$105+ Cheap flights from O'Hare Intl (ORD) to San Juan
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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Sep 4 — Sep 111
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to San Juan 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.Cheapflights Tip: The best prices from Chicago O'Hare Intl to San Juan are usually found in September or August, booked 56 days in advance, depart on a Tuesday or Monday and return on a Thursday
Cheap flight deals from O'Hare Intl to San Juan
Cheapest
Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to San JuanExplore the most affordable flight options available from O'Hare Intl to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 5, 2026.
Explore the most affordable flight options available from O'Hare Intl to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Thu 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/5![Frontier logo]()
$223
This Super.com deal was found by Cheapflights users on 8/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/1![Frontier logo]()
$224
This Super.com deal was found by Cheapflights users on 7/31. 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.
Tue 8/2512:44 am -
Nonstop5h 00m
Wed 9/27:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 8/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/2![Frontier logo]()
$226
This Super.com deal was found by Cheapflights users on 7/31. 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 8/2112:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 8/1![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Wed 9/27:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$230
This Super.com deal was found by Cheapflights users on 8/3. 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.
Sun 8/1612:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$232
This Frontier deal was found by Cheapflights users on 8/3. 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.
Mon 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
Best flights from O'Hare Intl to San JuanDiscover carefully curated flight deals from O'Hare Intl to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 5, 2026.
Discover carefully curated flight deals from O'Hare Intl to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 5, 2026.
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Wed 9/28:55 am -
Nonstop4h 49m
Tue 9/81:00 am -
1 stop9h 44m
Deal found 8/5![United Airlines logo]()
$252
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:35 pm -
1 stop7h 45m
Tue 9/85:05 am -
1 stop9h 34m
Deal found 7/31![JetBlue logo]()
$300
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Sat 9/195:00 am -
1 stop7h 45m
Sat 9/261:25 pm -
1 stop10h 04m
Deal found 8/4![United Airlines logo]()
$256
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am -
1 stop8h 05m
Sat 9/55:00 pm -
1 stop7h 44m
Deal found 7/31![JetBlue logo]()
$300
This JetBlue deal was found by Cheapflights users on 7/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:35 pm -
1 stop7h 45m
Fri 9/45:05 am -
1 stop9h 34m
Deal found 7/31![JetBlue logo]()
$300
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:55 am -
Nonstop4h 49m
Sat 9/123:56 pm -
Nonstop5h 09m
Deal found 7/31![United Airlines logo]()
$387
This JetBlue deal was found by Cheapflights users on 8/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:59 am -
1 stop7h 35m
Thu 10/14:29 pm -
1 stop7h 39m
Deal found 8/1![JetBlue logo]()
$400
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Sun 8/305:00 am -
1 stop7h 45m
Wed 9/22:20 pm -
1 stop10h 06m
Deal found 8/4![United Airlines logo]()
$416
This United Airlines deal was found by Cheapflights users on 8/2. 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.
Thu 10/228:55 am -
Nonstop4h 49m
Sun 10/253:55 pm -
Nonstop5h 31m
Deal found 8/2![United Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 8/4. 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 10/28:55 am -
Nonstop4h 49m
Sat 10/173:56 pm -
Nonstop5h 09m
Deal found 8/4![United Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 8/1. 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.
Wed 9/98:55 am -
Nonstop4h 49m
Thu 9/103:56 pm -
Nonstop5h 09m
Deal found 8/1![United Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 8/3. 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 10/15:30 am -
1 stop9h 12m
Sun 10/43:56 pm -
Nonstop5h 09m
Deal found 8/3![United Airlines logo]()
$462
Last-minute flights from O'Hare Intl to San JuanDiscover last-minute flight deals from O'Hare Intl to San Juan. Data last updated August 5, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to San Juan. Data last updated August 5, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/3. 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.
Sun 8/1612:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 8/3. 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.
Mon 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
This Super.com deal was found by Cheapflights users on 7/31. 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 8/2112:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$227
This Super.com deal was found by Cheapflights users on 7/31. 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.
Tue 8/2512:44 am -
Nonstop5h 00m
Wed 9/27:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$225
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:44 am -
Nonstop5h 00m
Tue 9/17:14 pm -
Nonstop5h 13m
Deal found 8/1![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$230
This Super.com deal was found by Cheapflights users on 8/1. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/1![Frontier logo]()
$224
This Super.com deal was found by Cheapflights users on 8/2. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 8/2![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Wed 9/27:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$229
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:44 am -
Nonstop5h 00m
Sun 9/67:14 pm -
Nonstop5h 13m
Deal found 7/31![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/5![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Thu 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
One-way flights from O'Hare Intl to San JuanSearch for one-way flight options from O'Hare Intl to San Juan. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
Search for one-way flight options from O'Hare Intl to San Juan. Find affordable one-way fares based on user searches. Data last updated August 5, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Sat 9/267:11 am -
1 stop8h 52m
Deal found 8/3![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Sat 9/127:11 am -
1 stop29h 23m
Deal found 8/3![Frontier logo]()
$109
This eDestinos deal was found by Cheapflights users on 8/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:44 am -
Nonstop5h 00m
Deal found 8/2![Frontier logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 8/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:11 am -
1 stop29h 23m
Deal found 8/2![Frontier logo]()
$111
This eDestinos deal was found by Cheapflights users on 8/3. 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.
