"It's the kind of city where you don't have to make plans," Cusack says. "You can go out in Chicago and the day or the night happens to you. You run into people and they say, 'Let's go over here, and let's do this.'?"
A guy who's spent all day on a bike requires sustenance, and in Chicago that most likely means steak. Cusack mentions arguably the greatest Chicago steak house in a city full of great steak houses: Gibsons Bar and Steakhouse, which he calls "the old standby."
"It's hard to get a better steak than [Gibsons] in Chicago," he says. "It's like Old Faithful. It has a real Chicago feeling."
But there's more to Chicago than just steak.
"There are great little Italian restaurants on Wells. Edwardo's is a great pizza place. They've got them all over. I get the stuffed spinach. Topo Gigio's Ristorante is a good Italian restaurant on Wells. Traditional. There are so many places … "
If it's a special occasion, Cusack might bike over to the holy temple of new American cuisine, with its tasting menu of infinite dishes, impeccable quality, and extraordinary price: Charlie Trotter's.
"Charlie Trotter's is a terrific place," he says. "There is also Spiaggia [a two-level, upscale Northern Italian restaurant], in the One Magnificent Mile building. It's a fantastic restaurant overlooking the city, right across from the Drake [Hotel]. I've gone there quite a bit. It's really superior."
Dinner done, it's time for drinks, music, nightlife - and the guy on the bike knows exactly where to pedal.
"Stanley's is a terrific bar," he says. "Stanley's is like mayhem, basically. Donnie Kruse is one of the owners, and he's kind of the mayor of Chicago. A lot of ballplayers go over there. It's kind of like a sports bar and they have live-band karaoke on [Sunday nights]. It's a really loose, fun crowd. They have a little restaurant in back and serve great food."