As for a "boutique" hotel in the Chicago Core I can't really help you. I have stayed at the Renaissance, which is near the South end of Michigan avenue (the Miracle Mile); just a little inland on the river. It is close to the House of Blues, which is a great spot. A couple of my favourite restaurants in Chicago are:

Scoozi, Italian/Mediterranean fare in set in a large old warehouse. Friendly and liveley atmosphere (a bit on the loud side), good food at a decent price.

For something a bit more upscale, my favourite is "Vivere", part of an italian village of restaurants.

Finally, if price really is no object, and your taste buds are inclined for Thai food....there is "Vong". Simply to die for, as well as mortgage your house.

Regards,

John Wiernikowski Hamilton, ON CANADA