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
Saturday, August 22nd, 2026
Outbound Flights
16h 41m·2 stops
$532 USD
ORDAug 22 18:59
→PITAug 22 21:47
AA 4402Embraer 175
8h 23m layover·Overnight
PITAug 23 06:10
→MIAAug 23 08:57
AA 2313Boeing 737
58m layover
MIAAug 23 09:55
→SJUAug 23 12:40
AA 1613Boeing 737
7h 24m·1 stop
$658 USDORDAug 22 05:00
→PHLAug 22 08:03
AA 2970Boeing 737MAX 8 Passenger
1h 22m layover
PHLAug 22 09:25
→SJUAug 22 13:24
AA 614Airbus A321neo
4h 55m·Nonstop
$767 USDORDAug 22 16:59
→SJUAug 22 22:54
AA 1865Boeing 737
7h 35m·1 stop
$771 USDORDAug 22 08:22
→MIAAug 22 12:35
AA 1250Airbus A321
1h 36m layover
MIAAug 22 14:11
→SJUAug 22 16:57
AA 967Boeing 737
7h 35m·1 stop
$771 USDORDAug 22 09:55
→MIAAug 22 14:08
AA 3056Boeing 737
1h 32m layover
MIAAug 22 15:40
→SJUAug 22 18:30
AA 1852Airbus A321
6h 40m·1 stop
$771 USDORDAug 22 05:00
→MIAAug 22 09:07
AA 2984Airbus A321
48m layover
MIAAug 22 09:55
→SJUAug 22 12:40
AA 1613Boeing 737
7h 38m·1 stop
$771 USDORDAug 22 06:00
→MIAAug 22 10:07
AA 2452Boeing 737MAX 8 Passenger
1h 38m layover
MIAAug 22 11:45
→SJUAug 22 14:38
AA 1341Airbus A321
7h 2m·1 stop
$771 USDORDAug 22 06:49
→CLTAug 22 09:55
AA 1784Airbus A321
1h 10m layover
CLTAug 22 11:05
→SJUAug 22 14:51
AA 783Airbus A321
7h 53m·1 stop
$771 USDORDAug 22 13:31
→PHLAug 22 16:48
AA 830Airbus A319
1h 27m layover
PHLAug 22 18:15
→SJUAug 22 22:24
AA 2433Boeing 737