$113+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
May 17 — May 241
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
Cheapest
Best
Last-minute
One-way
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 April 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 April 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Sun 4/192:00 pm
ORD
- SJU
1 stop8h 59m
Multiple Airlines
Wed 4/2910:59 am
SJU
- ORD
Nonstop5h 09m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Mon 5/185:30 pm
ORD
- SJU
1 stop7h 38m
Multiple Airlines
Mon 5/2511:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$225
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Thu 4/303:03 pm
SJU
- ORD
1 stop8h 36m
Frontier
Deal found 4/15![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 4/2710:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Mon 5/411:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Mon 4/2010:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Tue 4/2110:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/145:30 pm
ORD
- SJU
1 stop18h 45m
Multiple Airlines
Sun 5/178:04 pm
SJU
- ORD
1 stop28h 55m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$229
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/193:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Wed 5/276:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/14![Frontier logo]()
$230
This American Airlines deal was found by Cheapflights users on 4/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:00 am
ORD
- SJU
1 stop7h 43m
American Airlines
Wed 8/267:14 pm
SJU
- ORD
1 stop14h 46m
American Airlines
Deal found 4/13![American Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Fri 5/155:30 pm
ORD
- SJU
1 stop7h 38m
Multiple Airlines
Sat 5/238:04 pm
SJU
- ORD
1 stop13h 18m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 4/2810:00 am
ORD
- SJU
Nonstop4h 39m
Multiple Airlines
Wed 5/66:00 am
SJU
- ORD
2 stops14h 51m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Sun 5/312:38 pm
ORD
- SJU
1 stop10h 21m
Multiple Airlines
Sun 5/102:09 am
SJU
- ORD
1 stop11h 45m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$234
This CheapOair deal was found by Cheapflights users on 4/14. 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 4/295:05 am
ORD
- SJU
1 stop13h 17m
Spirit Airlines
Mon 5/411:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$235
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 April 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 April 17, 2026.
This Delta deal was found by Cheapflights users on 4/13. 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.
Wed 8/197:10 am
ORD
- SJU
1 stop8h 25m
Delta
Wed 9/22:40 pm
SJU
- ORD
1 stop10h 17m
Delta
Deal found 4/13![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/282:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sat 5/27:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/12![United Airlines logo]()
$267
This Priceline deal was found by Cheapflights users on 4/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/75:30 pm
ORD
- PSE
1 stop14h 32m
Frontier
Sun 5/1010:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 4/15![Frontier logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 4/2810:31 am
ORD
- BQN
1 stop14h 12m
Multiple Airlines
Thu 4/302:38 am
BQN
- ORD
2 stops33h 55m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$403
This Delta deal was found by Cheapflights users on 4/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/12:59 pm
ORD
- SJU
1 stop6h 18m
Delta
Sat 6/67:30 am
SJU
- ORD
1 stop12h 11m
Delta
Deal found 4/12![Delta logo]()
$236
This CheapOair deal was found by Cheapflights users on 4/12. 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.
Sat 6/135:25 pm
ORD
- PSE
1 stop15h 17m
Frontier
Sun 6/2110:27 am
PSE
- ORD
1 stop23h 54m
Frontier
Deal found 4/12![Frontier logo]()
$321
This Delta deal was found by Cheapflights users on 4/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:03 am
ORD
- SJU
1 stop11h 42m
Delta
Thu 8/131:06 pm
SJU
- ORD
1 stop8h 11m
Delta
Deal found 4/12![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/15. 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 5/72:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Mon 5/117:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/15![United Airlines logo]()
$362
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/175:30 pm
ORD
- PSE
1 stop14h 32m
Frontier
Sun 5/2410:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 4/14![Frontier logo]()
$346
This Delta deal was found by Cheapflights users on 4/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/28:03 am
ORD
- SJU
1 stop7h 42m
Delta
Sun 8/96:00 am
SJU
- ORD
1 stop7h 34m
Delta
Deal found 4/16![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/12. 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 4/302:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sun 5/37:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/12![United Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Sun 5/32:10 pm
ORD
- PSE
2 stops19h 26m
Multiple Airlines
Tue 5/511:14 am
PSE
- ORD
1 stop12h 00m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$405
This Delta deal was found by Cheapflights users on 4/15. 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.
Thu 7/165:15 am
ORD
- SJU
1 stop10h 30m
Delta
Thu 7/232:42 pm
SJU
- ORD
1 stop10h 11m
Delta
Deal found 4/15![Delta logo]()
$326
This CheapOair deal was found by Cheapflights users on 4/13. 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.
Wed 7/85:30 pm
ORD
- PSE
1 stop15h 22m
Frontier
Tue 7/2110:37 am
PSE
- ORD
1 stop13h 37m
Frontier
Deal found 4/13![Frontier logo]()
$361
This United Airlines deal was found by Cheapflights users on 4/15. 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 5/12:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Fri 5/87:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/15![United Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/2911:28 am
ORD
- BQN
2 stops13h 15m
Multiple Airlines
Sat 5/22:48 am
BQN
- ORD
1 stop11h 27m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$427
This CheapOair deal was found by Cheapflights users on 4/14. 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.
