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Chicago Flight + Hotel packages

Chicago Hotels

See all 976 Properties in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
    3.0 out of 5.0
     
     
    3.2 out of 5 (83 reviews)

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

    Congress Plaza Hotel$111

    Congress Plaza Hotel$111
    Warwick Allerton - Chicago

    Warwick Allerton - Chicago

    701 North Michigan Avenue, Chicago
      4.0 out of 5.0
       
       
      4.0 out of 5 (701 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$92

      Warwick Allerton - Chicago$92
      River Hotel

      River Hotel

      75 East Wacker Drive, Chicago
        4.0 out of 5.0
         
         
        4.0 out of 5 (466 reviews)

        Located in The Loop, this hotel is within a 5-minute walk of Downtown Chicago and Chicago Theatre. Wrigley Building and Tribune Tower are also within 10 ...

        River Hotel$79

        River Hotel$79
        Club Quarters Hotel, Central Loop

        Club Quarters Hotel, Central Loop

        111 West Adams Street, Chicago
          4.0 out of 5.0
           
           
          4.1 out of 5 (617 reviews)

          Club Quarters is a club-like hotel in the center of the Loop, Chicago’s central business district. A short walk to Symphony Center, the Art Institute, Board ...

          Club Quarters Hotel, Central Loop$75

          Club Quarters Hotel, Central Loop$75
          Hyatt Regency Chicago

          Hyatt Regency Chicago

          151 East Wacker Dr, Chicago
            4.0 out of 5.0
             
             
            4.1 out of 5 (827 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$95

            Hyatt Regency Chicago$95
            Best Western Grant Park Hotel

            Best Western Grant Park Hotel

            1100 S Michigan Ave, Chicago
              2.5 out of 5.0
               
               
              4.1 out of 5 (38 reviews)

              Favored for its location across from Grant Park, Museum Campus, Soldier Field, and Northerly Island, the Best Western Grant Park is also 1 mile from Millennium ...

              Best Western Grant Park Hotel$95

              Best Western Grant Park Hotel$95
              Edward Hotel Chicago

              Edward Hotel Chicago

              6600 N. Mannheim Rd, Rosemont
                3.0 out of 5.0
                 
                 
                4.0 out of 5 (142 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$63

                Edward Hotel Chicago$63
                Chicago's Essex Inn

                Chicago's Essex Inn

                800 S Michigan Ave, Chicago
                  3.5 out of 5.0
                   
                   
                  3.6 out of 5 (357 reviews)

                  Across from the greenery and attractions of Grant Park, the Essex Inn is 3 blocks from the Loop business district and Lake Michigan, 4 blocks from the Art Institute, ...

                  Chicago's Essex Inn$133

                  Chicago's Essex Inn$133
                  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 (798 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$105

                    Palmer House a Hilton Hotel$105
                    Wyndham Grand Chicago Riverfront

                    Wyndham Grand Chicago Riverfront

                    71 E Wacker Dr, Chicago
                      4.0 out of 5.0
                       
                       
                      4.2 out of 5 (283 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$95

                      Wyndham Grand Chicago Riverfront$95
                      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.