Cheap flights from Chicago to Portland
From 278 USD — compare hundreds of airlines
Vuelos directosMás barato: 2026-07 · 161 US$
Precios por fecha
191 US$
07-09
176 US$
07-10
176 US$
07-11
176 US$
07-12
176 US$
07-13
176 US$
07-14
176 US$
07-15
176 US$
07-16
176 US$
07-17
176 US$
07-18
176 US$
07-19
176 US$
07-20
Aerolíneas en esta ruta
Alaska AirlinesUnited AirlinesSilk AviaSouthwest Airlines
Preguntas frecuentes
What's the cheapest month to fly Chicago to Portland?
Usually 2026-07, from 161 USD.
Are there direct flights from Chicago to Portland?
We show both direct and connecting options — filter to compare.