$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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 19 — Apr 261
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
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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 March 20, 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 March 20, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$202
This Priceline deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$203
This Priceline deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/42:10 pm
ORD
- SJU
1 stop8h 33m
Frontier
Sat 5/96:00 am
SJU
- ORD
1 stop18h 13m
Frontier
Deal found 3/19![Frontier logo]()
$206
This CheapOair deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Sat 5/166:41 pm
SJU
- ORD
1 stop15h 56m
Frontier
Deal found 3/19![Frontier logo]()
$207
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:05 am
ORD
- SJU
1 stop12h 50m
Multiple Airlines
Thu 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$208
This Priceline deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/306:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/19![Spirit Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Thu 4/164:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$214
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1110:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$215
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/19![Spirit Airlines logo]()
$218
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 March 20, 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 March 20, 2026.
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:55 pm
ORD
- PSE
1 stop16h 12m
Frontier
Tue 5/1210:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 3/17![Frontier logo]()
$264
This Delta deal was found by Cheapflights users on 3/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/91:15 pm
ORD
- SJU
1 stop8h 33m
Delta
Tue 6/166:15 am
SJU
- ORD
1 stop11h 29m
Delta
Deal found 3/15![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Wed 4/292:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sat 5/21:00 am
SJU
- ORD
1 stop8h 44m
United Airlines
Deal found 3/15![United Airlines logo]()
$354
This Trip.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/189:16 am
ORD
- BQN
2 stops15h 27m
Multiple Airlines
Sun 4/192:38 am
BQN
- ORD
2 stops31h 58m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:15 pm
ORD
- SJU
2 stops17h 20m
Southwest
Tue 5/125:05 am
SJU
- ORD
2 stops14h 20m
Southwest
Deal found 3/15![Southwest logo]()
$450
This CheapOair deal was found by Cheapflights users on 3/15. 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.
Tue 5/193:55 pm
ORD
- PSE
1 stop17h 33m
Frontier
Mon 5/2510:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 3/15![Frontier logo]()
$304
This CheapOair deal was found by Cheapflights users on 3/15. 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.
Fri 5/155:30 pm
ORD
- PSE
1 stop14h 37m
Frontier
Tue 5/1910:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 3/15![Frontier logo]()
$304
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:55 pm
ORD
- PSE
1 stop16h 12m
Frontier
Wed 5/1310:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 3/17![Frontier logo]()
$335
This Delta deal was found by Cheapflights users on 3/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1212:10 pm
ORD
- SJU
1 stop9h 38m
Delta
Mon 6/152:35 pm
SJU
- ORD
1 stop6h 49m
Delta
Deal found 3/14![Delta logo]()
$406
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Wed 4/221:00 pm
ORD
- SJU
1 stop7h 24m
United Airlines
Mon 4/277:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/15![United Airlines logo]()
$414
This Kiwi.com deal was found by Cheapflights users on 3/15. 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.
Mon 4/66:10 pm
ORD
- BQN
2 stops30h 43m
Multiple Airlines
Tue 4/142:38 am
BQN
- ORD
1 stop11h 22m
Multiple Airlines
Deal found 3/15![Multiple Airlines logo]()
$449
This CheapOair deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Sun 5/102:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 3/19![Frontier logo]()
$341
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Thu 4/92:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Thu 4/167:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/15![United Airlines logo]()
$439
This CheapOair deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:30 pm
ORD
- PSE
1 stop14h 37m
Frontier
Wed 5/2710:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 3/19![Frontier logo]()
$355
This United Airlines deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/182:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Tue 4/217:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/18![United Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Tue 3/314:51 pm
ORD
- MAZ
2 stops15h 51m
Multiple Airlines
Sat 4/44:36 pm
MAZ
- ORD
1 stop14h 09m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/22:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Mon 5/43:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 3/19![United Airlines logo]()
$440
This CheapOair deal was found by Cheapflights users on 3/15. 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.
