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 14 days ago
Extremely Rare Availability
1% of dates checked are available within 10% of the lowest price

Tuesday, September 29th, 2026

Outbound Flights

5h 9m·Nonstop
$419 USD
United Airlines
SJUSep 29 15:56
→
ORDSep 29 20:05
UA 2088Airbus A321neo
7h 42m·1 stop
$423 USD
United Airlines
SJUSep 29 01:00
→
EWRSep 29 05:04
UA 2219Boeing 737MAX 9 Passenger
56m layover
United Airlines
EWRSep 29 06:00
→
ORDSep 29 07:42
UA 530Boeing 757
7h 37m·1 stop
$423 USD
United Airlines
SJUSep 29 16:55
→
IADSep 29 20:47
UA 2024Boeing 737MAX 9 Passenger
1h 31m layover
United Airlines
IADSep 29 22:18
→
ORDSep 29 23:32
UA 421Airbus A321neo
10h 41m·1 stop
$650 USD
United Airlines
SJUSep 29 07:00
→
IAHSep 29 10:45
UA 1644Boeing 737MAX 9 Passenger
3h layover
United Airlines
IAHSep 29 13:45
→
ORDSep 29 16:41
UA 1299Airbus A321neo
13h 57m·1 stop
$1,238 USD
United Airlines
SJUSep 29 18:45
→
EWRSep 29 22:46
UA 2036Boeing 737MAX 8 Passenger
7h 14m layover·Overnight
United Airlines
EWRSep 30 06:00
→
ORDSep 30 07:42
UA 530Boeing 757
8h 50m·1 stop
$1,376 USD
United Airlines
SJUSep 29 07:00
→
IAHSep 29 10:45
UA 1644Boeing 737MAX 9 Passenger
1h 10m layover
United Airlines
IAHSep 29 11:55
→
ORDSep 29 14:50
UA 1691Airbus A321neo
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