Why none of the Cubs vs. Sox games during the week, or Lollapalooza the next weekend (I can just see Big John being a Flosstradamus guy)? Stay in Wrigleyville after the game. All the tourists hear that it's packed after games and leave, and it's just locals with great beer prices. Leave the Sox game as soon as the game is over.
I really like the Architectural River Boat cruise. As for the touristy stuff, I found Sears (now Willis) Tower to be a waste of money. I did enjoy river walk and the Magnificent Mile shopping is worth walking...but it's overpriced and snooty. Check and see if there are any other festivals going on downtown, five summers ago I found a great Comedy Fest and at some street improv show Tim Meadows, Bob Odenkirk and Steve Carroll just come in and made themselves part of the show. There was a great food festival too.
You are from Alberta so I assume beef is your meat of choice...Ditka's restaurant was a surprisingly good steakhouse, and you get to see all the memorabilia . If you are all the beef your wife can handle we had vegetarian in our group and he enjoyed his meal too. If you want adventurous but busy (with reservations we were at a shared table), try The Girl and the Goat. I was apprehensive because there were things like a Pig Face and Tongue on the menu, but had the Bass and it was amazing.