Chicago and Grand Canyon Trip Advice

One of my favorite parts of blogging is interacting with all of you.  It’s fun sharing knowledge (or lack there of).
Nate and I are currently planning two trips.  We are going to Chicago for a long week-end with some dear friends of ours.  We are also looking at heading to the Grand Canyon in August-ish.
Here’s where we need you…
What are Chicago favorites?  Favorite restaurants? Places? Shopping? etc.  Nate and I have been to Chicago a handful of times but our friends haven’t.  Nate and I have have done a lot of the touristy stuff but feel free to share all of our wisdom.  Who knows what we’ve missed!  I’d also love recommendations of thrift stores/unique shops. 
Chicago 008
Next up: the Grand Canyon.  Flights to Phoenix from our local airport are ridiculously cheap right now.  Our plan is to fly into Phoenix and start our adventure from there.  We would like to spend a few days hiking in the Grand Canyon.  What are your favorite things to do in Arizona? Restaurants?  Suggestions on where to stay to fully enjoy the Grand Canyon?  Any other awesome things to do/see in Arizona?
via AAPG
Thanks in advance for your help! Bring on those suggestions!