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
Monday, August 24th, 2026
Outbound Flights
18h 48m·2 stops
$542 USD
ORDAug 24 18:50
→SDFAug 24 21:25
AA 4603Embraer 175
8h 50m layover·Overnight
SDFAug 25 06:15
→MIAAug 25 08:50
AA 2073Airbus A319
2h 55m layover
MIAAug 25 11:45
→SJUAug 25 14:38
AA 1341Airbus A321
7h 24m·1 stop
$698 USDORDAug 24 05:00
→PHLAug 24 08:03
AA 2970Boeing 737MAX 8 Passenger
1h 22m layover
PHLAug 24 09:25
→SJUAug 24 13:24
AA 614Airbus A321neo
4h 55m·Nonstop
$717 USDORDAug 24 17:20
→SJUAug 24 23:15
AA 1865Boeing 737
7h 38m·1 stop
$721 USDORDAug 24 06:00
→MIAAug 24 10:07
AA 2452Boeing 737MAX 8 Passenger
1h 38m layover
MIAAug 24 11:45
→SJUAug 24 14:38
AA 1341Airbus A321
7h 2m·1 stop
$751 USDORDAug 24 06:49
→CLTAug 24 09:55
AA 1784Airbus A321
1h 10m layover
CLTAug 24 11:05
→SJUAug 24 14:51
AA 783Airbus A321
8h 12m·1 stop
$751 USDORDAug 24 06:59
→MIAAug 24 11:10
AA 1875Airbus A321
2h 15m layover
MIAAug 24 13:25
→SJUAug 24 16:11
AA 967Boeing 737
7h 58m·1 stop
$823 USDORDAug 24 13:26
→PHLAug 24 16:43
AA 830Airbus A319
1h 32m layover
PHLAug 24 18:15
→SJUAug 24 22:24
AA 2433Boeing 737
6h 40m·1 stop
$972 USDORDAug 24 05:00
→MIAAug 24 09:07
AA 2984Airbus A321
48m layover
MIAAug 24 09:55
→SJUAug 24 12:40
AA 1613Boeing 737
7h 35m·1 stop
$1,206 USDORDAug 24 09:55
→MIAAug 24 14:08
AA 3056Boeing 737
1h 38m layover
MIAAug 24 15:46
→SJUAug 24 18:30
AA 1852Boeing 737MAX 8 Passenger