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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 15%* 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 Flight + Hotel Deals

Top Hotel Deals

See all 1,729 properties in Chicago
Congress Plaza Hotel £111
Reviewed on 24 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

    Property is fancy. Elevators need a facelift so as guest rooms

    Hotel Essex Chicago £103
    Reviewed on 24 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

      It was an excellent place to stay. However, there are hidden fees. There is an urban fee of $16 that includes water and gym use.

      Warwick Allerton - Chicago £93
      Reviewed on 23 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

        Bedroom was spacious and bed comfortable. Large adjustable TV screen. Was able to get into bath easily.

        Millennium Knickerbocker Chicago £99
        Reviewed on 21 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

          Location, cleanliness and nice staff, also how you check people for their key to get on the elevator

          Swissotel - Chicago £122
          Reviewed on 19 Aug 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

            Nice hotel, wonderful views. Few staff members working, long lines for front desk even to ask questions. Long wait for elevators, 6 elevators only one taking people up. Tried to cram 10 stops on one elevator and people don’t fit.

            Travelodge by Wyndham Downtown Chicago £99
            Reviewed on 22 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

              Great location, very beautiful room and excellent service

              Hilton Chicago O'Hare Airport £105
              Reviewed on 25 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

                I really liked the location. The staff was very friendly. The room was clean. The phone kept flashing with a message, and when I tried to get a message, I was told there were none. The TV wouldn't work. When I called the operator, she said she would send up engineering to take care of both problems. ...

                The Whitehall Hotel £89
                Reviewed on 21 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

                  Location and staff friendliness. Comfortable room. Excellent value. We would definitely consider this hotel again.

                  Top Deals on Flights

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