Tue 6/95:25 pm
ORD
- PSE
1 stop16h 31m
Frontier
Tue 6/2310:27 am
PSE
- ORD
1 stop13h 52m
Frontier
Deal found 4/14![Frontier logo]()
$366
This United Airlines deal was found by Cheapflights users on 4/12. 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 5/142:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Thu 5/217:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/12![United Airlines logo]()
$380
This CheapOair deal was found by Cheapflights users on 4/12. 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.
Fri 5/85:30 pm
ORD
- BQN
1 stop7h 32m
Frontier
Sun 5/102:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 4/12![Frontier logo]()
$368
This United Airlines deal was found by Cheapflights users on 4/15. 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 7/282:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Mon 8/37:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/15![United Airlines logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/2810:31 am
ORD
- MAZ
2 stops25h 13m
Multiple Airlines
Sat 5/27:35 am
MAZ
- ORD
1 stop14h 14m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$518
This Trip.com deal was found by Cheapflights users on 4/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/147:30 am
ORD
- PSE
2 stops24h 32m
Frontier
Thu 5/2110:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 4/16![Frontier logo]()
$401
This United Airlines deal was found by Cheapflights users on 4/16. 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.
Sat 5/302:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sat 6/67:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/16![United Airlines logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 5/85:30 pm
ORD
- BQN
1 stop7h 32m
Multiple Airlines
Thu 5/212:59 am
BQN
- ORD
1 stop20h 15m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$524
This CheapOair deal was found by Cheapflights users on 4/12. 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.
Thu 5/215:11 pm
ORD
- PSE
1 stop14h 56m
Frontier
Mon 5/2510:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 4/12![Frontier logo]()
$406
This CheapOair deal was found by Cheapflights users on 4/15. 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 5/225:11 pm
ORD
- PSE
1 stop14h 56m
Frontier
Sun 5/3110:02 am
PSE
- ORD
1 stop14h 11m
Frontier
Deal found 4/15![Frontier logo]()
$406
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/307:50 am
ORD
- CPX
2 stops27h 55m
Multiple Airlines
Mon 5/41:05 pm
CPX
- ORD
2 stops23h 14m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$600
This CheapOair deal was found by Cheapflights users on 4/12. 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.
Fri 5/295:11 pm
ORD
- BQN
1 stop7h 51m
Frontier
Fri 6/52:59 am
BQN
- ORD
1 stop21h 14m
Frontier
Deal found 4/12![Frontier logo]()
$451
This Mytrip deal was found by Cheapflights users on 4/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:28 am
ORD
- CPX
3 stops26h 15m
Multiple Airlines
Sun 5/33:03 pm
CPX
- ORD
2 stops28h 35m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$612
This United Airlines deal was found by Cheapflights users on 4/13. 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.
Wed 4/291:06 pm
ORD
- BQN
1 stop9h 03m
United Airlines
Sat 5/212:15 am
BQN
- ORD
1 stop9h 29m
United Airlines
Deal found 4/13![United Airlines logo]()
$596
Last-minute flights from O'Hare Intl to Puerto RicoDiscover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated April 17, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Sun 4/192:00 pm
ORD
- SJU
1 stop8h 59m
Multiple Airlines
Wed 4/2910:59 am
SJU
- ORD
Nonstop5h 09m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Mon 4/2010:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Tue 4/2110:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$228
This Frontier deal was found by Cheapflights users on 4/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Thu 4/303:03 pm
SJU
- ORD
1 stop8h 36m
Frontier
Deal found 4/15![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 4/2710:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Mon 5/411:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 4/16. 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 4/2810:00 am
ORD
- SJU
Nonstop4h 39m
Multiple Airlines
Wed 5/66:00 am
SJU
- ORD
2 stops14h 51m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$233
This CheapOair deal was found by Cheapflights users on 4/14. 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 4/295:05 am
ORD
- SJU
1 stop13h 17m
Spirit Airlines
Mon 5/411:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Sun 5/312:38 pm
ORD
- SJU
1 stop10h 21m
Multiple Airlines
Sun 5/102:09 am
SJU
- ORD
1 stop11h 45m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$234
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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.
Tue 5/510:49 am
ORD
- SJU
1 stop12h 30m
Spirit Airlines
Tue 5/1211:01 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/145:30 pm
ORD
- SJU
1 stop18h 45m
Multiple Airlines
Sun 5/178:04 pm
SJU
- ORD
1 stop28h 55m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 4/14. 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.
Fri 5/155:30 pm
ORD
- SJU
1 stop7h 38m
Multiple Airlines
Sat 5/238:04 pm
SJU
- ORD
1 stop13h 18m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 4/16. 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.
