> If I drive up which I would need to do with a bike I'm worried about parking and the liability of
> having a car in the city. Any ideas?
Despite the extortive parking rates in the downtown area, most suburban hotels and motels have free parking. The "OJ Hotel" on Cumberland, where I know you stayed at least once, is one of them. It's also more hilly in that part of the area than it is closer to the lake.
I've known people who have driven to Chicago, parked in the long term lot at Midway, and taken the train to the city as the long term rates are lower than the loop area daily rates. You can take a bike on the El except in rush hours and most (all?) CTA buses have bike racks.
The one time I drove to Pinkfest the car mostly stayed in the lot at the hotel.