$97+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Sep 16 — Sep 231
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Puerto Rico with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from O'Hare Intl to Puerto Rico
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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 August 17, 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 August 17, 2026.
This Super.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/12. 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.
Thu 10/17:11 am -
1 stop29h 23m
Mon 10/57:00 am -
1 stop8h 45m
Deal found 8/12![Frontier logo]()
$212
This Super.com deal was found by Cheapflights users on 8/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/15![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/162:32 pm -
1 stop9h 36m
Deal found 8/14![Multiple Airlines logo]()
$214
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Sun 8/307:14 pm -
Nonstop5h 13m
Deal found 8/13![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
2 stops25h 35m
Deal found 8/14![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 8/16![Frontier logo]()
$218
This deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:44 pm -
1 stop11h 27m
Wed 9/92:57 am -
1 stop8h 23m
Deal found 8/14![Frontier logo]()
$219
This CheapOair deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:44 am -
Nonstop5h 00m
Thu 9/37:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Fri 8/2812:44 am -
Nonstop5h 00m
Wed 9/912:59 am -
1 stop13h 31m
Deal found 8/16![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/112:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Mon 8/316:35 am -
1 stop31h 15m
Deal found 8/13![Frontier logo]()
$223
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 August 17, 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 August 17, 2026.
This Justfly.com deal was found by Cheapflights users on 8/12. 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.
Tue 12/12:50 pm -
1 stop8h 21m
Sat 12/56:01 am -
1 stop9h 25m
Deal found 8/12![JetBlue logo]()
$304
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/62:16 pm -
Nonstop4h 44m
Sat 11/142:05 am -
1 stop8h 57m
Deal found 8/13![United Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/2410:26 am -
2 stops21h 52m
Mon 9/2810:05 am -
1 stop13h 54m
Deal found 8/13![Frontier logo]()
$378
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/76:00 am -
1 stop8h 50m
Thu 1/146:30 pm -
1 stop7h 20m
Deal found 8/13![Delta logo]()
$472
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:11 pm -
1 stop13h 11m
Sun 10/257:45 pm -
2 stops28h 59m
Deal found 8/16![Multiple Airlines logo]()
$472
This JetBlue deal was found by Cheapflights users on 8/13. 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.
Fri 11/132:35 pm -
1 stop8h 24m
Tue 11/176:01 am -
1 stop9h 38m
Deal found 8/13![JetBlue logo]()
$353
This FlightHub deal was found by Cheapflights users on 8/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/74:44 pm -
1 stop16h 13m
Sat 11/1411:52 am -
1 stop22h 29m
Deal found 8/15![Frontier logo]()
$410
This JetBlue deal was found by Cheapflights users on 8/13. 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.
Thu 1/212:35 pm -
1 stop8h 24m
Thu 1/286:01 am -
1 stop9h 38m
Deal found 8/13![JetBlue logo]()
$402
This United Airlines deal was found by Cheapflights users on 8/12. 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 11/42:16 pm -
Nonstop4h 44m
Fri 11/132:05 am -
1 stop8h 57m
Deal found 8/12![United Airlines logo]()
$446
This Frontier deal was found by Cheapflights users on 8/12. 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.
Thu 8/277:44 pm -
1 stop13h 18m
Mon 8/3110:47 am -
1 stop13h 21m
Deal found 8/12![Frontier logo]()
$436
This Justfly.com deal was found by Cheapflights users on 8/15. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/232:35 pm -
1 stop8h 24m
Mon 2/16:01 am -
1 stop9h 38m
Deal found 8/15![JetBlue logo]()
$402
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:55 am -
Nonstop4h 49m
Wed 10/287:05 am -
1 stop8h 33m
Deal found 8/13![United Airlines logo]()
$446
This CheapOair deal was found by Cheapflights users on 8/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:35 pm -
1 stop8h 24m
Thu 10/225:01 am -
1 stop19h 43m
Deal found 8/15![JetBlue logo]()
$410
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Sun 9/68:55 am -
Nonstop4h 49m
Fri 9/111:00 am -
1 stop7h 41m
Deal found 8/15![United Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 8/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:30 pm -
1 stop9h 20m
Mon 9/143:56 pm -
Nonstop5h 09m
Deal found 8/13![United Airlines logo]()
$463
This Priceline deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am -
1 stop16h 33m
Mon 11/307:27 pm -
1 stop19h 44m
Deal found 8/16![Multiple Airlines logo]()
$632
This JetBlue deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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.
