Map room, Hop Leaf, and the Kuma Corner. Those are my three favorite places in Chi town. I don't live there though.
Kuma Corner is a great burger place. The wait is usually about 2 hours but they will never say it is longer than 45 minutes, ever. Just expect to wait a long time. They have awesome beer and the best bloody mary I have ever had.
In Dundee there are two great brewpubs. Emmett's Tavern and M.T. Barrels. I know Two Brothers brewery is also down near naperville. The closest LHBS to elgin is the one in St. Charles "The Homebrew Shop"