The Allerton Hotel has been a standout on Michigan Avenue since it arrived in the 1920s as one of the first high-rise buildings. Its distinctive “Tip Top Tap” illuminated sign was added in the 1940s, and the hotel has recently been given a multimillion-dollar revamp to keep it at the pinnacle of modernity and luxury. The winner of this package will experience these sumptuous surroundings firsthand as you spend an evening in a specialty suite for two, followed by a continental breakfast in the M Avenue restaurant.