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Does Expedia have Vacation 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 Vacation Package?

Smart jetsetters can save up to $583* by booking a package deal on Expedia.

Can I choose my airline with a Chicago Expedia Vacation 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 vacation will be easy!

Do I lose money if I change my mind after I have booked my Chicago Vacation 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 Vacation?

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 accommodations 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.



*Savings based on all vacation package bookings with Flight + Hotel on Expedia.com from January through December 2018, 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 around Chicago


Best Lodging Options Near Chicago

See all 1,918 Properties in Chicago
Congress Plaza Hotel $150
Reviewed on Sep 12, 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

    Beautiful building. Clean room, nice helpful people.

    Hotel Essex Chicago $121
    Reviewed on Sep 13, 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

      I liked the feel of it, very comfortable. I liked the closeness to attractions. I didn’t like the non complementary breakfast since it was so expensive but I did like the cafe downstairs and the decent price. I didn’t like the shower bc my bathroom got soaked as soon I got in LOL but very pretty ...

      Warwick Allerton - Chicago $135
      Reviewed on Sep 14, 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

        Clean room, comfy bed, very friendly staff, sustainably focused (though that could negatively economically impact housekeeping staff), minimal amenities (room service would be nice). Will definitely book again.

        Inn of Chicago $94
        Reviewed on Sep 4, 2019
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        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

          The Whitehall Hotel $114
          Reviewed on Sep 14, 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

            It was in Michigan Avenue close to a lot of Things

            Swissotel - Chicago $159
            Reviewed on Sep 12, 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

              I lked the room and the view, The bedding was particularly comfortable. I did not like the "resort fee." Jack up the room rate if you have to, but the amenities you offer were not ones I needed or could use, especially for a one night stay. You do not even have a swimming pool, for instance. Just ...

              Palmer House a Hilton Hotel $176
              Reviewed on Sep 12, 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

                Easy access to many amenities downtown, other nearby hotels and Millenium Park. Walking distance to great shopping and restaurants. The staff and service is great. It is a historic hotel, which offers a unique flavor and feeling for those seeking it.

                Sofitel Chicago Magnificent Mile $142
                Reviewed on Sep 14, 2019
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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

                  Upscale, very clean, and professional and courteous staff

                  Top Flight + Hotel Deals

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