This is why the hotel will be crazy expensive Yeah, on weekend dates in the summer, it will likely be $400/night plus parking. Offseason, though, I could see you getting a room for $100-$150. A boutique hotel built next to Wrigley field will not go for $100/night. It won't be a holiday inn express. Even in the offseason. EDIT: And they are partnering with Starwood for it, which specializes in upscale/luxury brands I've gotten rooms in nice hotels on off peak nights in the 100-150 range. That includes downtown Chicago. Yeah, a Sunday night in February is going to be cheap.