If you will use enough of it, the Citypass is actually a good deal. We were there in March, and hit Science and Industry, Shedd Aquarium, the Field Museum, and the Willis Tower. (The Citypass gives you a fastpass to the the observation deck - that alone was worth it when we were there - without it it was a 3 hour wait to get to the top!)
We had no issue using the "L" and buses to get around - worked great.
Real deep dish pizza and Chicago Beef Sandwiches... We did Lou Malnati's and Al's beef (we can get Giordanos and Portillos here).
And ignore the haters, are there terrible parts of Chicago - yep, just like every City. All in all we found nearly everyone we dealt with to be friendly and willing to provide advice if you asked for it...
We had no issue using the "L" and buses to get around - worked great.
Real deep dish pizza and Chicago Beef Sandwiches... We did Lou Malnati's and Al's beef (we can get Giordanos and Portillos here).
And ignore the haters, are there terrible parts of Chicago - yep, just like every City. All in all we found nearly everyone we dealt with to be friendly and willing to provide advice if you asked for it...