When in  Chicago you will have an unbelievably good time and meal at the purple pig on Michigan av Another absolutely do not miss is the girl in the goat on Randolph but you need to get reservations now for your visit in July.
Some great old standard that are the best in the nation shaws crab house eat in  the oyster bar not the restaurant on Hubbard. One of the all-time classiest restaurants in the city is Joe's Stone crab on rush.
Chicago is truly a great and fun city for restaurants when you get ready to go out you want to go to the rooftop at the wit.
Enjoy Chicago.

If you like the Red Head Piano Bar also try Pops for Champaign. For a 'jeans & t-shirt' good Chicago joint for crab legs try the Half Shell on Diversey. If you like prime rib, try Lawreys on Ontairo St.  

As said above, Shaws on Hubbard is awesome! And in the oyster bar they have live music on weekends. Plus right next door is a good jazz bar called Danny's.  

Www.wateriders.com

There are several good places, depending upon where you are staying. Al's or Mr. Beef on Orleans are good choices if downtown.

If you like history & straying from the beaten path, the Weird Chicago tour company offers bus & foot routes for haunted locations, true crime landmarks, & my personal favorite - the Red Light Tour

The Air & Water Show (Aug. 17 & 18) is pretty spectacular, as is the Pride Parade (June 30). Northalsted Market Days (Aug. 10 & 11) are like a less-crowded, less expensive Taste of Chicago IMO. Navy Pier has a variety of diversions that changes daily/weekly/monthly, plus bicycle rental if you care to meander along the lake shore. And of course Chinatown is always worth visiting.

Love this place.  They have a tasting lunch that is out of this world and its very reasonably priced.  Regardless, lunch or dinner, this is an amazing place.