Chicago

Chicago's entertainment varies from loud and loose to sophisticated and sedate. You'll find classic Chicago corner bars in most neighborhoods, along with trendier alternatives like wine bars and lounges. The strains of blues and jazz provide much of the backbeat to the city's groove, and an alternative country scene is flourishing. As far as dancing is concerned, take your pick from cavernous clubs to smaller spots with DJs spinning dance tunes; there's everything from hip-hop to swing. Wicker Park/Bucktown and River North have the hottest nightlife, but prime spots are spread throughout the city.

Shows usually begin at 9 pm; cover charges generally range from $3 to $20, depending on the day of the week (Friday and Saturday nights are the most expensive). The list of blues and jazz clubs includes several South Side locations: be cautious about transportation here late at night, because some of these neighborhoods can be unsafe. Drive your own car or ask the bartender to call you a cab.

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  • 1. Second City

    Near North | Comedy Clubs

    An institution since 1959, Second City has served as a launching pad for some of the hottest comedians around. Alumni include Dan Aykroyd, Tina...Read More

  • 2. The Annoyance Theatre & Bar

    Lakeview | Comedy Clubs

    This is home base for Annoyance Productions, an irreverent group best known for hits like Skinprov and Hitch*Cocktails . ...Read More

  • 3. Chicago Improv Festival

    Comedy Clubs

    The springtime Chicago Improv Festival, the nation's largest festival for improvisers, has stages devoted to group, pair, and single improv...Read More

  • 4. ComedySportz

    Lakeview | Comedy Clubs

    ComedySportz specializes in "competitive improv," in which two teams vie for the audience's favor. Book a family-friendly early performance...Read More

  • 5. I.O.

    Lincoln Park | Comedy Clubs

    Formerly called ImprovOlympic, I.O. is the city's home for long-form improvisation. The signature piece is "The Harold," in which a team of...Read More

  • 6. Zanies Comedy Night Club

    Near North | Comedy Clubs

    Zanies books outstanding national talent and is Chicago's best stand-up comedy spot. Jay Leno, Jerry Seinfeld, and Jackie Mason have all performed...Read More

  • 7. Barrel of Laughs

    Comedy Clubs

    Barrel of Laughs, in the city's southwest suburbs (a 30-minute drive from downtown), spotlights local and national comics. The dinner package...Read More

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