The Matchbox may claim to be the tiniest bar in Chicago, but the Clark Street Bar, situated inside The Clark Street Dog, may have it beat. Only about 10 stools line the bar and there is only one TV; an old-school jukebox entertains patrons with the likes of Bon Jovi.

Phil, the night bartender Tuesday through Saturday, is known for his off-beat personality and for hooking up regulars, most of whom are neighborhood residents who've been out at the other bars in the area and stop in for a boiled Vienna hot dog ($2.95) or a double cheeseburger ($4). Maybe they'll grab a domestic beer ($3.50) for a nightcap.

Average cost: <$10