The Blackhawks hope to even their playoff series Friday night against the Vancouver Canucks.
On Saturday at noon, the Bulls begin their first round playoff series at the United Center against the Indiana Pacers.
Then the Hawks return home for Game 3 in Chicago Sunday night.
This is actually the third year in a row that both teams have made the post-season.
The surprise in all this, however, seems to be that roles have changed -- it is the Bulls who have a No. 1 seed heading in, and it's the Stanley Cup Champion Blackhawks who are the underdogs.
Either way, the fact is that this sports city has something few others can boast about -- two winners.
The saving grace of winter hanging on in Chicago seems to be that the city's sports teams are hanging in there, together, in the playoffs.
It's a brisk business at the Blackhawks store on Michigan Avenue, where people are in a buying mood.
"It helps the fans, it really does, kind of give them a solidarity with the players, a little bit of team city identity," said Allan Wyatt of Longmont, Colo.
The Gunther family from Cleveland, Ohio, loves the feeling that winning is in the air.
"It is very fun. You can tell people are excited about it, there is almost like a sense it should be happening, We are Chicago, we're a sports city, so it is easy to get caught up in it," Dan Gunther said.
City icons are draped in Hawks colors, and if you want to catch a cab at fancy hotel, just ask Marius Smith with the Four Seasons Hotel.
"We're busy, everybody is moving around, people are enjoying the city more, People are coming here, and even though it is supposed to be warm and it is cold, people are still out here enjoying Chicago," Smith said.
As people ponder the force behind the last great dynasty that rocked Chicago sports, fans arrive to pick up playoff tickets they've ordered online. At the busiest intersections, longtime fans consider the possibilities.
"Chicago has always supported their franchises, and consequently for them, to be sitting where they are, I think it really is a lot of dedication being put in by the two organizations. That's why it is the Madhouse on Madison," said Melvin Funches of Chicago.
Longtime ESPN sportswriter Lester Munson says winter's staying power isn't such a bad thing.
"Having two teams in the playoffs, having this every 48 hours of peaks and valleys, and they win, and they lose who are they going to play next, this is going to be the kind of excitement we have not had in a long time," Munson said.
If the Blackhawks win Friday night in Vancouver, you can be sure it will be feverish around here this weekend, and we can guess the Bulls will likely put on a clinic against the Indiana Pacers Saturday afternoon.
The last time a city had multiple major league championships was 2004, with Boston's Red Sox and Patriots winning it all.
Before that, in 1988, Los Angeles had the Lakers and Dodgers winning in the same year. It has happened 12 times actually but never in Chicago.