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Chicago Holiday Packages

Save Time and Money with Chicago Holiday Packages

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.

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

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!

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

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.

Popular Activities for your Chicago Holiday

Holidays are pretty great already. But throwing yourself into the fantastic activities on offer always makes them better!

Your trip to Chicago is about to get a whole lot more exciting. There are plenty of activities available, including:

For a more complete list of activities, jump onto our Chicago things to do page.

Chicago Accommodation

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.

Nearest Airports to 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.

*Savings based on all holiday package bookings with Flight + Hotel on Expedia.com from January through December 2017, as compared to 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. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.


Guide to Exploring Chicago


Top Chicago Hotel Deals

See all 1,701 properties in Chicago
Congress Plaza Hotel SG$160
Reviewed on 16 Aug,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

    Great location. Did not try restaurants or bar. Nice bed and useful elevators. AC in room was loud and spewed water. It kept us up on the last night of our stay. We complained and were given a partial refund for our last night. Tub also clogged and handle fell off shower door.

    Warwick Allerton - Chicago SG$140
    Reviewed on 17 Aug,2019
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    Warwick Allerton - Chicago

    Warwick Allerton - Chicago

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

      This is a nice historic building in the middle of Magnificent Mile! Great price when we booked!

      Millennium Knickerbocker Chicago SG$132
      Reviewed on 17 Aug,2019
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      Millennium Knickerbocker Chicago

      Millennium Knickerbocker Chicago

      163 East Walton Place, Chicago, IL
         
        4.3 of 5
        4.0 out of 5.0 Stars

        I like the location. Also, the bed was very comfortable and there were a variety of different types of pillows.

        Hotel Essex Chicago SG$112
        Reviewed on 16 Aug,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

          So happy with my stay at the Essex. The staff were amazing and helpful, rooms very modern, bed was like a pillow! Bluetooth mirrors in the bathroom were a great touch. And the location/view could not be beaten!

          The Whitehall Hotel SG$131
          Reviewed on 17 Aug,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

            Friendly staff. Good location. Would definitely stay here again.

            Travelodge by Wyndham Downtown Chicago SG$131
            Reviewed on 16 Aug,2019
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            Travelodge by Wyndham Downtown Chicago

            Travelodge by Wyndham Downtown Chicago

            65 E Harrison St, Chicago, IL
               
              3.3 of 5
              2.0 out of 5.0 Stars

              Nice beds, good size room, and warm shower. WiFi also worked well.

              Palmer House a Hilton Hotel SG$192
              Reviewed on 16 Aug,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

                Love the historic restoration, comfort of king bed, corner room with 2 windows and nice size, good cocktails. Dislike broadcasted techno music in entire lobby, dining rooms, registration, bar, EVERYWHERE. It made me feel on edge. I think you need to offer free WiFi. And put in coffee maker in ...

                Hilton Chicago O'Hare Airport SG$153
                Reviewed on 12 Aug,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

                  Convenient and close to Airport. However the Telco reception seems quite bad and require to purchase the Wifi Services from the Hotel.

                  Chicago Packages

                  Chicago Flight Deals

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