Underground Wonder Bar (Chicago)

True to its title, the Underground Wonder Bar is an underground wonder of the Gold Coast. While it books itself as a jazz/blues club, you're likely to hear anything from reggae and rock to blues and jazz, all in the same night. Besides the bevy of locals and visiting musicians who fill the weekly roster (notice the wall of signed celebrity headshots), owner Lonie Walker and her "Big Bad Ass Company Band" perform at least half of the week nights.

Far from the Green Mill in ambience, the Wonder Bar audience is often encouraged to sing and dance along. If you chance to be there the night of someone's birthday, you'll experience Walker's traditional celebration, which falls somewhere between an intimate Bar Mitzvah party and a fraternity hazing: Surprisingly mess-free, it involves an attractive cocktail waitress, chocolate syrup, whipped cream, alcohol and singing. While the guests range from just-ripe 21-year-olds to middle-aged men in sport coats stopping in after work, the crowd is conversation-friendly. And when the musicians pump it up, even the silver ornaments and disco balls get shakin'.

There's no room for shyness in this corridor-shape bar, where guests weave through the center of the band to reach the restroom in back. Should you and your friend or lover prefer a candlelit table for two, arrive before the music starts. Otherwise, you'll find yourself squeezed between two rows of bar stools, soaking up the red light and squirming for a view of the voice behind the baby grand. On top of a cover charge (around ten bucks), you'll spend between $4-$10 on a beer, wine or your cocktail of choice.