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Visit downtown & the outskirts many times per year on business & pleasure (my brother has lived in area for 20 yrs).
Depending on where you are staying, downtown is usually a 40-60 minute drive from O'Hare. I usually take the train (Blue line connects airport & downtown).
Walking along Michigan Ave is great to take in local architecture but also check out the waterfront from Shedd Aquarium (south of river) north to Grant and Millennium Parks, Navy Pier just north of river (a lot of renovating these past couple yrs), up to Lincoln Park Zoo.
That's a lot of area to cover but you can't go wrong poking around that general area from sites, food, drink, etc.....
And don't forget the obligatory picture with "The Bean" (Cloud Gate) in Millennium Park
Willis Tower Skydeck is cool too. Scary as hel for me since I hate heights and you are basically walking into a see through glass cube but the views on a clear day are spectacular.
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