Congratulations! :) For Priceline, add the North Michigan Ave - River North Area. There are lots of hotels there and it is a fairly short walk to the Grand or Chicago stations on the Red Line. Tons of shopping and eating options. I stayed in the area two years ago (Marriott Magnificent Mile) and really enjoyed the atmosphere. Easy to get to most of the museums by subway, walking, or taxi. The Museum of Science and Industry is further south and requires a bus ride or a cab. Hotwire has a $201 3.5* hotel in that same general area and also a $216 4* hotel. Obviously above your price point, but that gives you an idea of the rates out there. I'd recommend spending the extra $$$ and staying downtown vs. the suburbs - you'll end up wasting a lot of time every day on the commuter trains and some of the train stations in Chicago are not particularly convenient to tourist attractions. Also, I highly recommend the Chicago Architecture Foundation boat tour - well worth the price and perfect if you want to do some sightseeing while off your feet. We really enjoyed it.