Chicago , General info:
7/10

Two airports -Midway or OHare (ORD).OHare is major airport; both convenient to downtown (called The Loop)

Chicago , Different stuff:
6/10

flee market - great fun!

Chicago , Don't miss:
5/10

sambucca

Chicago , Food:
9/10

Food in Chicago is excellent! There is so much variety. There are many places for steak (Carmine's, Wildfire). There is also great Italian (Sappori Trattoria). Many ethnic restaurants if you want tasty affordable alternatives. My advice - go to a BYOB with a bottle or two of wine and you'll save.

Chicago , Hotels:
7/10

Hotels along Michigan Avenue are fun yet expensive. For a cheaper place in a great location, try Congress Plaza hotel.

Chicago , Safety:
6/10

OK for the most part. Just plan out your route in advance. Take cabs, buses, or trains.