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
Friday, August 21st, 2026
Outbound Flights
18h 55m·2 stops
$599 USD
ORDAug 21 18:56
→MKEAug 21 19:59
AA 6357Canadair RJ 700
10h 36m layover·Overnight
MKEAug 22 06:35
→CLTAug 22 09:41
AA 2866Airbus A321
1h 24m layover
CLTAug 22 11:05
→SJUAug 22 14:51
AA 783Airbus A321
7h 24m·1 stop
$689 USDORDAug 21 05:00
→PHLAug 21 08:03
AA 2970Boeing 737MAX 8 Passenger
1h 22m layover
PHLAug 21 09:25
→SJUAug 21 13:24
AA 614Airbus A321neo
4h 55m·Nonstop
$727 USDORDAug 21 17:20
→SJUAug 21 23:15
AA 1865Boeing 737
6h 40m·1 stop
$731 USDORDAug 21 05:00
→MIAAug 21 09:07
AA 2984Airbus A321
48m layover
MIAAug 21 09:55
→SJUAug 21 12:40
AA 1613Boeing 737
7h 2m·1 stop
$731 USDORDAug 21 06:49
→CLTAug 21 09:55
AA 1784Airbus A321
1h 10m layover
CLTAug 21 11:05
→SJUAug 21 14:51
AA 783Airbus A321
7h 38m·1 stop
$731 USDORDAug 21 06:00
→MIAAug 21 10:07
AA 2452Boeing 737MAX 8 Passenger
1h 38m layover
MIAAug 21 11:45
→SJUAug 21 14:38
AA 1341Airbus A321
8h 12m·1 stop
$731 USDORDAug 21 06:59
→MIAAug 21 11:10
AA 1875Airbus A321
2h 15m layover
MIAAug 21 13:25
→SJUAug 21 16:11
AA 967Boeing 737
7h 38m·1 stop
$761 USDORDAug 21 09:55
→MIAAug 21 14:08
AA 3056Boeing 737
1h 39m layover
MIAAug 21 15:47
→SJUAug 21 18:33
AA 1852Boeing 737
7h 58m·1 stop
$761 USDORDAug 21 13:26
→PHLAug 21 16:43
AA 830Airbus A319
1h 32m layover
PHLAug 21 18:15
→SJUAug 21 22:24
AA 2433Boeing 737