Party like a New Year's millionaire at Trump's famed restaurant Sixteen. The sparkling restaurant, situated on the 16th floor of Trump Hotel with sweeping views of the Chicago River, Lake Michigan and the city skyline, is offering several New Year's Eve dinner options guaranteed to wow the most discerning palate – five courses to eight courses with wine and Champagne. Plus, guests enjoying the midnight toast will have prime viewing of the city's spectacular annual New Year's Eve fireworks display from Navy Pier. Dinner with wine ranges from $175 to $490 per person. Guests can also enjoy dessert and Champagne for only $75 per person while viewing the fireworks.
Where to stay: The ultra-chic Elysian Hotel in the Gold Coast district. How chic? Fashion legends Coco Chanel and Christian Dior inspired the décor – kick pleats in the drapery are reminiscent of Monsieur Dior while crystal chandeliers and lighting replicate Chanel's famous jewelry. Another fun fact: The hotel's restaurant Balsan is named after Chanel's alleged lover Etienne Balsan, who helped fund the designer's fashion enterprise. Rooms start at $300 per night.
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