Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Book with Confidence. Price Match Guarantee.

No Hotwire Cancellation Fee

We've Saved Customers over $3.1 Billion


Featured Chicago Boutique Hotels

See all 967 Properties in Chicago
The Whitehall Hotel

The Whitehall Hotel

105 E Delaware Pl, Chicago
    4.0 out of 5.0
     
     

    Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.

    The Whitehall Hotel$98

    The Whitehall Hotel$98
    Hotel Felix Chicago

    Hotel Felix Chicago

    111 W Huron St, Chicago
      4.0 out of 5.0
       
       

      Hotel Felix Chicago is 5 blocks from the Magnificent Mile, one of America’s most dazzling thoroughfares. It’s a 7-minute cab ride to the Navy Pier Ferris Wheel, ...

      Hotel Felix Chicago$96

      Hotel Felix Chicago$96
      ACME Hotel Company Chicago

      ACME Hotel Company Chicago

      15 East Ohio Street, Chicago
        3.0 out of 5.0
         
         

        Just north of the downtown Chicago business core, ACME Hotel Company Chicago is 2 blocks from the Magnificent Mile, 6 blocks from the Wrigley Building, and less ...

        ACME Hotel Company Chicago$104

        ACME Hotel Company Chicago$104
        Ivy Boutique Hotel

        Ivy Boutique Hotel

        233 E Ontario, Chicago
          4.5 out of 5.0
           
           

          Located in Near North Side, this luxury hotel is within a 10-minute walk of Downtown Chicago, Tribune Tower, and Chicago Water Tower. John Hancock Center and ...

          Ivy Boutique Hotel$134

          Ivy Boutique Hotel$134
          Hotel Lincoln

          Hotel Lincoln

          1816 N Clark Street, Chicago
            4.0 out of 5.0
             
             

            Located in Lincoln Park, this boutique hotel is within a 10-minute walk of Park West, Second City, and Chicago History Museum. Lincoln Park Zoo and North Avenue ...

            Hotel Lincoln$112

            Hotel Lincoln$112
            The Willows Hotel

            The Willows Hotel

            555 W Surf St, Chicago
              3.0 out of 5.0
               
               

              Situated among the Victorian greystone buildings of Chicago's Lakeview neighborhood, The Willows Hotel is within 1.5 miles of Lincoln Park Zoo and Wrigley Field. ...

              The Willows Hotel$118

              The Willows Hotel$118
              The Majestic Hotel

              The Majestic Hotel

              528 W Brompton Ave, Chicago
                3.0 out of 5.0
                 
                 

                Occupying a charming brownstone building, this boutique hotel is in the Lakeview neighborhood, 0.2 mile from Lincoln Park. Wrigley Field is 0.7 mile from the ...

                The Majestic Hotel$126

                The Majestic Hotel$126
                Dana Hotel and Spa

                Dana Hotel and Spa

                660 North State Street, Chicago
                  4.0 out of 5.0
                   
                   

                  The Dana Hotel and Spa is 3 blocks from upmarket shopping on the Magnificent Mile, in Chicago's River North area. Art lovers will enjoy the many local galleries, ...

                  Dana Hotel and Spa$134

                  Dana Hotel and Spa$134
                  Raffaello Hotel

                  Raffaello Hotel

                  201 E Delaware Pl, Chicago
                    4.0 out of 5.0
                     
                     

                    Located on Chicago's fabled Gold Coast, this boutique hotel is adjacent to the John Hancock Tower, steps from stylish shops, and about 1 mile from Navy ...

                    Raffaello Hotel$115

                    Raffaello Hotel$115
                    Kimpton Hotel Monaco Chicago

                    Kimpton Hotel Monaco Chicago

                    225 N Wabash Ave, Chicago
                      4.5 out of 5.0
                       
                       

                      Kimpton Hotel Monaco Chicago, a 14-story hotel in the Loop business district, is 4 blocks from Millennium Park and Lake Michigan, and a half-mile from the Art ...

                      Kimpton Hotel Monaco Chicago$136

                      Kimpton Hotel Monaco Chicago$136
                      Map

                      Recently Booked Hotels in Chicago

                      Courtyard by Marriott Chicago Wood Dale
                      3.0 out of 5.0
                      Last booking: 1 minute ago
                      The Talbott Hotel
                      4.0 out of 5.0
                      Last booking: 1 minute ago
                      Virgin Hotels Chicago
                      4.5 out of 5.0
                      Last booking: 1 minute ago
                      The Blackstone, Autograph Collection
                      4.0 out of 5.0
                      Last booking: 3 minutes ago
                      Best Western Plus North Joliet
                      2.5 out of 5.0
                      Last booking: 3 minutes ago
                      Hyatt House Chicago/Evanston
                      3.5 out of 5.0
                      Last booking: 3 minutes ago
                      Holiday Inn Chicago North-Evanston
                      3.0 out of 5.0
                      Last booking: 5 minutes ago
                      WoodSpring Suites Chicago Darien
                      2.5 out of 5.0
                      Last booking: 5 minutes ago
                      Motel 6 Elk Grove Village
                      2.0 out of 5.0
                      Last booking: 6 minutes ago