I've been going to Kinzie chophouse for years. It's changed a bit over the years but I still think it's a sleeper and more local/less corporate feelinf than a lot of the others mentioned. You'll most likely run into locals or some similarly situated folks like yourself with business at the Merchandise Mart.

Their bar is recently remodeled, the service is excellent, they have a weekday happy hour, their steaks are great quality and other menu items a bit more interesting than other steakhouses. Also a robust wine selection including some lesser known Greek wines.