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Chicago Flight + Hotel packages

Chicago Hotels

See all 994 Hotels in Chicago
Central Loop Hotel

Central Loop Hotel

111 West Adams Street, Chicago
    4.0 out of 5.0
     
     
    4.0 out of 5 (348 reviews)

    Situated in the heart of "the Loop," the contemporary Central Loop Hotel is steps from all of Chicago’s major business and cultural destinations such as Chicago ...

    Central Loop Hotel$125

    Central Loop Hotel$125
    River Hotel

    River Hotel

    75 East Wacker Drive, Chicago
      4.0 out of 5.0
       
       
      4.0 out of 5 (459 reviews)

      Located in The Loop, this hotel is within a 10-minute walk of Chicago Theatre, Wrigley Building, and Tribune Tower. Ford Center for the Performing Arts Oriental ...

      River Hotel$141

      River Hotel$141
      The Whitehall Hotel

      The Whitehall Hotel

      105 E Delaware Pl, Chicago
        4.0 out of 5.0
         
         
        3.8 out of 5 (992 reviews)

        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$110

        The Whitehall Hotel$110
        Wyndham Grand Chicago Riverfront

        Wyndham Grand Chicago Riverfront

        71 E Wacker Dr, Chicago
          4.0 out of 5.0
           
           
          4.2 out of 5 (276 reviews)

          This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district ...

          Wyndham Grand Chicago Riverfront$134

          Wyndham Grand Chicago Riverfront$134
          Edward Hotel Chicago

          Edward Hotel Chicago

          6600 N. Mannheim Rd, Rosemont
            3.0 out of 5.0
             
             
            3.9 out of 5 (133 reviews)

            Situated near the airport, this hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. ...

            Edward Hotel Chicago$78

            Edward Hotel Chicago$78
            Congress Plaza Hotel

            Congress Plaza Hotel

            520 South Michigan Avenue, Chicago
              3.0 out of 5.0
               
               
              3.2 out of 5 (77 reviews)

              Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

              Congress Plaza Hotel$88

              Congress Plaza Hotel$88
              Hotel Felix Chicago

              Hotel Felix Chicago

              111 W Huron St, Chicago
                4.0 out of 5.0
                 
                 
                4.0 out of 5 (196 reviews)

                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$104

                Hotel Felix Chicago$104
                Loews Chicago Hotel

                Loews Chicago Hotel

                455 North Park Drive, Chicago
                  4.5 out of 5.0
                   
                   
                  4.7 out of 5 (58 reviews)

                  Located in Near North Side, this luxury hotel is within a 10-minute walk of Tribune Tower and Wrigley Building. Navy Pier and Chicago Children's Museum are also ...

                  Loews Chicago Hotel$159

                  Loews Chicago Hotel$159
                  Hilton Chicago O'Hare Airport

                  Hilton Chicago O'Hare Airport

                  Ohare International Airport, Chicago
                    4.0 out of 5.0
                     
                     
                    3.9 out of 5 (184 reviews)

                    The only hotel on airport property, the Hilton Chicago O'Hare Airport is located 2 miles from the Donald E. Stephens Convention Center and the Rosemont Theatre, ...

                    Hilton Chicago O'Hare Airport$93

                    Hilton Chicago O'Hare Airport$93
                    Palmer House a Hilton Hotel

                    Palmer House a Hilton Hotel

                    17 E Monroe St, Chicago
                      4.0 out of 5.0
                       
                       
                      4.1 out of 5 (790 reviews)

                      This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...

                      Palmer House a Hilton Hotel$118

                      Palmer House a Hilton Hotel$118
                      Map

                      Experience the best of Chicago

                      With a global smorgasbord of restaurants, bars, music venues and architectural landmarks, Chicago is by no means a Second City. A Chicago vacation brings year-round thrills, whether you're catching the opening pitch at Wrigley Field or riding the famous El.

                      Before you admire your reflection in Cloud Gate (aka "The Bean") or hit a skyline cruise on Lake Michigan, allow Orbitz to help you with the planning. Enjoy the intel from our insider guide, from the top 10 attractions to tips from local experts.

                      Best time to take a vacation to Chicago

                      Tourists flock to Chicago during spring and summer, when Chicagoans emerge from hibernation into outdoor cafes, legendary sports stadiums and the city's gorgeous parks for music, food and cultural festivals including the Taste of Chicago and Lollapalooza.

                      If a Chicago vacation happens during the winter, pack a down coat and take advantage of off-peak rates at downtown Chicago hotels. The city's public transportation is among the best in the nation, making it easy to travel to museums, bars, restaurants, landmarks and even far-flung locations in the suburbs.

                      Insider tips for Chicago travel

                      Kit Kat Lounge

                      Shake up your Sunday brunch with the bottomless mimosas and drag shows at Kit Kat Lounge, Boys Town's favorite martini bar and lounge.

                      Alinea

                      If you're planning to visit this famous restaurant, book your reservation at least two months in advance. If you do score a table, don't be discouraged if you can't spot the restaurant immediately. It's in a grey brick storefront with no sign.

                      Cocktails

                      Looking for an offbeat place for cocktails in one of Chicago's hippest neighborhoods? Consider the Bedford in Wicker Park, located in a former bank building. Imbibe old-school cocktails in the actual vault, which is dotted by safe deposit boxes.

                      Boat tours

                      For a leisurely lesson on Chicago's architecture, catch a boat cruise from Navy Pier or at the bottom of the Wrigley Building.

                      Beaches

                      For great people watching and impressive skyline views, hit Oak Street Beach, where singles flock to play volleyball and sunbathe. Families stick to Montrose and Loyola beaches a little further north, which are a lot less crowded and pose better chances for finding a parking spot.

                      * Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from July 1, 2015 to June 30, 2016, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

                      * Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.