My boyfriend and I stayed 2 nights at the Hotel Blake in October 2009. We wanted something that was clean, up-to-date, and in a great location in downtown Chicago. Hotel Blake was perfect for our needs. The staff is very friendly and accommodating. The room was a good size, nice flat-screen TV, wonderful bathroom with one of those wide shower heads which was awesome. Bed was very comfortable and the decor was up-to-date. We had the continental breakfast one morning (it was included which was nice) and had great coffee and bagels (there were other food offerings but that's all we had). The hotel is VERY easily accessible to the Blue Line, which takes you straight to O'Hare Airport. It was about 45 minutes on the train to and from the airport and the train stop is about a block from the hotel. If you're debating about cab from O'Hare to hotel (not sure the distant to Midway), definitely skip it-- the train is something like $2.50 per person for one way on a 45 min train whereas a cab is about 30 min and $45.
We didn't get to try the Custom House, which is the restaurant in the hotel, but everywhere we went when people asked us where we were staying, everyone would say "oh their restaurant is great!"
We walked to downtown and Navy Pier-- probably about a mile-- if you're in Chicago to see the city, it's definitely worth walking to see everything. If you're on the lazy side, you may want to take a cab, but it's really cheap.
There is free wireless in the hotel, but if you didn't bring a computer, there is also free access to a computer and printer on the first floor.
Staff at the front desk are very helpful in recommending local restaurants and bars, and giving directions.
Stay at the Hotel Blake-- great deal and a hidden gem!