Your best Bet: ( imho)
Fly in to 06C, modern, friendly municipal airport with big concrete apron
take train into city ( Roselle station is 1/2 mile from 06C)
http://metrarail.com/metra/en/home/maps_schedules/metra_system_map/md-w/map.html
this drops you in the heart of the loop, summertime in Chicago is great. All kinds of new hotels this summer, ( look up new Hyatt @ Chicago Athletic assn.) or any chain in "River North" or Michigan Ave (1200 S address or north) would be central to all attractions.
Do not get a car- between the Metra and "EL", it works great.
Museum Campus, Millennium Park ,Michigan Ave ( Shopping) and anywhere for great restaurants.
Send me a PM , i'll give you my email- glad to help out. I'm in commercial construction, know area well.
-Jim