As stated before, Bill Cunningham is only shown on Tribune stations, since Tribune produces the show, & for now, has no syndicator distributing the show (they exited the syndication business in 2006). Until Tribune Company can find a distributor, Bill Cunningham won't air outside of the Tribune markets (Tribune owns no stations in Milwaukee, or in any part of Wisconsin for that matter). Chicago is the nearest market to you, & depending on how well WGN-TV can be picked up in the Milwaukee area (other than Racine & Kenosha Counties, where the signal is strong enough to pick up), you might get the station, & still see the show at 2pm CT.
According to this morning's Taylor on Radio Column The Bill Cunningham Show will be moving to The CW Network airing 3PM-4PM Eastern replacing Dr. Drew's Life Changers.