$118+ Cheap flights from San Juan to O'Hare Intl (ORD)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jul 19 — Jul 261
Round-trip
1 adult, Economy
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Find cheap flights from San Juan 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.Cheapflights Tip: The best prices from San Juan to Chicago O'Hare Intl are usually found in February or January, booked 82 days in advance, depart on a Thursday or Friday and return on a Monday
Cheap flight deals from San Juan to O'Hare Intl
Cheapest
Best
Last-minute
One-way
Cheapest flights from San Juan to O'Hare IntlExplore the most affordable flight options available from San Juan to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.
Explore the most affordable flight options available from San Juan to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/76:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/15![Frontier logo]()
$225
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.
Thu 9/36:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Sun 9/612:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/16![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/266:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Tue 9/112:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/15![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/216:00 am
SJU
- ORD
1 stop31h 25m
Frontier
Fri 9/412:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/15![Frontier logo]()
$229
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.
Thu 8/276:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Fri 8/2812:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/16![Frontier logo]()
$230
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
Sat 8/228:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/15![United Airlines logo]()
$232
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.
Wed 8/196:45 am
SJU
- ORD
1 stop31h 15m
Frontier
Sun 8/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/17![Frontier logo]()
$233
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.
Wed 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 9/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/17![Frontier logo]()
$234
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.
Thu 8/275:10 pm
SJU
- ORD
1 stop8h 25m
American Airlines
Sat 8/296:59 pm
ORD
- SJU
1 stop13h 44m
American Airlines
Deal found 6/17![American Airlines logo]()
$236
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.
Tue 8/187:24 pm
SJU
- ORD
1 stop13h 10m
American Airlines
Wed 8/265:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/17![American Airlines logo]()
$237
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 8/257:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Sat 8/2912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/18![Frontier logo]()
$238
Best flights from San Juan to O'Hare IntlDiscover carefully curated flight deals from San Juan to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
Discover carefully curated flight deals from San Juan to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 19, 2026.
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.
Wed 8/264:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Sun 8/308:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/18![United Airlines logo]()
$242
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/134:58 pm
SJU
- ORD
1 stop7h 46m
JetBlue
Mon 8/177:00 am
ORD
- SJU
1 stop10h 51m
JetBlue
Deal found 6/18![JetBlue logo]()
$436
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 9/33:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Sat 9/58:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/14![United Airlines logo]()
$317
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.
Fri 6/267:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Tue 6/306:29 pm
ORD
- SJU
1 stop10h 00m
United Airlines
Deal found 6/16![United Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 9/93:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Tue 9/225:00 am
ORD
- SJU
1 stop7h 53m
United Airlines
Deal found 6/14![United Airlines logo]()
$462
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:20 pm
SJU
- ORD
1 stop10h 06m
United Airlines
Sat 8/224:00 pm
ORD
- SJU
2 stops19h 54m
United Airlines
Deal found 6/15![United Airlines logo]()
$476
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 6/277:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Sat 7/48:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Deal found 6/16![United Airlines logo]()
$517
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 9/172:55 pm
SJU
- ORD
1 stop10h 33m
United Airlines
Mon 9/218:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/14![United Airlines logo]()
$552
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 9/54:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Tue 9/81:00 pm
ORD
- SJU
2 stops9h 50m
United Airlines
Deal found 6/15![United Airlines logo]()
$580
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:00 am
SJU
- ORD
2 stops12h 03m
Delta
Sun 9/610:50 am
ORD
- SJU
2 stops12h 02m
Delta
Deal found 6/18![Delta logo]()
$3,394
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:30 am
SJU
- ORD
2 stops11h 59m
Delta
Sun 9/137:00 am
ORD
- SJU
2 stops14h 00m
Delta
Deal found 6/18![Delta logo]()
$3,394
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:19 pm
SJU
- ORD
1 stop9h 33m
Delta
Mon 8/3110:30 am
ORD
- SJU
2 stops10h 59m
Delta
Deal found 6/18![Delta logo]()
$3,394
Last-minute flights from San Juan to O'Hare IntlDiscover last-minute flight deals from San Juan to O'Hare Intl. Data last updated June 19, 2026 and is based on user searches.
Discover last-minute flight deals from San Juan to O'Hare Intl. Data last updated June 19, 2026 and is based on user searches.
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.
Tue 6/2312:57 am
SJU
- ORD
Nonstop5h 07m
American Airlines
Mon 7/138:00 am
ORD
- SJU
1 stop13h 59m
American Airlines
Deal found 6/17![American Airlines logo]()
$382
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.
Wed 6/241:00 am
SJU
- ORD
1 stop7h 42m
United Airlines
Sat 6/2711:15 am
ORD
- SJU
1 stop9h 09m
United Airlines
Deal found 6/17![United Airlines logo]()
$315
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.
Wed 6/246:21 am
SJU
- ORD
1 stop8h 56m
American Airlines
Tue 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/19![American Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 6/247:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Mon 6/296:40 pm
ORD
- SJU
1 stop9h 49m
United Airlines
Deal found 6/15![United Airlines logo]()
$357
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.
Wed 6/246:21 am
SJU
- ORD
1 stop8h 56m
American Airlines
Sat 6/278:00 am
ORD
- SJU
1 stop13h 45m
American Airlines
Deal found 6/19![American Airlines logo]()
$366
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.
