Cheap flights from Chicago to San Juan
From 236 USD — compare hundreds of airlines
Vuelos directosMás barato: 2026-07 · 197 US$
Precios por fecha
197 US$
07-03
Aerolíneas en esta ruta
American AirlinesUnited AirlinesSilk Avia
Preguntas frecuentes
What's the cheapest month to fly Chicago to San Juan?
Usually 2026-07, from 197 USD.
Are there direct flights from Chicago to San Juan?
We show both direct and connecting options — filter to compare.