Map above should automatically show bike shops nearest you. Plan a route by several of them, ideally coordinated with other street team hitting other shops.
Possible additional attractive distribution locations: Yoga Studios, Hipster Bars.
Flyer distribution is a fun job if taken with confidence. I distribute by walking in and pretty much straight up saying "Hi, I'm from the World Naked Bike Ride, wanted to leave you some flyers and a little window poster." If help looks confused I immediately continue "This is the (Nth) year. You may know Chicago set the world's record" and by then someone'll go "oh yeah (so and so) did that" and you're in. The major franchises are more impersonal, but still often have a flyer rack near the door. And remember to sticker the bike racks outside any shop (or anywhere).
- Online calendars and mailing lists for web promo.
NEAR NORTH distribution - Bike shops from Andersonville East to Lakeview.
FAR NORTH distribution - Bike shops from Roger Park north to Evanston.
Google map plot for "bicycle"