Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

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

Warwick Allerton - Chicago

Warwick Allerton - Chicago

701 North Michigan Avenue, Chicago, IL
    4.0 out of 5.0
     
     
    4.0 out of 5 (3 reviews)

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

    from NZ$158

    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 away from Chicago Riverwalk and Michigan Avenue Bridge. Grant Park and Chicago Theatre are also within ...

      from NZ$155

      Swissotel - Chicago

      Swissotel - Chicago

      323 E Wacker Dr, Chicago, IL
        4.5 out of 5.0
         
         
        4.8 out of 5 (4 reviews)

        Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk and Michigan Avenue. Grant Park and Tribune Tower are also within 10 minutes. ...

        from NZ$175

        Congress Plaza Hotel

        Congress Plaza Hotel

        520 South Michigan Avenue, Chicago, IL
          3.5 out of 5.0
           
           
          3.8 out of 5 (10 reviews)

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

          from NZ$137

          Radisson Blu Aqua Hotel Chicago

          Radisson Blu Aqua Hotel Chicago

          221 N Columbus Dr, Chicago, IL
            4.5 out of 5.0
             
             
            4.0 out of 5 (1 reviews)

            Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk, Grant Park, and Aon Center. Chicago Theatre and Chicago Cultural Center ...

            from NZ$232

            Eurostars Magnificent Mile, previously Dana Hotel

            Eurostars Magnificent Mile, previously Dana Hotel

            660 North State Street, Chicago, IL
              4.0 out of 5.0
               
               
              5.0 out of 5 (1 reviews)

              Located in River North, this spa hotel is steps away from Chinese Consulate and State Street. Chicago Water Tower and Tribune Tower are also within 10 minutes. ...

              from NZ$163

              Palmer House a Hilton Hotel

              Palmer House a Hilton Hotel

              17 E Monroe St, Chicago, IL
                4.0 out of 5.0
                 
                 
                2.3 out of 5 (3 reviews)

                Located in The Loop, this spa hotel is within a 5-minute walk of Art Institute of Chicago and Millennium Park. Chicago Theatre and Willis Tower are also within ...

                from NZ$163

                Hilton Chicago O'Hare Airport

                Hilton Chicago O'Hare Airport

                Ohare International Airport, Chicago, IL
                  4.0 out of 5.0
                   
                   
                  3.0 out of 5 (3 reviews)

                  Located in O'Hare, this hotel is within 6 miles (10 km) of Fashion Outlets of Chicago, Donald E. Stephens Convention Center and Rosemont Theatre. Allstate Arena ...

                  from NZ$190

                  Inn of Chicago

                  Inn of Chicago

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

                    Located in Near North Side, this beach hotel is within a 5-minute walk of Michigan Avenue, Tribune Tower, and Northwestern Memorial Hospital. Chicago Water Tower ...

                    from NZ$125

                    DoubleTree by Hilton Chicago - Magnificent Mile

                    DoubleTree by Hilton Chicago - Magnificent Mile

                    300 E Ohio St, Chicago, IL
                      3.5 out of 5.0
                       
                       
                      3.5 out of 5 (2 reviews)

                      Located in Near North Side, this hotel is within a 10-minute walk of Michigan Avenue, Chicago Riverwalk and Tribune Tower. Chicago Water Tower and Northwestern ...

                      from NZ$148

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

                      ^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.

                      *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.