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Chicago Holiday Packages

Chicago, Illinois, is the perfect choice for an American holiday—it has a busy, powerful vibe similar to New York, with just as much to do and see. Chicago packages are your ticket to an American Midwest secret: “The Windy City” has some of the best food, shopping and nightlife in the U.S.—at least, according to the locals! Why not decide for yourself on your next holiday?

Things to Do in Chicago

Navy Pier is a can’t-miss activity for any holiday in Chicago. The 45m-tall Ferris wheel is sure to catch your attention; take a spin for great city views. Then do your best sailor swagger into the shops, where you just might find those perfect skyline-shaped chocolates. Don’t be “a-freud” to stop and chat with the statue of TV-psychologist Bob Newhart, whose couch is designed for therapeutic confessions (and photo ops). Hungry? Travel to the tropics inside Crystal Gardens, a one-acre greenhouse with palm trees, fountains and a variety of restaurants.

If you’re in the mood for some education, or the weather just isn’t on your side, explore indoors at one of Chicago’s museums. Always wanted to see the world from an ant’s perspective or learn about man-eating lions in Kenya? The Field Museum of Natural history, one of the largest in the world, is your playground. You could also book a Chicago car hire and head north to the Illinois Railway Museum or south to the Museum of Science and Industry.

Shopping, Dining & Nightlife

The money you’ve saved with our Chicago package deals is probably burning a hole in your pocket, so it’s time to decide: What’s your shopping style? The Magnificent Mile lives up to its name, with world-famous luxury brands and posh boutiques. In the Loop neighbourhood, rock collectors can find the perfect marquise cut on Jewelers Row, while bargain hunters can dig through discount racks on State Street. A Chicago holiday near Millennium Park is the perfect home base for shopaholic getaways, with both these neighbourhoods within walking distance.

You can show off your new diamonds at dinner without even leaving Mag Mile—it’s one of the best neighbourhoods for upscale dining. However, Chicago holidays are best spent exploring; go northwest to find up-and-coming Lincoln Park, filled to the brim with the vanguard of experimental cuisine. Get your hands on mozzarella balloons, inside-out eggs benedict and crispy pig’s ears, and your taste buds will never be the same.

Swanky sightseers can keep their holiday going into the wee hours in Gold Coast, an area that is, you guessed it, on the Lake Michigan coast and very exclusive. Head over to stylish Rush Street to get your groove on with live jazz, reggae or funk. For the younger (or just hipper) crowd, Wicker Park is all about trendy cocktails, groovy tunes and a laid-back vibe. Plus, it’s got a subway stop on the 24-hour Blue Line, so you can easily get back downtown without even springing for a cab.

What’s Next?

The next steps are easy—listen to your holiday self and book your getaway with Wotif. We have the best Chicago hotel packages, because you can mix and match with flights to the same destination to create your perfect escape. Check us out today.


Guide to Exploring Chicago

Top Chicago Hotels

See all 1,635 properties in Chicago

Estimated price for 1 night/2 adults

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
    3.5 out of 5.0
     
     
    3.7 out of 5 (9 reviews)

    Located in The Loop, this hotel is steps from Columbia College Chicago, Museum of Contemporary Photography, and Auditorium Building and Theatre. Fine Arts Building ...

    Congress Plaza HotelNZ$189

    11 Aug - 12 Aug

    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago, IL
      4.0 out of 5.0
       
       
      3.0 out of 5 (2 reviews)

      Located in The Loop, this eco-friendly hotel is steps from Chicago Riverwalk and Michigan Avenue Bridge. Chicago Theatre and Millennium Park are also within ...

      Hyatt Regency ChicagoNZ$345

      15 Aug - 16 Aug

      Travelodge by Wyndham Downtown Chicago

      Travelodge by Wyndham Downtown Chicago

      65 E Harrison St, Chicago, IL
        2.0 out of 5.0
         
         
        2.8 out of 5 (4 reviews)

        Located in The Loop, this hotel is steps from Lakefront Trail, Columbia College Chicago, and State Street. Buckingham Fountain and Grant Park are also within ...

        Travelodge by Wyndham Downtown ChicagoNZ$164

        28 Jul - 29 Jul

        Hotel Essex Chicago

        Hotel Essex Chicago

        800 S Michigan Ave, Chicago, IL
          4.0 out of 5.0
           
           
          5.0 out of 5 (1 reviews)

          Located in The Loop, this hotel is within a 5-minute walk of Lakefront Trail, State Street, and Columbia College Chicago. Grant Park and Buckingham Fountain ...

          Hotel Essex ChicagoNZ$190

          11 Aug - 12 Aug

          Central Loop Hotel

          Central Loop Hotel

          111 West Adams Street, Chicago, IL
            4.0 out of 5.0
             
             
            4.2 out of 5 (4 reviews)

            Located in The Loop, this boutique hotel is within a 5-minute walk of Chicago Board of Trade Building and State Street. Willis Tower and Skydeck Ledge are also ...

            Central Loop HotelNZ$202

            28 Jul - 29 Jul

            Warwick Allerton - Chicago

            Warwick Allerton - Chicago

            701 North Michigan Avenue, Chicago, IL
              4.0 out of 5.0
               
               
              4.5 out of 5 (2 reviews)

              This family-friendly Chicago hotel is located in the entertainment district, just steps from Northwestern Memorial Hospital and Michigan Avenue. Chicago Water ...

              Warwick Allerton - ChicagoNZ$195

              15 Aug - 16 Aug

              Kinzie Hotel

              Kinzie Hotel

              20 W Kinzie St, Chicago, IL
                4.0 out of 5.0
                 
                 

                Located in River North, this hotel is steps from House of Blues Chicago and State Street. Tribune Tower and Wrigley Building are also within 10 minutes. Grand ...

                Kinzie HotelNZ$237

                18 Aug - 19 Aug

                The St. Clair Hotel – Magnificent Mile

                The St. Clair Hotel – Magnificent Mile

                162 East Ontario Street, Chicago, IL
                  2.5 out of 5.0
                   
                   
                  4.0 out of 5 (1 reviews)

                  Located in Near North Side, this hotel is within 1 mi (2 km) of Navy Pier, Millennium Park, and Art Institute of Chicago. Cloud Gate and Grant Park are also ...

                  The St. Clair Hotel – Magnificent MileNZ$190

                  11 Aug - 12 Aug

                  Hilton Chicago- Michigan Ave Cultural Mile

                  Hilton Chicago- Michigan Ave Cultural Mile

                  720 S Michigan Ave, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    5.0 out of 5 (1 reviews)

                    Located in The Loop, this historic hotel is within a 5-minute walk of Columbia College Chicago and Grant Park. Art Institute of Chicago and Millennium Park are ...

                    Hilton Chicago- Michigan Ave Cultural MileNZ$282

                    12 Aug - 13 Aug

                    The Whitehall Hotel

                    The Whitehall Hotel

                    105 E Delaware Pl, Chicago, IL
                      4.0 out of 5.0
                       
                       
                      3.5 out of 5 (4 reviews)

                      Located in Near North Side, this romantic hotel is steps from 900 North Michigan Shops, John Hancock Center, and Water Tower Place. Chicago Water Tower and Michigan ...

                      The Whitehall HotelNZ$196

                      28 Jul - 29 Jul

                      ^Savings based on all package bookings made with Flight + Hotel on Wotif.co.nz from January 1, 2018 to December 31, 2018, 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.