Fri 6/267:00 am
SJU
- ORD
1 stop11h 42m
American Airlines
Tue 6/308:05 am
ORD
- SJU
1 stop13h 55m
American Airlines
Deal found 6/17![American Airlines logo]()
$341
This Frontier deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 6/279:37 pm
SJU
- ORD
1 stop11h 26m
Frontier
Fri 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/15![Frontier logo]()
$369
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/275:56 pm
SJU
- ORD
1 stop7h 08m
Delta
Sat 7/45:30 am
ORD
- SJU
1 stop10h 16m
Delta
Deal found 6/18![Delta logo]()
$378
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:00 am
SJU
- ORD
1 stop18h 19m
Frontier
Mon 7/2012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/16![Frontier logo]()
$367
One-way flights from San Juan to O'Hare IntlSearch for one-way flight options from San Juan to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
Search for one-way flight options from San Juan to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated June 19, 2026.
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.
Wed 8/2610:33 am
SJU
- ORD
1 stop15h 02m
American Airlines
Deal found 6/17![American Airlines logo]()
$118
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” 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 8/195:10 pm
SJU
- ORD
1 stop8h 25m
American Airlines
Deal found 6/14![American Airlines logo]()
$119
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.
Tue 7/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” 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 8/46:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/15![Frontier logo]()
$121
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.
Fri 8/147:00 am
SJU
- ORD
1 stop13h 46m
American Airlines
Deal found 6/18![American Airlines logo]()
$123
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$127
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$128
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$136
Find flight deals from San Juan to O'Hare Intl
Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to O'Hare Intl (ORD). 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 19, 2026.
Round-trip from | $225 (Kiwi.com) |
|---|---|
One-way from | $118 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $422 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Juan to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 19, 2026.
Use the filters below to find and compare flights from San Juan to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/26
4:55 pm-11:40 pm
1 stop7h 45m
Chicago O'Hare Intl
Sun 8/30
8:55 am-2:44 pm
Nonstop4h 49m
$242
Quickest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/3
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Sat 9/5
8:55 am-2:44 pm
Nonstop4h 49m
$317
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 6/26
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Tue 6/30
6:29 pm-5:29 am
1 stop10h 00m
$357
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 8/13
4:58 pm-11:44 pm
1 stop7h 46m
Chicago O'Hare Intl
Mon 8/17
7:00 am-6:51 pm
1 stop10h 51m
$436
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 9/9
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Tue 9/22
5:00 am-1:53 pm
1 stop7h 53m
$462
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/19
2:20 pm-11:26 pm
1 stop10h 06m
Chicago O'Hare Intl
Sat 8/22
4:00 pm-12:54 pm
2 stops19h 54m
$476
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 6/27
7:40 am-11:53 am
Nonstop5h 13m
Chicago O'Hare Intl
Sat 7/4
8:49 am-2:44 pm
Nonstop4h 55m
$517
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/17
2:55 pm-12:28 am
1 stop10h 33m
Chicago O'Hare Intl
Mon 9/21
8:55 am-2:44 pm
Nonstop4h 49m
$552
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 9/5
4:55 pm-11:40 pm
1 stop7h 45m
Chicago O'Hare Intl
Tue 9/8
1:00 pm-11:50 pm
2 stops9h 50m
$580
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 9/3
7:00 am-6:03 pm
2 stops12h 03m
Chicago O'Hare Intl
Sun 9/6
10:50 am-11:52 pm
2 stops12h 02m
$3,394
Showing 1-10 of 21 resultsSorted by cheapest first
Best time to book a flight from San Juan to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from San Juan with our price prediction graph.
PR1-ORD
SJU-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 San Juan to Chicago O'Hare Intl Airport
PR1-ORD
SJU-ORD
What is the cheapest month to book a flight from San Juan to Chicago O'Hare Intl Airport?
Currently, May is the cheapest month in which you can book a flight from San Juan to Chicago O'Hare Intl Airport (average of $64). Flying from San Juan to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $123). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SJU to ORD?
Find hourly flight availability from San Juan 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 June 19, 2026.
It’s typically best to fly out from San Juan to Chicago O'Hare Intl Airport in the evening. Doing so could potentially save you 13% on the flight price compared to flying in the morning, which is usually more expensive.
Weekly flight availability from San Juan to Chicago O'Hare Intl Airport
Explore weekly flight availability from San Juan 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 June 19, 2026.
The most flights from PR1 to ORD are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).
How much does it cost to fly round-trip from San Juan to Chicago O'Hare Intl Airport?
How often are flights from San Juan to Chicago delayed?
About 8% of weekly flights between San Juan 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 San Juan to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Thursday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on San Juan 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 San Juan to Chicago O'Hare Intl Airport?
To ensure you get the cheapest price possible for a flight from San Juan to Chicago O'Hare Intl Airport, you should look to book at least 81 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 San Juan to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from San Juan to O'Hare Intl. Price data was last updated on June 13, 2026.
Travelers seeking maximum savings on their San Juan to Chicago O'Hare Intl Airport flight should consider departing on Sunday at noon when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated June 19, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from San Juan 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.
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Food
7.2
Comfort
7.8
Entertainment
7.8
Overall
7.8
Crew
8.5
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentRakshith,May 2026
TPE - SEA
Related info for your journey
Find useful and relevant information for your journey from San Juan to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Gurnee
Delavan
Oakbrook Terrace
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Racine
Warrenville
Rockford
Great Lakes
Northbrook
Waukegan
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Other flights to O'Hare Intl
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Top 6 airlines flying from San Juan to O'Hare Intl
Discover the top 6 airlines that operate flights from San Juan to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$252 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$432 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$263 | Average$483 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$457 | FlexibilityNo cancel fee | On-time63% |