San Juan (SJU) to Chicago (ORD) flight deal in business from $358
Luis Muñoz Marín International Airport
San Juan, Puerto Rico
O'Hare International Airport
Chicago, United States
$558 USD
-36%$358 USD
Verified 15 days agoJanuary 2027
Mon
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Extremely Rare Availability
1% of dates checked are available within 10% of the lowest price
Sunday, January 10th, 2027
Outbound Flights
5h 22m·Nonstop
$734 USD
SJUJan 10 08:35
→ORDJan 10 11:57
UA 2089Boeing 737MAX 8 Passenger
5h 28m·Nonstop
$734 USD
SJUJan 10 16:52
→ORDJan 10 20:20
UA 2088Boeing 737MAX 8 Passenger
10h 42m·1 stop
$738 USD
SJUJan 10 02:05
→EWRJan 10 05:24
UA 2219Boeing 737
3h 36m layover

EWRJan 10 09:00
→ORDJan 10 10:47
UA 2290Boeing 737MAX 9 Passenger
13h 56m·1 stop
$1,238 USD
SJUJan 10 19:35
→EWRJan 10 22:53
UA 2036Boeing 737MAX 8 Passenger
7h 7m layover·Overnight

EWRJan 11 06:00
→ORDJan 11 07:31
UA 530Boeing 737
9h 32m·1 stop
$1,376 USD
SJUJan 10 02:05
→EWRJan 10 05:24
UA 2219Boeing 737
2h 36m layover

EWRJan 10 08:00
→ORDJan 10 09:37
UA 2488Boeing 737
10h 59m·1 stop
$1,376 USD
SJUJan 10 10:15
→IAHJan 10 13:25
UA 2495Boeing 737MAX 8 Passenger
3h 5m layover

IAHJan 10 16:30
→ORDJan 10 19:14
UA 2296Boeing 737
8h 52m·1 stop
$1,376 USD
SJUJan 10 13:00
→EWRJan 10 16:17
UA 2461Boeing 737MAX 9 Passenger
1h 48m layover

EWRJan 10 18:05
→ORDJan 10 19:52
UA 254Boeing 737
7h 25m·1 stop
$1,376 USD
SJUJan 10 17:50
→IADJan 10 20:55
UA 2024Boeing 737MAX 8 Passenger
1h 15m layover

IADJan 10 22:10
→ORDJan 10 23:15
UA 421Boeing 737