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

Sunday, December 20th, 2026

Outbound Flights

5h 22m·Nonstop
$549 USD
United Airlines
SJUDec 20 08:10
→
ORDDec 20 11:32
UA 2089Boeing 737MAX 8 Passenger
8h 25m·1 stop
$592 USD
United Airlines
SJUDec 20 02:05
→
EWRDec 20 05:24
UA 2219Boeing 737
1h 36m layover
United Airlines
EWRDec 20 07:00
→
ORDDec 20 08:30
UA 2754Boeing 737
5h 28m·Nonstop
$636 USD
United Airlines
SJUDec 20 16:52
→
ORDDec 20 20:20
UA 2088Boeing 737MAX 8 Passenger
7h 25m·1 stop
$636 USD
United Airlines
SJUDec 20 17:50
→
IADDec 20 20:55
UA 2024Boeing 737MAX 8 Passenger
1h 15m layover
United Airlines
IADDec 20 22:10
→
ORDDec 20 23:15
UA 421Boeing 737
11h 34m·1 stop
$1,238 USD
United Airlines
SJUDec 20 08:30
→
IADDec 20 11:35
UA 2022Boeing 737MAX 8 Passenger
5h 25m layover
United Airlines
DCADec 20 17:00
→
ORDDec 20 18:04
UA 654Airbus A320
12h 3m·1 stop
$1,238 USD
United Airlines
SJUDec 20 08:30
→
IADDec 20 11:35
UA 2022Boeing 737MAX 8 Passenger
5h 40m layover
United Airlines
IADDec 20 17:15
→
ORDDec 20 18:33
UA 2497Boeing 737
14h 55m·1 stop
$1,238 USD
United Airlines
SJUDec 20 19:35
→
EWRDec 20 22:53
UA 2036Boeing 737MAX 8 Passenger
8h 7m layover·Overnight
United Airlines
EWRDec 21 07:00
→
ORDDec 21 08:30
UA 2754Boeing 737
7h 42m·1 stop
$1,376 USD
United Airlines
SJUDec 20 08:30
→
IADDec 20 11:35
UA 2022Boeing 737MAX 8 Passenger
1h 30m layover
United Airlines
IADDec 20 13:05
→
ORDDec 20 14:12
UA 2331Boeing 737
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