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Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

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Chicago Holiday

What are the best places to visit in Chicago?

Preparing for your trip to Chicago? Need some info about what to see when you arrive? That's where we can assist!

Take it from us, your bucket list will be heaps shorter after a trip to Chicago! Famed attractions like the Art Institute of Chicago and Willis Tower should be some of your first ports of call. The McCormick Place and the University of Illinois Chicago also draw in crowds of travellers from all across the globe.

You're going to find yourself surrounded by terrific things to do and see, including Navy Pier and the Lincoln Park Zoo. If you're dying to get the most out of your stay, also check out Lincoln Park and the Chicago Cultural Centre.

Millennium Park is an oasis amid the bustle of everyday life. Pull off your shoes and feel the cool grass beneath your feet or simply lie on your back and spot shapes in the clouds. Adventurers in this destination have heaps of options. Those who are a little queasy around heights might want to look away, but anyone who's curious about skyscrapers can't miss John Hancock Centre. Towering high above the ground, it's a beloved fixture of the area's skyline. Still have some time on your hands? Want to catch a sunrise among some spectacular scenery? Skydeck Ledge boasts glorious views that deserve to be photographed.

What are the most popular activities for a Chicago holiday?

When we hark back to our travels, we usually remember experiences rather than our swish hotel room and its view of the pool. Are you ready to create some new travel memories?

Your trip to Chicago is about to get a lot more exciting. There are heaps of activities available, such as:

To check out all the activities on offer, head to our Chicago things to do page.

What types of accommodation options are available in Chicago?

With no less than 165 accommodation in Chicago, finding a place to stay won't be difficult. But why wait around? Book now via Expedia and kick-start your next cheap holiday or luxury getaway.

Begin the quest for a dreamy Chicago base by looking into the latest offers at the Chicago Premier Suites (540 N State Street) and The Peninsula Chicago (108 East Superior Street). Alternatively, the Trump International Hotel & Tower Chicago (401 N Wabash Ave) and the Old Chicago Inn (3222 N Sheffield Ave) are two properties well worth investigating if you're travelling on the cheap.

If you'd rather stay nearby the Art Institute of Chicago, The Langham, Chicago and the JW Marriott Chicago are excellent options.

Is there an airport in Chicago?

We know the airport won't be the most memorable moment of your holiday, but there's nothing like the excitement of knowing that your well-deserved trip to Chicago is just a flight away! Once you unbuckle your seatbelt at Midway International Airport (MDW), you'll be 9 miles from the heart of town.




Guide to Exploring Chicago


Chicago Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Top Chicago Hotel & Accommodation Deals

See all 2,101 properties in Chicago
LondonHouse Chicago, Curio Collection by Hilton NZ$160
Reviewed on 11 Jul. 2020
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LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

85 East Wacker Drive, Chicago, IL
     
    4.6 of 5
    4.5 out of 5.0 Stars

    The property is in a great location and very nicely updated. Out bathroom was not the cleanest, but not terrible either.

    Sofitel Chicago Magnificent Mile NZ$285
    Reviewed on 12 Jul. 2020
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    Sofitel Chicago Magnificent Mile

    Sofitel Chicago Magnificent Mile

    20 E Chestnut St, Chicago, IL
       
      4.6 of 5
      4.5 out of 5.0 Stars

      Great gym. Bad housekeeping service. Attention at front desk is far too be kind. If feels like the girls at the front desk were making you a favor. Same goes to the girls at the bar.

      Kinzie Hotel NZ$191
      Reviewed on 8 Jul. 2020
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      Kinzie Hotel

      Kinzie Hotel

      20 W Kinzie St, Chicago, IL
         
        4.5 of 5
        4.0 out of 5.0 Stars

        Great location, friendly staff. So many great food options nearby and the Riverwalk.

        Best Western Grant Park Hotel NZ$102
        Reviewed on 12 Jul. 2020
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        Best Western Grant Park Hotel

        Best Western Grant Park Hotel

        1100 S Michigan Ave, Chicago, IL
           
          4.1 of 5
          2.5 out of 5.0 Stars

          Clean room,nice host, bug free, nice view, working vending machines

          The Godfrey Hotel Chicago NZ$206
          Reviewed on 12 Jul. 2020
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          The Godfrey Hotel Chicago

          The Godfrey Hotel Chicago

          127 West Huron, at LaSalle, Chicago, IL
             
            4.3 of 5
            4.5 out of 5.0 Stars

            The hotel was nice and clean! Very nice hotel and walking or uber/Lyft ride to the city walk or navy pier. The Rooftop bar was really nice too!

            Radisson Blu Aqua Hotel Chicago NZ$334
            Reviewed on 11 Jul. 2020
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            Radisson Blu Aqua Hotel Chicago

            Radisson Blu Aqua Hotel Chicago

            221 N Columbus Dr, Chicago, IL
               
              4.4 of 5
              4.5 out of 5.0 Stars

              The hotel is in the perfect location, minutes to the river walk, navy pier and shopping on Michigan Ave and State Street. The rooms were nice and clean and the staff and restaurant were great. I’d recommend this place to friends and family. My wife and I will definitely return.

              The Whitehall Hotel NZ$159
              Reviewed on 11 Jul. 2020
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              The Whitehall Hotel

              The Whitehall Hotel

              105 E Delaware Pl, Chicago, IL
                 
                4.1 of 5
                4.0 out of 5.0 Stars

                The service was great and i loved the room service

                Trump International Hotel & Tower Chicago NZ$537
                Reviewed on 7 Jul. 2020
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                Trump International Hotel & Tower Chicago

                Trump International Hotel & Tower Chicago

                401 N Wabash Ave, Chicago, IL
                   
                  4.8 of 5
                  5.0 out of 5.0 Stars

                  Check-in with Terasa was quick and easy. She, like all the staff, was excellent! Housekeeping was Outstanding! Yen, was so Attentive and Kind! The Men at the Valet and Bellhops were Top Notch! Perfect Location! 5 Stars all around!

                  Top Activities in Chicago

                  See all 226 activities in Chicago