$115+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Sep 30 — Oct 71
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
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 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 August 31, 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 August 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Sat 9/57:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/30![Frontier logo]()
$166
This CheapOair deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/27:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/29![Frontier logo]()
$173
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Tue 9/17:14 pm -
Nonstop5h 13m
Thu 9/312:44 am -
Nonstop5h 00m
Deal found 8/30![Frontier logo]()
$177
This Priceline deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/29![Frontier logo]()
$178
This eDestinos deal was found by Cheapflights users on 8/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/30![Frontier logo]()
$179
This Orbitz deal was found by Cheapflights users on 8/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:14 pm -
Nonstop5h 13m
Mon 9/712:44 am -
Nonstop5h 00m
Deal found 8/30![Frontier logo]()
$188
This eDestinos deal was found by Cheapflights users on 8/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/30![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 am -
1 stop8h 45m
Sat 10/248:04 am -
1 stop28h 27m
Deal found 8/26![Frontier logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/17:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/29![Frontier logo]()
$203
This Priceline deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Fri 9/1811:08 am -
1 stop12h 51m
Tue 9/223:50 pm -
1 stop17h 24m
Deal found 8/28![Frontier logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:08 am -
1 stop12h 51m
Tue 9/223:50 pm -
1 stop17h 24m
Deal found 8/28![Frontier logo]()
$332
This Super.com deal was found by Cheapflights users on 8/30. 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.
Sun 9/2711:08 am -
1 stop12h 51m
Sun 10/43:50 pm -
1 stop17h 23m
Deal found 8/30![Frontier logo]()
$333
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 August 31, 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 August 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:08 am -
1 stop12h 51m
Wed 9/237:25 am -
2 stops25h 48m
Deal found 8/28![Frontier logo]()
$371
This United Airlines deal was found by Cheapflights users on 8/30. 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.
Fri 9/253:56 pm -
Nonstop5h 09m
Sun 10/48:55 am -
Nonstop4h 49m
Deal found 8/30![United Airlines logo]()
$382
This Cheapflightsfares deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:20 pm -
1 stop10h 24m
Sun 11/152:35 pm -
1 stop8h 58m
Deal found 8/29![JetBlue logo]()
$491
This CheapOair deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 11/712:22 pm -
1 stop22h 24m
Sun 11/152:35 pm -
1 stop8h 58m
Deal found 8/26![Multiple Airlines logo]()
$509
This FlightHub deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1811:08 am -
1 stop12h 51m
Mon 9/213:50 pm -
1 stop17h 04m
Deal found 8/28![Frontier logo]()
$390
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 10/12:55 pm -
1 stop10h 28m
Sun 10/48:55 am -
Nonstop4h 49m
Deal found 8/28![United Airlines logo]()
$410
This FlightHub deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:12 am -
1 stop12h 47m
Mon 9/213:50 pm -
1 stop17h 04m
Deal found 8/28![Frontier logo]()
$409
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/253:56 pm -
Nonstop5h 09m
Sun 9/278:55 am -
Nonstop4h 49m
Deal found 8/26![United Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 8/30. 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.
Thu 9/103:56 pm -
Nonstop5h 09m
Sun 9/138:55 am -
Nonstop4h 49m
Deal found 8/30![United Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 9/142:44 am -
1 stop21h 15m
Tue 9/293:50 pm -
1 stop17h 24m
Deal found 8/29![Frontier logo]()
$450
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/161:25 pm -
2 stops19h 18m
Mon 10/195:55 pm -
2 stops18h 50m
Deal found 8/26![United Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 11/58:25 am -
Nonstop5h 22m
Thu 11/52:16 pm -
Nonstop4h 44m
Deal found 8/29![United Airlines logo]()
$469
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/303:56 pm -
Nonstop5h 09m
Sat 10/38:55 am -
Nonstop4h 49m
Deal found 8/28![United Airlines logo]()
$472
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 11/241:09 am -
1 stop9h 53m
Mon 11/302:30 pm -
1 stop7h 27m
Deal found 8/27![United Airlines logo]()
$511
This United Airlines deal was found by Cheapflights users on 8/30. 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.
