He'll bike by the city's landmarks, starting at the Marshall Field's building, where his parents used to take him to see the big tree at Christmas. Then there's the Sears Tower and the John Hancock Center, where Cusack will jump off the bike and hop into an elevator, arriving at the top of the Hancock, where a diorama of the history of Chicago competes with the heavenly view. "The John Hancock is great because you can see the whole city from all the way around," he says.

Back on the street, he heads into Bucktown, once a scruffy quarter named for the immigrant families who kept goats in their yards and now Chicago's hottest neighborhood. Cusack fans would recognize it from his 2000 movie High Fidelity, in which John starred with his sister Joan as a Chicago record-store owner charting his top five romantic breakups.

"You can take your bike through Bucktown, which is terrific," Cusack says. "Just a cool area with lots of great coffee shops and clubs and restaurants. We shot all over there for High Fidelity. It's where Double Door [a live-music venue] is. There are great record stores in Bucktown. Tiny little record stores like the one in High Fidelity. They are all over. You can also find great funky art and stuff like that."

When the lunch hour looms, Cusack bikes to Leo's. "Leo's Lunchroom," he says. "That's a great little place for lunch, a tiny little diner, down on … I can't remember where it is [in Bucktown]. I know how to get there on a bike."

Afterward, he might spin by some of the museums. "MCA is right downtown," he says of the Museum of Contemporary Art, dedicated to the avant-garde. "It's fantastic. And there's the Art Institute of Chicago - unbelievable."