Mon 5/185:30 pm
ORD
- SJU
1 stop7h 38m
Multiple Airlines
Mon 5/2511:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$225
This Frontier deal was found by Cheapflights users on 4/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/193:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Wed 5/276:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/14![Frontier logo]()
$230
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 April 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 April 17, 2026.
This American Airlines deal was found by Cheapflights users on 4/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/106:40 am
ORD
- SJU
1 stop14h 25m
American Airlines
Deal found 4/16![American Airlines logo]()
$113
This eDestinos deal was found by Cheapflights users on 4/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/242:20 pm
ORD
- SJU
1 stop9h 09m
Frontier
Deal found 4/16![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 4/15. 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.
Tue 4/281:27 pm
ORD
- SJU
1 stop28h 55m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$117
This Super.com deal was found by Cheapflights users on 4/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2112:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 4/16![Frontier logo]()
$118
This Super.com deal was found by Cheapflights users on 4/14. 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.
Mon 4/2710:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/189:20 am
ORD
- SJU
1 stop6h 32m
Spirit Airlines
Deal found 4/13![Spirit Airlines logo]()
$120
This Super.com deal was found by Cheapflights users on 4/16. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/710:22 am
ORD
- SJU
1 stop12h 35m
Frontier
Deal found 4/16![Frontier logo]()
$122
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/133:55 pm
ORD
- PSE
1 stop16h 12m
Frontier
Deal found 4/14![Frontier logo]()
$123
This Delta deal was found by Cheapflights users on 4/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:15 am
ORD
- SJU
1 stop7h 20m
Delta
Deal found 4/12![Delta logo]()
$123
This Super.com deal was found by Cheapflights users on 4/14. 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 5/74:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$124
This Expedia deal was found by Cheapflights users on 4/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/284:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$125
This Orbitz deal was found by Cheapflights users on 4/12. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:00 am
ORD
- BQN
1 stop16h 43m
Frontier
Deal found 4/12![Frontier logo]()
$128
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 April 17, 2026.
Round-trip from | $224 (CheapOair) |
|---|---|
One-way from | $113 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $381 |
Good round-trip deal | $343 or less |
Good one-way deal | $189 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 April 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
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 8/19
7:10 am-4:35 pm
1 stop8h 25m
San Juan Luis Munoz Marin Intl
Wed 9/2
2:40 pm-11:57 pm
1 stop10h 17m
$226
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 6/1
2:59 pm-10:17 pm
1 stop6h 18m
San Juan Luis Munoz Marin Intl
Sat 6/6
7:30 am-6:41 pm
1 stop12h 11m
$236
Quickest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/28
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Sat 5/2
7:40 am-11:53 am
Nonstop5h 13m
$267
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Thu 5/7
5:30 pm-9:02 am
1 stop14h 32m
Ponce Mercedita
Sun 5/10
10:02 am-11:13 pm
1 stop14h 11m
$316
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Sat 6/13
5:25 pm-9:42 am
1 stop15h 17m
Ponce Mercedita
Sun 6/21
10:27 am-9:21 am
1 stop23h 54m
$321
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 8/6
8:03 am-8:45 pm
1 stop11h 42m
San Juan Luis Munoz Marin Intl
Thu 8/13
1:06 pm-8:17 pm
1 stop8h 11m
$326
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 8/2
8:03 am-4:45 pm
1 stop7h 42m
San Juan Luis Munoz Marin Intl
Sun 8/9
6:00 am-12:34 pm
1 stop7h 34m
$326
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 7/16
5:15 am-4:45 pm
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Thu 7/23
2:42 pm-11:53 pm
1 stop10h 11m
$326
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Sun 5/17
5:30 pm-9:02 am
1 stop14h 32m
Ponce Mercedita
Sun 5/24
10:02 am-11:13 pm
1 stop14h 11m
$346
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Wed 7/8
5:30 pm-9:52 am
1 stop15h 22m
Ponce Mercedita
Tue 7/21
10:37 am-11:14 pm
1 stop13h 37m
$361
Showing 1-10 of 54 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, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Puerto Rico (average of $115). Flying from Chicago O'Hare Intl Airport to Puerto Rico in November is currently the most expensive (average of $545). 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 April 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 22% 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 April 11, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Puerto Rico flight should consider departing on Monday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 April 17, 2026.
The most flights from ORD to PR0 are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).
How often are flights from Chicago to Puerto Rico delayed?
About 20% of weekly flights between Chicago and Puerto Rico have experienced delays in the past year, with the average delay time being 142 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 18% 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 April 17, 2026.
Read reviews from past customers who have flown United Airlines,JetBlue, andAmerican Airlines from Chicago O'Hare Intl Airport to Puerto Rico. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Entertainment
7.1
Boarding
7.7
Food
6.6
Comfort
7.3
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Puerto Rico. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
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 April 17, 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 April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$115 | Average$300 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$235 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$314 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$143 | Average$347 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$510 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$312 | Average$517 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$484 | FlexibilityNo cancel fee | On-time63% |