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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 42%* 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 vacation 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 travelers 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 Center.

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 Center. 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?

Vacations 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.

What types of accommodation options are available in Chicago?

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

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 vacation, 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 center of town.




Guide to Exploring around Chicago


Best Lodging Options Near Chicago

See all 1,825 Properties in Chicago
Congress Plaza Hotel NT$4,387
Reviewed on 2019/9/19
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

    Situation Rooms spacious Quiet I have no more to say

    Hotel Essex Chicago NT$3,631
    Reviewed on 2019/9/19
    See details
     
    Hotel Essex Chicago

    Hotel Essex Chicago

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

      Staff was very courteous and helpful. Rooms were clean and very adequate.

      The Whitehall Hotel NT$3,476
      Reviewed on 2019/9/19
      See details
       
      The Whitehall Hotel

      The Whitehall Hotel

      105 E Delaware Pl, Chicago, IL
         
        4.1 of 5
        4.0 out of 5.0 Stars

        Nice to have been met by a doorman. We saw the lake!! from our corner room. A lovely room, gorgeous bathroom. Staff was wonderful, especially the evening bar manager (black hair, lovely and kind personality). Very comfortable, and such a historic building kept in great condition.

        Inn of Chicago NT$2,517
        Reviewed on 2019/9/4
        See details
         
        Inn of Chicago

        Inn of Chicago

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

          Nice staff, nice lobby, nice neighborhood, room's furnitures are old but clean

          Warwick Allerton - Chicago NT$3,687
          Reviewed on 2019/9/19
          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

            Location is excellent. It was a pleasant stay, everyone was super friendly.

            Palmer House a Hilton Hotel NT$5,437
            Reviewed on 2019/9/17
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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

              great location, great staff and amenities, beautiful property

              The St. Clair Hotel – Magnificent Mile NT$3,160
              Reviewed on 2019/9/19
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              The St. Clair Hotel – Magnificent Mile

              The St. Clair Hotel – Magnificent Mile

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

                It was at a perfect location for all the things we went to Chicago to see/do. Convenient to the bus and sub way lines and places to eat. Room was a bit small, but very clean. Had a few issues connecting to the wi-fi also. Would stay here again next time traveling to Chicago.

                Hyatt Regency Chicago NT$6,165
                Reviewed on 2019/9/9
                See details
                 
                Hyatt Regency Chicago

                Hyatt Regency Chicago

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

                  Perfect location for all attractions. Walkable distance to everything

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