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C. AMERICA & CARIBBEAN

C. AMERICA & CARIBBEAN

San Juan, Puerto Rico → Chicago, USA

Flight deals from San Juan, Puerto Rico to Chicago, USA | Secret Flying

July 22, 2026

Non-stop from San Juan, Puerto Rico to Chicago, USA for only $247 USD roundtrip

Non-stop flights from San Juan, Puerto Rico to Chicago, USA for only $247 USD roundtrip with United Airlines.

Flight deals from San Juan, Puerto Rico to Chicago, USA | Secret Flying

August 22, 2023

🔥 San Juan, Puerto Rico to Chicago, USA for only $166 USD roundtrip (Jan-Feb dates)

Cheap flights from San Juan, Puerto Rico to Chicago, USA for only $166 USD roundtrip with United Airlines.