Entering theWit isn’t so dissimilar from entering a dance club. Everything is ultramodern and sparkly. Staff and guests alike are bubbly. Pants are tight. This slightly quirky hotel loves its urban setting and makes the most of it: Two-story-high lobby windows look directly onto a bustling El station. Part of the Doubletree family (free cookies!), theWit is popping with personality. It's playful and bright with splashy colors, natural light streams in from the floor-to-ceiling windows, art fills each room, and touch-screen phones allow you to choose which Chicago voice you want to awaken you: 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 little taste of Miami Beach with a retractable roof that’s open year-round. Room service comes from the onsite, locally focused restaurant, State and Lake.