not sure what you mean by entertaining but I would recommend sears towers or hancock building for great city views, there is an untouchables tour that goes by places from the infamous past of Chicago, st valentines day massacre, biograph theatre (dillenger shooting) etc.  

also biily goats,( inspiration for Saturday nite live cheezbooger, cheezebooger sketch)

don't know about hobby scene, haven't lived there in over 15 years but Chicago and suburbs all have vice departments. would be very careful.
pm me if you want to discuss more about places to visit

Navy Pier, Frank Lloyd Wright house, Willis (not Sears anymore) Tower, Ride the Seadog speed boats (pick the red one) on Lake Michigan, Chicago Art Institute, Ravinia for live music, Cubs game. There should be something in there that you like.

Getting arrested in Chicago is not fun.

I suggest that you pose this same question on the Chicago board. Also, if you have access yet to the Provider's Only Board, that may be a good place to get the scoop from other providers.

Posted By: NicoleAble

I'm heading to Chicago for the first time ever next week -- where are some entertaining places to visit? Any words from the ladies? What's it like to provide there? I heard that screening must be at a all time high.  
   
  I would appreciate any and ALL advice  
   
   
 Thankx xxoxooxo  
 Nicole  
 

I know enough to know there's a lot happening in Chicago but for specifics on what to do and what not to do you need to talk to the people who live there.

If you like soccer Mexico and Cuba are playing at soldier field next week.  

Posted By: NicoleAble

I'm heading to Chicago for the first time ever next week -- where are some entertaining places to visit? Any words from the ladies? What's it like to provide there? I heard that screening must be at a all time high.  
   
  I would appreciate any and ALL advice  
   
   
 Thankx xxoxooxo  
 Nicole