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Chicago Flight + Hotel packages

Chicago Hotels

See all 1,166 Properties in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
    3.0 out of 5.0
     
     
    3.4 out of 5 (122 reviews)

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

    Congress Plaza Hotel$119

    Congress Plaza Hotel$119
    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 (818 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$165

      Palmer House a Hilton Hotel$165
      Warwick Allerton - Chicago

      Warwick Allerton - Chicago

      701 North Michigan Avenue, Chicago
        4.0 out of 5.0
         
         
        4.0 out of 5 (716 reviews)

        Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from ...

        Warwick Allerton - Chicago$134

        Warwick Allerton - Chicago$134
        Hyatt Regency McCormick Place

        Hyatt Regency McCormick Place

        2233 S Martin Luther King Dr, Chicago
          4.0 out of 5.0
           
           
          4.1 out of 5 (229 reviews)

          Connected via enclosed skybridge to the McCormick Place convention complex, the Hyatt Regency is adjacent to a Metro station, with easy access to Chicago's downtown ...

          Hyatt Regency McCormick Place$179

          Hyatt Regency McCormick Place$179
          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 (196 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$108

            Hilton Chicago O'Hare Airport$108
            Comfort Inn Arlington Heights - O'Hare

            Comfort Inn Arlington Heights - O'Hare

            2120 S Arlington Heights Rd, Arlington Heights
              2.5 out of 5.0
               
               
              4.3 out of 5 (35 reviews)

              Situated near the airport, this hotel is within 1 mi (2 km) of Ned Brown Forest Preserve and Heritage Park. Arlington Lakes Golf Club and Metropolis Performing ...

              Comfort Inn Arlington Heights - O'Hare$68

              Comfort Inn Arlington Heights - O'Hare$68
              Freehand Chicago

              Freehand Chicago

              19 East Ohio Street, Chicago
                3.5 out of 5.0
                 
                 
                3.9 out of 5 (41 reviews)

                Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

                Freehand Chicago$130

                Freehand Chicago$130
                Hyatt Regency Chicago

                Hyatt Regency Chicago

                151 East Wacker Dr, Chicago
                  4.0 out of 5.0
                   
                   
                  4.1 out of 5 (853 reviews)

                  This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

                  Hyatt Regency Chicago$222

                  Hyatt Regency Chicago$222
                  River Hotel

                  River Hotel

                  75 East Wacker Drive, Chicago
                    4.0 out of 5.0
                     
                     
                    4.0 out of 5 (476 reviews)

                    Located in The Loop, this hotel is within a 5-minute walk of Downtown Chicago, Chicago Theatre, and Wrigley Building. Tribune Tower and Ford Center for the Performing ...

                    River Hotel$148

                    River Hotel$148
                    Inn of Chicago

                    Inn of Chicago

                    162 E Ohio St, Chicago
                      3.0 out of 5.0
                       
                       
                      3.4 out of 5 (339 reviews)

                      Inn of Chicago is a half-block from the Magnificent Mile and 2 blocks from the landmark Tribune Tower. Millennium Park, Navy Pier, and the Art Institute of Chicago ...

                      Inn of Chicago$111

                      Inn of Chicago$111
                      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 January through December 2017, 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. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

                      * 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.