ORD and OAK are approximately 1,831 miles apart by great-circle distance.
No. Roame's current schedule feed lists service with stops from ORD to OAK, but no nonstop service.
Airlines represented in the current schedule are Southwest Airlines (WN).
Aircraft listed in the current schedule include Boeing 737-800 Winglets (73H) and Boeing 737 MAX 8 (7M8).