Avoid Viagra Triangle...name says it all. Starts with Gibson's as the bottom "point" of the triangle and on up Rush Street. Chop House has steaks at least as good, and probably better. Restaurant in Trump Tower (virtually next door to Hotel 71) has gotten excellent reviews if you're in the mood to splurge. The live Theatre district will be just south of your hotel, over the river a few blocks; walking distance. Maybe call ahead for shows and ticket availability? Cadillac Theatre has awesome seating, tilt, lots of legroom. Coming in on a Sunday night (and staying a Monday night?) means your entertainment options might be limited or at least not as "lively".
The Transformer movie crew is in town and planning on shooting July 19-21 at Hotel 71. Did you get a deal?
Transformers
Shopping of course up Michigan Avenue, north of the river, and on the south side of the river along State Street. Grant Park and Millenium Park are straight east of the State Street shopping district, as is the Art Institute. The Cultural Center (on the corner of Randolph and Michigan) is having an architectural exhibit about Louis Sullivan complete with hands-on exhibits.
Exhibit Info The old Carson Pirie Scott Store has had its cast iron Sullivan-designed facade restored and can be seen along State Street. And of course the AIA has displays and tours in the old Santa Fe building on South Michigan (I want to say 222 S. Michigan, but could be wrong).
I hope you're not driving in Chicago, if so bring a credit card with a big limit on it to pay for parking, and don't miss the hidden signage and search until you find it for the paying meter box (1 per block).
Walk north up Dearborn to Lincoln Park for a look at turn of the century mansions.
A possibility for breakfast is Ina's on West Randolph. Always rave reviews.
Museum of Science and Industry seems to be more emptiness and cobwebs than museum anymore. If you have kids along, they may like some of the interactive exhibits. The submarine is cool, though extra charge, as is some of the space equipment. Field Museum has a gem exhibit your wife might enjoy.
Have fun.