$141+ Cheap flights from Puerto Rico to O'Hare Intl (ORD)
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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Aug 4 — Aug 111
Round-trip
1 adult, Economy
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Find cheap flights from Puerto Rico to O'Hare Intl with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Puerto Rico to O'Hare Intl
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Cheapest flights from Puerto Rico to O'Hare IntlExplore the most affordable flight options available from Puerto Rico to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 5, 2026.
Explore the most affordable flight options available from Puerto Rico to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/3112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$212
This Frontier deal was found by Cheapflights users on 7/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Wed 8/1212:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/4![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Sun 8/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/4![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Fri 8/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Mon 8/2412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Tue 8/2512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$217
This Frontier deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Fri 8/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/2![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Sat 8/2212:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/1![Frontier logo]()
$219
This Booking.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/2412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$220
This eDestinos deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 7/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$221
This Expedia deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 7/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/5. 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 8/246:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Sat 8/2912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/5![Frontier logo]()
$224
Best flights from Puerto Rico to O'Hare IntlDiscover carefully curated flight deals from Puerto Rico to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 5, 2026.
Discover carefully curated flight deals from Puerto Rico to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 5, 2026.
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Sat 8/2910:40 am
ORD
- SJU
1 stop8h 58m
United Airlines
Deal found 6/30![United Airlines logo]()
$242
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Tue 8/255:30 am
ORD
- SJU
1 stop7h 12m
Delta
Deal found 7/3![Delta logo]()
$246
This Frontier deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:19 pm
BQN
- ORD
1 stop11h 51m
Frontier
Wed 8/195:59 pm
ORD
- BQN
1 stop7h 11m
Frontier
Deal found 7/3![Frontier logo]()
$392
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:01 am
BQN
- ORD
1 stop10h 23m
JetBlue
Wed 8/192:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 7/2![JetBlue logo]()
$392
This United Airlines deal was found by Cheapflights users on 7/4. 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.
Thu 8/202:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
Tue 8/255:30 am
ORD
- SJU
1 stop9h 12m
United Airlines
Deal found 7/4![United Airlines logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/155:41 pm
CPX
- ORD
2 stops19h 34m
Multiple Airlines
Sat 7/1812:44 am
ORD
- CPX
1 stop8h 38m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$675
This United Airlines deal was found by Cheapflights users on 7/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Wed 9/28:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 7/4![United Airlines logo]()
$327
This Delta deal was found by Cheapflights users on 7/5. 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.
Sun 8/237:00 am
SJU
- ORD
1 stop6h 40m
Delta
Sat 8/296:40 am
ORD
- SJU
1 stop8h 58m
Delta
Deal found 7/5![Delta logo]()
$366
This Frontier deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2112:04 pm
BQN
- ORD
1 stop12h 06m
Frontier
Sat 8/85:13 pm
ORD
- BQN
1 stop7h 57m
Frontier
Deal found 6/30![Frontier logo]()
$396
This United Airlines deal was found by Cheapflights users on 7/4. 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.
Fri 8/214:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Thu 8/278:50 am
ORD
- SJU
1 stop10h 48m
United Airlines
Deal found 7/4![United Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:00 am
SJU
- ORD
1 stop10h 41m
United Airlines
Wed 9/210:40 am
ORD
- SJU
1 stop8h 58m
United Airlines
Deal found 7/1![United Airlines logo]()
$336
This SmartFares deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/213:20 pm
BQN
- ORD
1 stop10h 24m
JetBlue
Thu 1/77:00 am
ORD
- BQN
1 stop16h 33m
JetBlue
Deal found 7/2![JetBlue logo]()
$599
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/2512:19 pm
BQN
- ORD
2 stops20h 34m
Frontier
Fri 7/315:13 pm
ORD
- BQN
1 stop7h 57m
Frontier
Deal found 7/4![Frontier logo]()
$570
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/193:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Fri 9/258:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 7/2![United Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 7/4. 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.
