where is the best place in chicago to go out on a date?

Answer 1

Well not knowing much about you like age and how long you have been dating, how much you would like to spend.

Here are a couple of suggestions:
See the Blue Man Group (about $60 a ticket)
Go for a Walk in Millennium Park - better in summer (there is a good Italian Restaurant across the street, don't know the name but it has a red awning)
Navy Pier - There is a lot to there
Shedds Aquarium (see the dolphin show)

Answer 2

Ask in the Travel - Chicago section.