Chicago (ORD) to San Juan (SJU) flight deal in economy from $237

United AirlinesUAUnited Airlines
Round Trip•Economy
United StatesORD

O'Hare International Airport

Chicago, United States
Puerto RicoSJU

Luis Muñoz Marín International Airport

San Juan, Puerto Rico
$527 USD
-55%$237 USD
Verified 16 days ago
Extremely Rare Availability
3% of dates checked are available within 10% of the lowest price

Monday, December 21st, 2026

7 round-trip options

Returning
Sat, Dec 26, 2026•5 Day Trip
$757 USD
Google Flights
Returning
Sun, Dec 27, 2026•6 Day Trip
$911 USD
Google Flights
Returning
Mon, Dec 28, 2026•7 Day Trip
$911 USD
Google Flights
Returning
Wed, Dec 30, 2026•9 Day Trip
$842 USD
Google Flights
Returning
Fri, Jan 1, 2027•11 Day Trip
$999 USD
Google Flights
Returning
Sat, Jan 2, 2027•12 Day Trip
$1,657 USD
Google Flights
Returning
Sun, Jan 3, 2027•13 Day Trip
$1,579 USD
Google Flights