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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 Inn of Chicago - Magnificent Mile from $78 USD Inn of Chicago's dramatic, sleek, contemporary design belies the history and charm of its landmark building. ... 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 More Great Deals on Chicago Hotels Hotel 71 from $107 USD The Loop Sheraton Chicago Hotel and Towers from $109 USD Magnificent Mile and River North Hyatt Regency Chicago from $119 USD The Loop 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 Millennium Knickerbocker Hotel Chicago from $159 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