I’m 28 and taking my 15 year old half-brother with me on a short vacation trip to Chicago over Thanksgiving break (leaving the Friday before and coming back Thanksgiving Eve). We will primarily be doing the attractions on the CityPass.

I have 1.2 million Hilton points (and 3 weekend night certs to use) and almost half a million Marriott points.

I stayed at the Waldorf on a job when I was 22 years old (very impressed with the hotel at that time) and again 6 years later this past June (Gold Coast suite, which is bigger than my apartment and the 2nd highest option available) and not so impressed sadly....but after staying at many 5-stars for work, maybe it just didn't seem as cool as it did when I was younger. I have no exposure to the Conrad (any Conrad actually).

Which of these 3 hotels would you recommend? I'm likely leaning towards the Waldorf or the Conrad so I can burn through Hilton points.