Tue 6/95:14 pm
ORD
- PSE
1 stop14h 42m
Frontier
Tue 6/169:55 am
PSE
- ORD
1 stop14h 46m
Frontier
Deal found 3/15![Frontier logo]()
$386
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Mon 4/132:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Thu 4/161:00 am
SJU
- ORD
1 stop7h 43m
United Airlines
Deal found 3/16![United Airlines logo]()
$445
This CheapOair deal was found by Cheapflights users on 3/16. 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.
Thu 6/45:30 pm
ORD
- PSE
1 stop14h 37m
Frontier
Mon 6/810:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 3/16![Frontier logo]()
$386
This Kiwi.com deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/38:56 pm
ORD
- CPX
1 stop14h 49m
Multiple Airlines
Tue 4/74:33 pm
CPX
- ORD
1 stop14h 12m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$573
This United Airlines deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Wed 4/293:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 3/19![United Airlines logo]()
$454
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/125:14 pm
ORD
- PSE
1 stop14h 42m
Frontier
Wed 6/179:55 am
PSE
- ORD
1 stop14h 46m
Frontier
Deal found 3/17![Frontier logo]()
$386
This CheapOair deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/194:57 pm
ORD
- BQN
1 stop7h 46m
Multiple Airlines
Fri 4/244:10 pm
BQN
- ORD
2 stops16h 31m
Multiple Airlines
Deal found 3/19![Multiple Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Mon 5/112:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sat 5/167:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/16![United Airlines logo]()
$463
This CheapOair deal was found by Cheapflights users on 3/14. 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.
Fri 6/125:14 pm
ORD
- PSE
1 stop14h 42m
Frontier
Mon 6/159:55 am
PSE
- ORD
1 stop14h 46m
Frontier
Deal found 3/14![Frontier logo]()
$386
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Fri 5/82:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sat 5/167:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/15![United Airlines logo]()
$466
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/91:00 pm
ORD
- BQN
1 stop9h 09m
United Airlines
Sun 6/1412:15 am
BQN
- ORD
1 stop9h 27m
United Airlines
Deal found 3/17![United Airlines logo]()
$561
This United Airlines deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/132:21 pm
ORD
- BQN
1 stop7h 48m
United Airlines
Sat 6/2012:15 am
BQN
- ORD
1 stop8h 27m
United Airlines
Deal found 3/17![United Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Mon 4/201:06 pm
ORD
- BQN
1 stop9h 03m
United Airlines
Wed 4/2212:15 am
BQN
- ORD
1 stop9h 45m
United Airlines
Deal found 3/15![United Airlines logo]()
$576
Last-minute flights from O'Hare Intl to Puerto RicoDiscover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated March 20, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated March 20, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 4/81:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/19![Spirit Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 3/16. 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.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/19![Spirit Airlines logo]()
$213
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/19![Spirit Airlines logo]()
$218
This eDestinos deal was found by Cheapflights users on 3/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:05 pm
ORD
- SJU
1 stop26h 44m
Frontier
Wed 4/1510:54 am
SJU
- ORD
1 stop29h 14m
Frontier
Deal found 3/15![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/117:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Thu 4/164:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$214
This CheapOair deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1110:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$215
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$202
This Priceline deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/137:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$203
This CheapOair deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:05 am
ORD
- SJU
1 stop12h 50m
Multiple Airlines
Thu 4/163:31 pm
SJU
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 3/18![Multiple Airlines logo]()
$208
This Priceline deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/306:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/17![Multiple Airlines 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 March 20, 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 March 20, 2026.
This Super.com deal was found by Cheapflights users on 3/15. 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.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$97
This WAYA deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:51 pm
ORD
- SJU
1 stop7h 28m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$98
This eDestinos deal was found by Cheapflights users on 3/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:18 pm
ORD
- SJU
1 stop8h 45m
Frontier
Deal found 3/15![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3010:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/19![Spirit Airlines logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$105
This eDestinos deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:04 pm
ORD
- SJU
1 stop27h 44m
Frontier
Deal found 3/17![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 3/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 3/19![Spirit Airlines logo]()
$108
This Super.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 3/18![Spirit Airlines logo]()
$109
This Super.com deal was found by Cheapflights users on 3/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
- SJU
1 stop8h 40m
Frontier
Deal found 3/18![Frontier logo]()
$110
This CheapOair deal was found by Cheapflights users on 3/15. 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.
