Want to really impress your clients/mistresses/manstresses/political representatives? Snag the 12-seat table in St. Elmo's wine cellar. It's private, swanky and affords ease of access to the steakhouse's 10,000-plus bottles, including "super" bottle options that are very, very expensive ($8000 for a hefty double magnum of Cristal) to the altogether more reasonable (plenty of sub-$50 bottles, with extensive representation from Australia, Italy, Spain and the Bordeaux and Rhone regions). Wine Spectator has given St. Elmo its Award of Excellence for several years running.
127 S. Illinois St., 635-0636, stelmos.com
2nd: Corner Wine Bar