$93+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Mar 5 — Mar 121
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 April or January, booked 49 days in advance, depart on a Monday or Tuesday and return on a Friday
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 February 3, 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 February 3, 2026.
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:23 pm
ORD
- SJU
1 stop21h 35m
Spirit Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Tue 3/1710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 3/1812:55 pm
SJU
- ORD
1 stop7h 56m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$185
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:05 am
ORD
- SJU
1 stop7h 56m
Multiple Airlines
Tue 2/2412:32 pm
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$186
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:50 pm
ORD
- SJU
1 stop6h 53m
Frontier
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Frontier
Deal found 2/2![Frontier logo]()
$187
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
- SJU
1 stop16h 38m
Frontier
Wed 2/255:25 pm
SJU
- ORD
1 stop19h 21m
Frontier
Deal found 2/2![Frontier logo]()
$188
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:34 pm
ORD
- SJU
1 stop22h 24m
Spirit Airlines
Wed 4/2211:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$189
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 2/236:51 pm
ORD
- SJU
2 stops18h 40m
Spirit Airlines
Tue 3/1010:52 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$191
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 1/31. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 4/110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Sun 4/121:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$195
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 February 3, 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 February 3, 2026.
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/22:20 pm
ORD
- SJU
Nonstop4h 40m
United Airlines
Fri 3/68:30 am
SJU
- ORD
Nonstop5h 22m
United Airlines
Deal found 2/2![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:25 pm
ORD
- SJU
1 stop7h 47m
Delta
Wed 4/296:15 am
SJU
- ORD
1 stop11h 27m
Delta
Deal found 2/2![Delta logo]()
$246
This Expedia deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:30 am
ORD
- SJU
1 stop14h 13m
Frontier
Sun 3/83:19 pm
SJU
- ORD
1 stop9h 19m
Frontier
Deal found 2/2![Frontier logo]()
$247
This Spirit deal was found by Cheapflights users on 2/2. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/268:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Tue 3/3111:03 am
SJU
- ORD
1 stop8h 28m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$276
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Sun 4/262:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Thu 4/303:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 2/1![United Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Sat 5/22:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Wed 5/67:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 2/1![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/189:52 am
ORD
- SJU
1 stop9h 20m
Delta
Sat 2/286:15 am
SJU
- ORD
1 stop9h 55m
Delta
Deal found 2/2![Delta logo]()
$266
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Sat 5/22:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Tue 5/53:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 2/1![United Airlines logo]()
$237
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/143:21 pm
ORD
- SJU
1 stop6h 37m
Delta
Wed 2/256:37 pm
SJU
- ORD
1 stop7h 19m
Delta
Deal found 2/2![Delta logo]()
$266
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/198:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Mon 3/2311:03 am
SJU
- ORD
1 stop22h 22m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Tue 3/38:55 am
ORD
- SJU
Nonstop4h 45m
United Airlines
Tue 3/107:30 am
SJU
- ORD
Nonstop5h 22m
United Airlines
Deal found 2/2![United Airlines logo]()
$304
This United Airlines deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/232:20 pm
ORD
- SJU
Nonstop4h 40m
United Airlines
Wed 3/44:52 pm
SJU
- ORD
Nonstop5h 28m
United Airlines
Deal found 2/1![United Airlines logo]()
$344
Last-minute flights from O'Hare Intl to San JuanDiscover last-minute flight deals from O'Hare Intl to San Juan. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to San Juan. Data last updated February 3, 2026 and is based on user searches.
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:05 am
ORD
- SJU
1 stop7h 56m
Multiple Airlines
Tue 2/2412:32 pm
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$186
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 am
ORD
- SJU
1 stop16h 38m
Frontier
Wed 2/255:25 pm
SJU
- ORD
1 stop19h 21m
Frontier
Deal found 2/2![Frontier logo]()
$188
This Booking.com deal was found by Cheapflights users on 2/2. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$193
This Gotogate deal was found by Cheapflights users on 2/2. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:50 pm
ORD
- SJU
1 stop16h 04m
Frontier
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Frontier
Deal found 2/2![Frontier logo]()
$187
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 2/236:51 pm
ORD
- SJU
2 stops18h 40m
Spirit Airlines
Tue 3/1010:52 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$195
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$189
This CheapOair deal was found by Cheapflights users on 2/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:23 pm
ORD
- SJU
1 stop21h 35m
Spirit Airlines
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Mon 3/1610:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 3/1812:55 pm
SJU
- ORD
1 stop7h 56m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$185
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 February 3, 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 February 3, 2026.
