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 16 days agoAugust 2026
Mon
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Good Availability
56% of dates checked are available within 10% of the lowest price
Tuesday, August 18th, 2026
Outbound Flights
13h 49m·2 stops
$615 USD
ORDAug 18 22:35
→GRRAug 19 00:41
AA 3544Embraer 175
5h 33m layover
GRRAug 19 06:14
→PHLAug 19 08:08
AA 5310Canadair RJ 900
1h 17m layover
PHLAug 19 09:25
→SJUAug 19 13:24
AA 614Airbus A321neo
7h 24m·1 stop
$680 USDORDAug 18 05:00
→PHLAug 18 08:03
AA 2970Boeing 737MAX 8 Passenger
1h 22m layover
PHLAug 18 09:25
→SJUAug 18 13:24
AA 614Airbus A321neo
4h 55m·Nonstop
$727 USDORDAug 18 17:20
→SJUAug 18 23:15
AA 1865Boeing 737
6h 40m·1 stop
$731 USDORDAug 18 05:00
→MIAAug 18 09:07
AA 2984Airbus A321
48m layover
MIAAug 18 09:55
→SJUAug 18 12:40
AA 1613Boeing 737
7h 2m·1 stop
$731 USDORDAug 18 06:49
→CLTAug 18 09:55
AA 1784Airbus A321
1h 10m layover
CLTAug 18 11:05
→SJUAug 18 14:51
AA 783Airbus A321
7h 38m·1 stop
$731 USDORDAug 18 09:55
→MIAAug 18 14:08
AA 3056Boeing 737
1h 39m layover
MIAAug 18 15:47
→SJUAug 18 18:33
AA 1852Boeing 737
7h 38m·1 stop
$731 USDORDAug 18 06:00
→MIAAug 18 10:07
AA 2452Boeing 737MAX 8 Passenger
1h 38m layover
MIAAug 18 11:45
→SJUAug 18 14:38
AA 1341Airbus A321
8h 12m·1 stop
$731 USDORDAug 18 06:59
→MIAAug 18 11:10
AA 1875Airbus A321
2h 15m layover
MIAAug 18 13:25
→SJUAug 18 16:11
AA 967Boeing 737
9h 44m·1 stop
$731 USDORDAug 18 11:40
→PHLAug 18 14:52
AA 1743Boeing 737
3h 23m layover
PHLAug 18 18:15
→SJUAug 18 22:24
AA 2433Boeing 737