"We’re sure whatever show you’re seeing at Second City will be great, but just in case you need a guarantee that one part of your night won’t bomb, go to Somerset. This is one of the absolute best restaurants in Chicago, and also the fanciest spot on our list. Its upscale American menu manages to be interesting but still appeal to just about everyone - and nothing you eat will disappoint. Make sure to tell the server you have a time constraint, and you’ll easily get out in time for the show. It’s about a five-minute cab ride or 15-minute walk from here to Second City." - adrian kane