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Looking for the absolute best places to eat, sleep, shop, and socialize in the capital of jazz? Earning the discriminating vote of ShermansTravel.com editors, these picks comprise the city's can't-miss attractions, hotels, restaurants, bars, and shops – from the best way to appreciate the city’s architecture (a river cruise) to the best place to catch a set of live music (Green Mill).
2008 SMART LUXURY WINNER
Old-World Class
The Pen is that rare luxury hotel that is frequented by world travelers and locals alike. You’ll see couples on dates in the gold-domed lobby, sampling decadent desserts or catching a jazz performance, and local power brokers sipping finely crafted cocktails at the bar. The superior rooms are the largest anywhere in the city, and the hotel is parked in the center of the city’s prime shopping district. Best season for value: spring.
Great Value Alternative: City Suites has Art Deco rooms close to Wrigley Field and the best nightlife in the city. From $200/night; www.cityinns.com
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