$123+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jul 21 — Jul 281
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 Monday or Tuesday and return on a Thursday
Cheap flight deals from O'Hare Intl to San Juan
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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 June 21, 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 June 21, 2026.
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 8/154:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Fri 8/2812:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/19![American Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 8/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 8/77:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$260
This Frontier deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 9/37:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/20![Frontier logo]()
$261
This Frontier deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/20![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/248:57 pm
SJU
- ORD
1 stop27h 11m
Frontier
Deal found 6/20![Frontier logo]()
$264
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/2710:40 am
ORD
- SJU
1 stop8h 58m
United Airlines
Sun 8/304:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Deal found 6/20![United Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Sat 8/156:40 am
ORD
- SJU
1 stop8h 58m
Delta
Sat 8/292:31 pm
SJU
- ORD
1 stop6h 59m
Delta
Deal found 6/20![Delta logo]()
$266
This American Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/275:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Deal found 6/20![American Airlines logo]()
$267
This Priceline deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:44 am
ORD
- SJU
Nonstop5h 00m
Multiple Airlines
Tue 9/86:50 am
SJU
- ORD
1 stop7h 49m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/247:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/20![Frontier logo]()
$269
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 June 21, 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 June 21, 2026.
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 8/2011:23 am
ORD
- SJU
1 stop10h 06m
Delta
Mon 8/242:59 pm
SJU
- ORD
1 stop6h 56m
Delta
Deal found 6/20![Delta logo]()
$358
This United Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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 9/108:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Mon 9/142:55 pm
SJU
- ORD
1 stop10h 33m
United Airlines
Deal found 6/19![United Airlines logo]()
$462
This KAYAK deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:00 am
ORD
- SJU
1 stop16h 57m
American Airlines
Thu 7/912:59 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/18![American Airlines logo]()
$480
This Delta deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Sat 7/49:48 am
ORD
- SJU
1 stop11h 39m
Delta
Tue 7/712:50 pm
SJU
- ORD
1 stop8h 43m
Delta
Deal found 6/20![Delta logo]()
$431
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/258:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Thu 10/13:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/20![United Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Sat 9/191:00 am
SJU
- ORD
1 stop7h 41m
United Airlines
Deal found 6/16![United Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/108:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Sun 9/134:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Deal found 6/20![United Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/178:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Mon 9/213:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/18![United Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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
ORD
- SJU
Nonstop4h 49m
United Airlines
Mon 9/143:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/20![United Airlines logo]()
$487
This United Airlines deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 9/248:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Mon 9/283:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/20![United Airlines logo]()
$547
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/188:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Sun 9/202:20 pm
SJU
- ORD
1 stop10h 07m
United Airlines
Deal found 6/18![United Airlines logo]()
$562
This United Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 10/138:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Sat 10/173:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/17![United Airlines logo]()
$568
Last-minute flights from O'Hare Intl to San JuanDiscover last-minute flight deals from O'Hare Intl to San Juan. Data last updated June 21, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to San Juan. Data last updated June 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$267
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Fri 7/107:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$277
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Sat 7/117:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 6/16![United Airlines logo]()
$279
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 7/97:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$276
This eDestinos deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 7/157:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/20![Frontier logo]()
$290
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/17![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/20![Frontier logo]()
$291
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/17![Frontier logo]()
$282
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/2012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/17![Frontier logo]()
$283
This Kiwi.com deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 7/2012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 8/46:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/17![Frontier logo]()
$286
This Super.com deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 7/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$287
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 June 21, 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 June 21, 2026.
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:33 am
ORD
- SJU
1 stop10h 56m
Delta
Deal found 6/17![Delta logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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 9/25:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/18![American Airlines logo]()
$124
This American Airlines deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
ORD
- SJU
1 stop7h 38m
American Airlines
Deal found 6/19![American Airlines logo]()
$126
This American Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” 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 8/86:45 am
ORD
- SJU
1 stop14h 39m
American Airlines
Deal found 6/17![American Airlines logo]()
$128
This Frontier deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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 7/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/20![Frontier logo]()
$129
This eDestinos deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” 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.
Tue 7/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/20![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/16![Frontier logo]()
$131
This Delta deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” 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.
Fri 8/149:54 am
ORD
- SJU
1 stop11h 35m
Delta
Deal found 6/19![Delta logo]()
$133
This Super.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” 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 7/1912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/21![Frontier logo]()
$137
This eDestinos deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” 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.
Mon 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/18![Frontier logo]()
$140
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/16![American Airlines logo]()
$141
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 June 21, 2026.
Round-trip from | $257 (American Airlines) |
|---|---|
One-way from | $123 (Delta) |
Popular in | December |
Cheapest in | September |
Average price | $451 |
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 June 21, 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 - SJU
ORDSJU
Chicago O'Hare Intl
Thu 8/20
11:23 am-10:29 pm
1 stop10h 06m
San Juan Luis Munoz Marin Intl
Mon 8/24
2:59 pm-8:55 pm
1 stop6h 56m
$358
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 7/4
9:48 am-10:27 pm
1 stop11h 39m
San Juan Luis Munoz Marin Intl
Tue 7/7
12:50 pm-8:33 pm
1 stop8h 43m
$431
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 9/10
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Mon 9/14
2:55 pm-12:28 am
1 stop10h 33m
$462
Quickest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 9/25
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Thu 10/1
3:56 pm-8:05 pm
Nonstop5h 09m
$462
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 9/17
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Sat 9/19
1:00 am-7:41 am
1 stop7h 41m
$462
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 9/10
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Sun 9/13
4:55 pm-11:40 pm
1 stop7h 45m
$467
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 9/17
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Mon 9/21
3:56 pm-8:05 pm
Nonstop5h 09m
$467
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 7/6
5:00 am-10:57 pm
1 stop16h 57m
San Juan Luis Munoz Marin Intl
Thu 7/9
12:59 am-5:04 am
Nonstop5h 05m
$480
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 9/2
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Mon 9/14
3:56 pm-8:05 pm
Nonstop5h 09m
$487
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 9/24
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Mon 9/28
3:56 pm-8:05 pm
Nonstop5h 09m
$547
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, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Juan (average of $120). Flying from Chicago O'Hare Intl Airport to San Juan in August is currently the most expensive (average of $753). 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 June 21, 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 26% 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 June 21, 2026.
The most flights from ORD to PR1 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 much does it cost to fly round-trip from Chicago O'Hare Intl Airport to San Juan?
How often are flights from Chicago to San Juan delayed?
About 22% 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?
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 19% 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 June 20, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San Juan flight should consider departing on Saturday 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 June 21, 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.
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
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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Complete your trip
Complete your trip to San Juan by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to San Juan by cabin class
Find flights from O'Hare Intl to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and San Juan flights
Browse other O'Hare Intl and San Juan flight options. Last updated on June 21, 2026.
Other flights from O'Hare Intl
Browse through other flights departing from O'Hare Intl. Flights are based on user searches made on Cheapflights and were last updated on June 21, 2026.
Popular flight searches
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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 June 21, 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$147 | Average$331 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$261 | Average$509 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$301 | Average$503 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$482 | FlexibilityNo cancel fee | On-time63% |