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Travel Reservations Instantly Check Rates and Availability & Book Online... Top Hotels Deals in Chicago, IL Book Flight + Hotel together and save! Breeze into the Windy City with a reservation at one of many Chicago hotels near the Sears Tower, Magnificent Mile, and more.    Four Points by Sheraton Chicago Downtown Magnificent Mile from $100 USD Whether checking out Magnificent Mile shops or seeking an indoor rest by the pool, Four Points Chicago has it all, High Speed Internet and Free Bottled ... more InterContinental Chicago from $125 USD InterContinental Chicago is the only downtown Chicago hotel with a front entrance onto the Magnificent Mile. ... more The Allerton Hotel on Magnificent Mile from $88 USD As one of the first high-rises to grace fashionable Michigan Avenue, Allerton became synonymous with high style. ... more Tremont Hotel from $99 USD Tremont is home to Mike Ditka's with two floors of fine dining and Mike's prized collection of sports memorabilia. ... more Hotel 71 from $107 USD Hotel 71 is a sleek and sophisticated boutique-style hotel swimmingly located on the Chicago River. ... more More Great Deals on Chicago Hotels Sheraton Chicago Hotel and Towers from $109 USD Magnificent Mile and River North Hyatt Regency Chicago from $119 USD The Loop Affinia Chicago from $135 USD Magnificent Mile and River North The Blackstone A Renaissance Hotel from $138 USD The Loop Residence Inn By Marriott Chicago Downtown Magnificent Mile from $139 USD Magnificent Mile and River North W Chicago - Lakeshore from $149 USD Magnificent Mile and River North The James Chicago from $169 USD Magnificent Mile and River North The Sutton Place Hotel Chicago from $170 USD More Cities with Great Deals

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