$94+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Apr 9 — Apr 161
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 March 10, 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 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:24 pm
ORD
- SJU
1 stop25h 38m
Frontier
Fri 5/298:10 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 3/9![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 5/47:50 am
ORD
- SJU
1 stop17h 16m
Spirit Airlines
Fri 5/83:21 am
SJU
- ORD
1 stop11h 44m
Spirit Airlines
Deal found 3/6![Spirit Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 8/1812:59 am
ORD
- SJU
Nonstop4h 57m
Frontier
Wed 8/268:10 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 3/5![Frontier logo]()
$195
This Frontier deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/95:14 pm
ORD
- SJU
1 stop7h 42m
Frontier
Sat 6/278:10 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 3/6![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/192:10 pm
ORD
- SJU
1 stop21h 23m
Frontier
Sat 4/2511:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/5![Frontier logo]()
$197
This Travelocity deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity 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
Fri 4/176:00 am
SJU
- ORD
1 stop17h 54m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:59 am
ORD
- SJU
Nonstop4h 57m
Frontier
Thu 8/278:10 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 3/9![Frontier logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Sat 4/183:47 pm
SJU
- ORD
1 stop7h 52m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$200
This Frontier deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:00 pm
ORD
- SJU
1 stop9h 18m
Frontier
Thu 4/1611:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/5![Frontier logo]()
$202
This CheapOair deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/202:20 pm
ORD
- SJU
1 stop9h 09m
Frontier
Sat 4/2511:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/5![Frontier logo]()
$204
This Priceline deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/315:14 pm
ORD
- BQN
1 stop17h 37m
Frontier
Sun 6/712:46 pm
BQN
- ORD
1 stop11h 55m
Frontier
Deal found 3/5![Frontier logo]()
$244
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 10, 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 10, 2026.
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/297:10 am
ORD
- SJU
1 stop8h 13m
Delta
Tue 5/52:45 pm
SJU
- ORD
1 stop8h 36m
Delta
Deal found 3/5![Delta logo]()
$266
This CheapOair deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/1410:25 am
ORD
- PSE
1 stop23h 11m
Frontier
Sun 5/319:55 am
PSE
- ORD
1 stop14h 46m
Frontier
Deal found 3/5![Frontier logo]()
$314
This United Airlines deal was found by Cheapflights users on 3/4. 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.
Tue 5/52:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Mon 5/117:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/4![United Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/112:40 pm
ORD
- SJU
2 stops8h 15m
Southwest
Fri 5/155:35 am
SJU
- ORD
2 stops17h 20m
Southwest
Deal found 3/8![Southwest logo]()
$404
This Trip.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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
Mon 4/272:38 am
BQN
- ORD
1 stop11h 22m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/229:50 am
ORD
- SJU
1 stop9h 34m
Delta
Thu 4/302:45 pm
SJU
- ORD
1 stop10h 14m
Delta
Deal found 3/5![Delta logo]()
$266
This Travelocity deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:38 am
ORD
- PSE
1 stop25h 53m
Frontier
Sun 4/1911:21 am
PSE
- ORD
1 stop13h 38m
Frontier
Deal found 3/8![Frontier logo]()
$391
This Orbitz deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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.
