Trump International Hotel and Tower Chicago
Cost: Kids in the City package starts at $415 per night. Fall rates will start at $475 per night.
Family friendly might not be the first thing that comes to mind when you think Trump Hotels, but our staff reviewer took her three little boys for a weekend and found everything they encountered geared to their family. From cookies in the room with each child's name on them to individual backpacks with things for the kids to do, the entire staff bent over backwards to make the family comfortable. The Trump Kids program offers special spa treatments, swim classes, and interactive video games.