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:30 am
ORD
- SJU
1 stop16h 23m
Frontier
Deal found 2/1![Frontier logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sun 5/33:52 pm
ORD
- SJU
1 stop24h 38m
Frontier
Deal found 2/2![Frontier logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 2/2. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
ORD
- SJU
1 stop12h 50m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$95
This Mytrip deal was found by Cheapflights users on 2/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:18 am
ORD
- SJU
1 stop7h 40m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$97
This Expedia deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1012:44 pm
ORD
- SJU
1 stop8h 49m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$98
This Expedia deal was found by Cheapflights users on 2/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:44 pm
ORD
- SJU
1 stop8h 25m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$99
This Super.com deal was found by Cheapflights users on 2/2. 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.
Sat 2/218:15 am
ORD
- SJU
1 stop16h 38m
Frontier
Deal found 2/2![Frontier logo]()
$100
This Frontier deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/302:20 pm
ORD
- SJU
1 stop9h 09m
Frontier
Deal found 2/2![Frontier logo]()
$101
This CheapOair deal was found by Cheapflights users on 2/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:23 pm
ORD
- SJU
1 stop21h 35m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:23 pm
ORD
- SJU
1 stop15h 16m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$103
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 February 3, 2026.
Round-trip from | $184 (CheapOair) |
|---|---|
One-way from | $93 (CheapOair) |
Popular in | December |
Cheapest in | April |
Average price | $358 |
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 February 3, 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
O'Hare Intl
Fly to
San Juan
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 3/2
2:20 pm-9:00 pm
Nonstop4h 40m
San Juan Luis Munoz Marin Intl
Fri 3/6
8:30 am-11:52 am
Nonstop5h 22m
$237
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 4/26
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Thu 4/30
3:56 pm-8:15 pm
Nonstop5h 19m
$237
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/2
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Wed 5/6
7:40 am-11:53 am
Nonstop5h 13m
$237
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 5/2
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Tue 5/5
3:56 pm-8:15 pm
Nonstop5h 19m
$237
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/21
2:25 pm-11:12 pm
1 stop7h 47m
San Juan Luis Munoz Marin Intl
Wed 4/29
6:15 am-4:42 pm
1 stop11h 27m
$246
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 3/4
8:30 am-12:43 am
1 stop14h 13m
San Juan Luis Munoz Marin Intl
Sun 3/8
3:19 pm-11:38 pm
1 stop9h 19m
$247
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 2/18
9:52 am-9:12 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Sat 2/28
6:15 am-2:10 pm
1 stop9h 55m
$266
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 2/14
3:21 pm-11:58 pm
1 stop6h 37m
San Juan Luis Munoz Marin Intl
Wed 2/25
6:37 pm-11:56 pm
1 stop7h 19m
$266
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 3/26
8:56 pm-2:29 am
Nonstop4h 33m
San Juan Luis Munoz Marin Intl
Tue 3/31
11:03 am-6:31 pm
1 stop8h 28m
$276
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 3/3
8:55 am-3:40 pm
Nonstop4h 45m
San Juan Luis Munoz Marin Intl
Tue 3/10
7:30 am-11:52 am
Nonstop5h 22m
$304
Showing 1-10 of 24 results
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
How far ahead should I book a flight from Chicago O'Hare Intl Airport to San Juan?
Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to San Juan. Price data was last updated on January 30, 2026.
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 49 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 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 $126). Flying from Chicago O'Hare Intl Airport to San Juan in December is currently the most expensive (average of $224). 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 February 3, 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 at noon.
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 January 31, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San Juan flight should consider departing on Tuesday evenings 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.
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 February 3, 2026.
The most flights from ORD to PR1 are scheduled on a Monday (11 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).
How often are flights from Chicago to San Juan delayed?
About 17% of weekly flights between Chicago and San Juan have experienced delays in the past year, with the average delay time being 140 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, American Airlines have had the lowest number of delays on this route, with just 14% of flights being delayed.
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 February 3, 2026.
See what other customers who have flown with United Airlines, American Airlines, and JetBlue 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.
Boarding
7.7
Food
6.6
Entertainment
7.1
Crew
8.1
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Boarding
7.7
Food
6.6
Entertainment
7.1
Crew
8.1
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Boarding
7.7
Food
6.6
Entertainment
7.1
Crew
8.1
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Boarding
7.7
Food
6.6
Entertainment
7.1
Crew
8.1
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Boarding
7.7
Food
6.6
Entertainment
7.1
Crew
8.1
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Boarding
7.7
Food
6.6
Entertainment
7.1
Crew
8.1
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
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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Alternative routes for O'Hare Intl to San Juan
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from O'Hare Intl to San Juan
Discover the top 7 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 February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$284 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$238 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$394 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$137 | Average$308 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$250 | Average$509 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$354 | Average$530 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$390 | Average$486 | FlexibilityNo cancel fee | On-time63% |