Chicago (ORD) to San Juan (SJU) flight deal in business from $354
ORDO'Hare International Airport
Chicago, United States
SJULuis Muñoz Marín International Airport
San Juan, Puerto Rico
$560 USD
-37%$354 USD
Verified 19 days agoOctober 2026
Mon
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Extremely Rare Availability
2% of dates checked are available within 10% of the lowest price
Saturday, October 3rd, 2026
Outbound Flights
4h 49m·Nonstop
$444 USD
ORDOct 3 08:55
→SJUOct 3 14:44
UA 1996Airbus A321neo
7h 45m·1 stop
$550 USDORDOct 3 05:00
→EWROct 3 08:12
UA 2759Boeing 737
1h 35m layover
EWROct 3 09:47
→SJUOct 3 13:45
UA 1556Boeing 737MAX 9 Passenger
9h 15m·1 stop
$550 USDORDOct 3 13:35
→EWROct 3 16:58
UA 2183Boeing 737MAX 9 Passenger
2h 49m layover
EWROct 3 19:47
→SJUOct 3 23:50
UA 1543Boeing 737MAX 9 Passenger
7h 50m·1 stop
$636 USDORDOct 3 15:00
→EWROct 3 18:28
UA 1236Airbus A321neo
1h 19m layover
EWROct 3 19:47
→SJUOct 3 23:50
UA 1543Boeing 737MAX 9 Passenger
9h 6m·1 stop
$664 USDORDOct 3 10:32
→IAHOct 3 13:28
UA 2638Airbus A321neo
1h 38m layover
IAHOct 3 15:06
→SJUOct 3 20:38
UA 701Boeing 737MAX 9 Passenger
13h 22m·1 stop
$1,238 USDORDOct 3 21:35
→EWROct 4 00:57
UA 1209Airbus A321neo
7h 3m layover
EWROct 4 08:00
→SJUOct 4 11:57
UA 2143Boeing 767
13h 49m·1 stop
$1,238 USDORDOct 3 21:45
→IADOct 4 00:50
UA 1922Boeing 737MAX 9 Passenger
7h 50m layover
IADOct 4 08:40
→SJUOct 4 12:34
UA 2021Boeing 737MAX 8 Passenger
18h 38m·1 stop
$3,258 USDORDOct 3 22:00
→DENOct 3 23:54
UA 767Airbus A321neo
9h 52m layover·Overnight
DENOct 4 09:46
→SJUOct 4 17:38
UA 1339Boeing 737MAX 8 Passenger