Chicago (ORD) to San Juan (SJU) flight deal in business from $379
ORDO'Hare International Airport
Chicago, United States
SJULuis Muñoz Marín International Airport
San Juan, Puerto Rico
$587 USD
-35%$379 USD
Verified about 3 hours agoOctober 2026
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Limited Availability
10% of dates checked are available within 10% of the lowest price
Wednesday, October 28th, 2026
Outbound Flights
4h 44m·Nonstop
$379 USD
ORDOct 28 14:16
→SJUOct 28 20:00
UA 695Airbus A321neo
7h 11m·1 stop
$383 USDORDOct 28 05:00
→EWROct 28 08:07
UA 2455Boeing 737
1h 8m layover
EWROct 28 09:15
→SJUOct 28 13:11
UA 2143Boeing 767
6h 45m·1 stop
$383 USDORDOct 28 05:55
→EWROct 28 08:59
UA 656Boeing 737MAX 9 Passenger
51m layover
EWROct 28 09:50
→SJUOct 28 13:40
UA 1556Boeing 737MAX 9 Passenger
8h 6m·1 stop
$586 USDORDOct 28 14:30
→EWROct 28 17:52
UA 1236Airbus A321neo
1h 44m layover
EWROct 28 19:36
→SJUOct 28 23:36
UA 1543Boeing 737MAX 9 Passenger
4h 48m·Nonstop
$676 USDORDOct 28 08:52
→SJUOct 28 14:40
UA 1996Airbus A321neo
12h 2m·1 stop
$1,300 USDORDOct 28 21:48
→EWROct 29 00:59
UA 1209Airbus A321neo
6h 1m layover
EWROct 29 07:00
→SJUOct 29 10:50
UA 1460Boeing 737MAX 9 Passenger