By no means the best!
3 night stay at Trump in May
Very nice high end property in a very great location for walking the city.
Hit or miss with service staff at front desk, most are friendly but a few are not.
 I was really turned off by a gentleman at the front desk who refused to extend our check out by 2 hours. He was a real jerk and does not understand hospitality at all. He was condescending and arrogant.
Donald needs to say " YOUR FIRED" to that jerk.
 Keep in mind when we arrived for our guaranteed 3pm check in on day one the room was not ready so we were asked by the manager to "hang out". We said sure not to worry.
This was the only reason I felt they should extend a courtesy 2 hours upon our departure. To be fair to the hotel, the manager called me 15 minutes after the "incident" and said they would honor a 2 hour extension. At this point it was too late and we already felt kicked out.
Day 1 - My shower handle fell off in my hand and I could not turn off the cold water, on top of that the floor drain was clogged and wouldn't drain. I had a real mess while trying to get ready for a dinner meeting. I called the front desk for help and they asked if I wanted a plumber to come up and fix it, but having only an hour to shower, dress and get to my meeting I could not afford to have a plumber come out and check out the situation, It was clearly not an easy fix so I asked to move nearby if possible.
 After about 25min sitting in the room waiting, I was shown to a new room located on the spa floor, I guess they call that an upgrade from my original room on the 19th floor but I would have preferred to stay on the 19th floor as I had two closets a microwave, ref ridge, stove and a fully stocked kitchenette plus my traveling companion was next door. Well all of that was convenient for about 45 mins.
On to the 14th floor " spa rooms"
The spa room was a joke in my opinion and should be the run of the house category. 
I didn't complain I just took the room and made the best of it. 
The next day I attempt to use my in room "spa bathtub" but the drain does not close properly and can not hold water. That was lame, I took a shower instead and while I was out for the day they came and fixed it. I bet that bath would be awesome, sorry I missed it.
****Super noisy room
Tip...Avoid any room near 1416 on the spa floor - there is a janitorial or service station door across the hallway that slams at least every 30 minutes if not more often all night long and it's very loud. I can't believe this has never been addressed but it's awful.
Simple observation........The door staff is MIA more than they are at the door, I think their goal is to open the door and greet guests as they come and go. We opened the door ourselves 9 out of 10 times and never saw a doorman.
On the brighter side, the upstairs lobby bar was fantastic and their limo service to airport was easily arranged by the concierge who was pleasant. I'd say overall my experience was a 3 star A-OK. As the one in charge of booking the hotels I'd book elsewhere next time for the sake of my employees and myself. 
 In Chicago I'd recommend both the Park Hyatt or Pennisula on NOMI. Their Hospitality shines through much better and they treat guests like they are in their home. 
The "H" in Hospitality was missing at Trump. I wanted to give them a try and I'm glad I did but now feel like been there done that rather than the need to be loyal.