Ferris Buller's Day OFF... If you have seen the film then try and recreate it...
Here was my effort to which you can dip in and out as your personal taste dictates.
1. At 08:30 be at 18 W Monroe: La Salle Bank Theatre Box Office: Wait in the cold until 10:00 when 10 rush tickets will be sold at $25 per seat. 40 are available on line if you have a PC. See web site for details. I was there on a Sat so there were two performances and at 0900 I was number 11 in line! What you get is a front row seat that had me in the centre 2m from the performers. I was blown away by the show. Disadvantages are the stage is about 1m high so you cannot see the back of the stage and very occasionally some of the performance. Also when the star performer is illuminated you are too... yes you are that close.
2. After buying your tickets go straight to the Art Institute of ORD. $12 to get in... pass on the $6 headphones. See the Monet's which I love and the painting in dots of the girl famous in Ferris Bullers Day off.
3. Atwood Cafe, 1 West Washington, atwoodcafe.com, Slightly art deco in style. Eat at the bar and have a "Spring Fling" cocktail.
4. See show at 1400 if on a Sat
5. Walk past the Hancock Tower to Drake hotel and have an executive cocktail, a double, and chill. Its downstairs and really cool place.
6. Walk to the Hancock tower and goto the 96th? floor for a cocktail overlooking the city. The cocktail is not as good as the Drake but the view is top class.
7. Evening entertainment depends on if you are in a group or not. As a large group I would recommend Howl at the moon as it looks a laugh.
As a couple I would either do Andy's Jazz Bar. This is pure Jazz with two sessions and the food was OK too.
Or try The House of Blues downstairs *upstairs you have to pay, when I visited it was more light rock than Jazz but a good night all the same.
As a single I would consider Sullivans steak house opposite Howl to the moon.
Other bits to try would be the science museum for the sub tour, Wriggly field if there is a game on and the Sears Tower...where I think there is a scene from the film. Also the WEBER, as in the BBQ, restaurant did a good burger and had a good feel to the place.