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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 $583* 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 550 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.

What are the most popular activities for a Chicago holiday?

When we hark back to our travels, we usually remember experiences rather than our swish hotel room and its view of the pool. Are you ready to create some new travel memories?

Your trip to Chicago is about to get a lot more exciting. There are heaps of activities available, such as:

To check out all the activities on offer, head to our Chicago things to do page.

What types of accommodation options are available in Chicago?

With no less than 165 accommodation in Chicago, finding a place to stay won't be difficult. But why wait around? Book now via Expedia and kick-start your next cheap holiday or luxury getaway.

Begin the quest for a dreamy Chicago base by looking into the latest offers at the Chicago Premier Suites (540 N State Street) and The Peninsula Chicago (108 East Superior Street). Alternatively, the Trump International Hotel & Tower Chicago (401 N Wabash Ave) and the Old Chicago Inn (3222 N Sheffield Ave) are two properties well worth investigating if you're travelling on the cheap.

If you'd rather stay nearby the Art Institute of Chicago, The Langham, Chicago and the JW Marriott Chicago are excellent options.

Is there an airport in Chicago?

We know the airport won't be the most memorable moment of your holiday, but there's nothing like the excitement of knowing that your well-deserved trip to Chicago is just a flight away! Once you unbuckle your seatbelt at Midway International Airport (MDW), you'll be 9 miles from the heart of town.




Guide to Exploring Chicago


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 Chicago Hotel & Accommodation Deals

See all 2,273 properties in Chicago
The Whitehall Hotel AU$116
Reviewed on 21 Feb. 2020
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

    Hotel was in a really nice area and the staff was extremely friendly, they made the whole trip great

    Congress Plaza Hotel AU$150
    Reviewed on 21 Feb. 2020
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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

      Overall this hotel is pretty good. The rooms are nice, it’s in a great location but it just feels a bit rundown? Shower was a nightmare to operate and the water didn’t run very hot. Heating couldn’t be turned down to anything cooler than absolutely boiling...

      Best Western Grant Park Hotel AU$113
      Reviewed on 24 Feb. 2020
      See details
       
      Best Western Grant Park Hotel

      Best Western Grant Park Hotel

      1100 S Michigan Ave, Chicago, IL
         
        4.1 of 5
        2.5 out of 5.0 Stars

        In the room there wasnt frigde or macrowave, I went with my baby

        River Hotel AU$127
        Reviewed on 17 Feb. 2020
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        River Hotel

        River Hotel

        75 East Wacker Drive, Chicago, IL
           
          4.2 of 5
          4.0 out of 5.0 Stars

          The view was nice. But I would have liked a better view of the city

          Sofitel Chicago Magnificent Mile AU$194
          Reviewed on 24 Feb. 2020
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          Sofitel Chicago Magnificent Mile

          Sofitel Chicago Magnificent Mile

          20 E Chestnut St, Chicago, IL
             
            4.6 of 5
            4.5 out of 5.0 Stars

            Very nice modern hotel great location walking distance from shopping and restaurants

            Radisson Blu Aqua Hotel Chicago AU$270
            Reviewed on 24 Feb. 2020
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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

              Loved the fitness center, lap pool and the hot tub. The location is great and our room was very nice.

              Warwick Allerton - Chicago AU$134
              Reviewed on 22 Feb. 2020
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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

                Right in the center of downtown Chicago. Walking distance to all the best restaurants

                Omni Chicago Suites - Magnificent Mile AU$303
                Reviewed on 21 Feb. 2020
                See details
                 
                Omni Chicago Suites - Magnificent Mile

                Omni Chicago Suites - Magnificent Mile

                676 N Michigan Ave, Chicago, IL
                   
                  4.5 of 5
                  4.5 out of 5.0 Stars

                  Great hotel and location. Friendly staff. Would stay again

                  Top 10 Things To Do In Chicago

                  See all 265 activities in Chicago