O'Hare International Airport
Chicago, United States
Luis Muñoz Marín International Airport
San Juan, Puerto Rico
$219 USD
-51%$108 USD
Verified Nov 29, 2025 at 12:03 PMRare Availability
9% of dates checked are available within 10% of the lowest price
Wednesday, January 28th, 2026
Outbound Flights
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4h 40m·Nonstop
$364 USD
ORDJan 28 14:20
→SJUJan 28 21:00
UA 695Airbus A321neo
7h 1m·1 stop
$368 USD
ORDJan 28 15:35
→EWRJan 28 18:51
UA 2133Boeing 737
46m layover

EWRJan 28 19:37
→SJUJan 29 00:36
UA 1543Boeing 737MAX 9 Passenger
8h 56m·1 stop
$368 USD
ORDJan 28 05:40
→IAHJan 28 08:41
UA 537Boeing 737MAX 9 Passenger
1h 29m layover

IAHJan 28 10:10
→SJUJan 28 16:36
UA 1192Boeing 737MAX 9 Passenger
4h 45m·Nonstop
$394 USD
ORDJan 28 08:55
→SJUJan 28 15:40
UA 1996Airbus A321neo
15h 13m·1 stop
$433 USD
ORDJan 28 19:42
→EWRJan 28 22:58
UA 1324Boeing 737
9h 2m layover·Overnight

EWRJan 29 08:00
→SJUJan 29 12:55
UA 2143Boeing 767
14h 55m·1 stop
$433 USD
ORDJan 28 20:00
→LGAJan 28 23:21
UA 2214Boeing 737
8h 39m layover·Overnight

EWRJan 29 08:00
→SJUJan 29 12:55
UA 2143Boeing 767
18h 46m·1 stop
$563 USD
ORDJan 28 19:50
→IAHJan 28 22:58
UA 2426Airbus A321neo
11h 12m layover·Overnight

IAHJan 29 10:10
→SJUJan 29 16:36
UA 1192Boeing 737MAX 9 Passenger
23h 24m·1 stop
$585 USD
ORDJan 28 20:58
→DCAJan 28 23:59
UA 3563Embraer 175
17h 33m layover·Overnight

IADJan 29 17:32
→SJUJan 29 22:22
UA 2025Boeing 737MAX 9 Passenger