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Chicago Flight + Hotel packages

Chicago Hotels

See all 974 Hotels in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
    3.0 out of 5.0
     
     
    3.2 out of 5 (80 reviews)

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

    Congress Plaza Hotel$151

    Congress Plaza Hotel$151
    Warwick Allerton - Chicago

    Warwick Allerton - Chicago

    701 North Michigan Avenue, Chicago
      4.0 out of 5.0
       
       
      4.0 out of 5 (697 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$83

      Warwick Allerton - Chicago$83
      River Hotel

      River Hotel

      75 East Wacker Drive, Chicago
        4.0 out of 5.0
         
         
        4.0 out of 5 (461 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$108

        River Hotel$108
        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 (616 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$93

          Club Quarters Hotel, Central Loop$93
          Kimpton Hotel Allegro

          Kimpton Hotel Allegro

          171 W Randolph St, Chicago
            4.0 out of 5.0
             
             
            4.1 out of 5 (349 reviews)

            Located in the Loop's theater district, Kimpton Hotel Allegro is next to the Cadillac Palace Theatre, 4 blocks from Millennium Park, and 1 mile from the Magnificent ...

            Kimpton Hotel Allegro$82

            Kimpton Hotel Allegro$82
            Hyatt Regency Chicago

            Hyatt Regency Chicago

            151 East Wacker Dr, Chicago
              4.0 out of 5.0
               
               
              4.1 out of 5 (825 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$104

              Hyatt Regency Chicago$104
              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 (37 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$92

                Best Western Grant Park Hotel$92
                Edward Hotel Chicago

                Edward Hotel Chicago

                6600 N. Mannheim Rd, Rosemont
                  3.0 out of 5.0
                   
                   
                  4.0 out of 5 (140 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
                  Chicago's Essex Inn

                  Chicago's Essex Inn

                  800 S Michigan Ave, Chicago
                    3.5 out of 5.0
                     
                     
                    3.6 out of 5 (353 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$79

                    Chicago's Essex Inn$79
                    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 (793 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
                      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.