$128+ Cheap flights from O'Hare Intl (ORD) to San Juan
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to San Juan with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Chicago O'Hare Intl to San Juan are usually found in August or February, booked 56 days in advance, depart on a Tuesday or Monday and return on a Thursday
Cheap flight deals from O'Hare Intl to San Juan
Cheapest
Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to San JuanExplore the most affordable flight options available from O'Hare Intl to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 4, 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 November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:52 pm -
1 stop22h 08m
Mon 11/303:43 am -
1 stop23h 16m
Deal found 10/30![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Thu 12/105:24 pm -
1 stop6h 49m
Sat 12/197:28 am -
1 stop13h 40m
Deal found 10/31![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/610:29 pm -
1 stop13h 00m
Sun 12/202:29 am -
1 stop11h 31m
Deal found 10/31![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:24 pm -
1 stop6h 49m
Fri 12/186:00 am -
1 stop12h 59m
Deal found 11/3![Frontier logo]()
$249
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:19 am -
1 stop12h 40m
Fri 11/207:12 pm -
Nonstop5h 09m
Deal found 11/1![Frontier logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Mon 11/167:55 am -
1 stop29h 24m
Mon 11/237:58 pm -
1 stop13h 49m
Deal found 11/2![Frontier logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:42 pm -
1 stop21h 35m
Sun 11/226:00 am -
1 stop11h 57m
Deal found 11/1![Frontier logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Thu 11/126:00 am -
1 stop15h 28m
Thu 11/266:31 pm -
1 stop15h 15m
Deal found 11/1![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 11/2. 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.
Sun 11/226:20 am -
1 stop13h 29m
Thu 11/266:31 pm -
1 stop15h 15m
Deal found 11/2![Frontier logo]()
$254
This eDestinos deal was found by Cheapflights users on 11/1. 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 eDestinos is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Thu 11/56:00 am -
1 stop15h 28m
Mon 11/97:26 pm -
1 stop23h 41m
Deal found 11/1![Frontier logo]()
$255
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/145:24 pm -
1 stop6h 49m
Mon 12/2110:26 pm -
Nonstop5h 07m
Deal found 10/31![Frontier logo]()
$256
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 November 4, 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 November 4, 2026.
This United Airlines deal was found by Cheapflights users on 11/2. 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 1/112:16 pm -
Nonstop4h 44m
Thu 1/148:05 am -
1 stop8h 19m
Deal found 11/2![United Airlines logo]()
$262
This JetBlue deal was found by Cheapflights users on 11/2. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
1 stop7h 09m
Fri 12/46:38 am -
1 stop8h 52m
Deal found 11/2![JetBlue logo]()
$284
This United Airlines deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/92:16 pm -
Nonstop4h 44m
Tue 12/154:55 pm -
Nonstop5h 31m
Deal found 10/30![United Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Wed 11/119:21 am -
1 stop10h 03m
Fri 11/138:25 am -
Nonstop5h 22m
Deal found 11/2![United Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:34 am -
1 stop8h 50m
Tue 11/174:55 pm -
Nonstop5h 31m
Deal found 11/3![United Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/262:16 pm -
Nonstop4h 44m
Thu 1/288:05 am -
1 stop9h 44m
Deal found 11/3![United Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 10/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/302:16 pm -
Nonstop4h 44m
Mon 12/74:55 pm -
Nonstop5h 31m
Deal found 10/31![United Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/252:16 pm -
Nonstop4h 44m
Wed 12/94:55 pm -
Nonstop5h 31m
Deal found 11/3![United Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Wed 12/22:16 pm -
Nonstop4h 44m
Mon 12/74:55 pm -
Nonstop5h 31m
Deal found 11/2![United Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 11/1. 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 11/88:52 am -
Nonstop4h 48m
Tue 11/104:55 pm -
Nonstop5h 31m
Deal found 11/1![United Airlines logo]()
$431
This United Airlines deal was found by Cheapflights users on 11/1. 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 1/302:16 pm -
Nonstop4h 44m
Mon 2/15:50 pm -
1 stop7h 54m
Deal found 11/1![United Airlines logo]()
$442
Last-minute flights from O'Hare Intl to San JuanDiscover last-minute flight deals from O'Hare Intl to San Juan. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to San Juan. Data last updated November 4, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 11/1. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:00 am -
1 stop15h 28m
Mon 11/97:26 pm -
1 stop23h 41m
Deal found 11/1![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Thu 11/126:00 am -
1 stop15h 28m
Mon 11/237:58 pm -
1 stop13h 49m
Deal found 11/1![Frontier logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1310:19 am -
1 stop12h 40m
Fri 11/207:12 pm -
Nonstop5h 09m
Deal found 11/1![Frontier logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop15h 28m
Sun 11/2210:54 pm -
1 stop27h 49m
Deal found 10/30![Frontier logo]()
$252
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Mon 11/167:55 am -
1 stop29h 24m
Mon 11/237:58 pm -
1 stop13h 49m
Deal found 11/2![Frontier logo]()
$251
This Frontier deal was found by Cheapflights users on 11/2. 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.
