Chicago (ORD) to San Juan (SJU) flight deal in business from $447
ORDO'Hare International Airport
Chicago, United States
SJULuis Muñoz Marín International Airport
San Juan, Puerto Rico
$512 USD
-13%$447 USD
Verified 15 days agoAugust 2026
Mon
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Sun
Good Availability
56% of dates checked are available within 10% of the lowest price
Sunday, August 2nd, 2026
Outbound Flights
14h 1m·2 stops
$640 USD
ORDAug 2 22:32
→GRRAug 3 00:36
AA 1096Airbus A319
6h 8m layover
GRRAug 3 06:44
→PHLAug 3 08:44
AA 5494Canadair RJ 900
44m layover
PHLAug 3 09:28
→SJUAug 3 13:33
AA 903Boeing 737
4h 58m·Nonstop
$717 USDORDAug 2 17:50
→SJUAug 2 23:48
AA 3192Boeing 737
7h 20m·1 stop
$751 USDORDAug 2 06:30
→CLTAug 2 09:37
AA 1784Airbus A321
1h 26m layover
CLTAug 2 11:03
→SJUAug 2 14:50
AA 783Airbus A321
9h 59m·1 stop
$782 USDORDAug 2 12:00
→CLTAug 2 15:08
AA 2681Boeing 737
4h layover
CLTAug 2 19:08
→SJUAug 2 22:59
AA 2830Airbus A321
8h 42m·1 stop
$793 USDORDAug 2 13:17
→CLTAug 2 16:29
AA 3280Boeing 737
2h 39m layover
CLTAug 2 19:08
→SJUAug 2 22:59
AA 2830Airbus A321
7h 33m·1 stop
$823 USDORDAug 2 05:00
→PHLAug 2 08:05
AA 2970Boeing 737MAX 8 Passenger
1h 23m layover
PHLAug 2 09:28
→SJUAug 2 13:33
AA 903Boeing 737
7h 2m·1 stop
$823 USDORDAug 2 06:10
→MIAAug 2 10:22
AA 1380Boeing 737MAX 8 Passenger
55m layover
MIAAug 2 11:17
→SJUAug 2 14:12
AA 2584Airbus A321
7h 48m·1 stop
$823 USDORDAug 2 06:59
→MIAAug 2 11:12
AA 835Airbus A321
1h 51m layover
MIAAug 2 13:03
→SJUAug 2 15:47
AA 2581Boeing 737
8h 54m·1 stop
$823 USDORDAug 2 08:30
→MIAAug 2 12:45
AA 1250Airbus A321
2h 55m layover
MIAAug 2 15:40
→SJUAug 2 18:24
AA 3165Boeing 737