Fri 10/92:55 pm
SJU
- ORD
1 stop10h 28m
United Airlines
Fri 10/168:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 7/4![United Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:00 am
SJU
- ORD
1 stop9h 45m
United Airlines
Sun 10/48:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/30![United Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/151:25 pm
SJU
- ORD
2 stops17h 42m
United Airlines
Tue 9/297:15 am
ORD
- SJU
2 stops15h 35m
United Airlines
Deal found 7/1![United Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/38:25 am
SJU
- ORD
Nonstop5h 24m
United Airlines
Thu 11/52:16 pm
ORD
- SJU
Nonstop4h 44m
United Airlines
Deal found 7/1![United Airlines logo]()
$482
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:15 am
BQN
- ORD
2 stops32h 06m
United Airlines
Sun 9/62:31 pm
ORD
- BQN
1 stop7h 38m
United Airlines
Deal found 7/1![United Airlines logo]()
$633
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:15 am
BQN
- ORD
2 stops15h 40m
United Airlines
Sun 9/139:40 pm
ORD
- BQN
2 stops24h 29m
United Airlines
Deal found 7/1![United Airlines logo]()
$640
This United Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/812:15 am
BQN
- ORD
1 stop8h 27m
United Airlines
Wed 10/141:35 pm
ORD
- BQN
1 stop8h 34m
United Airlines
Deal found 7/3![United Airlines logo]()
$647
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:15 am
BQN
- ORD
2 stops19h 23m
United Airlines
Sat 9/127:20 am
ORD
- BQN
2 stops14h 49m
United Airlines
Deal found 7/1![United Airlines logo]()
$652
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/281:19 pm
MAZ
- ORD
1 stop7h 46m
United Airlines
Fri 10/25:00 am
ORD
- MAZ
2 stops10h 11m
United Airlines
Deal found 7/2![United Airlines logo]()
$1,101
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:48 am
CPX
- ORD
2 stops13h 38m
United Airlines
Wed 9/28:55 am
ORD
- CPX
1 stop7h 26m
United Airlines
Deal found 7/1![United Airlines logo]()
$1,553
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:51 am
VQS
- ORD
1 stop9h 14m
United Airlines
Sat 9/58:55 am
ORD
- VQS
1 stop8h 35m
United Airlines
Deal found 7/1![United Airlines logo]()
$5,472
Last-minute flights from Puerto Rico to O'Hare IntlDiscover last-minute flight deals from Puerto Rico to O'Hare Intl. Data last updated July 5, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to O'Hare Intl. Data last updated July 5, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 7/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Wed 8/1212:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/4![Frontier logo]()
$213
This eDestinos deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/87:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 7/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$221
This Expedia deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/107:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 7/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Sun 8/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/4![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Tue 8/2512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Mon 8/2412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Sat 8/2212:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/1![Frontier logo]()
$219
This Booking.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/2412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Fri 8/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/2![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 7/5. 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 8/246:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Sat 8/2912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/5![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Sun 8/3012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/307:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/3112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/3![Frontier logo]()
$212
One-way flights from Puerto Rico to O'Hare IntlSearch for one-way flight options from Puerto Rico to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated July 5, 2026.
Search for one-way flight options from Puerto Rico to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated July 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/30![Frontier logo]()
$141
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:55 pm
SJU
- ORD
1 stop10h 50m
United Airlines
Deal found 7/1![United Airlines logo]()
$143
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:00 am
SJU
- ORD
1 stop9h 58m
American Airlines
Deal found 7/1![American Airlines logo]()
$146
This Super.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$147
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:10 pm
SJU
- ORD
1 stop7h 20m
American Airlines
Deal found 6/30![American Airlines logo]()
$148
This Expedia deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/2![Frontier logo]()
$149
This Trip.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/143:10 am
BQN
- ORD
1 stop21h 00m
Frontier
Deal found 7/2![Frontier logo]()
$151
This eDestinos deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$151
This Super.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/3![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/113:10 am
BQN
- ORD
1 stop21h 00m
Frontier
Deal found 7/1![Frontier logo]()
$153
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:25 am
SJU
- ORD
1 stop10h 21m
American Airlines
Deal found 7/1![American Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/123:10 am
BQN
- ORD
1 stop21h 00m
Frontier
Deal found 7/1![Frontier logo]()
$177
Find flight deals from Puerto Rico to O'Hare Intl
Keep the following information in mind while searching for Puerto Rico to O'Hare Intl flight deals. Data was last updated July 5, 2026.
Round-trip from | $212 (Kiwi.com) |
|---|---|
One-way from | $141 (Kiwi.com) |
Popular in | June |
Cheapest in | February |
Average price | $333 |
Good round-trip deal | $350 or less |
Good one-way deal | $203 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Puerto Rico to O'Hare Intl 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 July 5, 2026.
