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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 $200* 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 & Accommodation Deals

See all 1,966 properties in Chicago
Warwick Allerton - Chicago AU$148
Reviewed on 11 Nov. 2019
See details
 
Warwick Allerton - Chicago

Warwick Allerton - Chicago

701 North Michigan Avenue, Chicago, IL
     
    4.1 of 5
    4.0 out of 5.0 Stars

    Rooms small, but workable and clean. Great location especially for shopping, etc.

    Hyatt Regency Chicago AU$145
    Reviewed on 12 Nov. 2019
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    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago, IL
       
      4.4 of 5
      4.0 out of 5.0 Stars

      Great atmosphere. Location is perfect and staff is very helpful. The food is very good.

      Swissotel - Chicago AU$159
      Reviewed on 12 Nov. 2019
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      Swissotel - Chicago

      Swissotel - Chicago

      323 E Wacker Dr, Chicago, IL
         
        4.4 of 5
        4.5 out of 5.0 Stars

        It was a beautiful hotel. They messed up reservation but made good by upgrade to river view which was pretty. We thought there was a pool but found out they closed it up 3 yrs ago. Need to update info.

        Congress Plaza Hotel AU$128
        Reviewed on 9 Nov. 2019
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        Congress Plaza Hotel

        Congress Plaza Hotel

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

          Great location. easy access to Bus and train and acceptable restauants. Only complaint...I asked for a 5:00 AM wake up and DID NOT receive it. When I called to report this all I got was a weak sorry sir. I am not a sir. Not getting the call was a BIG problem. Dek clerk has NOT clue. Other than that, ...

          Radisson Blu Aqua Hotel Chicago AU$232
          Reviewed on 12 Nov. 2019
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          Radisson Blu Aqua Hotel Chicago

          Radisson Blu Aqua Hotel Chicago

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

            Beautiful hotel. Great location! We would recommend this highly! Thanks for the hospitality!

            Eurostars Magnificent Mile, previously Dana Hotel AU$153
            Reviewed on 13 Nov. 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

              Every staff member was extremely helpful and gracious.

              Palmer House a Hilton Hotel AU$153
              Reviewed on 11 Nov. 2019
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              Palmer House a Hilton Hotel

              Palmer House a Hilton Hotel

              17 E Monroe St, Chicago, IL
                 
                4.2 of 5
                4.0 out of 5.0 Stars

                The location is ideal for seeing the play Hamilton. Just about one block down the street to the theater. My most high praise goes out to the barber shop where I received excellent service. Brady! He's the man! I got an old school shave and it was awesome! If you're not in a hurry and want to treat ...

                Hilton Chicago O'Hare Airport AU$178
                Reviewed on 11 Nov. 2019
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                Hilton Chicago O'Hare Airport

                Hilton Chicago O'Hare Airport

                Ohare International Airport, Chicago, IL
                   
                  3.9 of 5
                  4.0 out of 5.0 Stars

                  Very convenient for an early flight out of O’Hare. Facilities need to be updated.

                  Top Chicago Flight & Hotel Packages

                  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 10 Things To Do In Chicago

                  See all 147 activities in Chicago