Thu 9/106:00 am -
1 stop6h 56m
Mon 9/144:23 pm -
1 stop7h 45m
Deal found 8/14![JetBlue logo]()
$479
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Thu 12/105:00 am -
1 stop7h 40m
Sun 12/138:10 am -
Nonstop5h 22m
Deal found 8/16![United Airlines logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Fri 9/48:37 am -
2 stops24h 45m
Mon 9/75:41 pm -
1 stop6h 46m
Deal found 8/16![Multiple Airlines logo]()
$738
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Sun 11/292:16 pm -
Nonstop4h 44m
Sat 12/54:52 pm -
Nonstop5h 28m
Deal found 8/16![United Airlines logo]()
$509
This JetBlue deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 2/32:35 pm -
1 stop8h 24m
Sun 2/76:01 am -
1 stop9h 38m
Deal found 8/14![JetBlue logo]()
$538
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/105:46 pm -
2 stops29h 25m
Thu 1/286:01 am -
1 stop9h 38m
Deal found 8/12![JetBlue logo]()
$538
This United Airlines deal was found by Cheapflights users on 8/12. 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 12/32:20 pm -
Nonstop4h 40m
Sun 12/138:10 am -
Nonstop5h 22m
Deal found 8/12![United Airlines logo]()
$539
This CheapOair deal was found by Cheapflights users on 8/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:00 am -
1 stop15h 59m
Tue 9/15:01 am -
1 stop19h 43m
Deal found 8/13![JetBlue logo]()
$541
This United Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/308:55 am -
Nonstop4h 49m
Tue 10/63:56 pm -
Nonstop5h 09m
Deal found 8/14![United Airlines logo]()
$567
This United Airlines deal was found by Cheapflights users on 8/15. 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.
Tue 10/208:55 am -
Nonstop4h 49m
Sat 10/241:05 am -
1 stop9h 40m
Deal found 8/15![United Airlines logo]()
$572
This JetBlue deal was found by Cheapflights users on 8/12. 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.
Sat 8/293:20 pm -
1 stop8h 13m
Tue 9/12:30 pm -
1 stop10h 14m
Deal found 8/12![JetBlue logo]()
$584
This United deal was found by Cheapflights users on 8/13. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/35:00 am -
2 stops10h 21m
Wed 1/610:48 am -
2 stops12h 12m
Deal found 8/13![Multiple Airlines logo]()
$1,064
This United Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/255:00 am -
1 stop7h 45m
Sun 9/273:56 pm -
Nonstop5h 09m
Deal found 8/14![United Airlines logo]()
$578
This United Airlines deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:09 pm -
1 stop10h 00m
Thu 10/2912:09 am -
1 stop8h 39m
Deal found 8/16![United Airlines logo]()
$616
Last-minute flights from O'Hare Intl to Puerto RicoDiscover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated August 17, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated August 17, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 8/16![Frontier logo]()
$218
This Super.com deal was found by Cheapflights users on 8/13. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Sun 8/307:14 pm -
Nonstop5h 13m
Deal found 8/13![Frontier logo]()
$215
This CheapOair deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$220
This Super.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Mon 8/316:35 am -
1 stop31h 15m
Deal found 8/13![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Fri 8/2812:44 am -
Nonstop5h 00m
Wed 9/912:59 am -
1 stop13h 31m
Deal found 8/16![Frontier logo]()
$221
This deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:44 pm -
1 stop11h 27m
Wed 9/92:57 am -
1 stop8h 23m
Deal found 8/14![Frontier logo]()
$219
This Super.com deal was found by Cheapflights users on 8/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/15![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/112:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/14![Frontier logo]()
$222
This CheapOair deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/162:32 pm -
1 stop9h 36m
Deal found 8/14![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
2 stops25h 35m
Deal found 8/14![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 9/88:05 am -
1 stop30h 12m
Wed 9/168:45 am -
1 stop31h 00m
Deal found 8/12![Frontier logo]()
$224
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 August 17, 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 August 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:04 am -
1 stop30h 14m
Deal found 8/13![Frontier logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/128:04 am -
1 stop30h 14m
Deal found 8/13![Frontier logo]()
$99
This CheapOair deal was found by Cheapflights users on 8/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Deal found 8/13![Frontier logo]()
$100
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/148:04 am -
1 stop28h 27m
Deal found 8/13![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 8/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/712:44 am -
Nonstop5h 00m
Deal found 8/12![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 8/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Deal found 8/12![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:11 am -
1 stop29h 23m
Deal found 8/14![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Thu 10/158:04 am -
1 stop28h 27m
Deal found 8/16![Frontier logo]()
$110
This eDestinos deal was found by Cheapflights users on 8/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:44 am -
Nonstop5h 00m
Deal found 8/13![Frontier logo]()
$112
This Cheapflightsfares deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” 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 11/92:35 pm -
1 stop8h 24m
Deal found 8/14![JetBlue logo]()
$150
This CheapOair deal was found by Cheapflights users on 8/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/147:00 am -
1 stop16h 11m
Deal found 8/12![JetBlue logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 8/15. 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.
