Cheap flights from Oakland to Chicago
From 274 USD — compare hundreds of airlines
Direct flightsCheapest: 2026-07 · 310 US$
Prices by date
310 US$
03/07
Airlines on this route
FAQ
What's the cheapest month to fly Oakland to Chicago?
Usually 2026-07, from 310 USD.
Are there direct flights from Oakland to Chicago?
We show both direct and connecting options — filter to compare.