Right now this is still in maybe mode. One of the options on our list of anniversary travels is visiting Chicago. Since I have only traveled through the south side going to Michigan, what is there to do in Chicago? We would be there for about 3 nights.

Also, is it wise to walk from the train station to a downtown hotel? Google Maps says the walk would be about 30 minutes if there would be anything to see. But I know I wouldn't advise anyone walking anywhere from the Memphis train station!

 

You really didn't say when you would be getting in to Chicago. The train station is hopping through the day with people going to work. In the evening it slows a bit. If I were you I'd take a cab to the hotel. If you feel it's safe enough then you could walk back to the train.
You also didn't say where downtown you will be staying. For sure there's the Magnificent Mile (Shopping & Eating), the Art, History, and Science Museums. On the lake front (AKA Lake Shore Drive) there's; the Bean in Grant park, Navy pier (Shopping & Eating) the aquarium, an open air amphitheater, and if that's not enough there's the theaters, to include Blueman Group at the Briar Street Theater.
Enjoy but you'll only scratch the surface of what Chicago has to offer in 3 days.

 

That trip never happened. Wound up going the other direction to New Orleans. By car. Might have had a better time in Chicago. NO is nice, but somewhat dirty.

 

If you hadn't guessed I Love Chicago and the 12 years we lived up there. But my wife is from New Orleans and we get there frequently. Love it too. Bourbon Street is only a small part of the Big Easy.
Not sure why I just saw this post? Just noticed it was from AUG 2014???