Saw this post a bit late...have lived and worked in loop for a decade now...
Things to do in order of preference...
Touristy stuff
1. Millennium park
2. Michigan Ave/Water Tower/Hancock
3. Navy Pier
4. CSO River Architecture tour
5. Sky deck at Willis Tower
5. Theater District: Randolph
Museum Stuff
1. Field museum - sue
2. Shedd Aquarium
3. Museum of Science
Off the beaten track
1. Grab a drink at Palmer house. '20 architecture
2. Deep Dish pizza
3. Catch a game at Wrigley
4. Those tourist Capone/dark night tours
5. The bar strip on Clark
And if you are adventurous
1. Take out BBQ in da 'hood at Uncle Johns ... Google it... Best BBQ In town
Things to do in order of preference...
Touristy stuff
1. Millennium park
2. Michigan Ave/Water Tower/Hancock
3. Navy Pier
4. CSO River Architecture tour
5. Sky deck at Willis Tower
5. Theater District: Randolph
Museum Stuff
1. Field museum - sue
2. Shedd Aquarium
3. Museum of Science
Off the beaten track
1. Grab a drink at Palmer house. '20 architecture
2. Deep Dish pizza
3. Catch a game at Wrigley
4. Those tourist Capone/dark night tours
5. The bar strip on Clark
And if you are adventurous
1. Take out BBQ in da 'hood at Uncle Johns ... Google it... Best BBQ In town