San Francisco is always 2 hours behind Chicago. When it's 9:00 AM in Chicago, it's 7:00 AM in San Francisco. Both cities observe DST on the same schedule, maintaining the 2-hour difference year-round.
Chicago uses CST/CDT while San Francisco uses PST/PDT (Pacific Time).
Late morning SF works well! 9:00 AM - 3:00 PM SF corresponds to 11:00 AM - 5:00 PM Chicago. Good overlap for business hours.
San Francisco and Chicago are both major business hubs. United operates frequent 4-hour flights from its hubs in both cities.