Sat 9/127:21 pm -
2 stops37h 52m
Deal found 8/15![Frontier logo]()
$181
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 August 17, 2026.
Round-trip from | $211 (Super.com) |
|---|---|
One-way from | $97 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $320 |
Good round-trip deal | $323 or less |
Good one-way deal | $123 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 August 17, 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
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Tue 12/1
2:50 pm-1:11 am
1 stop8h 21m
Ponce Mercedita
Sat 12/5
6:01 am-1:26 pm
1 stop9h 25m
$304
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 11/6
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Sat 11/14
2:05 am-9:02 am
1 stop8h 57m
$326
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Fri 11/13
2:35 pm-12:59 am
1 stop8h 24m
Ponce Mercedita
Tue 11/17
6:01 am-1:39 pm
1 stop9h 38m
$353
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Thu 9/24
10:26 am-9:18 am
2 stops21h 52m
Ponce Mercedita
Mon 9/28
10:05 am-10:59 pm
1 stop13h 54m
$378
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Thu 1/21
2:35 pm-12:59 am
1 stop8h 24m
Ponce Mercedita
Thu 1/28
6:01 am-1:39 pm
1 stop9h 38m
$402
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Sat 1/23
2:35 pm-12:59 am
1 stop8h 24m
Ponce Mercedita
Mon 2/1
6:01 am-1:39 pm
1 stop9h 38m
$402
ChicagoAguadilla
ORD Chicago O'Hare Intl - BQN Aguadilla Borinquen
ORDBQN
Chicago O'Hare Intl
Sat 11/7
4:44 pm-10:57 am
1 stop16h 13m
Aguadilla Borinquen
Sat 11/14
11:52 am-8:21 am
1 stop22h 29m
$410
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Thu 10/15
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
Thu 10/22
5:01 am-11:44 pm
1 stop19h 43m
$410
ChicagoPonce
ORD Chicago O'Hare Intl - PSE Ponce Mercedita
ORDPSE
Chicago O'Hare Intl
Thu 8/27
7:44 pm-10:02 am
1 stop13h 18m
Ponce Mercedita
Mon 8/31
10:47 am-11:08 pm
1 stop13h 21m
$436
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/4
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Fri 11/13
2:05 am-9:02 am
1 stop8h 57m
$446
Showing 1-10 of 60 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
ORD-CPX
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
ORD-CPX
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Puerto Rico?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $350). Flying from Chicago O'Hare Intl Airport to Puerto Rico in December is currently the most expensive (average of $537). 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 August 17, 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 31% 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 August 17, 2026.
The most flights from ORD to PR0 are scheduled on a Monday (7 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (3 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 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?
Wednesday 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 August 15, 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 August 17, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, 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.
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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 August 17, 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 2,558,603 searches. Data last updated August 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$366 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$326 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$415 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$264 | Average$525 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$297 | Average$491 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$372 | Average$485 | FlexibilityNo cancel fee | On-time63% |