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
Monday, August 31st, 2026
Outbound Flights
14h 25m·2 stops
$558 USD
ORDAug 31 21:15
→PITAug 31 23:59
AA 4527Embraer 175
6h 11m layover·Overnight
PITSep 1 06:10
→MIASep 1 08:57
AA 2313Boeing 737
58m layover
MIASep 1 09:55
→SJUSep 1 12:40
AA 1613Boeing 737
7h 24m·1 stop
$659 USDORDAug 31 05:00
→PHLAug 31 08:03
AA 2970Boeing 737MAX 8 Passenger
1h 22m layover
PHLAug 31 09:25
→SJUAug 31 13:24
AA 614Airbus A321neo
4h 55m·Nonstop
$727 USDORDAug 31 17:20
→SJUAug 31 23:15
AA 1865Boeing 737
7h 2m·1 stop
$731 USDORDAug 31 06:49
→CLTAug 31 09:55
AA 1784Airbus A321
1h 10m layover
CLTAug 31 11:05
→SJUAug 31 14:51
AA 783Airbus A321
7h 58m·1 stop
$731 USDORDAug 31 13:26
→PHLAug 31 16:43
AA 830Airbus A319
1h 32m layover
PHLAug 31 18:15
→SJUAug 31 22:24
AA 2433Boeing 737
7h 38m·1 stop
$761 USDORDAug 31 06:00
→MIAAug 31 10:02
AA 2452Boeing 737MAX 8 Passenger
1h 43m layover
MIAAug 31 11:45
→SJUAug 31 14:38
AA 1341Airbus A321
8h 12m·1 stop
$833 USDORDAug 31 06:59
→MIAAug 31 11:10
AA 1875Airbus A321
2h 15m layover
MIAAug 31 13:25
→SJUAug 31 16:11
AA 967Boeing 737
8h 56m·1 stop
$833 USDORDAug 31 08:37
→MIAAug 31 12:50
AA 1250Airbus A321
2h 57m layover
MIAAug 31 15:47
→SJUAug 31 18:33
AA 1852Boeing 737
7h 38m·1 stop
$1,216 USDORDAug 31 09:55
→MIAAug 31 14:08
AA 3056Boeing 737
1h 39m layover
MIAAug 31 15:47
→SJUAug 31 18:33
AA 1852Boeing 737