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      Comedy Show at Castle – Up to 54% Off Standup

      Comedy Night with Benji Brown

      Castle (711.2 miles)

      Star of Wild ‘N Out and The Rickey Smiley Show and Ghana-born comedian get crowds rolling

      $53.74 $25

      The Second City's Deep Cuts or Improv All-Stars – Up to 43% Off

      The Second City's Deep Cuts or Improv All-Stars

      UP Comedy Club (711.3 miles)

      Annoyance Theatre founder Mick Napier directs a cast of top improv talent; revue about living in the Internet age collects past sketches

      $24.50 $17

      Morning Show Comedians – Up to 62% Off Navy Pier Showcase

      Navy Pier Four Star Comedy presents Morning Show Comedians

      Pepsi Skyline Stage At Navy Pier (710.2 miles)

      WGN Morning News' Mike Toomey, Ana Belaval, and Pat Tomasulo moonlight as standup comedians, showing off their skills at Navy Pier

      $33.30 $12.50

      $10 for Live Comedy at The Comedy Shrine Theater

      The Comedy Shrine Theater

      The Comedy Shrine Theater (742.6 miles)

      Comics and resident improvisers fill standup showcases and a Whose Line Is It Anyway? tribute

      $20 $10

      Yakov Smirnoff – Up to 41% Off Standup

      Yakov Smirnoff

      Rialto Square Theatre (738.5 miles)

      Soviet-born comedy icon who found fame comparing the US with the USSR is still yukking it up with society-deconstructing wordplay

      $47.25 $28

      Up to 50% Off Improv Show with Popcorn

      Laugh Out Loud Theater

      Streets of Woodfield (730.3 miles)

      Improvisers can perform a show with spontaneous scenes, games, and songs

      $22 $11

      Take in 33rd-Floor City Views During an Intimate Jazz Soiree

      Intimate Jazz Mixer

      Chicago (711.1 miles)

      Jazz vocalist Erin McDougald and her ensemble serenade guests as they mingle, sip cocktails, and watch the sun set over the Chicago skyline

      $70