Wed 3/254:18 pm
ORD
- PSE
1 stop17h 22m
Frontier
Deal found 3/15![Frontier logo]()
$132
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 March 20, 2026.
Round-trip from | $202 (Cheapflightsfares) |
|---|---|
One-way from | $97 (Super.com) |
Popular in | December |
Cheapest in | October |
Average price | $416 |
Good round-trip deal | $311 or less |
Good one-way deal | $167 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 March 20, 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 - PSE
ORDPSE
Chicago O'Hare Intl
Wed 5/6
3:55 pm-9:07 am
1 stop16h 12m
Ponce Mercedita
Tue 5/12
10:02 am-11:13 pm
1 stop14h 11m
$264
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Tue 5/19
3:55 pm-10:28 am
1 stop17h 33m
Ponce Mercedita
Mon 5/25
10:02 am-11:13 pm
1 stop14h 11m
$304
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Fri 5/15
5:30 pm-9:07 am
1 stop14h 37m
Ponce Mercedita
Tue 5/19
10:02 am-11:13 pm
1 stop14h 11m
$304
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 6/9
1:15 pm-10:48 pm
1 stop8h 33m
San Juan Luis Munoz Marin Intl
Tue 6/16
6:15 am-4:44 pm
1 stop11h 29m
$326
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Wed 5/6
3:55 pm-9:07 am
1 stop16h 12m
Ponce Mercedita
Wed 5/13
10:02 am-11:13 pm
1 stop14h 11m
$335
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 5/8
5:30 pm-2:02 am
1 stop7h 32m
Aguadilla Borinquen
Sun 5/10
2:59 am-11:13 pm
1 stop21h 14m
$341
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/29
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Sat 5/2
1:00 am-8:44 am
1 stop8h 44m
$354
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Fri 5/22
5:30 pm-9:07 am
1 stop14h 37m
Ponce Mercedita
Wed 5/27
10:02 am-11:13 pm
1 stop14h 11m
$355
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Tue 6/9
5:14 pm-8:56 am
1 stop14h 42m
Ponce Mercedita
Tue 6/16
9:55 am-11:41 pm
1 stop14h 46m
$386
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Thu 6/4
5:30 pm-9:07 am
1 stop14h 37m
Ponce Mercedita
Mon 6/8
10:02 am-11:13 pm
1 stop14h 11m
$386
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-MAZ
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-MAZ
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Puerto Rico?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $124). Flying from Chicago O'Hare Intl Airport to Puerto Rico in December is currently the most expensive (average of $224). 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 March 20, 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 25% on your trip compared to booking a flight at noon.
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 March 14, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Puerto Rico flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 March 20, 2026.
The most flights from ORD to PR0 are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 19% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 141 minutes.
What is the most punctual flight time for Chicago to Puerto Rico flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Puerto Rico flights?
Over the last year, American Airlines have had the lowest number of delays on this route, with just 17% of flights being delayed.
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 March 20, 2026.
Read reviews from past customers who have flown United Airlines,JetBlue, andAmerican Airlines from Chicago O'Hare Intl Airport to Puerto Rico. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Puerto Rico by cabin class
Find flights from O'Hare Intl to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Puerto Rico flights
Browse other O'Hare Intl and Puerto Rico flight options. Last updated on March 20, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from O'Hare Intl to Puerto Rico
Discover the top 7 airlines that operate flights from O'Hare Intl to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$296 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$236 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$313 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$143 | Average$347 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$514 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$312 | Average$521 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$377 | Average$484 | FlexibilityNo cancel fee | On-time63% |