457,451 searches. Data last updated October 13, 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 Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/16
10:30 am-11:54 pm
1 stop11h 24m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$135
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 12/12
2:59 pm-1:59 am
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$143
Quickest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 10/30
2:16 pm-8:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$152
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sun 12/13
2:59 pm-1:59 am
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$159
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/9
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$169
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/11
1:00 pm-1:13 am
1 stop10h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$178
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 11/10
8:52 am-3:40 pm
Nonstop4h 48m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$179
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 10/19
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$208
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 11/13
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$219
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 11/3
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$219
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-BQN
ORD-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 Chicago O'Hare Intl Airport to Puerto Rico
ORD-PR0
ORD-BQN
ORD-SJU
ORD-PSE
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Puerto Rico?
Currently, February is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $339). Flying from Chicago O'Hare Intl Airport to Puerto Rico in December is currently the most expensive (average of $534). 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 October 13, 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 evening. If you’re flexible enough to do this you can expect to save up to 30% on your trip compared to booking a flight in the morning.
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 October 13, 2026.
The most flights from ORD to PR0 are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 22% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 148 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?
Wednesday tends to have the lowest number of delays on this route, whereas Monday 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 59 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 October 10, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Puerto Rico flight should consider departing on Sunday evenings when fares are most often at their lowest. Friday mornings 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 October 13, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andJetBlue 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
8.6
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Crew
8.6
Boarding
8.1
Entertainment
7.5
Overall
7.9
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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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Alternative routes for O'Hare Intl to Puerto Rico
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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 October 13, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from O'Hare Intl to Puerto Rico
Discover the top 6 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 7,457,451 searches. Data last updated October 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$366 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$484 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$153 | Average$416 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$263 | Average$532 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$285 | Average$488 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$372 | Average$482 | FlexibilityNo cancel fee | On-time63% |