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
Sunday, August 30th, 2026
Outbound Flights
4h 55m·Nonstop
$440 USD
ORDAug 30 17:20
→SJUAug 30 23:15
AA 1865Boeing 737
6h 40m·1 stop
$444 USDORDAug 30 05:00
→MIAAug 30 09:07
AA 2984Airbus A321
48m layover
MIAAug 30 09:55
→SJUAug 30 12:40
AA 1613Boeing 737
7h 4m·1 stop
$444 USDORDAug 30 06:49
→CLTAug 30 09:55
AA 1784Airbus A321
1h 10m layover
CLTAug 30 11:05
→SJUAug 30 14:53
AA 783Airbus A321
7h 38m·1 stop
$444 USDORDAug 30 06:00
→MIAAug 30 10:02
AA 2452Boeing 737MAX 8 Passenger
1h 43m layover
MIAAug 30 11:45
→SJUAug 30 14:38
AA 1341Airbus A321
8h 56m·1 stop
$444 USDORDAug 30 08:37
→MIAAug 30 12:50
AA 1250Airbus A321
2h 57m layover
MIAAug 30 15:47
→SJUAug 30 18:33
AA 1852Boeing 737
7h 20m·1 stop
$503 USDORDAug 30 08:37
→MIAAug 30 12:50
AA 1250Airbus A321
1h 21m layover
MIAAug 30 14:11
→SJUAug 30 16:57
AA 967Boeing 737
9h 44m·1 stop
$503 USDORDAug 30 11:40
→PHLAug 30 14:52
AA 1743Boeing 737
3h 23m layover
PHLAug 30 18:15
→SJUAug 30 22:24
AA 2433Boeing 737
7h 38m·1 stop
$761 USDORDAug 30 09:55
→MIAAug 30 14:08
AA 3056Boeing 737
1h 39m layover
MIAAug 30 15:47
→SJUAug 30 18:33
AA 1852Boeing 737