Mon 5/46:00 am
ORD
- MAZ
2 stops11h 43m
JetBlue
Mon 5/117:35 am
MAZ
- ORD
2 stops15h 01m
JetBlue
Deal found 3/7![JetBlue logo]()
$782
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/6![United Airlines logo]()
$410
This Priceline deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/84:21 pm
ORD
- BQN
1 stop8h 32m
Frontier
Thu 4/162:38 am
BQN
- ORD
1 stop15h 31m
Frontier
Deal found 3/5![Frontier logo]()
$391
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Wed 4/293:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 3/9![United Airlines logo]()
$412
This CheapOair deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 5/209:41 am
ORD
- BQN
2 stops15h 05m
Multiple Airlines
Mon 6/112:46 pm
BQN
- ORD
1 stop11h 55m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$466
This CheapOair deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:57 am
ORD
- BQN
1 stop17h 46m
Frontier
Sun 5/102:38 am
BQN
- ORD
1 stop12h 39m
Frontier
Deal found 3/8![Frontier logo]()
$413
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/46:00 am
ORD
- SJU
2 stops17h 15m
Southwest
Mon 6/1510:20 pm
SJU
- ORD
2 stops15h 55m
Southwest
Deal found 3/9![Southwest logo]()
$506
This United Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/297:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/7![United Airlines logo]()
$423
This CheapOair deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:00 am
ORD
- BQN
2 stops18h 46m
Multiple Airlines
Tue 5/262:58 am
BQN
- ORD
1 stop21h 43m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$472
This United Airlines deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 6/52:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Mon 6/157:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/6![United Airlines logo]()
$425
This CheapOair deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/215:14 pm
ORD
- PSE
1 stop14h 42m
Frontier
Mon 5/259:55 am
PSE
- ORD
1 stop14h 46m
Frontier
Deal found 3/8![Frontier logo]()
$426
This CheapOair deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 4/258:31 am
ORD
- PSE
2 stops22h 18m
Multiple Airlines
Fri 5/111:31 am
PSE
- ORD
1 stop28h 52m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$480
This CheapOair deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/1311:21 am
ORD
- PSE
1 stop22h 19m
Frontier
Sun 3/1511:35 am
PSE
- ORD
1 stop28h 53m
Frontier
Deal found 3/9![Frontier logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/218:56 pm
ORD
- MAZ
1 stop11h 46m
Multiple Airlines
Wed 3/254:36 pm
MAZ
- ORD
1 stop14h 09m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$490
This United Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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
Tue 4/287:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/7![United Airlines logo]()
$463
This CheapOair deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3010:20 am
ORD
- PSE
1 stop25h 17m
Frontier
Thu 4/212:39 pm
PSE
- ORD
1 stop11h 57m
Frontier
Deal found 3/8![Frontier logo]()
$426
This Priceline deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:31 am
ORD
- PSE
2 stops22h 18m
Multiple Airlines
Sun 4/1911:21 am
PSE
- ORD
1 stop26h 54m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$533
This United Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/97:30 am
ORD
- BQN
2 stops14h 39m
United Airlines
Tue 5/1212:15 am
BQN
- ORD
3 stops21h 23m
United Airlines
Deal found 3/5![United Airlines logo]()
$485
This United Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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
Wed 5/67:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/5![United Airlines logo]()
$503
This Orbitz deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/232:05 pm
ORD
- PSE
1 stop19h 26m
Multiple Airlines
Tue 4/288:39 am
PSE
- ORD
2 stops24h 02m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$557
This Expedia deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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.
Sat 3/2811:00 am
ORD
- MAZ
2 stops21h 42m
JetBlue
Sat 4/44:36 pm
MAZ
- ORD
2 stops16h 29m
JetBlue
Deal found 3/5![JetBlue logo]()
$970
This United Airlines deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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
Sun 5/317:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/7![United Airlines logo]()
$506
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 3/3012:45 pm
ORD
- PSE
1 stop22h 52m
Multiple Airlines
Thu 4/212:39 pm
PSE
- ORD
1 stop11h 57m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$562
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 10, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Puerto Rico. Data last updated March 10, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 3/314:18 pm
ORD
- BQN
1 stop8h 24m
Frontier
Mon 4/69:14 pm
BQN
- ORD
1 stop27h 22m
Frontier
Deal found 3/7![Frontier logo]()
$314
This Priceline deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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.
