Sad to say I was very disappointed
I want to begin my review by saying that before I even stepped a foot inside this hotel, I had huge expectations. I really wanted to love this hotel and my experience there. The photos and previous reviews had all been so lovely...and my husband and I were celebrating an anniversary and much needed get away from small children.
I will say the building, location and the courtyard is unbeatable. The staff were friendly and smiley...but then the experience quickly turned sour. Once inside (from the grand courtyard), the lobby (though modern and pretty) felt cold and cramped to me (yes it was a chilly October day)...no warmth (as I always experience entering The Ritz or Peninsula or The Four Seasons). The room was also unimpressive. Though modern and beautifully furnished, it again felt cold...although there was a beautiful fireplace in the room (which I will get to later). There were stains in our carpet; plain and non-luxurious bedding with only 2 pillows and virtually no toiletries in the bathroom(no kleenex so I had to use toilet paper to remove my makeup).
As I said, we were celebrating a anniversary. So, we brought our own champagne and called to request a bucket of ice so that we could enjoy a glass before going out to dinner. We sat and waited and waited...after more than 45 minutes of waiting, we drank luke warm champagne before going to dinner.
When we returned to our room to relax, we tried to wear the robe and slippers but to our surprise, their slippers were made for children...literally. My husband had to jam his feet into them. We found it amusing and called to request some bigger slippers. After about 30 minutes, housekeeping brought up the same size slippers...so my husband trodded around with half his feet hanging out the back.
Then, we really wanted to take advantage of a good night rest (with small children at home-a much desired luxury)....only to be surprisingly awakened at 4a.m by the rooms alarm...we shot up out of bed thinking there was a fire!! We called front desk and the technician who came to our room said it was the carbon monoxide alarm, apparently set off from the fireplace (15 minutes of a roaring fire I soarly came to regret). We sat awake...sad and tired...
In the morning, we called down to order breakfast to be brought to our room...(last chance to impress us!)...but no...they brought my husband's food but forgot to bring mine...I sat and watched my husband eat and then ate alone a half hour later. 
To rub salt to our wounds, we found a cigarette in our car when our car was brought to us...hmmm, it seems like the Waldorf Chicago does not want our future business. I do NOT recommend this hotel if you are expecting luxury or 5 star service.