Sun 11/226:20 am -
1 stop13h 29m
Thu 11/266:31 pm -
1 stop15h 15m
Deal found 11/2![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:52 pm -
1 stop22h 08m
Mon 11/303:43 am -
1 stop23h 16m
Deal found 10/30![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/610:29 pm -
1 stop13h 00m
Sun 12/202:29 am -
1 stop11h 31m
Deal found 10/31![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Thu 12/105:24 pm -
1 stop6h 49m
Sat 12/197:28 am -
1 stop13h 40m
Deal found 10/31![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/135:24 pm -
1 stop6h 49m
Fri 12/186:00 am -
1 stop12h 59m
Deal found 11/3![Frontier logo]()
$249
This Cheapflightsfares deal was found by Cheapflights users on 11/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/145:24 pm -
1 stop6h 49m
Fri 12/1810:26 pm -
Nonstop5h 07m
Deal found 11/1![Frontier logo]()
$256
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 November 4, 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 November 4, 2026.
This Mytrip deal was found by Cheapflights users on 11/2. 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.
Sun 11/157:55 am -
1 stop27h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$128
This American Airlines deal was found by Cheapflights users on 11/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/175:01 pm -
Nonstop4h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$129
This Super.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/1312:17 am -
Nonstop4h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$130
This Super.com deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:59 pm -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![JetBlue logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1010:31 pm -
Nonstop4h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$132
This JetBlue deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/152:59 pm -
1 stop9h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$133
This eDestinos deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:00 am -
1 stop15h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Fri 11/134:42 pm -
1 stop16h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 11/2. 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.
Thu 12/318:59 am -
1 stop13h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$137
This Frontier deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:20 am -
1 stop13h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$138
This American Airlines deal was found by Cheapflights users on 11/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/307:50 pm -
1 stop14h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$139
This Mytrip deal was found by Cheapflights users on 10/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/810:00 am -
2 stops13h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$140
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 November 4, 2026.
Round-trip from | $245 (Kiwi.com) |
|---|---|
One-way from | $128 (Mytrip) |
Popular in | December |
Cheapest in | August |
Average price | $462 |
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 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 12/15
2:59 pm-2:05 am
1 stop9h 06m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 12/14
2:59 pm-1:59 am
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
Quickest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/9
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 11/13
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 11/7
8:52 am-3:40 pm
Nonstop4h 48m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 12/9
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$219
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 12/12
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$258
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/30
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$259
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 1/11
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Thu 1/14
8:05 am-2:24 pm
1 stop8h 19m
$262
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/18
7:00 am-4:09 pm
1 stop7h 09m
San Juan Luis Munoz Marin Intl
Fri 12/4
6:38 am-1:30 pm
1 stop8h 52m
$284
Showing 1-10 of 19 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, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to San Juan (average of $338). Flying from Chicago O'Hare Intl Airport to San Juan in December is currently the most expensive (average of $529). 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 November 4, 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 29% 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 November 4, 2026.
The most flights from ORD to PR1 are scheduled on a Monday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).
How much does it cost to fly round-trip from Chicago O'Hare Intl Airport to San Juan?
Airfare is below average for this route at the moment.
Chicago O'Hare Intl Airport to San Juan flights typically cost between $357 and $598 in January.The cheapest round-trip price found within the last 5 days was $245 on Frontier (Jan 9-Jan 14).
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 148 minutes.
What is the most punctual flight time for Chicago to San Juan flights?
Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to San Juan flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 18% of flights being delayed.
How far ahead should I book a flight from Chicago O'Hare Intl Airport to San Juan?
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to San Juan, you should look to book at least 55 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to San Juan?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to San Juan. Price data was last updated on October 31, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to San Juan flight should consider departing on Sunday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Juan. Reviews last updated November 4, 2026.
See what other customers who have flown with Southwest,United Airlines, andJetBlue 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.
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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
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Complete your trip
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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 November 4, 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 November 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$515 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$366 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$152 | Average$355 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$262 | Average$506 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$285 | Average$486 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$377 | Average$485 | FlexibilityNo cancel fee | On-time63% |