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
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Good Availability
56% of dates checked are available within 10% of the lowest price
Wednesday, August 19th, 2026
Outbound Flights
4h 55m·Nonstop
$445 USD
ORDAug 19 17:20
→SJUAug 19 23:15
AA 1865Boeing 737
7h 24m·1 stop
$449 USDORDAug 19 05:00
→PHLAug 19 08:03
AA 2970Boeing 737MAX 8 Passenger
1h 22m layover
PHLAug 19 09:25
→SJUAug 19 13:24
AA 614Airbus A321neo
7h 38m·1 stop
$449 USDORDAug 19 06:00
→MIAAug 19 10:07
AA 2452Boeing 737MAX 8 Passenger
1h 38m layover
MIAAug 19 11:45
→SJUAug 19 14:38
AA 1341Airbus A321
7h 38m·1 stop
$449 USDORDAug 19 09:55
→MIAAug 19 14:08
AA 3056Boeing 737
1h 39m layover
MIAAug 19 15:47
→SJUAug 19 18:33
AA 1852Boeing 737
8h 12m·1 stop
$449 USDORDAug 19 06:59
→MIAAug 19 11:10
AA 1875Airbus A321
2h 15m layover
MIAAug 19 13:25
→SJUAug 19 16:11
AA 967Boeing 737
10h 2m·2 stops
$449 USDORDAug 19 10:53
→DCAAug 19 13:54
AA 1187Airbus A319
1h layover
DCAAug 19 14:54
→MIAAug 19 17:48
AA 1299Boeing 737
1h 23m layover
MIAAug 19 19:11
→SJUAug 19 21:55
AA 1689Boeing 737
6h 40m·1 stop
$508 USDORDAug 19 05:00
→MIAAug 19 09:07
AA 2984Airbus A321
48m layover
MIAAug 19 09:55
→SJUAug 19 12:40
AA 1613Boeing 737
7h 2m·1 stop
$766 USDORDAug 19 06:49
→CLTAug 19 09:55
AA 1784Airbus A321
1h 10m layover
CLTAug 19 11:05
→SJUAug 19 14:51
AA 783Airbus A321