The Blackhawks found themselves down two goals late in the third period before capitalizing on two mistakes by Toronto to force overtime and win in a shootout.
Jonathan Toews and Artemi Panarin scored in the shootout to give Chicago a 5-4 win over the Maple Leafs on Saturday night.
Artem Anisimov scored his second goal of the game on a rebound with 2:28 left to cut it to 4-3, then Richard Panik knocked in a loose puck in front of the goal 60 seconds later.
"We needed it," Toews said. "It wasn't pretty for a while there in the third sometimes. It looked like wherever we were going they were there and shut us down. Everything was going against us again."
But Anisimov connected as Blackhawks goalie Scott Darling was heading to the bench for an extra attacker. Darling was on the bench when Panik tied it with his team-leading sixth goal.
"We found a way to score a couple late ones," coach Joel Quenneviille said. "We're certainly fortunate to come back in a game like that.
"That was a little different way of going about it."
Toronto rookie William Nylander scored twice for his first multi-goal game, with the 20-year-old's second goal putting the Maple Leafs ahead 4-2 early in the third. But Toronto blew a lead in the final period for the third straight game and dropped its third straight, going 0-1-2 on a road trip.
And the Maple Leafs failed again to win at Chicago for the first time since February 2003.
"I thought we made two mistakes down the stretch," coach Mike Babcock said. "I didn't think we were on our heels at all. It was two blatant ones there, too. You can't give those up."
James van Riemsdyk scored a tie-breaking goal late in the second period and Tyler Bozak also connected for Toronto. Rookie Auston Matthews, the NHL's top 2016 draft pick, set up both of Nylander's goals and had the lone Toronto goal in the shootout.
"You just try to get open and he finds you pretty well there," Nylander said.
And Babcock and the Leafs weren't totally upset in settling for one point.
"All in all, I'm very pleased with the way we played here," Babcock said. "I thought Matthews had some great shifts. I think we're going in the right direction trending the right way."
Rookie Tyler Motte also scored for Chicago. Motte connected for the second straight game after getting his first NHL goal in a 3-2 loss at Columbus on Friday.
Chicago's Brian Campbell had three assists.
Toronto's Frederik Andersen made 31 saves through overtime. Darling blocked 30 shots.
Chicago forward Marian Hossa returned to the lineup after missing Friday's game. He scored his 500th NHL goal in a 7-4 win over Philadelphia on Tuesday, but left in the third period after blocking a shot.
Anisimov opened the scoring 3:36 in, completing a 2-on-1 break created when Panarin beat Nazem Kadri with a nifty move after entering the Toronto zone.
Bozak tied it 1-all with 14 seconds left in the first on a deflection from the slot despite being covered. Jake Gardiner's low shot ticked off Bozak's stick.
Nylander's power-play goal at 9:28 second put Toronto ahead 2-1.
Motte tied it 2-all 1:40 later. Andersen stopped Motte's initial deflection of Campbell's shot, but Motte batted in the rebound.
Van Riemsdyk made it 3-2 with 1:44 left in the second when he swept in a loose rebound from the edge of the crease.
Nylander connected again 4:46 into the third period, firing into a half-open net from the slot after taking Matthews' slick feed to make it 4-2.
NOTES: Blackhawks D Trevor van Riemsdyk, James' brother, will miss about a month with an upper-body injury, coach Joel Quenneville said before the game. The defenseman left Friday's game in Columbus in the second period, holding his right arm after crashing into the net. He appeared in 82 games last season, but van Riemsdyk was a healthy scratch for three games following Chicago's season opener and returned to the lineup against the Blue Jackets. ... Quenneville said there's no change in F Andrew Desjardins' (lower-body) status and doesn't know when he'll resume skating. ... Toronto D Martin Marincin (lower body) missed his second game.
Maple Leafs: Return home to face Tampa Bay on Tuesday.
Blackhawks: Face Calgary at home on Monday.