Sat 4/114:21 pm
ORD
- SJU
1 stop14h 35m
Frontier
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Frontier
Deal found 3/5![Frontier logo]()
$202
This CheapOair deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/116:10 pm
ORD
- SJU
1 stop16h 39m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$210
This Travelocity deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity 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
Fri 4/176:00 am
SJU
- ORD
1 stop17h 54m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Sat 4/183:47 pm
SJU
- ORD
1 stop7h 52m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$200
This CheapOair deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/6![Multiple Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/192:10 pm
ORD
- SJU
1 stop21h 23m
Frontier
Sat 4/2511:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/5![Frontier logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” 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 4/193:08 pm
ORD
- SJU
1 stop22h 19m
Frontier
Wed 4/291:59 am
SJU
- ORD
1 stop10h 04m
Frontier
Deal found 3/6![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/192:10 pm
ORD
- SJU
1 stop21h 23m
Frontier
Mon 4/271:59 am
SJU
- ORD
2 stops16h 01m
Frontier
Deal found 3/5![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/202:20 pm
ORD
- SJU
1 stop9h 09m
Frontier
Sat 4/2511:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/5![Frontier logo]()
$204
This Cheapflightsfares deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:05 am
ORD
- SJU
1 stop13h 17m
Spirit Airlines
Wed 4/2912:57 pm
SJU
- ORD
1 stop12h 27m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$207
This Cheapflightsfares deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/267:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Sat 5/24:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$206
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 10, 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 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2410:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$94
This Super.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$95
This Cheapflightsfares deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/267:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” 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 5/75:16 pm
ORD
- SJU
1 stop6h 37m
Frontier
Deal found 3/7![Frontier logo]()
$100
This CheapOair deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:05 pm
ORD
- PSE
1 stop16h 45m
Frontier
Deal found 3/9![Frontier logo]()
$101
This Booking.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/113:00 pm
ORD
- SJU
1 stop9h 18m
Frontier
Deal found 3/5![Frontier logo]()
$101
This Cheapflightsfares deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 4/147:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2510:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$105
This CheapOair deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/84:21 pm
ORD
- PSE
1 stop18h 28m
Frontier
Deal found 3/9![Frontier logo]()
$107
This Priceline deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/251:27 pm
ORD
- SJU
1 stop21h 56m
Frontier
Deal found 3/9![Frontier logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” 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 5/47:50 am
ORD
- SJU
1 stop17h 16m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$108
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 10, 2026.
Round-trip from | $192 (Kiwi.com) |
|---|---|
One-way from | $94 (Cheapflightsfares) |
Popular in | December |
Cheapest in | October |
Average price | $408 |
Good round-trip deal | $282 or less |
Good one-way deal | $142 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 10, 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 4/29
7:10 am-4:23 pm
1 stop8h 13m
San Juan Luis Munoz Marin Intl
Tue 5/5
2:45 pm-10:21 pm
1 stop8h 36m
$266
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/22
9:50 am-8:24 pm
1 stop9h 34m
San Juan Luis Munoz Marin Intl
Thu 4/30
2:45 pm-11:59 pm
1 stop10h 14m
$266
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Thu 5/14
10:25 am-10:36 am
1 stop23h 11m
Ponce Mercedita
Sun 5/31
9:55 am-11:41 pm
1 stop14h 46m
$314
Quickest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/5
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Mon 5/11
7:40 am-11:53 am
Nonstop5h 13m
$331
ChicagoPonce
ORD - PSE
ORDPSE
Chicago O'Hare Intl
Thu 4/16
7:38 am-10:31 am
1 stop25h 53m
Ponce Mercedita
Sun 4/19
11:21 am-11:59 pm
1 stop13h 38m
$391
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Wed 4/8
4:21 pm-1:53 am
1 stop8h 32m
Aguadilla Borinquen
Thu 4/16
2:38 am-5:09 pm
1 stop15h 31m
$391
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 5/11
2:40 pm-11:55 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Fri 5/15
5:35 am-9:55 pm
2 stops17h 20m
$404
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 5/11
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Sat 5/16
7:40 am-11:53 am
Nonstop5h 13m
$410
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 4/23
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Wed 4/29
3:56 pm-8:15 pm
Nonstop5h 19m
$412
ChicagoAguadilla
ORD - BQN
ORDBQN
Chicago O'Hare Intl
Fri 5/8
6:57 am-1:43 am
1 stop17h 46m
Aguadilla Borinquen
Sun 5/10
2:38 am-2:17 pm
1 stop12h 39m
$413
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-MAZ
ORD-BQN
ORD-CPX
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Puerto Rico
ORD-PR0
ORD-SJU
ORD-PSE
ORD-MAZ
ORD-BQN
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 10, 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 26% 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 February 21, 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 10, 2026.
The most flights from ORD to PR0 are scheduled on a Monday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (11 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 10, 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
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Food
6.6
Boarding
7.7
Overall
7.4
Crew
8.1
Comfort
7.3
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 10, 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$296 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$236 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$337 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$311 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$253 | Average$514 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$313 | Average$522 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$377 | Average$487 | FlexibilityNo cancel fee | On-time63% |