San Juan (SJU) to Chicago (ORD) flight deal in business from $358

United AirlinesUAUnited Airlines
One Way•Business Class
Puerto RicoSJU

Luis Muñoz Marín International Airport

San Juan, Puerto Rico
United StatesORD

O'Hare International Airport

Chicago, United States
$558 USD
-36%$358 USD
Verified 13 days ago
Extremely Rare Availability
1% of dates checked are available within 10% of the lowest price

Tuesday, September 1st, 2026

Outbound Flights

7h 45m·1 stop
$358 USD
United Airlines
SJUSep 1 16:55
→
IADSep 1 20:47
UA 2024Boeing 737MAX 9 Passenger
1h 40m layover
United Airlines
IADSep 1 22:27
→
ORDSep 1 23:40
UA 421Boeing 737MAX 8 Passenger
10h·1 stop
$435 USD
United Airlines
SJUSep 1 01:00
→
EWRSep 1 05:04
UA 2219Boeing 737MAX 9 Passenger
3h 12m layover
United Airlines
EWRSep 1 08:16
→
ORDSep 1 10:00
UA 2488Boeing 737
5h 9m·Nonstop
$500 USD
United Airlines
SJUSep 1 15:56
→
ORDSep 1 20:05
UA 2088Airbus A321neo
9h 13m·1 stop
$553 USD
United Airlines
SJUSep 1 01:00
→
EWRSep 1 05:04
UA 2219Boeing 737MAX 9 Passenger
2h 26m layover
United Airlines
EWRSep 1 07:30
→
ORDSep 1 09:13
UA 2754Airbus A321neo
7h 40m·1 stop
$588 USD
United Airlines
SJUSep 1 01:00
→
EWRSep 1 05:04
UA 2219Boeing 737MAX 9 Passenger
56m layover
United Airlines
EWRSep 1 06:00
→
ORDSep 1 07:40
UA 530Boeing 737
8h 50m·1 stop
$1,376 USD
United Airlines
SJUSep 1 07:00
→
IAHSep 1 10:45
UA 1644Boeing 737MAX 9 Passenger
1h 10m layover
United Airlines
IAHSep 1 11:55
→
ORDSep 1 14:50
UA 2417Boeing 737
Google Flights