Sun 8/912:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 8/3. 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.
Thu 8/2712:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 7/31. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Deal found 7/31![Frontier logo]()
$114
This Frontier deal was found by Cheapflights users on 8/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:44 am -
Nonstop5h 00m
Deal found 8/1![Frontier logo]()
$116
This eDestinos deal was found by Cheapflights users on 8/3. 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.
Fri 8/1412:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 8/3. 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.
Wed 8/2612:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$118
Find flight deals from O'Hare Intl to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to San Juan (PR1). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 5, 2026.
Round-trip from | $222 (Kiwi.com) |
|---|---|
One-way from | $105 (Kiwi.com) |
Popular in | December |
Cheapest in | September |
Average price | $344 |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to San Juan 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 August 5, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 9/2
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Tue 9/8
1:00 am-9:44 am
1 stop9h 44m
$252
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 9/19
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Sat 9/26
1:25 pm-10:29 pm
1 stop10h 04m
$256
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 8/11
2:35 pm-11:20 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Tue 9/8
5:05 am-1:39 pm
1 stop9h 34m
$300
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 8/12
7:00 am-4:05 pm
1 stop8h 05m
San Juan Luis Munoz Marin Intl
Sat 9/5
5:00 pm-11:44 pm
1 stop7h 44m
$300
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Thu 8/13
2:35 pm-11:20 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Fri 9/4
5:05 am-1:39 pm
1 stop9h 34m
$300
Quickest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 9/8
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Sat 9/12
3:56 pm-8:05 pm
Nonstop5h 09m
$387
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 9/23
10:59 am-7:34 pm
1 stop7h 35m
San Juan Luis Munoz Marin Intl
Thu 10/1
4:29 pm-11:08 pm
1 stop7h 39m
$400
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sun 8/30
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Wed 9/2
2:20 pm-11:26 pm
1 stop10h 06m
$416
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Thu 10/22
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Sun 10/25
3:55 pm-8:26 pm
Nonstop5h 31m
$457
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 10/2
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Sat 10/17
3:56 pm-8:05 pm
Nonstop5h 09m
$457
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from O'Hare Intl with our price prediction graph.
ORD-PR1
ORD-SJU
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 San Juan
ORD-PR1
ORD-SJU
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to San Juan?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Juan (average of $349). Flying from Chicago O'Hare Intl Airport to San Juan in December is currently the most expensive (average of $536). 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 SJU?
Find hourly flight availability from O'Hare Intl to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 5, 2026.
It’s optimal to fly from Chicago O'Hare Intl Airport to San Juan in the evening. By choosing this option you can save up to 30% on the cost of your flight, compared to a flight in the morning.
Weekly flight availability from Chicago O'Hare Intl Airport to San Juan
Explore weekly flight availability from O'Hare Intl to San Juan. 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 5, 2026.
The most flights from ORD to PR1 are scheduled on a Monday (10 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (7 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to San Juan?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to San Juan flights typically cost between $254 and $430 in September.The cheapest round-trip price found within the last 5 days was $222 on Frontier (Sep 17-Sep 24).
How often are flights from Chicago to San Juan delayed?
About 23% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 139 minutes.
What is the most punctual flight time for Chicago to San Juan 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?
Wednesday 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 San Juan flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 18% of flights being delayed.
How far ahead should I book a flight from Chicago O'Hare Intl Airport to San Juan?
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to San Juan, you should look to book at least 55 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to San Juan?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to San Juan. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San Juan flight should consider departing on Sunday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated August 5, 2026.
See what other customers who have flown with Southwest,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to San Juan have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
8.0
Entertainment
7.5
Crew
8.6
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to San Juan. 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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O'Hare Intl and San Juan flights
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Top 6 airlines flying from O'Hare Intl to San Juan
Discover the top 6 airlines that operate flights from O'Hare Intl to San Juan. 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 August 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$366 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$234 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$149 | Average$342 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$262 | Average$510 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$302 | Average$494 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$486 | FlexibilityNo cancel fee | On-time63% |