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Craving A Unique Night In The City? Try This Chicago Itinerary On For Size.

There’s no place quite like downtown Chicago for amazing food, fun, and nightlife. Why not grab 31 of your closest friends and charter a trolley for the ultimate restaurant/pub crawl? In addition to a multitude of hop-on, hop-off public tours, THE CHICAGO TROLLEY & DOUBLE DECKER CO. also specializes in upscale private events perfect for tasting your way through the Windy City (chicagotrolley.com). More evening entertainment awaits with BLUE MAN GROUP (above), the quintessential trio mixing music, art, and theatrics (blueman.com). Party into the night at the ultra-hip JBAR, which conveniently anchors the south end of Rush Street and — even moreconveniently — is next to The James hotel, with posh, modern rooms and dreamy beds that will be much appreciated at night’s end (jameshotels.com). The morning after, be sure to fuel up at the FOUR SEASONS HOTEL CHICAGO’s impressive brunch, with multiple rooms full of tempting courses and a memorable view of downtown from the upscale dining room (fourseasons.com).