$105+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Sep 4 — Sep 111
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 August 5, 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 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
This Super.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/1![Frontier logo]()
$224
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/2![Frontier logo]()
$226
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$227
This Priceline deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/2512:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Mon 8/3112:44 am -
Nonstop5h 00m
Wed 9/27:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Wed 8/2612:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/312:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Mon 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/3012:44 am -
Nonstop5h 00m
Mon 9/217:00 am -
1 stop8h 45m
Deal found 7/31![Frontier logo]()
$234
This Justfly.com deal was found by Cheapflights users on 7/30. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:35 pm -
1 stop8h 24m
Fri 8/285:01 am -
1 stop9h 38m
Deal found 7/30![JetBlue logo]()
$304
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 5, 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 5, 2026.
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/18:50 am -
1 stop10h 48m
Sat 9/121:00 am -
1 stop9h 13m
Deal found 8/3![United Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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.
Thu 9/35:20 pm -
Nonstop4h 55m
Sat 9/512:55 am -
Nonstop5h 05m
Deal found 8/4![American Airlines logo]()
$287
This Delta deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:07 am -
1 stop12h 45m
Sun 9/67:00 am -
1 stop6h 40m
Deal found 8/4![Delta logo]()
$296
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Tue 8/112:35 pm -
1 stop7h 45m
Tue 9/85:05 am -
1 stop9h 34m
Deal found 7/31![JetBlue logo]()
$300
This Priceline deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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.
Wed 10/146:05 am -
1 stop25h 58m
Wed 10/215:01 am -
1 stop9h 38m
Deal found 8/1![Multiple Airlines logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/49:10 pm -
1 stop28h 00m
Mon 9/73:05 am -
2 stops18h 03m
Deal found 7/30![Frontier logo]()
$435
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/132:35 pm -
1 stop7h 45m
Fri 9/45:05 am -
1 stop9h 34m
Deal found 7/31![JetBlue logo]()
$300
This JetBlue deal was found by Cheapflights users on 7/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/122:35 pm -
1 stop8h 24m
Tue 8/185:01 am -
1 stop9h 38m
Deal found 7/30![JetBlue logo]()
$304
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/58:55 am -
Nonstop4h 49m
Sat 9/123:56 pm -
Nonstop5h 09m
Deal found 8/4![United Airlines logo]()
$342
This JetBlue deal was found by Cheapflights users on 7/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:35 pm -
1 stop8h 24m
Fri 8/285:01 am -
1 stop9h 38m
Deal found 7/30![JetBlue logo]()
$304
This Delta deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/301:29 pm -
1 stop9h 20m
Mon 10/57:30 am -
1 stop10h 29m
Deal found 8/1![Delta logo]()
$371
This United Airlines deal was found by Cheapflights users on 8/4. Clicking the “Pick Dates” 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 9/910:40 am -
1 stop8h 58m
Wed 9/163:56 pm -
Nonstop5h 09m
Deal found 8/4![United Airlines logo]()
$342
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/115:00 am -
1 stop7h 45m
Sat 9/191:00 am -
1 stop9h 12m
Deal found 8/3![United Airlines logo]()
$346
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:00 pm -
2 stops16h 01m
Fri 9/1810:05 am -
1 stop13h 54m
Deal found 7/30![Multiple Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Sat 8/296:00 am -
1 stop9h 33m
Tue 9/221:16 pm -
1 stop9h 21m
Deal found 7/31![Delta logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/1310:26 am -
2 stops21h 52m
Sun 9/2010:05 am -
1 stop25h 15m
Deal found 7/31![Frontier logo]()
$474
This United Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/88:55 am -
Nonstop4h 49m
Sat 9/123:56 pm -
Nonstop5h 09m
Deal found 7/31![United Airlines logo]()
$387
This JetBlue deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/15:01 am -
1 stop9h 38m
Deal found 8/3![JetBlue logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 10/77:25 am -
2 stops24h 38m
Sun 10/119:58 am -
1 stop14h 57m
Deal found 8/3![Frontier logo]()
$507
This JetBlue deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/312:35 pm -
1 stop8h 24m
Fri 9/45:01 am -
1 stop9h 38m
Deal found 8/3![JetBlue logo]()
$428
This Expedia deal was found by Cheapflights users on 7/30. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
2 stops31h 39m
Mon 9/215:41 pm -
2 stops30h 27m
Deal found 7/30![Multiple Airlines logo]()
$598
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/153:20 pm -
2 stops15h 29m
Sat 8/295:01 am -
1 stop10h 23m
Deal found 7/30![JetBlue logo]()
$475
This Expedia deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:59 am -
2 stops24h 41m
Wed 9/235:41 pm -
2 stops30h 27m
Deal found 8/2![Multiple Airlines logo]()
$699
This JetBlue deal was found by Cheapflights users on 7/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/72:35 pm -
1 stop8h 58m
Wed 9/94:23 pm -
1 stop7h 45m
Deal found 7/30![JetBlue logo]()
$517
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/78:45 am -
2 stops13h 24m
Tue 9/812:15 am -
1 stop9h 58m
Deal found 8/2![United Airlines logo]()
$650
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/293:20 pm -
2 stops15h 29m
Sat 9/58:39 am -
2 stops16h 05m
Deal found 7/30![JetBlue logo]()
$522
This United Airlines deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 8/2912:16 pm -
1 stop9h 53m
Fri 9/412:15 am -
2 stops19h 22m
Deal found 8/2![United Airlines logo]()
$669
This Priceline deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:00 am -
2 stops10h 43m
Thu 8/2010:07 am -
2 stops14h 37m
Deal found 8/1![Multiple Airlines logo]()
$825
This United Airlines deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/296:15 am -
2 stops15h 54m
