Top Hotel 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 Willis Tower, Magnificent Mile, and more.    Hotel 71 from $159 USD Immerse yourself in the convenient location and urban sophistication of Hotel 71-a quiet haven in the heart of downtown Chicago only steps from The Magnificent ... more The Sutton Place Hotel Chicago from $117 USD The Sutton Place Chicago offers an experience of luxury from top to bottom. ... more Club Quarters Central Loop from $89 USD Experience peace and calm in a members-only, club-like atmosphere in Chicago's Central Loop. ... more Club Quarters Wacker at Michigan from $89 USD Club Quarters is an exclusive and club-like hotel that ensures privacy and tranquility. ... more Central Loop Hotel from $89 USD The Central Loop Hotel is located at the corner of Adams and Clark Streets in the center of the Loop, Chicago's business and cultural district, making ... more More Great Deals on Chicago Hotels River Hotel from $109 USD Loop/ Magnificent Mile/ River North Hilton Chicago Michigan Avenue Cultural Mile from $119 USD Loop/ Magnificent Mile/ River North The Palmer House Hilton from $127 USD Loop/ Magnificent Mile/ River North Congress Plaza Hotel from $129 USD Loop/ Magnificent Mile/ River North Embassy Suites Chicago - Downtown/Lakefront from $149 USD Loop/ Magnificent Mile/ River North Chicago - The Drake from $151 USD Loop/ Magnificent Mile/ River North The Westin Michigan Avenue Chicago from $155 USD Loop/ Magnificent Mile/ River North Chicago Marriott Downtown Magnificent Mile from $169 USD Loop/ Magnificent Mile/ River North W Chicago Lakeshore from $179 USD Loop/ Magnificent Mile/ River North More Cities with Great Deals