A crowd estimated to be in the hundreds gathered outside while the Hawks were packed in a roped-off area inside.
Center John Madden brought the Cup through the adoring crowd. Camera phones were firing as the Hawks poured beer in the Cup and drank from it.
After about 45 minutes, the party moved from Tavern to Gibson's for a brief visit before heading off to Rockit Bar.
Eleven-year-old Joshua was among the hundreds of elated fans who gathered wherever the chalice traveled. He said he touched the Cup three times as it passed by.
"It felt awesome," he said. "It just felt like I was part of the team.
Fans who didn't get a chance to catch a glimpse of the Cup during its impromptu tour through town should make plans to attend the parade and rally planned for Friday morning.
The Blackhawks took a chartered jet home early Thursday morning and arrived to Chicago Fire Department trucks blasting celebratory arcs of water over the aircraft.