Mon 8/3112:15 am -
1 stop8h 25m
Deal found 8/3![United Airlines logo]()
$671
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:20 pm -
2 stops16h 08m
Tue 9/89:52 pm -
2 stops26h 16m
Deal found 7/30![JetBlue logo]()
$579
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 5, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated August 5, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Mon 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$227
This Justfly.com deal was found by Cheapflights users on 7/30. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/212:35 pm -
1 stop8h 24m
Fri 8/285:01 am -
1 stop9h 38m
Deal found 7/30![JetBlue logo]()
$304
This Priceline deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/2512:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Wed 8/2612:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$230
This Super.com deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/1![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/3012:44 am -
Nonstop5h 00m
Mon 9/217:00 am -
1 stop8h 45m
Deal found 7/31![Frontier logo]()
$234
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/2![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Mon 8/3112:44 am -
Nonstop5h 00m
Wed 9/27:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/312:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
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 5, 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 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/267:11 am -
1 stop8h 52m
Deal found 8/3![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 9/127:11 am -
1 stop29h 23m
Deal found 8/3![Frontier logo]()
$109
This eDestinos deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Sat 8/2912:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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 9/307:11 am -
1 stop29h 23m
Deal found 8/2![Frontier logo]()
$111
This eDestinos deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Sun 8/912:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am -
Nonstop5h 00m
Deal found 7/31![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Deal found 7/31![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 8/1. Clicking the “Pick Dates” 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 8/2012:44 am -
Nonstop5h 00m
Deal found 8/1![Frontier logo]()
$116
This eDestinos deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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 8/1412:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 8/3. Clicking the “Pick Dates” 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.
Wed 8/2612:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 8/2. Clicking the “Pick Dates” 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.
Wed 9/93:50 pm -
1 stop17h 23m
Deal found 8/2![Frontier logo]()
$176
This Priceline deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 9/17:44 pm -
1 stop29h 26m
Deal found 7/31![Frontier logo]()
$184
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 5, 2026.
Round-trip from | $222 (Kiwi.com) |
|---|---|
One-way from | $105 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $328 |
Good round-trip deal | $315 or less |
Good one-way deal | $130 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 5, 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
Tue 9/1
8:50 am-8:38 pm
1 stop10h 48m
San Juan Luis Munoz Marin Intl
Sat 9/12
1:00 am-9:13 am
1 stop9h 13m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 9/3
5:20 pm-11:15 pm
Nonstop4h 55m
San Juan Luis Munoz Marin Intl
Sat 9/5
12:55 am-5:00 am
Nonstop5h 05m
$287
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/1
10:07 am-11:52 pm
1 stop12h 45m
San Juan Luis Munoz Marin Intl
Sun 9/6
7:00 am-12:40 pm
1 stop6h 40m
$296
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 8/11
2:35 pm-11:20 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Tue 9/8
5:05 am-1:39 pm
1 stop9h 34m
$300
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 8/13
2:35 pm-11:20 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Fri 9/4
5:05 am-1:39 pm
1 stop9h 34m
$300
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Wed 8/12
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
Tue 8/18
5:01 am-1:39 pm
1 stop9h 38m
$304
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Mon 8/24
2:35 pm-11:59 pm
1 stop8h 24m
Ponce Mercedita
Fri 8/28
5:01 am-1:39 pm
1 stop9h 38m
$304
Quickest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 9/5
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Sat 9/12
3:56 pm-8:05 pm
Nonstop5h 09m
$342
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 9/9
10:40 am-8:38 pm
1 stop8h 58m
San Juan Luis Munoz Marin Intl
Wed 9/16
3:56 pm-8:05 pm
Nonstop5h 09m
$342
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 9/11
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Sat 9/19
1:00 am-9:12 am
1 stop9h 12m
$346
Showing 1-10 of 50 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
ORD-MAZ
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 $539). 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 5, 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 August 5, 2026.
The most flights from ORD to PR0 are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 23% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 139 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 1, 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 5, 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.
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Crew
8.6
Boarding
8.1
Food
7.0
Comfort
8.0
Entertainment
7.5
Overall
8.0
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 5, 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$366 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$327 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$387 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$262 | Average$523 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$302 | Average$494 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$486 | FlexibilityNo cancel fee | On-time63% |