Use the filters below to find and compare flights from Puerto Rico to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/26
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Sat 8/29
10:40 am-8:38 pm
1 stop8h 58m
$242
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/20
5:49 pm-11:57 pm
1 stop7h 08m
Chicago O'Hare Intl
Tue 8/25
5:30 am-1:42 pm
1 stop7h 12m
$246
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/20
2:20 pm-11:26 pm
1 stop10h 06m
Chicago O'Hare Intl
Tue 8/25
5:30 am-3:42 pm
1 stop9h 12m
$289
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/26
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Wed 9/2
8:55 am-2:44 pm
Nonstop4h 49m
$327
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 8/21
4:55 pm-11:40 pm
1 stop7h 45m
Chicago O'Hare Intl
Thu 8/27
8:50 am-8:38 pm
1 stop10h 48m
$336
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 9/1
7:00 am-4:41 pm
1 stop10h 41m
Chicago O'Hare Intl
Wed 9/2
10:40 am-8:38 pm
1 stop8h 58m
$336
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sun 8/23
7:00 am-12:40 pm
1 stop6h 40m
Chicago O'Hare Intl
Sat 8/29
6:40 am-4:38 pm
1 stop8h 58m
$366
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Sat 8/15
12:19 pm-11:10 pm
1 stop11h 51m
Chicago O'Hare Intl
Wed 8/19
5:59 pm-2:10 am
1 stop7h 11m
$392
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Sat 8/15
5:01 am-2:24 pm
1 stop10h 23m
Chicago O'Hare Intl
Wed 8/19
2:35 pm-12:33 am
1 stop8h 58m
$392
AguadillaChicago
BQN - ORD
BQNORD
Aguadilla Borinquen
Tue 7/21
12:04 pm-11:10 pm
1 stop12h 06m
Chicago O'Hare Intl
Sat 8/8
5:13 pm-2:10 am
1 stop7h 57m
$396
Showing 1-10 of 43 resultsSorted by cheapest first
Best time to book a flight from Puerto Rico to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Puerto Rico with our price prediction graph.
SJU-ORD
BQN-ORD
CPX-ORD
MAZ-ORD
VQS-ORD
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 Puerto Rico to Chicago O'Hare Intl Airport
PR0-ORD
SJU-ORD
BQN-ORD
CPX-ORD
MAZ-ORD
What is the cheapest month to book a flight from Puerto Rico to Chicago O'Hare Intl Airport?
Currently, May is the cheapest month in which you can book a flight from Puerto Rico to Chicago O'Hare Intl Airport (average of $64). Flying from Puerto Rico to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $123). 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 PR to ORD?
Find hourly flight availability from Puerto Rico to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 5, 2026.
A simple way to save on the total cost of your ticket is to fly from Puerto Rico to Chicago O'Hare Intl Airport in the evening. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight in the morning.
Weekly flight availability from Puerto Rico to Chicago O'Hare Intl Airport
Explore weekly flight availability from Puerto Rico to O'Hare Intl. 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 July 5, 2026.
The most flights from PR0 to ORD 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 Puerto Rico to Chicago delayed?
About 8% of weekly flights between Puerto Rico and Chicago have experienced delays in the past year, with the average delay time being 184 minutes.
What is the most punctual flight time for Puerto Rico to Chicago flights?
Historically, flights departing at night 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 Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Puerto Rico to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 4% of flights being delayed.
How far ahead should I book a flight from Puerto Rico to Chicago O'Hare Intl Airport?
Booking 81 days in advance of your planned departure date is, on average, the best time to get cheap flights from Puerto Rico to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Puerto Rico to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from Puerto Rico to O'Hare Intl. Price data was last updated on July 4, 2026.
Travelers seeking maximum savings on their Puerto Rico to Chicago O'Hare Intl Airport flight should consider departing on Sunday at noon 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.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated July 5, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from Puerto Rico to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Overall
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Overall
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Overall
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Overall
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Overall
7.8
Crew
8.5
Boarding
8.1
Food
7.2
Comfort
7.8
Entertainment
7.8
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Related info for your journey
Find useful and relevant information for your journey from Puerto Rico to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Oak Brook
Gurnee
Delavan
Oakbrook Terrace
Downers Grove
Des Plaines
South Holland
Libertyville
Hoffman Estates
Warrenville
Rockford
Racine
Great Lakes
Northbrook
Waukegan
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Complete your trip
Complete your trip to O'Hare Intl by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Puerto Rico to O'Hare Intl by cabin class
Find flights from Puerto Rico to O'Hare Intl, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on July 5, 2026.
Puerto Rico and O'Hare Intl flights
Browse other Puerto Rico and O'Hare Intl flight options. Last updated on July 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 6 airlines flying from Puerto Rico to O'Hare Intl
Discover the top 6 airlines that operate flights from Puerto Rico to O'Hare Intl. 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 July 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$275 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$204 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$434 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$261 | Average$482 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$457 | FlexibilityNo cancel fee | On-time63% |