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 14 days ago
Extremely Rare Availability
3% of dates checked are available within 10% of the lowest price

Friday, August 21st, 2026

7 round-trip options

Returning
Wed, Aug 26, 2026•5 Day Trip
$319 USD
Google Flights
Returning
Fri, Aug 28, 2026•7 Day Trip
$319 USD
Google Flights
Returning
Sat, Aug 29, 2026•8 Day Trip
$323 USD
Google Flights
Returning
Sun, Aug 30, 2026•9 Day Trip
$400 USD
Google Flights
Returning
Tue, Sep 1, 2026•11 Day Trip
$323 USD
Google Flights
Returning
Wed, Sep 2, 2026•12 Day Trip
$319 USD
Google Flights
Returning
Fri, Sep 4, 2026•14 Day Trip
$319 USD
Google Flights