I am glad someone commented on the difference in 'downtown Chicago' and 'price' .. downtown in the summer will be definately tourist season and on the more expensive side.

The Palmer House is a great location .. and kept very updated .. but an older hotel. The Hilton on South Michigan Avenue is also old and grand and has a fabulous Sunday brunch!

That said, anything on the Mag Mile will be $$$$ but right in the thick of things to do and see as well as cab to.

You may want to try the Holiday Inn Mart Plaza ... on weekends they are a bit out of the way .. during the week a very very heavy business hotel owing to their near-loop location.

I was already beaten to my favorite suggestion ... Indian Lakes. It IS suburban (tho I think has shuttle to the airport which would provide access to the city by public transit) and has wonderful facilities (pool, golf and catering). I think they may also offer shuttle to Woodfield Mall .. or one rental car for the group would be realistic.

Another option would be any of the larger hotels by ORD airport (Marriott or Hyatt or Embassy suites or ...). They offer shuttles to ORD and weekends may be reasonable in price.

The other thought is Great America in Gurnee. A day or two at the park for everyone and then hotel nearby ... or a slight drive might be kewl.

Chicago-land has a great deal to offer .. city, suburbs, shopping, museums, sightseeing, dining ... It kinda comes down to what the group wants to do. TOOOOO much museum in the schedule may turn off people .. and too much crowd (Navy Pier or Taste of Chicago) may also turn off people. Your end-date is close the the Venetian Night festival along the lakefront (mid Aug) that is really neat .. but again loads of people.

I would possibly send a questionaire to the people and give them 'ideas' of things they can do .. and let them decide if they want Aquarium and Field Museum or high end mall shopping or outlet mall shopping or golf or ...

You have your work cut out for you!