I lived in Chicago for four years and loved every minute of it.

The new millenium park is supposed to be amazing (it was built after I left). You will want to see the new cloud gate sculpture, it beautiful.

You have to walk Michigan avenue for the shopping and be sure and stop to get some Garretts popcorn...the best especially the caramel.

One of my fave things to take visitors on was the architectural boat tour. Its a lovely way to see the city via the river and very educational and nice to sit on the boat and watch the sights and people.

And Chicgao has a great threater district so you might want to check and see what broadway shows are playing.

And maybe you should entice him with some sports and get bleacher seats to a Cubs game. Or is you are going in the fall check out the a NFL Bears game - I hear the new soldier field is great.

Take the elevator to the top of the JOhn Hancock building...the view is amazing on a clear day. So the Sears tower.

A little out of the city os the museum of science and industry - great museum to walk around. There is also the museum of art in millenium park called the Art Institute of Chicago (its world class) and the modern museum of art near the Hancock tower. OMG and how could I forget the field museum and Shedd aquarium right off Grant Park.

The Lincoln Park zoo if fun to walk around and be sure to go to Old Town a great quaint are to walk around with great restuarants.

And check into getting Oprah tix.

And there are a ton of great restaurants!

If you are in the city on a Wednesday or a Sayurday be sure to go to the Navy Pier for the fireworks. I used to live right near there and could watch em from my apartment.

FOr an out of the city drive take a ride up to Lake Geneva not far from the city but great in the summer and I am sure there are some lovely inns to stay overnight there.

Take a ride to Milwaukee and take in a Brewers game or tour one of the brewies there. I also hear there is a great museum up there but I cannot remember the name.

Here's a link to the visitor bureau

http://www.choosechicago.com/Pages/default.aspx


Those are my thoughts.