The Gwen is my hands-down favorite in Chicago. It's romantic, you can hang out in the lobby bar and/or rooftop bar and enjoy yourselves. And it's very convenient to everything else you want to do in the city.

The Robey is another cool hotel. It's away from the tourist parts of the city, in the bucktown neighborhood. But it's cool, has a rooftop terrace with drinks and views. And the neighborhood has plenty to do for a leisurely day.