The Black Bear Lodge at Stratton Mountain Resort
Price was $723, price is now $722 per person
Roundtrip flight included
Chicago (ORD) to Rutland (RUT)
This smoke-free resort features a golf course and 10 restaurants. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Families will appreciate the arcade/game room, kid-friendly dining, and babysitting.