Let's start with food. Pizza #1 was from Chicago Pizza and Oven Grinder Company. Pretty much as I remember it, including the 90 minute wait. They take reservations now, but I had not expected everyone to be hungry after 12 hours of flying...
Donuts from Stan's Donuts and Coffee. Note to future self: In the future, just buy six of the same donut to avoid the high likelihood of fights over donuts.
Hot dog and Italian beef from Al's Italian Beef. Sorry, no link. Either their website is dead or American Airline's satellite link has failed. Seeing as my father never took me here, it's probably not very good, but this non-Chicagoan was fooled.
Pizza #2 was a tough decision. Giordano's has always been my preferred traditional Chicago pizza, but the Internet says it's for tourists. My family says go to Lou Malnati's, but the beer list tops out at Stella Artois. Beer is very important when travelling with my children. Pequod's seemed to care at least a little about my happiness and had a reasonable selection. We were starving by the time the pan finally made it out of the oven which may explain why it was the best pizza ever.
Our hotel claims to have invented the brownie. That's a photo of a regular old fashioned. They also make a brownie old fashioned (not pictured).