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.