"You can go down toward Halsted and see all the blues clubs and jazz clubs. I like to go to the Green Mill. We shot that in High Fidelity. It's this great old jazz club. It's in a really old building that is just fantastic. They say Al Capone drank there. You feel like you can see how the whole place must have been bustling in the '20s or something. Then the neighborhood decayed, and now it is coming back up. It's been around for so long, you can sort of feel the history. The acoustics aren't great, but the room feels so great. It has a big, long, old bar, and it's a great place to hang out."
As the night descends, the air fills with big bass and deep voices: Chicago blues. The clubs are lined up along Rush Street and beyond - all within biking distance of one another, all great, says Cusack.
"Kingston Mines is a tiny little blues place, the best place to hear the blues," he says. "The Checkerboard Lounge on the deep South Side [now closed], that's pretty intense. You can hear the best blues in the world in these cramped little places. They have small, tiny little stages and the best blues players in the world."
He is cycling back in time now, remembering the legends he's seen.
"We used to go hear Sugar Blue play all the time," he says. "We would go out to dinner, then go over to Checkerboard Lounge and hear Sugar Blue playing with his band from around 11 p.m. on. Then, after he's done playing, you go to the Green Mill. It's open until four. You can go barhopping all night."
In the end, Cusack says Chicago is more than its beautiful skyline, its historic architecture, its hearty food, its gutsy blues. Chicago is its people, a brand of Midwesterner as tough and resilient as the seasons.
"They survive all those tough winters and then everybody sort of explodes and goes crazy when the spring and summer come because they are so happy about it," he says. "You have the dead of summer and the dead of winter. There is not a better place to be."
He believes the best gauge of the people is their sports teams.
"I watched all six championships for the Bulls," he says. "You could always go to any bar on any given night in the winter and the whole city would stop for Michael Jordan. Everyone would hold their breath to see what he would do. The whole city went nuts for all six championships.
"I would also go to the old Soldier Field on Sundays and see the Bears. I was there for every playoff game when they went to the Super Bowl, when the Bears had that magical season in 1985. I was there for the last game, when they beat the Giants. The colder it got, the happier the fans got. Then, as soon as they knew they were going to the Super Bowl, it started to snow. The whole city was in this state of bliss. … I was also there the year before when the Cubs were two innings away from going to the World Series. I've been to every playoff game the Cubs have played, too, which haven't been that many … "
Cusack considers this about Chicago, his city of winning, losing, and waiting, always knowing that victory will eventually come.
"Hey, man, it's like enduring the winters," he says. "We will endure and persevere until the spring comes."