Apr
One website: hotels.com!
I used this website when we went to Florida in November. It was great, easy and convenient. So I checked there when we decided to go to Chicago. I waited a couple days before I made hotel arrangements and the day I happened to be looking there was a promotional price on a 4 star hotel, Chicago Affinia.
This hotel was fricking awesome. The room was a great size, especially for Chicago, where rooms seem to be a bit small. It was barely a 1/2 block from the North end of the Magnificent Mile. The staff was incredible. Making the guests feel special since they remembered us every time we walked in, getting cabs for us and suggesting places.
The best part? I paid $80 a night, $185 for the 2 nights we were staying. If I would have booked the room through their website? $450 for both nights. Um no way could I afford that, even though it would have been worth it. They even checked us in early when we arrived at 1pm.
Here are pics of our room:

Chicago Affinia
We missed our train out on Monday, so we had to stay another night. I asked the Affinia how much it would be and she said the lowest they could do was $149. And trust me the place was worth it, but after spending so much money already I called hotels.com and spoke to an agent. She found me another promotional price at the Allerton Hotel (which we could see from our room at the Affinia). We got a room for $85 a night that overlooked the Mag Mile and was also 4 stars. It was definitely smaller but a nice room with a view. They checked us in at 11am instead of the 3pm check in time, which was definitely a bonus.
