Chicago - Which hotel on 3-4 day stay in Chicago if choosing between SPG, Marriott or Hilton?

Looking for a 3-4 day weekend getaway with the wife (without kids!) Friday June 15-Mon or Tues Jun 18. I want to use points for the trip. I am gold on SPG, HHonors and Marriott. I was thinking of Conrad or Wit for 4 nights using AXON AMex Hilton for 140,000. I also have Westin Chicago River North for cash and points for 4800 and $90. I was thinking of W as well, but since I only have gold status with SPG, the free breakfast with Hilton properties sound better and I presume I would have better success at room upgrades with Hilton properties? The Marriott properties all seem to be Category 7 so I rather save my miles unless there is property that is really recommended.

My wife and I are in our late 30's. Looking to explore the city by foot, eat at moderate priced restaurants and just relax! We are from Boston.

I was initially planning 3 nights but with AXON award, I will stretch trip to 4 since it is cheaper than booking 3 nights.

Any suggestions appreciated.

I'd probably go with the Conrad as its as good as any of the other properties and a little less points and free breakfast. Look at paid rates though. None of the awards are that cheap. I have pricelined the Hyatt downtown for $71 on July 4th weekend. I'd prefer to be north of the river rather than south if possible. Anywhere on Michigan between the river and oak st. is ideal.

I want to use points for the trip. always good to use points but the redemptions IMO are horrid for Chicago, so I'd Hotwire or PL, like hindukid did:
I have pricelined the Hyatt downtown for $71 on July 4th weekend.Seeing as you both are young and like to walk, I personally don't think you can go wrong with any of the chains you've mentioned.

always good to use points but the redemptions IMO are horrid for Chicago, so I'd Hotwire or PL, like hindukid did:


I agree!