San Juan (SJU) to Chicago (ORD) flight deal in business from $379

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
$559 USD
-32%$379 USD
Verified about 4 hours ago
Limited Availability
16% of dates checked are available within 10% of the lowest price

Wednesday, October 28th, 2026

Outbound Flights

5h 31m·Nonstop
$379 USD
United Airlines
SJUOct 28 15:55
→
ORDOct 28 20:26
UA 2088Airbus A321neo
8h 57m·1 stop
$383 USD
United Airlines
SJUOct 28 01:05
→
EWROct 28 05:24
UA 2219Boeing 737MAX 9 Passenger
1h 51m layover
United Airlines
EWROct 28 07:15
→
ORDOct 28 09:02
UA 2431Airbus A321neo
8h 11m·1 stop
$383 USD
United Airlines
SJUOct 28 16:50
→
IADOct 28 20:56
UA 2024Boeing 737MAX 9 Passenger
1h 51m layover
United Airlines
IADOct 28 22:47
→
ORDOct 29 00:01
UA 421Boeing 737MAX 8 Passenger
5h 22m·Nonstop
$531 USD
United Airlines
SJUOct 28 07:25
→
ORDOct 28 11:47
UA 2089Airbus A321neo
14h 13m·1 stop
$1,300 USD
United Airlines
SJUOct 28 18:35
→
EWROct 28 22:54
UA 2036Boeing 737MAX 9 Passenger
7h 6m layover·Overnight
United Airlines
EWROct 29 06:00
→
ORDOct 29 07:48
UA 530Airbus A321neo
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