Chara was the first to lift the Cup after the Bruins' decisive 4-0 victory in Vancouver over the Canucks in Game 7 of the championship series Wednesday.
He raised it to the sky again when he was the last player off the team's plane following a noisy overnight flight that landed at Logan International Airport at about 8:30 a.m. Thursday.
Then he lifted and shook it one more time when the team got off the bus in front of TD Garden minutes later.
"We are pretty OK with that weight," the 6-foot-9 Chara said before walking over to some of the roughly 500 fans who had gathered outside the team's home rink, allowing them to touch the coveted trophy that hasn't been in Bruins hands in 39 years.
"We are all very honored to be winners," he said.
Team President Cam Neely, one of the team's all-time great players and a Vancouver native, was one of the first off the bus, followed seconds later by grinning coach Claude Julien, rarely seen with a smile, pumping his fist.
The tired but smiling team, some wearing their white championship hats and still sporting their playoff beards, filtered off to the cheers of adoring fans.
"We got it done, we brought it back to Boston and this is where it belongs," Julien said.
The city plans a parade for the Bruins on Saturday morning. It will be the city's seventh championship parade in the past decade, following championship celebrations for the Patriots, Red Sox and Celtics.
Goalie Tim Thomas, the Conn Smythe Trophy winner as the finals MVP, said the team's accomplishment hasn't quite sunk in.
"When you get here and see the fans, it begins to sink in a little bit," he said.
"We won the Stanley Cup last night but in a part of my mind I still can't believe it. ... It's very hard to get your mind around it."
Brad Marchand, who scored two goals in the clincher, said the Bruins went to Vancouver not knowing what would happen and returned as the best team in the world.
The Bruins lost the first two games of the series held in Vancouver, as well as Game 5 there, but held serve at home, setting up the winner-take-all seventh game.
Associated Press writer Mark Pratt contributed to this report.