But now, since it's July, the middle of baseball season, Cusack's bike will head, almost automatically, to Wrigley Field.
"I'll bike from my apartment, meet somebody for lunch," he says. "If the game is at 1:20 p.m., you can leave the restaurant at 1:05 and ride your bike right up to Wrigley Field, lock it outside in this bike rack they have out there, and walk in. Wrigley Field is amazing, right in the heart of the city."
His restaurant choices are dependent on their proximity to the field.
"I could say, 'Hey, I'll meet you over at Smith & Wollensky,' and we would bike over there, have some food, and then make a mad dash to Wrigley Field."
A lifelong ritual, returning to Wrigley Field represents much more than baseball to Cusack.
"It totally connects me to Chicago and my childhood," he says. "My father took me there. We would sit behind third base, not in the box seats, but the grandstand. Then, when I got old enough, I would take the El, the elevated train, from Evanston, change to the Purple Line, and then we would go to Wrigley Field. I remember just as we'd pull into the park, the whole train would be rocking with excitement. You could see the scoreboard, the flags waving, and I would usually have about three or four bucks. It would take 50 cents to get down there, then it was $1.50 to sit in the bleachers, so that would take about $2, which would give me about a buck and a half for food and a ride home. Usually, I would spend the whole thing and we would have to hop the train on the way back."
Afterward, he suggests following the fans to Chicago's many loud, rabid sports bars - although it's something Cusack doesn't get to do much anymore.
"Yeah, those are a little trickier to go into if you are famous," he says. "Famous and alcohol can be not so good, but I like to go into [the bars]. There are great ones all around Wrigley Field. You can go into any of those and have a great time."