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
Tue
Wed
Thu
Fri
Sat
Sun
Good Availability
56% of dates checked are available within 10% of the lowest price
Sunday, August 9th, 2026
Outbound Flights
15h 10m·2 stops
$614 USD
ORDAug 9 08:05
→SDFAug 9 10:35
AA 3582Embraer 170
6h 20m layover
SDFAug 9 16:55
→CLTAug 9 18:40
AA 5450Canadair RJ 900
1h 50m layover
CLTAug 9 20:30
→SJUAug 10 00:15
AA 2830Airbus A321
4h 55m·Nonstop
$717 USDORDAug 9 17:20
→SJUAug 9 23:15
AA 1865Boeing 737
6h 40m·1 stop
$721 USDORDAug 9 05:00
→MIAAug 9 09:07
AA 2984Airbus A321
48m layover
MIAAug 9 09:55
→SJUAug 9 12:40
AA 1613Boeing 737
7h 38m·1 stop
$721 USDORDAug 9 06:00
→MIAAug 9 10:07
AA 2452Boeing 737MAX 8 Passenger
1h 38m layover
MIAAug 9 11:45
→SJUAug 9 14:38
AA 1341Airbus A321
7h 4m·1 stop
$721 USDORDAug 9 06:49
→CLTAug 9 09:55
AA 1784Airbus A321
1h 10m layover
CLTAug 9 11:05
→SJUAug 9 14:53
AA 783Airbus A321
8h 48m·1 stop
$751 USDORDAug 9 07:09
→MIAAug 9 11:20
AA 1875Airbus A321
2h 51m layover
MIAAug 9 14:11
→SJUAug 9 16:57
AA 967Boeing 737
9h 44m·1 stop
$823 USDORDAug 9 11:40
→PHLAug 9 14:52
AA 1743Boeing 737
3h 23m layover
PHLAug 9 18:15
→SJUAug 9 22:24
AA 2433Boeing 737
7h 20m·1 stop
$1,041 USDORDAug 9 08:37
→MIAAug 9 12:50
AA 1250Airbus A321
1h 21m layover
MIAAug 9 14:11
→SJUAug 9 16:57
AA 967Boeing 737
7h 38m·1 stop
$1,041 USDORDAug 9 09:55
→MIAAug 9 14:08
AA 3056Boeing 737
1h 39m layover
MIAAug 9 15:47
→SJUAug 9 18:33
AA 1852Boeing 737