Chicago, IL

Anyone who has spent any time in Chicago quickly falls in love with this charming city. I lived there twice in my career and both my kids were born there, so it has a special place in my heart. Despite winters that can be quite brutal (ever been stuck in O'Hare in February?), Chicago has much to recommend it as a terrific weekend destination. You'll find world class accommodations and dining, one of the best art museums in the world, a rich cultural tradition, the…