Entering The Wit isn’t so dissimilar from entering a dance club. Everything is ultramodern and sparkly. Staff and guests alike are bubbly. Pants are tight. Whether that’s your thing or not, it’s fascinating to see what Hilton—which The Wit is—can do with a boutique property. Playful and bright with splashy colors, natural light streams in from the floor-to-ceiling windows, art fill each room, and touch-screen phones allow you to choose which Chicago voice you want to awaken you: Barack Obama or Al Capone, maybe? In the hallways, you can hear the sounds of birds chirping by day and crickets and owls at night. Wit stands for “Whatever it Takes,” and clearly the staff does their best to have fun with that. Hotel guests also get first-in-line privileges to the ROOF, a Chicago hot spot with a retractable roof that’s open year round. Room service comes from the onsite, locally focused restaurant, State and Lake.