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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Sun
Good Availability
56% of dates checked are available within 10% of the lowest price
Monday, August 3rd, 2026
Outbound Flights
13h 39m·2 stops
$701 USD
ORDAug 3 08:20
→PITAug 3 11:07
AA 4478Embraer 175
4h 29m layover
PITAug 3 15:36
→CLTAug 3 17:15
AA 2309Boeing 737MAX 8 Passenger
1h 53m layover
CLTAug 3 19:08
→SJUAug 3 22:59
AA 2830Airbus A321
16h 42m·2 stops
$701 USDORDAug 3 21:08
→PITAug 3 23:52
AA 4539Embraer 175
5h 11m layover·Overnight
PITAug 4 05:03
→CLTAug 4 06:35
AA 349Airbus A321
4h 28m layover
CLTAug 4 11:03
→SJUAug 4 14:50
AA 783Airbus A321
16h 42m·2 stops
$701 USDORDAug 3 21:08
→PITAug 3 23:52
AA 4539Embraer 175
6h 46m layover·Overnight
PITAug 4 06:38
→CLTAug 4 08:10
AA 384Boeing 737MAX 8 Passenger
2h 53m layover
CLTAug 4 11:03
→SJUAug 4 14:50
AA 783Airbus A321
4h 58m·Nonstop
$727 USDORDAug 3 17:50
→SJUAug 3 23:48
AA 3192Boeing 737
7h 33m·1 stop
$731 USDORDAug 3 05:00
→PHLAug 3 08:05
AA 2970Boeing 737MAX 8 Passenger
1h 23m layover
PHLAug 3 09:28
→SJUAug 3 13:33
AA 903Boeing 737
8h 42m·1 stop
$731 USDORDAug 3 13:17
→CLTAug 3 16:29
AA 3280Boeing 737
2h 39m layover
CLTAug 3 19:08
→SJUAug 3 22:59
AA 2830Airbus A321
8h 43m·1 stop
$761 USDORDAug 3 05:07
→CLTAug 3 08:10
AA 2842Airbus A321
2h 53m layover
CLTAug 3 11:03
→SJUAug 3 14:50
AA 783Airbus A321
7h 20m·1 stop
$833 USDORDAug 3 06:30
→CLTAug 3 09:37
AA 1784Airbus A321
1h 26m layover
CLTAug 3 11:03
→SJUAug 3 14:50
AA 783Airbus A321
7h 19m·1 stop
$907 USDORDAug 3 10:05
→MIAAug 3 14:18
AA 1474Boeing 737
1h 22m layover
MIAAug 3 15:40
→SJUAug 3 18:24
AA 3165Boeing 737
7h 2m·1 stop
$907 USDORDAug 3 06:10
→MIAAug 3 10:22
AA 1380Boeing 737MAX 8 Passenger
55m layover
MIAAug 3 11:17
→SJUAug 3 14:12
AA 2584Airbus A321
7h 48m·1 stop
$907 USDORDAug 3 06:59
→MIAAug 3 11:12
AA 835Airbus A321
1h 51m layover
MIAAug 3 13:03
→SJUAug 3 15:47
AA 2581Boeing 737