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

See all 1,961 properties in Chicago
LondonHouse Chicago, Curio Collection by Hilton SG$150
Reviewed on 3 Aug,2020
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LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

     
    4.6 of 5
    4.5 out of 5.0 Stars

    This is a beautiful wonderfully located we staffed property I would recommend to vacation travelers and business travelers.

    Sofitel Chicago Magnificent Mile SG$196
    Reviewed on 2 Aug,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

      The location is great, one block from Michigan Ave, very convenient. The price is reasonable, nice view from the hotel.

      Best Western Grant Park Hotel SG$84
      Reviewed on 28 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

        Having stayed at the hotel seven days earlier and having been told that check in was at noon, (and checking in at noon) we arrived at noon to check in and were told that check in is at 3. I asked if that had changed in the past week and was told no, that's how it has always been. Because of covid, ...

        Kinzie Hotel SG$133
        Reviewed on 4 Aug,2020
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        Kinzie Hotel

        Kinzie Hotel

           
          4.5 of 5
          4.0 out of 5.0 Stars

          Everthing is great about this hotel. It is in a nice location. People who work there are very friendly. Our room was very clean and it had a nice view.

          Radisson Blu Aqua Hotel Chicago SG$308
          Reviewed on 4 Aug,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

            It was perfect just the way I imagined. I loved the bar overall and the lobby sitting is beautiful .Highly recommend 10000/10.

            The Godfrey Hotel Chicago SG$214
            Reviewed on 3 Aug,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

              Close to restaurants and shopping stores! Food was very excellent and everything was walking distance. Parking could be a bit pricey

              Home2 Suites by Hilton Chicago River North SG$151
              Reviewed on 28 Jul,2020
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              Home2 Suites by Hilton Chicago River North

              Home2 Suites by Hilton Chicago River North

                 
                4.4 of 5
                2.5 out of 5.0 Stars

                Very clean. Easy to get to the Mile. Beds were soft

                Trump International Hotel & Tower Chicago SG$411
                Reviewed on 3 Aug,2020
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                Trump International Hotel & Tower Chicago

                Trump International Hotel & Tower Chicago

                   
                  4.8 of 5
                  5.0 out of 5.0 Stars

                  Hotel is in a great location! Very clean and comfortable. Staff was friendly for the most part. Amenities offered were satisfactory.

                  Top Activities in Chicago

                  See all 160 things to do in Chicago