Mon 11/164:55 pm -
Nonstop5h 31m
Thu 12/32:16 pm -
Nonstop4h 44m
Deal found 8/30![United Airlines logo]()
$517
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/23:56 pm -
Nonstop5h 09m
Mon 10/58:55 am -
Nonstop4h 49m
Deal found 8/29![United Airlines logo]()
$517
This United Airlines deal was found by Cheapflights users on 8/30. 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.
Thu 1/211:09 am -
2 stops12h 18m
Fri 1/222:25 pm -
1 stop7h 32m
Deal found 8/30![United Airlines logo]()
$555
This United Airlines deal was found by Cheapflights users on 8/30. 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.
Thu 9/2412:15 am -
1 stop10h 27m
Mon 9/281:55 pm -
1 stop8h 14m
Deal found 8/30![United Airlines logo]()
$581
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/71:00 am -
1 stop9h 00m
Mon 10/128:55 am -
Nonstop4h 49m
Deal found 8/26![United Airlines logo]()
$596
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/52:55 pm -
1 stop9h 31m
Tue 9/812:29 pm -
2 stops10h 21m
Deal found 8/28![United Airlines logo]()
$640
This United Airlines deal was found by Cheapflights users on 8/30. 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 10/33:56 pm -
Nonstop5h 09m
Thu 10/88:55 am -
Nonstop4h 49m
Deal found 8/30![United Airlines logo]()
$687
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 10/11:19 pm -
2 stops11h 13m
Mon 10/55:00 am -
2 stops10h 11m
Deal found 8/26![United Airlines logo]()
$1,277
Last-minute flights from Puerto Rico to O'Hare IntlDiscover last-minute flight deals from Puerto Rico to O'Hare Intl. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Puerto Rico to O'Hare Intl. Data last updated August 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Tue 9/17:14 pm -
Nonstop5h 13m
Thu 9/312:44 am -
Nonstop5h 00m
Deal found 8/30![Frontier logo]()
$177
This Priceline deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/29![Frontier logo]()
$178
This Orbitz deal was found by Cheapflights users on 8/30. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:14 pm -
Nonstop5h 13m
Mon 9/712:44 am -
Nonstop5h 00m
Deal found 8/30![Frontier logo]()
$188
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$171
This FlightHub deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$172
This eDestinos deal was found by Cheapflights users on 8/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/30![Frontier logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Sat 9/57:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/30![Frontier logo]()
$166
This Priceline deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:52 am -
1 stop13h 07m
Wed 9/303:50 pm -
1 stop17h 23m
Deal found 8/31![Frontier logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1711:08 am -
1 stop12h 51m
Tue 9/223:50 pm -
1 stop17h 24m
Deal found 8/28![Frontier logo]()
$332
This Priceline deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Fri 9/1811:08 am -
1 stop12h 51m
Tue 9/223:50 pm -
1 stop17h 24m
Deal found 8/28![Frontier logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 am -
1 stop8h 45m
Sat 10/248:04 am -
1 stop28h 27m
Deal found 8/26![Frontier logo]()
$197
This Super.com deal was found by Cheapflights users on 8/30. 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.
Sun 9/2711:08 am -
1 stop12h 51m
Sun 10/43:50 pm -
1 stop17h 23m
Deal found 8/30![Frontier logo]()
$333
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 August 31, 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 August 31, 2026.
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:41 pm -
1 stop11h 19m
Deal found 8/31![American Airlines logo]()
$115
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/263:41 pm -
1 stop9h 20m
Deal found 8/27![American Airlines logo]()
$116
This Super.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/31![Frontier logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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 10/306:15 am -
1 stop10h 22m
Deal found 8/29![Frontier logo]()
$122
This Travelocity deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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.
Tue 9/87:14 pm -
Nonstop5h 13m
Deal found 8/28![Frontier logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Thu 10/17:00 am -
1 stop8h 45m
Deal found 8/30![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 11/197:00 am -
1 stop10h 37m
Deal found 8/28![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” 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 9/67:00 am -
1 stop7h 49m
Deal found 8/28![JetBlue logo]()
$127
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/106:00 am -
1 stop13h 07m
Deal found 8/26![American Airlines logo]()
$128
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” 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 9/512:55 am -
Nonstop5h 05m
Deal found 8/27![American Airlines logo]()
$129
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” 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.
