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Chicago

Does Expedia have holiday package deals to Chicago?

Yes! Expedia has some fantastic Chicago travel packages Combining your bookings is one of the simplest ways to save cash and time — and get your adventure off on the right foot.

How much can I save with a Chicago holiday package?

Smart jetsetters can save up to 80%* by booking a package deal on Expedia.

Can I choose my airline with a Chicago Expedia holiday package?

Our enormous global database lists more than 750,000 properties worldwide and 400 partner airlines. With such a broad range of options, crafting your dream holiday will be easy!

Do I lose money if I change my mind after I have booked my Chicago holiday package?

Still undecided? There are no hidden fees from us if you change your mind for almost any reservation.

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.

A holiday is a great time to slow down and unwind. It's also the ideal time to embark on some new experiences!

Kick-start your trip to Chicago by checking out some of these activities:

Jump onto our Chicago things to do page for a full list.

What types of accommodation options are available in Chicago?

You can expect a large range of accommodation when you head to Chicago. With 165 properties on offer, it won't be an issue booking a cosy place to sleep for your next luxury getaway or cheap holiday.

The Chicago Premier Suites (540 N State Street) and The Peninsula Chicago (108 East Superior Street) are two of the higher-end options in Chicago. Book a room at either and you're bound to have some of the nicest rooms in town. Looking for somewhere cheaper? The Trump International Hotel & Tower Chicago (401 N Wabash Ave) and the Old Chicago Inn (3222 N Sheffield Ave) are a couple of places that won't break the bank.

Of course, another great option is to stay just a stone's throw from the Art Institute of Chicago. You can do this by making a reservation at The Langham, Chicago, which is just 0.6 miles (1 km) away. Also in demand is the JW Marriott Chicago, a mere 0.5 miles (0.8 km) away.

Is there an airport in Chicago?

The airport probably isn't going to be the most exhilarating moment of your holiday, but there's nothing like the feeling of knowing that your well-earned trip to Chicago is a mere plane ride away! Once you hit the ground at Midway International Airport (MDW), you'll be 9 miles (14 km) from the centre of town.




Guide to Exploring Chicago


Top Chicago Hotel Deals

See all 1,399 properties in Chicago
Congress Plaza Hotel SG$165
Reviewed on 13 Oct,2019
See details
 
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
     
    3.7 of 5
    3.5 out of 5.0 Stars

    Location is great and was truly grateful for upgrade to a lake view room

    Hotel Essex Chicago SG$116
    Reviewed on 10 Oct,2019
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    Hotel Essex Chicago

    Hotel Essex Chicago

    800 S Michigan Ave, Chicago, IL
       
      4.4 of 5
      4.0 out of 5.0 Stars

      The room was beautiful! The furnishings were modern and everything was very clean. I was a little surprised how much noise I was able to hear from the hall, though, and since my room was right outside the elevator, there was quite a bit of noise throughout the night.

      The St. Clair Hotel – Magnificent Mile SG$132
      Reviewed on 11 Oct,2019
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      The St. Clair Hotel – Magnificent Mile

      The St. Clair Hotel – Magnificent Mile

      162 East Ontario Street, Chicago, IL
         
        4.0 of 5
        2.5 out of 5.0 Stars

        Room was very small, very clean with great beds. Service also very good

        Inn of Chicago SG$88
        Reviewed on 10 Oct,2019
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        Inn of Chicago

        Inn of Chicago

        162 E Ohio St, Chicago, IL
           
          3.6 of 5
          3.0 out of 5.0 Stars

          Great location , very clean and friendly. I loved the area, walked from one end of the town to the other with ease, the close to Old Navy Pier,

          DoubleTree by Hilton Chicago - Magnificent Mile SG$142
          Reviewed on 7 Oct,2019
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          DoubleTree by Hilton Chicago - Magnificent Mile

          DoubleTree by Hilton Chicago - Magnificent Mile

          300 E Ohio St, Chicago, IL
             
            4.2 of 5
            3.5 out of 5.0 Stars

            Clean, beautiful rooms. Friendly helpful staff. Great location downtown. The only negatives are no free breakfast and if you park with the hotel it’s an extra 55 dollars a day.

            Eurostars Magnificent Mile, previously Dana Hotel SG$161
            Reviewed on 9 Oct,2019
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            Eurostars Magnificent Mile, previously Dana Hotel

            Eurostars Magnificent Mile, previously Dana Hotel

            660 North State Street, Chicago, IL
               
              4.4 of 5
              4.0 out of 5.0 Stars

              it is close to everything and everyone is very professional.

              The Whitehall Hotel SG$128
              Reviewed on 11 Oct,2019
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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

                Old school hotel, beautiful, clean hotel and friendly staff. Nice neighbourhood.

                Wyndham Grand Chicago Riverfront SG$218
                Reviewed on 12 Oct,2019
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                Wyndham Grand Chicago Riverfront

                Wyndham Grand Chicago Riverfront

                71 E Wacker Dr, Chicago, IL
                   
                  4.3 of 5
                  4.0 out of 5.0 Stars

                  The property was beautiful and in a prime location to explore Chicago. My two biggest criticisms would be that room service was advertised but it would only be from 6:30 to 11:30 AM, breakfast only. Lunch and dinner would be available for pickup in the hotel restaurant. This wasn't a huge deal or ...

                  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 things to do in Chicago

                  See all 166 things to do in Chicago