Cheap flights from Chicago to Oakland
From 301 USD — compare hundreds of airlines
Vuelos directosMás barato: 2026-07 · 220 US$
Precios por fecha
220 US$
07-02
Aerolíneas en esta ruta
Southwest Airlines
Preguntas frecuentes
What's the cheapest month to fly Chicago to Oakland?
Usually 2026-07, from 220 USD.
Are there direct flights from Chicago to Oakland?
We show both direct and connecting options — filter to compare.