Fri 9/412:55 am -
Nonstop5h 05m
Deal found 8/29![American Airlines logo]()
$131
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” 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 9/212:55 am -
Nonstop5h 05m
Deal found 8/26![American Airlines logo]()
$132
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 August 31, 2026.
Round-trip from | $196 (Kiwi.com) |
|---|---|
One-way from | $115 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $287 |
Good round-trip deal | $346 or less |
Good one-way deal | $216 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 7,457,451 searches. Data last updated August 31, 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
AguadillaChicago
BQN Aguadilla Borinquen - ORD Chicago O'Hare Intl
BQNORD
Aguadilla Borinquen
Fri 9/18
11:08 am-10:59 pm
1 stop12h 51m
Chicago O'Hare Intl
Wed 9/23
7:25 am-10:13 am
2 stops25h 48m
$371
Quickest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/25
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Sun 10/4
8:55 am-2:44 pm
Nonstop4h 49m
$382
AguadillaChicago
BQN Aguadilla Borinquen - ORD Chicago O'Hare Intl
BQNORD
Aguadilla Borinquen
Fri 9/18
11:08 am-10:59 pm
1 stop12h 51m
Chicago O'Hare Intl
Mon 9/21
3:50 pm-9:54 am
1 stop17h 04m
$390
AguadillaChicago
BQN Aguadilla Borinquen - ORD Chicago O'Hare Intl
BQNORD
Aguadilla Borinquen
Sat 9/19
11:12 am-10:59 pm
1 stop12h 47m
Chicago O'Hare Intl
Mon 9/21
3:50 pm-9:54 am
1 stop17h 04m
$409
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 10/1
2:55 pm-12:23 am
1 stop10h 28m
Chicago O'Hare Intl
Sun 10/4
8:55 am-2:44 pm
Nonstop4h 49m
$410
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/25
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Sun 9/27
8:55 am-2:44 pm
Nonstop4h 49m
$422
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/10
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Sun 9/13
8:55 am-2:44 pm
Nonstop4h 49m
$440
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 10/16
1:25 pm-7:43 am
2 stops19h 18m
Chicago O'Hare Intl
Mon 10/19
5:55 pm-1:45 pm
2 stops18h 50m
$440
AguadillaChicago
BQN Aguadilla Borinquen - ORD Chicago O'Hare Intl
BQNORD
Aguadilla Borinquen
Mon 9/14
2:44 am-10:59 pm
1 stop21h 15m
Chicago O'Hare Intl
Tue 9/29
3:50 pm-10:14 am
1 stop17h 24m
$450
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 11/5
8:25 am-11:47 am
Nonstop5h 22m
Chicago O'Hare Intl
Thu 11/5
2:16 pm-9:00 pm
Nonstop4h 44m
$469
Showing 1-10 of 38 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
MAZ-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
MAZ-ORD
What is the cheapest month to book a flight from Puerto Rico to Chicago O'Hare Intl Airport?
Currently, February is the cheapest month in which you can book a flight from Puerto Rico to Chicago O'Hare Intl Airport (average of $223). Flying from Puerto Rico to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $439). 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 August 31, 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 at noon. If you’re flexible enough to do this you can expect to save up to 16% 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 August 31, 2026.
The most flights from PR0 to ORD are scheduled on a Monday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (6 on average).
How often are flights from Puerto Rico to Chicago delayed?
About 9% 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 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 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 August 29, 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. Wednesday 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 August 31, 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.
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Comfort
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Crew
8.5
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
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
Naperville
Glenview
Lake Geneva
Schaumburg
Oakbrook Terrace
Delavan
Oak Brook
Libertyville
Des Plaines
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
South Holland
Elgin
Racine
Skokie
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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 August 31, 2026.
Puerto Rico and O'Hare Intl flights
Browse other Puerto Rico and O'Hare Intl flight options. Last updated on August 31, 2026.
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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 7,457,451 searches. Data last updated August 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$282 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$216 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$425 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$267 | Average$470 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$427 | FlexibilityNo cancel fee | On-time63% |