A NYC friend is visiting Chicago with her high school son this spring and looking for a reasonably priced, well-located hotel in Chicago. She found three options for about $150 per night: Swissotel Chicago, Fairmont Chicago and Ambassador East. Friends from Des Moines report having good luck with Swissotel although they thought it was a little pricey for what you got.
Another option I suggested to my NYC friend is maybe taking her son on a college visit to U of Chicago, which as part of its offerings has a deal with Hilton Chicago to provide discounted rates.
TakeBetsywithyou 